This is a preview.Get full access.

Founding Sales

The Early-Stage Go-To-Market Handbook

Pete Kazanjy

A detailed and tactical guide to accelerate learning and success on the early-stage sales journey, from founder to early salesperson to sales leadership. Written by a sales expert for startup founders and first-time sales staff.
560 pages and 98 links


Updated August 22, 2022
Courtney NashEditor


What Inspired This Book?4 minutes, 5 links

In Spring of 2010, our startup, Unvarnished, launched to a massive cataclysm of press coverage, venture capital interest, and general gnashing of teeth.

As the world’s first serious attempt at a community-contributed reputation system for professionals, or a “Yelp for professionals,” we were featured on the Today Show, covered by many national newspapers, and enjoyed traffic spikes that would be the envy of any newly launched startup.

By January of 2011, we had concluded that our concept was a failure, and we needed to try something new.

At the behest of our board members, Josh Kopelman and Phin Barnes of First Round Capital and Saar Gur of CRV, we started looking at other potential ways to solve the same problem (hiring well is hard, and there is likely a data-centric way to help with that).

And while our first concept was a failure, the next one wasn’t.

In April 2011 we started building TalentBin, the earliest versions of which was a recruiting product based on referrals from employee networks to help recruiters better proactively mine the networks of their staff to assist in recruiting their hardest-to-fill openings.

Rather than sit in a cave, pretending we were building the next great thing before revealing it to the world, we were dead set on getting outside, and getting this in the hands of our intended customers as early as possible.

And that meant selling.

Unfortunately, we didn’t have any sales professionals on the team—or anyone with any sales experience, really. We had my cofounder, Jason, who started his career as a software engineer, before progressing to, variously, interaction design, then product management, then product management leadership, with a sprinkling of professional poker playing in between. And we had three engineers, who, while very smart and hardworking, weren’t about to hit the phones all day every day.

It quickly became apparent that the sales piece would fall to me, and not because of my overwhelming qualification for the role—my background was as a product marketing and marketing generalist, with some product management for kicks. Rather, everyone else had things that only they could do, so I had better get my ass in gear.

What followed in the ensuing three years was a massive exercise in painful growth and learning as TalentBin went from hypothesis, to early minimum viable product, to strong product-market fit and sales scaling, to acquisition by Monster Worldwide in early 2014.

And for me, this meant a transition from a generalist business founder, to TalentBin’s first evangelical sales rep, trying to get someone, anyone, to use our product, for free, through Summer and Fall 2011. Starting in that Fall, I moved on to become our first smiling and dialing account executive, asking for the sale with real money and a straight face, and then to the first beginnings of sales management as I brought on our first Market Development Rep to fill my calendar in January 2012. I then haltingly added account executives and market development reps through 2012, and continued all the way through robust, repeatable, scalable B2B SaaS sales, with account management and customer success apparatuses, in 2013 into 2014. When it was all said and done, we had a team of ~20 sales and customer success staff and were cranking along at a ~$6M/year run rate.

It was not without its misfires, train wrecks, and victories, individual and team. Most importantly, there were countless learnings at each step of the process.

The goal of this book is to share those with those who are beginning, midway, or even at the end of a similar journey.

Who Is This Book For?

Importantly, like any good sales conversation, first, we’re going to qualify this opportunity. This book is specifically targeted for founders who find themselves at the point where they need to transition into a selling role. And not the “founders are always selling” chestnut you constantly hear, but actually turning their attention to revenue-generating activities.

And not just any revenue-generating activities, like monetizing your software with ads, or freemium ~$9.99-a-month recurring revenues. Those are all fine on their own, but not our focus here. Rather, this book is specifically for founders who are leading organizations that have a B2B, direct sales model that involves sales professionals engaging in verbal, commercial conversations with buyers.

Moreover, many examples in this book will be targeted specifically to the realm of B2B SaaS software, and specifically as regards new, potentially innovative or disruptive offerings that are being brought to market for the first time.

In short, direct sales of the sort a B2B SaaS software startup would engage in.

If you are looking to be a first time salesperson, transitioning in from another type of role, or fresh out of school, in an organization that meets those characteristics above, you will get value out of this book.

Similarly, if you are a first time sales manager, either of the founder type or a sales individual contributor who is transitioning into that role, again, in an organization who meets the criteria above, you will also get value from this book.

Why Am I Uniquely Qualified to Tell This Story?

Then there’s the open question of why I am even qualified to be dispensing this sort of advice.

Aside from the above existence proof of success—albeit not hundreds of millions of dollars in revenue—I believe that a book written for non-sales people becoming sales people requires the point of view of that very same non-sales person who became a sales person, and then a sales leader.

While I did not learn at the knee of more senior sales professionals inside an existing organizational framework—say by starting as a Business Development Rep at Salesforce before moving into a Jr. Account Executive role and progressing from there—I believe that this was actually a benefit. It compelled the derivation of many best practices, which both aids with strong internalization (when you derive the answer, it sticks with you much more robustly) and opens up opportunities for innovation, as everything is on the table for questioning.

While this approach was time costly, and opportunity costly, in that I made many mistakes that likely would have been avoided by just cloning an existing reference architecture from a Salesforce or SuccessFactors or or Oracle, I also was able to approach the craft of selling, and later, the scaling, operationalization, and management thereof, with the sort of fresh child’s eyes that, coupled with a product management and engineering mindset, beget new innovation and adoption of the state of the art.

As I have since become both a sales leader at a larger, legacy sales organization and have become the sales guru that many startups and venture investors in my network come to for help, I think we ended up winning the tradeoff. We were able to innovate and adopt new, better approaches, cherry pick the best stuff from established sales orgs, and avoid any of the baggage that often accompanies calcified processes from sales organizations who, say, grew to scale in the 80s, 90s, or 00s.

Who Helped?

By no means was this a solitary enterprise. On our sales team we celebrated having an engineering mindset and felt that we were the product managers of our sales apparatus.

Chief among those who helped accelerate these learnings and overcome our errors were my sales staff, particularly Brad Snider, our first account executive; Rob Perez, our second account executive, whom we poached as an overlooked Sales Development Rep at LinkedIn; and Manny Ortega, who began as a particularly operations-minded Market Development Rep before transitioning more fully into a sales operations role before our acquisition. And on the customer success and enablement side, we went through a similar process of learning spearheaded by our head of customer success, Adam Abeles.

The First Round Capital CEO community was also invaluable, in that I was able to glean learnings from Q&A from the likes of Angus Davis, CEO of Swipely, and sales automation typhoon, Sean Black, former head of sales for Trulia, and later CEO of Crunched, amongst others.

And then there were certainly other organizations that we poached approaches from heavily. LinkedIn, ironically, as a primary competitor, was a particular pacesetter with regard to certain sales operations practices, from whom we heavily borrowed. And there were the writings of Aaron Ross, whose Predictable Revenue was influential in the later architecture of our sales org as it went from being me and a sole market development rep, to scaling up to a larger market development apparatus. Lastly Eric Ries’ The Lean Startup and Steve Blank’s Four Steps to the Epiphany were both influential in the beginning of our product development and hypothesis construction—in fact, I consider Founding Sales a cultural descendant of both books.


This book was the culmination of many people’s efforts. Thank you to my editor, Christina Bailly, for reducing redundancy and unnecessary loquaciousness. Thank you to my designer, and wife, Tracy Moeller, for laying out the book for print and epublishing, designing the cover, and building the entire website. Thank you to the First Round Capital portfolio community that supported me at the earliest stages of my journey, specifically Sean Black and Angus Davis for their peer support. And while we’re on the topic, thank you to First Round Capital and Charles River Ventures for funding TalentBin, and now Atrium, and providing the initial capital for the companies in which these lessons were learned.

Thank you to my TalentBin team, including my cofounder, Jason Heidema, and engineering leaders, Ignacio Andreu and Rodrigo Leroux, for providing a market-leading product on which I could learn to sell. And thank you to the early TalentBin sales team, including Rob Perez, Brad Snider, Manny Ortega, Akio Aida, Marcus Knight, and Jared McGriff, for being the combination guinea pigs/mad scientists with me as we figured this out. Thank you to Adam Abeles, who lead TalentBin’s customer success function, as well. And thank you to my extended peer education network of Modern Sales experts, including Jeremey Donovan, Trish Bertuzzi, Jason Jordan, and Jacco van der Kooij, for constantly pushing forward the frontier of Modern Sales, and teaching me along the way.

And thank you again to my wife, Tracy Moeller, for being my partner in my entrepreneurial journeys. Last, but not least, thank you to my parents, Cathey and Bob Kazanjy, for instilling in me a lifelong love of learning and critical inquiry without which none of this would be possible.

Founding Sales is dedicated to my brother, Michael T. Kazanjy, and my son, Michael P. Kazanjy.

How to Use This Book

importantThis book is written in stages, in that your sales efforts, like your product development efforts, will typically take a stepwise path where subsequent stages build on the prior stages.

You can read through the entire book if you want—each chapter has estimated reading times, and all in it shouldn’t take more than an hour or two per chapter. That said, usually you should only go as far as the stage that you’re at—in that worrying about things like, say, sales hiring, before you even have your sales narrative, slides, or outreach collateral in place, is going to be a premature optimization, and likely a distraction.

The goal of the book is to be a resource you can come back to frequently, like a textbook, when you need to refresh yourself on something or when you’re about to enter a new stage of your sales maturity process and need to see what’s coming next.

The Two Main Stages of Your Sales Efforts

While the entire early-stage sales transformation involves massive learnings, they will largely fall into two distinct buckets: first, figuring it out and then second, once figured out, scaling it. This is related to the notion of product-market fit, that Eric Ries, Steve Blank, and Marc Andreessen have made common parlance in the software industry. Figuring it out comes before substantial product-market fit, mainly. Scaling it is after. Both require different sales approaches, and applying the approaches designed for the latter while you’re still in the first bucket can be disastrous.

In the first epoch, it’s a tight, iterative process where you’re evangelically selling (there may not even be money involved) your solution (or perhaps even would-be solution, before you’ve even started building it) to would-be customers, and sorting out if indeed they have the pain that you’re looking to address, how big that pain is, and what they’d be willing to pay to resolve it. This stage involves its own set of approaches, which largely won’t be very scalable but will support those early learnings.

importantThe second epoch comes only after you’ve passed the first (for reasons we’ll discuss more in depth later). This is when you know your solution is viable, it solves customer pain, they are willing to pay money, and now it’s simply a question of scaling the number of humans who are doing the selling and, by extension, scaling all inputs and outputs associated with that activity. This book will be split accordingly, with the foundations and materials for early sales coming first, followed by setting up customer success programs and then scaling your sales management and execution efforts.

And while much of what will be discussed in the coming pages will be largely prescriptive in nature, the goal will be to present the sections in a way to provide a framework for understanding and thought, to aid you in your own solutions. Yes, taking what has worked before and adopting it wholesale will shorten your learning curve, but if you don’t understand the underpinnings, there’s always the risk of engaging in “cargo cult” sales activities—where you don’t quite know why you’re doing the thing you’re doing, but it worked over there, so it must work over here, right? Lastly, by no means is what follows the be-all, end-all, be all of early-stage direct sales. So if you can, adopt an engineering mindset as regards your sales approach and consider yourself the product manager of your go-to-market strategy, stealing best practices where they make sense, rejecting that which is no longer applicable or doesn’t fit, and building anew where needed.

Evangelical Sales Is Not Scaling Sales10 minutes

When you’re first starting out, there are many things you will do in your sales role that don’t look anything like sales you see in the movies, at a large sales organization, and so forth.

The goal of the first section of this book will be to discuss what those stage-appropriate activities look like, to ensure that you actually get to the second part: scaling what works.

One hallmark of this section will be doing the activities yourself. A lot of time founders think that once they’ve built a product, they can “sprinkle some sales pros on it” and poof, it’ll work. This is an incredibly destructive misconception, largely popularized by both founders and funders who don’t actually know terribly much about sales and are falsely pattern matching off of bad blog posts, movies, and sales books targeted to behaviors they’ve seen at later-stage organizations. This misconception has historically resulted in delayed or never-reached product-market fit. Steve Blank talks about it substantially in his Four Steps to the Epiphany. Much like startups are not just littler versions of large organizations, startup sales is not a smaller version of large, established sales orgs.

There’s an old saying that an organization can’t really start scaling until they’ve fired their first VP of Sales. This conception falsely presents this as a failure of that VP of Sales. Rather, this is more a failure of the founders in thinking that they could hand a sales professional who’s not a product manager a nascent product, and magically she would be able to sell the hell out of it.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Part I: Foundations

Mindset Changes for First-Time Sales Professionals29 minutes

One of the biggest things to adjust to when approaching sales for the first time is the often counterintuitive shift required to your mindset. This is especially true for founders with a background in non-sales disciplines like engineering, product management, finance, or even marketing.

I like to joke with new members of my team that doing sales changes neural pathways in your brain—but it’s really not a joke. They end up agreeing with me a few months in. A lot of the behaviors required for sales success are a massive departure from the ones you’ve valued in your career to date, even from generally accepted ways of being in society. But while they may feel uncomfortable at first, they’ve led, time and time again, to sales success.

This isn’t to say you need to run out and adopt all of these behaviors immediately, right out of the gate. My goal is simply to lay out a number of the sales mindsets that you will encounter. I want to validate, ahead of time, that when you do run into these, yes, you’re seeing what you think you are, and you shouldn’t be surprised. While a change, these new ways of thinking and interacting should be expected, and welcomed. And yes, if you can start driving yourself toward these attitudes in a proactive way, you will increase your success.

With that said, here are some of the mindset changes that will help you in the transition from founder to sales professional.

Embrace Plenty, Not Scarcity

Generally speaking, we’re taught that we should conserve resources. We’re told not to waste things. We’re all probably guilty of this—saving those extra MP3s in our iPhone’s music app, or leaving that email in our inbox, telling ourselves that we’re eventually going to get around to it. Don’t throw away that half sandwich; you can keep it in the fridge for later.

Stop that, now. Reject a mindset of scarcity—and, hence, hoarding—and embrace a mindset of plenty. The thinking should be, “Even if this one does not work out, there’s a line of thousands standing behind it that I need to get to.” So if a deal is stalling, if the customer doesn’t have the budget, if it turns out an account is not a perfect fit, and so on, great, fine, close it out. On to the next. You’ll get them the next time around.

The thing that is scarce in sales is time. To quote one of TalentBin’s key early sales staff, Brad Snider, spending “good time with good opportunities” is paramount. And, by extension, that means not spending time on opportunities that aren’t going to pan out. We’ll talk more about this later as it relates to qualifying accounts, and there certainly is an art and science piece to judging whether an account is worth it.

You should be ruthless with respect to truncating unproductive conversations with marginal opportunities, especially at the earliest of stages, when the world is a greenfield of untouched accounts in front of you.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Put Activity Above All Else

Everyone’s a fan of working smarter, not harder in the modern knowledge-worker economy. Well, sometimes you just have to grind. Sales, like recruiting, is all about activity and leverage. Generally speaking, activity in equals value out. There are certainly ways to ensure that your activity is high quality; you can also leverage it with technology to get more in less time and higher impact out of each unit of activity. We’ll dig into that more later. But to quote Joseph Stalin (likely apocryphally), “Quantity has a quality all its own,” and internalizing that is key.

More time on the phone. More demos. More proposals sent. More emails sent. More dials. More keystrokes. All of the above is activity, and activity is the goal.

This is often in direct contravention to typical notions of quality work: Thinking deeply about the perfect response to that email. Spending five minutes to game out a call before you make it. Reading, and rereading, that email to understand every nuance. Studying up on the materials to make sure that your pitch is perfect.

No more. Just as you need to shift your mindset from scarcity to plenty, the reality is that in order to move opportunities down the pipeline and close deals, activity is job one. Jump first, prepare midair. Template all communication. Drive activity, and output will follow.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Be Direct and Get Down to Business

Society often gets along through polite obfuscation. Through indirection. Through politesse, and circuitousness. Not in sales land, friend.

Much of sales is about getting down to brass tacks: Do you have the problem I’m trying to solve? Are you in agreement that it needs a solution? Are you prepared to spend money to solve it?

In the pursuit of efficiently attacking your account, you, as a sales professional, have full license to be direct in asking these sorts of questions. In fact, you can go all the way up to directly stating to your prospect, with full confidence, that your solution and their problem are an excellent fit and that they should buy X amount of your product to help their business. Asking for the sale is not optional, and it will quickly become second nature.

As Alec Baldwin states so entertainingly in that famous ABC scene in Glengarry Glen Ross, “A guy don’t walk on the lot lest he wants to buy.” People go to singles bars with very specific goals in mind. Your prospects would not be on the phone with you, taking your demo, if they didn’t have some buying intent.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Build Many Shallow Relationships

For the first-time sales pro, the scale of person-to-person interaction is a massive adjustment. Think about how many distinct people you typically interact with in a given week. If you’re like most professionals, it’s likely a constellation of one or two dozen people with whom you have frequent, ongoing interactions that build over time and with whom you have substantial history.

With sales, it’s the opposite. If you’re doing it right—see comments above about the importance of activity orientation—you’re having dozens of new interactions a week, and maintaining a pipeline of anywhere from a few dozen to north of a hundred ongoing, concurrent conversations.

It’s a substantial change of pace, and it also puts substantial stressors on you to be able to quickly build and maintain rapport with a new contact, while juggling key deal information, over the cycle of the sale. (Why do you think the weather and sports teams are the sales pro’s best friends? Instant conversation topics.) It puts the onus on the sales pro to keep readily accessible details of these individuals, their organizations, and their pains, as well as general rapport notes—which, of course, is not possible for a normal human brain. It can be exhausting, and it can be taxing. That’s why record keeping and CRM excellence (more on this later) are paramount.

This isn’t to say that these relationships are fake or that they’re not valuable or meaningful. They just demand a different way of interacting with other professionals than what you’re likely used to. To make the most of them, and manage them correctly, requires a change of mindset.

Assume the Sale Is Inevitable, and It Just Might Be

Approach your sales conversations with the stance that the prospect will inevitably be a customer. This is more applicable when you’re at the scaling stage, when it is now clear that the solution that you’re presenting has product-market fit. But it can be helpful even at the earlier stages of your go-to-market period.

What do I mean by a mindset of inevitability? If you have indeed qualified an account as a good fit, then the mindset should look something like this: “This is going to happen. It makes sense for you. This solution is the future, and it will make you more successful now and going forward. So we can do it now or we can do it later, but it’s going to happen, either with me or with a competitor of mine.”

A few helpful things come out of this mindset: First, it frames the conversation as when instead of if. This naturally makes the conversation more consultative and focused around business needs—“This solution exists to solve this problem, and we have validated that you have this problem, so clearly this solution makes sense. Let’s figure out when and how it should be implemented.” Second, it provides a confidence boost to the sales professional, related to the necessary expertness and fearlessness that we’ll talk about next. Third, it sets the groundwork for an ongoing relationship with the prospect; even if they don’t close this time through the funnel (and odds are, they won’t), they will be prepped for the next pass. It will also reinforce your own record-keeping processes, since you’ll know that recording these interactions will enable your future self the next time this prospect passes through the funnel.

It may feel odd to take on such a presumptuous mindset, and by no means is this a suggestion to be arrogant or off-putting in your dealings. But approaching each interaction with certainty will drive success in your conversations.

Expect to Win, but Be Unfazed by Rejection

In most of your professional interactions, you probably achieve some semblance of your goal most of the time, largely because you wouldn’t be engaged in the activity in question if you didn’t think you had a reasonable expectation of success.

This is definitely not the case in sales. You’re going to get shot down most of the time—you will not close the deal on that particular pass through the pipeline. For whatever reason: there won’t be enough budget, the timing will be off, the prospect will be happy with their current tools, a competitor will win the deal, the prospect will just disappear, and so on. It happens. Depending on your industry, and the point at which sales gets a prospect in the funnel, if yours is a new, innovative solution, a 20–30% win rate is solid.

The mindset change required to contend with this is the ability to hold what are essentially two seemingly opposed ideas in your head at once. You need to have and project full confidence that you’re going to win the deal but at the same time be unfazed when you do not. Being unfazed by rejection, and not internalizing it as a negative reflection on you or your offering, is key to maintaining the tempo and confidence required for sales success.

This is not to say that you should not learn from those losses; the reason for the loss should be recorded to benefit product iteration and also for reference the next time you engage with the account. Be intellectually honest about where the loss came from: Was it timing? Did you get beaten by a competitor because you didn’t follow up appropriately? Or because the product had a feature deficit? And make sure that the answer gets shared with others, so they don’t have to learn the same hard lesson you did by eating a loss. But after honestly reviewing and recording the loss cause, put it aside and move on. You should still expect to win the next one.

Record Everything—But Efficiently

As an outcome of sales strategies we’ve already covered—the sheer magnitude of professional interactions you’ll have and the importance of high activity—the reality is that you’re going to classify most of your opportunities as closed-lost. For that reason, a mindset of constant record keeping is paramount for success.

Previously, you could perhaps rely on your own memory to recall what it is that you were working on or what your last conversation with a given person had covered. No longer.

Instead, you need to admit to yourself that there’s no way that you can retain all this information, not just day to day and week to week when dealing with your current pipeline, but month to month and quarter to quarter as you revisit and resurrect previously closed opportunities. On my sales teams, we call it “setting future-you up for success.” When you come back to look at this account in a week, month, or quarter, what information will you wish you had? Record that now while it’s available, and make the ephemeral permanent.

And while your CRM will be the primary repository of this information, this mindset shift includes a variety of tactics (CRM excellence being one of them). In my sales teams, every person has a lab notebook to allow them to take notes during a call (especially during the discovery section), including size of opportunity, qualification details, and so on, to later be transferred to the CRM (not wholesale, but the salient points).

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Be Expert and Authoritative. It Begets Fearlessness.

Modern sales is not about trying to sell snake oil to a mark.

Rather, sales professionals are the grease of the market. They seek out inefficiencies in the world in the form of qualified prospects who have the business pain that the proposed solution resolves. Then they engage and consult with the prospect, and propose the implementation of the solution, to help fix that business pain.

As such, expertness in the vertical in which you are selling is an absolute requirement. You need to be a student of the game you are playing and, ideally, even more expert than the prospects to whom you are selling. This means absorbing as much information as possible about the field, the business processes that exist within it, the common organizational players, and the other solutions that already help with these business processes or compete with yours.

This expertness will make you fearless in your interactions. It will help with your activity orientation, removing your desire to over-prep for conversations and empowering you to just call, just email, just act. It will help with your ability to be direct, to operate from a position of inevitability, and to quickly establish rapport by demonstrating authority.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Make Yourself at Home in a Glass House

The level of transparency in a well-instrumented sales organization is a massive change for most people. From win and loss notes and closing ratios to leaderboards and error checking, everything is right there, available for everyone to see.

If you’re doing a good job, you will have all customer-facing interaction instrumented and recorded—every single email, every presentation, and every call—either in its entirety in the case of presentations and email, or in some partial capacity when it comes to calls and conversations. You should get comfortable with teammates jumping into those records and asking questions about why a call went this way or that way. Your creation of this transparent data is of paramount importance for the success of the organization, from both a go-to-market and a product-development standpoint.

Similarly, activity levels, or lack thereof, should be clearly documented and inescapable. If a rep spaced out today for some reason, the lack of calls and emails will be fully observable. And if your CRM is really well done, it will be observable down to the granularity of which hours of the day that rep was lagging.

So too with error checking. If your CRM is well executed, you will have reporting that shows exactly which opportunities and accounts have been missing activity for a certain period of time and are in danger. The only question that will remain is why you haven’t hopped on top of that! In fact, your CRM reporting should yield valuable insights all the way down to every single closed-won and closed-lost opportunity. For every win, you can see the strategy that sold five seats instead of two. For every lost opportunity, you’ll see what went wrong: budget, competition, a prospect not yet convinced of your solution’s value, and so on. But you lose this insight without transparency.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Remember, Sales IS About Math

When people think about what is needed for sales success, they jump to a lot of what people consider to be right brain activities. Storytelling, persuasion, rapport building, and such. Socialization, drinking, and dinner. Shooting from the hip and making it up as you go. They often don’t consider, or at least not as much, that sales is something that involves lots of metrics, math, and reporting. Guess what? You can’t escape math in sales either—especially if you want to have success at any amount of scale greater than a single rep.

All that instrumentation and recording that we talked about needs monitoring and analysis. Want to know how many emails to how many prospects are generally needed to get a demo on the board? You’re going to need the relevant Salesforce reports for that. Or want to know how many opportunities are required to close a deal, and what each of those opportunities is worth? Better have your win rates instrumented and reported on. Did you want to understand if you can afford to hire a sales development rep to feed your calendar? You’re going to need to know your average contract value. Did you want to know which of your sales reps are most efficient at converting opportunities into wins? You’ll need to split those win rates by rep, and probably add a revenue component to your calculation too. The sales leader who struggles with Salesforce reporting and Excel pivot tables is going to have a rough time in a high-velocity, high-scale sales environment.

Sales in the movies may be about dinners, suits, and booze, and there’s certainly still an expense-account-dinner component to it. But all of that activity is underpinned by a healthy helping of metrical excellence. You won’t be able to avoid it, so you might as well start getting cozy with it.

Foster Mindsets That Build on Each Other

These certainly aren’t the only mindset changes that you’ll notice starting to take hold. However, they are the ones that are initially the most crucial for your transition from founder to sales professional. Moreover, as you may have seen as you read, these first mindset shifts have a complementary, multiplicative impact on each other. Success begets success.

If you record everything, you can be direct and non-scarcity-minded, quickly identifying opportunities to spend your time on now. You’ll be free to move on from imperfect opportunities, knowing that you can come back later to get them because you did a great job of recording the customer interaction and creating backstops for future engagement—all of which will raise your activity levels and efficiency.

Or if you expect to win, are unfazed by loss, and have adopted the mindset of expertise, it’s easier to adopt a stance of inevitability. That, in turn, will help you be fearless and authoritative in your interactions, and more consultative, which will lead to higher close rates.

Or if you expect that you will have high volumes of shallow relationships, you will be prepared to be more direct and efficient in surfacing relevant business details. That will focus you on the importance of efficient record keeping, which will better empower your future self to pick these conversations back up if they do not close this time through the funnel.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Sales Narrative and Product Marketing Basicsan hour

The first step on the road to a repeatable, scalable sales process is to build your narrative. Craft the story you will be presenting to your would-be customers, which will eventually take the form of slides, email templates, spoken messaging, website copy, videos, and so forth—before you start creating those artifacts, you have to have the framework.

Your sales narrative will likely be a recasting of other material your organization may already have created. If you already have a concrete product narrative that captures customer pain and your proposed solution, then turning it into a customer-facing sales narrative shouldn’t be too hard.

Consider this possible product narrative for Groupon:

“It’s hard for small local businesses to acquire new customers. So we fix that by aggregating new customers with the help of compelling coupon offerings.”

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Use a Problem-Solution Narrative Structure

While there are a variety of ways to construct your customer-facing narrative, for early-stage, new-technology sales organizations, I’m a fan of the problem-solution-specifics narrative framing.

Identify the problem, who has it, how it is currently solved (or not), and why that’s unsatisfactory. Follow on with what has changed to make this problem solvable in a new way, what that means for the problem in question, how your new solution works to solve this problem, and what the quantitative and qualitative proof points are that validate this line of argumentation. Those will be the core components of a sales narrative, along with potential additions, like competitive messaging (why is your proposed approach better than other proposed approaches?) and all manner of embellishments (like digging into the specifics and features of your solution).

If this sounds like a fundraising pitch, you shouldn’t be surprised. A funding pitch typically has all of the same trappings, plus macroeconomic rollups of certain parts. For example, “How many people have the proposed problem and what are they willing to pay to solve it?” would be a market-sizing exercise, which isn’t relevant to a customer-facing sales pitch but requires the same precursory information.

Framing your narrative in this way will also be helpful as you develop your marketing collateral, in that each part builds on the part before. Think of it as an inductive approach: If someone disagrees with your framing of the problem, great, it’s the first thing you’ve discussed—you can focus on that (or end the interaction) rather than rehearsing other parts of your pitch that are not relevant. Or if the person you’re talking to agrees that this problem exists, but not that he has it, again, great—you can save time by not pitching someone who doesn’t care. Narrative framing nicely complements the efficiency mindset that should pervade sales, as covered previously in the chapter on sales mindset changes.

Building a Cohesive Sales Narrative

Once you understand how to think about all the necessary components—and have them mapped out—you can put it all together into a cohesive narrative.

What Is the Problem?

You need to identify the business pain you’re seeking to solve as crisply as possible, so your audience can quickly evaluate whether what you’re talking about is relevant to them.

Consider the following examples of possible business pain scenarios.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.


Pricing is a funny thing. It could be considered part of your narrative, or it could be considered part of your sales materials. In a way, it’s the conclusion of the narrative arc for your solution: “And because of all this, you should pay us this for the right to access our solution.” While pricing is something that is likely to change—usually going up as you gain more functionality, or getting more nuanced as you segment your solution—it’s definitely something that you’ll want to have nailed down, at least in an initial version, when you start having sales conversations.

importantFirst, I think it’s important to charge, even at the outset. If you don’t charge, people won’t take you seriously or think hard about whether your solution provides them value. They also likely won’t use the solution. It’s no skin off their backs, and they’re not paying for it, so why should they invest time in it? This isn’t to say that you have to charge an arm and a leg or that you can’t do a freemium approach, where there is a free initial period or volume of usage. And it doesn’t mean that you can’t have a set of lighthouse customers early on that pay for their license fees with engaged, ongoing, validated feedback. But you definitely should charge for your solution. Founders frequently kick the can down the road on this issue because they don’t want to hear someone say no to them. But you’re not doing yourself a favor by avoiding that moment. So figure out an initial price point, and then ask for it. Your solution provides real value to the customer (if it doesn’t, bigger problem), and your engineers need to eat. So charge.

I like to approach pricing in an iterative capacity, biasing toward giving away more value than is captured—at least to start. The goal here is that, early on, you want to get customers in the product, using it and testing your value promises; if your solution is priced to perfection, it will likely hurt your close rates and make acquiring those customers more challenging at the margin. This doesn’t mean that you’ll stick with lowish pricing forever. Rather, as you progress, with each incremental conversation, you’ll be getting more information about how the market reacts to your pricing. If you present your product for ~$100 per seat per month, and no one bats an eye, well, maybe next time make it ~$150! At TalentBin we started out asking for ~$99 a month just to test the water, then moved that to ~$199, ~$299, ~$399, and then ~$499 a month, with an annual contract, paid up front. But we pushed this up over time (not to mention, the product was getting better by leaps as we went).

Once you start to raise prices, don’t worry about those early customers that you have at 20% or 50% of your eventual pricing; there are tens of thousands of other customers in the world that will pay full price. Just grandfather those existing folks in and thank them for their early votes of confidence. No reason to punish them for being early believers. In fact, this can be a means by which to get people to jump and buy now: “Well, it’s five hundred a month right now, but as we add functionality, that may go up. Of course, if you buy now, you would be grandfathered in at that price.”

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Putting Your Narrative Together

You don’t have to take these constituent parts and write them into a page-long meditation, put it on a shelf, and never touch it again or have a holistic messaging document that you deliver verbatim. But it’s good to have a concept of what the narrative looks like, summed up, all together. Again, the narrative actually exists separate from whatever medium you end up collateralizing it in, whether slides, video, messaging, and so on. Whatever collateral you use, though, you need to be able to tell a coherent story.

Test yourself by experimenting with an elevator pitch, or how you might explain your story to someone you met at a cocktail party who has intimacy with the space you’re working in. This won’t be a full treatise, but rather the first skeleton of your story. Then, based on your interaction with the listener, as they ask more questions here or there, you can expand—because you’re deeply familiar with the details that underlie the cursory overview.

Another great exercise is to try writing it down to see if you can incorporate all of the pieces we’ve covered. So what would this look like? Let’s consider a couple approaches.

The TalentBin Narrative
This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Early-Stage Sales Materials Basics2 hours, 18 links

While there’s a galaxy’s worth of different sales materials that you could create and use for pitching prospects, we’re going to focus on the very basics in this chapter. What you need at this early stage is a set of materials that you can use to engage, pitch, and close your first set of customers: slides for a sales presentation, email templates and phone scripts for prospecting and appointment setting, demo scripting, and basic video content. It’s a necessarily limited set of materials, but it will set you up for later success in creating more varied and more involved collateral items, as you’ll start building a set of reusable and customizable assets for use across other materials.

cautionBefore we get started, I want to take a second to talk about a common misconception among new sales professionals that can hamper critical early-stage progress. Because their prior experience with sales comes from what they’ve seen in movies and the materials they’ve seen on mature organizations’ websites, they often believe that everything they produce has to be spit-shined and sparkly before it can get in front of a customer, or must be triple-checked and signed off on by everyone before they can present it, or that it has to be reviewed by legal. And so on.

While these constraints may be necessary for larger organizations with slower-moving offerings (and even then, I don’t buy it), this mindset is extremely damaging for an early-stage sales organization. When you’re getting started, speed is key. The shorter the feedback loop between hearing an objection from a customer and building a slide to combat that objection, the better. The less time between shipping an amazing new feature and recording a rough-around-the-edges video demo of it, the more appointments you will set. The faster you build a new slide documenting the feature and how it supports your value prop, or update your Why We Matter slide when a prestigious publication mentions you, the more mileage you will get. This is how you will win.

When there is a trade-off between a “perfect” deck and one that is good enough to persuade the customer, opt for speed. Having a handful of five-minute screencasts explaining each of your major features up on YouTube—recorded directly from your laptop while you speak into its microphone, complete with “ums,” “uhs,” and sneezes—will be more impactful for your efforts, to start, than one sparkling, pristine explainer video.

Sales Presentations

For the more visually inclined, I have put together a presentation of this section on sales presentations (Ha!), complete with lots of examples.

importantYou’ll note that we’re starting with slides. While a killer demo and a great verbal description are no doubt helpful, and explainer videos are nifty, nothing works in a sales context like slides. They’re visual, so you can mix in images, charts, and so on that underscore your point, alongside text that explains it.

You can speak over them, live. You can send them to someone who missed the presentation. You can use them in prospecting, to send to someone who isn’t sure they want to take a demo. You can record an overview video in which you talk over them. You can post them online to generate leads. You can screenshot one and email it to make a point. You can chop a deck down to a smaller mini-deck to make a more targeted point. You can remix slides to create presentations with different thrusts.

And importantly, a slide deck is what customers expect to see. It’s the means by which they’re used to consuming commercially oriented product information. This is not unlike how VCs are used to consuming would-be investment information via a pitch deck. There are just certain patterns of information presentation and consumption that have become standards, and in the B2B enterprise sales world, the go-to format is your sales presentation.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Key Scenarios for Narrative Sales Presentations

While you’ll iterate your slide deck continually, in alignment with your sales narrative and feedback from the market, there are some particular things you should keep an eye out for in certain sections.

The Problem and Who Has It

Starting with the problem section is helpful to your sales deck in the same way it helped start off your larger sales narrative: if the person to whom you’re presenting, when shown the problem your solution addresses, says, “Huh, I actually don’t have that problem,” then delightful! You’ve saved yourself and them the trouble of presenting a solution that doesn’t fit their business pain.

Of course, even better if you didn’t get all the way to the presentation before realizing that key piece of data (more on that in Early Prospecting. But better late than never to save your and your prospect’s time.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Sales Outreach Materials

Once you’ve got your deck nailed, the next step is going to be driving opportunities to present it to potential clients. And the precursor to that will be emails and phone calls. So having some basic templates there will be helpful.

A set of basic emails that handles inbound inquiries, and can be used for targeted outreach, is a key piece of your sales materials.

As with your deck, these emails will be medium-specific encapsulations of your narrative, whose end goal is to drive recipients to an online or offline presentation and demo. And as with your deck, these can start at the most basic and extend from there as your messaging gets more specific.

We’ll start with the idea of outbound outreach. While inbound leads (that you heavily qualify) are the highest-quality source of potential deals, it’s unlikely when you’re first starting out that you’ll have inbound demand of any merit before you start doing outbound.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Sales Demo Scripts

We’ll talk more about the actual process of giving a combined sales presentation and demo later. But before we get into the blocking and tackling of presentation and demo, it’s good to have a concept of the content you want to demonstrate when your prospects agree to a formal sales presentation.

As with the other materials discussed, this should be done with a mind toward your narrative. And because a live demo will typically come after you’ve shared some initial slides from your sales deck, follow the framing you presented in your deck. Your demo will reiterate much of it, but with much better context, customization, and visuality.

What is that framing? Well, as with your sales deck, it’s the bucketing of key use cases and the features that enable them. Ideally, you should already have those use cases identified, as they are likely referred to in your sales deck. But think about the combination of most common, most important, and most impressive use cases your solution enables. Then rank them, such that you start with the most important and most compelling ones—because you never know when a demo will have to end early! Beyond that, I like to think of a demo as telling the story of how your solution is used, again starting with major pain points.


This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Video Materials for Early-Stage Sales

I’m a big fan of video to help accelerate appointment setting in early-stage sales. Internet video is a fantastic tool; it’s highly accessible and provides for a richness of communication that far outstrips email templates or even visual exhibits. And thanks to mobile phones with fast data plans, video collateral can be watched anywhere, at the moment it shows up in a prospect’s email inbox or Twitter feed. As such, having a one-, two-, all the way up to five-minute overview of your offering to share with would-be prospects is extremely helpful.

MVP Overview Video

importantThe goal here is not to sell the product. Rather, as with your email templates and phone scripts, the goal of these videos is to sell the prospect on the next step—getting on the phone for discovery, presentation, and a demo. And as with your slides and email templates, your video overview does not have to be perfect. It just has to exist. One of the easiest ways to create a viable overview video is to put together a highly shortened sales presentation and demo and record it on your laptop, while you narrate.

exampleWhen TalentBin was extending its go-to-market from exclusively technical and design recruiting to include the healthcare vertical as well, we created a newly refreshed pitch deck focused on the realities of the healthcare recruiting market, and how TalentBin fit in there. Then I recorded a brief overview pitch that included the basics. Just use Camtasia, Snagit, QuickTime, or Loom to record your screen while you speak over your slides, and give a lightweight demo (as appropriate). It’s helpful to know the keystrokes to pause the recording in case you need to cough, or you stumble and need to pause and regain your footing.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Other Types of Early-Stage Sales Collateral

As you might imagine, there is a whole universe of other types of marketing collateral that you can invest in. PDFs! Webinars! Infographics! Blog listicles! Content marketing! Oh my! What we’ve covered are the basics that you want to get going before you start in on anything else. This isn’t to say that you can’t start selling if you don’t have a video overview. But it will make it easier for you to set appointments if you can embed one in your email templates. And you don’t need to have a formal demo script in place before you start taking customer meetings. But it can help make them more effective. You should be thinking about collateral as features in your go-to-market plans—each one involves time, energy, and cost, and that should be weighed against how frequently it will be used and the value its use provides.

One-Off Requests

Often you will get a request from a prospect for some sort of collateral that you don’t have. “Do you have a one-pager overview on this?” “Do you have customer success stories?” Most of the time you should think about the question under the question (more on this in Handling Objections. Consider whether an existing piece of collateral already handles their request before running off and manufacturing something new. Often that will be the case, so you can simply reply, “You’re looking for what others who have used the product have said about it? Great! We have a number of testimonials on slides near the end of this deck I’m attaching!” or “The first ten slides of this attached deck give a great overview for anyone you’d like to share it with. Oh, and this video overview is quite helpful too.”

On-Demand Collateral

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Part II: From Lead to Sale

Early Prospectingan hour, 7 links

Now that you have your materials pulled together and are ready to engage with some prospects, you need some prospects to engage with! And that means prospecting, going out and looking for some relevant potential customers. Later on we’ll be talking about how to do this at scale, and we’ll also be covering how to get prospects to come to you—what’s known as inbound marketing, which has been heavily popularized by folks like HubSpot.

Those more advanced forms of customer acquisition can be challenging for early-stage startups. Your customers may not realize that there is a solution to their business pain—or that they even have the pain in question. And if that’s the case, it can be tough to drive them inbound to you, at least to start.

That’s why, for now, your goal is to proactively find 50–100 potential clients that have the distinct pain point that your solution resolves, and to get the product in front of them for a commercial conversation about their business pains and how your solution can potentially help. Rest assured, we will definitely be iterating this approach, and you will learn things from your initial set of supposed prospects that help you tune your definition of whom you should actually be selling to. But this is your first shot.

The Ideal Customer Profile

One of the biggest issues founders and first-time salespeople have is trying to sell to people who don’t have the problem their solution solves. Instead they prioritize other characteristics—availability being the biggest temptation—when identifying prospects. You see this when founders sell to their incubator-mates or people they know from prior companies, or even friends and family.

The whole purpose of B2B product development is to identify a business pain in the market and build a product or service that resolves that business pain. And the purpose of B2B sales is to identify companies and individuals that have that business pain, propose the product as a means by which to resolve it, and eventually come to a mutually beneficial agreement to exchange money for that product—which then resolves the business pain, as promised. That’s how it’s supposed to work.

The opposite of this approach is trying to sell your solution to anything with a heartbeat, regardless of whether or not they or their company has the pain point the solution resolves. It’s approaches like this that give sales a slimy name. But what’s worse (aside from peeing in the pool for all the other people who are doing B2B sales and just generally irritating people), it’s actually terrible for your business. All you have in B2B sales is your time. And when you spend your time on prospects who don’t need your product, they won’t close. So you’re spending your scarce time (and salary expense, and runway) on prospects who are unlikely to buy. Think about that. Your goal in sales is to scalably acquire customers and revenue. So spending time on people who won’t close is the equivalent of setting revenue on fire.

Running the numbers quickly, you see how bad this can be. Imagine you’re aimless in your outreach targeting and qualification because your ideal customer profile is undefined or sloppy. Maybe you do 20 demos for people who don’t have your pain point. Maybe each of those demos requires, on average, 30 minutes of prep, an hour of execution, and another 30 minutes of follow-up immediately after the fact. To say nothing of further down-funnel follow-up, chasing the opportunity. That’s a full week of your time flushed down the drain, where it will never turn into revenue. You could have spent that time selling to people who might actually buy. Or working on your sales materials. Or doing a better job servicing your existing customers and making sure they are successful.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Who Has My Pain Point?

Remember your sales narrative, which was based on hypotheses about how your offering solves the pain points of potential customers? Parts of your ideal customer profile were defined there. But now, instead of expressing this in a narrative format, you want to boil it down to abstracted characteristics. You want to get to the point that you can rattle off a set of metadata characteristics that describe the relative level of attractiveness of a prospect.

exampleIn TalentBin’s case, this would be something like, “This account has five technical recruiters and twenty open technical hires, including iOS, Java, and Android roles, and uses LinkedIn Recruiter.” What are the characteristics in there? First, we have the existence of technical recruiters—without at least one recruiter or sourcer to actively use the tool, customers are unlikely to have success. Passive-candidate recruiting is too time-consuming and challenging to be done on the side by an HR generalist or a hiring manager. The fact that there are five recruiters indicates that this is a juicier-looking account, where there is an opportunity to sell up to five seats of TalentBin. And when it comes to business pain, there’s a lot: 20 engineering hires is a tall order. Even better, iOS, Java, and Android roles are the kind that TalentBin does particularly well at compared to LinkedIn (versus, say, .NET or C#). Lastly, if we can figure out whether the account has multiple seats of LinkedIn Recruiter—a market alternative to TalentBin—we’ll know how much they’re willing to spend on passive-recruiting tooling to make those five recruiters more effective. If they all have seats, we know that there’s around ~$50K of budget already allocated for LinkedIn Recruiter, which we can take a bite of.

exampleIn the case of Immediately, makers of a really cool sales-focused mobile email client and CRM tool for Gmail and Salesforce, it might look something like, “This account uses Gmail, Salesforce, and Marketo. They have fifty sales reps scattered across the United States, selling software that costs on average ~$50K. And it looks like the Vice President of Sales has a Sales Operations Manager reporting to her.” What are the characteristics Immediately is looking for? Well, as of 2015, the software needs Gmail and Salesforce to work. So if an organization doesn’t use Salesforce and Gmail, the conversation is dead in the water. Those are required characteristics. This account also uses Marketo, which indicates a level of sophistication within the sales and marketing organization, and a willingness to pay for expensive tooling that accelerates revenue acquisition. There are 50 reps, each of whom represents a potential user, so this seems like a potentially valuable opportunity.

Moreover, because the reps are spread all over the U.S.—rather than co-located in a single area, indicating a call center—it would seem that these are outside sales reps. And outside sales reps are less frequently in front of a laptop, which makes a compelling sales-first mobile email client and CRM all the more important for them. Beyond that, the software this prospect sells is expensive; incremental wins are very valuable to them. A solution like Immediately, which helps reps handle more deals and avoid dropped balls while mobile, is all the more important when each of those potential dropped balls represents ~$50K of revenue. Lastly, because someone is managing sales operations, we know there is someone who is specifically charged with making those 50 sales reps more effective and for maintaining a clean and effective CRM. He will likely be very interested in something that not only makes those reps more effective, but also helps him with the pain point of getting 50 distributed professionals to enter information into the CRM to help with data cleanliness, forecasting, and so forth.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Account Sourcing

Now that we’ve discussed the various places where you could go and look for accounts, let’s get very specific about doing this in practice, shooting for that goal of 50–100 targets.

Prospect Data Management

Later we’ll get into CRM and where to house your list of accounts and contacts to attack, but my recommendation at this stage is to just use a Google Sheet as your initial repository of prospects. This doesn’t mean that you’ll use this spreadsheet as your CRM (though you probably could for this limited scale of engagement), but you do want a place to house the structured prospect data. You can use a spreadsheet template, with both role-specific prospecting and hiring-specific prospecting.

You’ll note that there are typically distinct columns for pieces of information that we might eventually want to query on or use in a mail merge campaign.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Point of Contact Discovery

Now that you know how to find promising accounts, either by company-centric or people-centric demand signifiers, your next question is “Who should I be engaging at this company, and how can I reach them?” You want to find the right point of contact—ideally, the relevant decision-maker for the account. Note that this is different from people-centric sourcing of accounts. In that case, you were looking for potential users of your solution, like data scientists or field sales reps, at the account in question. That doesn’t necessarily mean that those data scientists or sales reps are the correct points of contact to sell to. This goes back to your sales narrative: you want to target and engage the person who is responsible for solving the pain your solution resolves and who has the decision-making authority, and budgetary control, to resolve that pain. You may also choose to involve people who would be users of the solution, but that is more for the purposes of marketing to them to build a groundswell of support and help convince the decision-maker in question.

How can you identify these decision-makers? Conveniently, it’s often their title that gives it away. By extension, you can use LinkedIn (or, or others) to search for those titles, constrained to a given account. You should be paying attention to what these titles look like as you are prospecting, and you’ll eventually converge on the right set. If you’re selling a recruiting solution, perhaps it’s the VP of Talent, Director of Recruiting, or Recruiting Manager. Or if you’re selling an e-commerce solution, it might be the Chief Marketing Officer, Digital Marketing Manager, and so on. If you sell sales tooling, it could be the VP of Sales, Chief Revenue Officer, VP of Sales Operations, Director of Sales Effectiveness, or Sales Operations Manager. The right title can vary based on stage—an early-stage company is less likely to have a Sales Operations Manager, so the responsibilities of sales operations might fall to the VP of Sales.

As such, I typically like to take the approach of cascading points of contact. If an account has a VP of Sales, a Director of Sales Operations, and a Sales Operations Manager, I prefer to grab all of them as potential points of contact. This can be even more scaled at a later juncture—perhaps you’ll grab not just all the decision-makers, but potentially all the users too, for later engagement via drip email marketing. LinkedIn is very helpful for finding these individuals. Just do a boolean title search, like (“account” OR “sales” OR “sales operations”) AND (“Director” OR “Vice” OR “VP”),” which will return people that have any of the words in the first set plus any of the words in the second. That will give you a good list to start with. Then look more deeply at each profile to figure out which person, or group of people, you really want to target.

If I thought that Zendesk were a good account to target for a sales enablement or acceleration solution, I would go looking in these contacts, which were uncovered by the search referenced above.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Prospect Outreach and Demo Appointment Setting2 hours, 6 links

Now that you’ve got your list of highly targeted potential accounts and associated points of contact, it’s time to tackle the business of actually selling. You were probably wondering when we’d get around to that! Up until this point, we’ve mainly been dealing with tooling to enable you to sell. But as covered in Mindset Changes for First-Time Sales Professionals, the best tooling in the world is useless without the actual activity of emailing, calling, presenting, demoing, and closing. That’s where the true work of selling is done, and because of this, it’s often the scariest to people who have never done it before. They believe deep down, secretly, that planning and planning, building more and more tools, can shield them from potential rejection. But experienced salespeople know, in the words of the great American philosopher Mike Tyson, that “everyone has a plan until they get punched in the mouth.” Sure, getting punched in the mouth is no fun, but you can’t win if you don’t get in the ring. Let’s smile and get ready!

What we’ll cover in the following chapters will prepare you for the various motions of selling, from appointment setting to pitching via sales presentation and product demonstration, all the way through closing and pipeline management. Note, though, that simply reading about these actions isn’t enough, and don’t expect to be naturally comfortable with, and excellent at, any of them. It will take practice and many repetitions before you have your pitch nailed and are eminently comfortable with all the objections prospects will throw at you. But this is totally to be expected, and the best way to get to that point is to just start!

Stages of the Sales Cycle

I like to think of the sales cycle bucketed into several major stages: First, there’s outreach and engagement, where you’re engaging a prospect account with the goal of setting an appointment. Next comes pitching, where you begin a commercial conversation with a prospect with the goal of eliciting more information about the particulars of their situation and persuading them that your solution fits their pain. And the stages continue all the way to closing—getting the prospect to sign on the line that is dotted, and the associated pipeline management. Each stage has its own set of actions, and its own goals, which we’ll cover in depth.

cautionYou will be the one taking all of these actions. This is another place where early-stage founders get tripped up. They hope that they can just hire a salesperson who will figure this all out. Go to Costco, buy a bin of sales dust. Sprinkle some sales dust on product. Poof: IPO. This is simply not the case. Sales professionals are adept at taking a proven product to market with a proven message and a proven set of materials—with minimal variation. They are not there to prove those things out on their own.

importantThe selling you will be engaged in is what is known as evangelical sales—a mix of product management, product marketing, and sales. In evangelical sales, there is a tight feedback loop between your interactions with the prospect and modifications of both the selling materials (product marketing) and even the features of the product itself (product management). It will be an iterative approach, with a number of false starts. But that tight feedback loop is indispensable in tuning your go-to-market in a way that allows you to start winning customers and, later, to package your approach in a way that can be replicated by an army of sales professionals. But the only way you’ll get there later is by doing it yourself now.

In this chapter, we’re going to touch on the first part of that cycle, outreach and engagement, with the goal of getting appointments on your calendar. A little later, we’ll cover the mechanics of presenting to a prospect, demoing, and then working the deal as it moves down the funnel. Both are important, in that if you don’t do the first, you won’t have the opportunity for the second. And even if you’re somehow amazing at closing business from the first step, if you aren’t able to reliably fill the top of your funnel, you’ll struggle to acquire the number of customers you’d prefer. A .500 batter who only gets a single at-bat a game isn’t nearly as productive as one who has three or four a game. So let’s make sure you’re getting those at-bats.

Setting Yourself Up for Success

As noted above, there is a particular tempo to enterprise sales’ distinct stages. In this first stage, the goal is to set up a commercial conversation about the prospect’s business pains and how your solution could potentially solve them, a.k.a. a pitch or demo. The goal at this stage is not to sell the solution. You’re simply selling a conversation—the opportunity to learn more, and tell more—the same way that the goal of a first date is not to get married, but rather to get to a second date (assuming there is a potential fit!). You try to get married on the first date, it’s gonna be an awkward scene. Same with sales.

As a non-sales person approaching this, you have an advantage of sorts over pure sales professionals seeking to set appointments. Because your offering is early stage, and you are not a salesperson, you can often approach these conversations as research or customer development—trying to understand pain points, and how they are currently solved. There is a balance here, as it is important to make sure that these conversations always remain in the realm of the commercial; you don’t want prospects thinking this conversation has nothing to do with addressing their business pains and potentially solving them, for a price. But because you’re the founder, CTO, CEO, or what have you, you can use that to your advantage and in doing so reduce the friction of getting these meetings on the calendar.

Management and Early CRM

Given the activity-centric nature of sales, you’re going to have many balls in the air concurrently. As noted in Mindset Changes for First-Time Sales Professionals, this is a new experience for most professionals. And while you may be used to being able to keep all your open items and projects “in your head,” this is extraordinarily challenging to do in sales. Every potential conversation, every conversation that is in flight, and all previous interactions are simply too much for someone to remember at once. Yes, yes, I’m sure you’re very smart and clever, but there’s no way you can keep it all straight in your head. And if you can, you’re not dealing with enough prospects concurrently! This is why modern sales organizations rely on customer relationship management (CRM) software to handle this issue—not only to help reps keep track of things but to support management functions too, like activity reporting, win-rate tracking, and even financial reporting on how many deals are happening.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Emailing Prospects

cautionEmail is your friend. It is an extremely powerful means of directed outreach toward prospects, when done correctly. It has the benefit of a strong ecosystem of automation and instrumentation tools, benefiting from over a decade of innovation in the space. And it is especially powerful in conjunction with calling and voicemail delivery. But be careful. When done incorrectly, it can make you look like you have no idea what you’re doing and poison potential client relationships. Bad emails are one of the main reasons why sales gets a bad name. So let’s make sure to do it right, okay?

As covered in the previous chapters Early-Stage Sales Materials Basics and Early Prospecting, you need to have both a set of prospects (who have been prequalified) and their email addresses, along with a set of email templates that characterize why you think they have the business pain your solution solves, describe what you think you can do about it, and conclude with a call to action to engage in a one-to-one commercial conversation—the mythical demo we seek to arrange.

One email probably won’t be enough to get the appointment on the calendar. As much as we’d like to think our words are magical and our arguments breathtakingly compelling, it’s probably going to take more than one shot to gain a response from the prospect—which is why we have more than one email template! People don’t want to read a book dropped in their inbox (he says, while writing a book). Rather, they want quick snippets of information, hyper-targeted to them, providing them insight and value. You can achieve this through personalization, but also by breaking up your messaging into multiple distinct emails. Splitting up the buckets of your narrative into separate short emails, constrained to a single thought, can be a very effective way to drip messaging about the pain you’re addressing. With this approach, you can demonstrate that you sniffed out that the prospect has that pain,and that the reason you’re emailing is to verify this, help them solve it, and be a hero. It’s hard to do that in a single monolithic email. Think of it as akin to what flash sale sites like One Kings Lane, Gilt, and Groupon figured out with their daily emails: delivering targeted, relevant content, one bit at a time, over time, is a great way to drive a prospect to eventual conversion.

The key, of course, is to ensure that you’re not showing up in the prospect’s inbox like a carnival barker, with exclamation points every sentence, bombastic claims, and all sorts of HTML layout elements. Yuck. Instead, using conversational, calm, text-based messaging, demonstrate your focus on their challenges. These emails should have the tone and candor of a message from one CEO to another (even if it’s actually from a founder to the manager of a function within the target organization). Moreover, small, lightweight, chunked emails help you take advantage of modern email marketing tooling, like lightweight drip marketing, which we’ll tackle in a bit.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Calling Prospects

Cold-calling is the epitome of everything that scares first-time sales staff. While not face-to-face exactly, it’s a synchronous interaction with the very person who can reject your solution, which, of course, your own personal worth is pretty heavily tied to. Why would I possibly want to put myself in a situation where someone could stomp on my product and, by extension, me? For a lot of reasons, actually—because synchronous verbal communication, miraculously, is a really rich way of communicating and gathering information. It’s almost like it might be one of the linchpins of the last few hundred thousand years of human evolution!

The trick to calling on your prospects, unsurprisingly, is similar to the trick for engendering email responsiveness: make sure that your solution is relevant to their situation, get your point across with clear messaging, and demonstrate that you are concerned about their situation with a customized, prospect-centric approach.

So let’s shed that fear of cold-calling right now. Yes, it will take some getting used to. But remember, you’re calling highly qualified contacts who have the problem you solve, and you’re seeking to help them solve that problem. Who wouldn’t welcome that?

Call Timing

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Setting up the Appointment

Meeting Invites

Once you have an appointment time and contact information, you need to send the relevant details for the meeting. For very early-stage customer conversations (like your first dozen customers), I’m a fan of going to visit the individual in person. As discussed in Early Prospecting, this is why initially targeting accounts in your own geography is helpful, even if the price point of your solution means that your scaled go-to-market will likely be via inside sales. If an in-person meeting is not tenable, you’ll need a means of digital presentation. Zoom and are good for this, as we’ll discuss more later.

Whether the meeting will be digital or in person, all of the relevant coordinates need to be included in the meeting invite you send to the prospect. You absolutely must send a calendar meeting invite. You cannot rely on the prospect to put the relevant details on his calendar, and this is a convenient way to both put the meeting on his calendar and deliver the pertinent meeting details. Put the location details (whether online or offline) in the location section of the meeting invite, in addition to the description section (yes, repeat them)—something like, “Online meeting via Use this link to join: […]” Be sure to put a brief agenda in the description section, after the duplicate location coordinates. Lastly, make sure to include a rich title description that reminds both the prospect and you of the goal of the meeting, like, “Twitter and TalentBin Online Demo” or, “HIRABL and Robert Half In-Person Demo.”

Consider including teaser material, like a demo video hyperlink, in the body of the meeting invite. This will help prospects get excited about attending but shouldn’t give them enough information that they feel it can stand in for the actual demo.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Prospecting Cadence

It’s a rare situation where your first email or first call results in a prospect getting back to you and agreeing to an appointment. Instead, you’ll need to implement a series of outreach actions targeting your prospects, typically alternating between emails, calls, and voice mails. In sales, this interleaving of outreach actions over time is known as a cadence.

You can of course implement this yourself via your lightweight Google Sheet CRM or in a more formal fashion through an actual CRM. Or, if you want to get really crazy, there is a set of solutions that are designed specifically to orchestrate this outreach cadence—two primary players being Outreach and SalesLoft. Both have pricing that accommodates an individual inexpensively and can help you be much more efficient in your appointment-setting workflow.

Regardless of whether you’re doing it yourself or using an orchestration system, typically you want to alternate emailing and calling. That might be an initial email and call on day one, followed by a call on day two, and then maybe a call and a voicemail on day three. From there, you might skip a day, and then email on day five, followed by an “I’m breaking up with you” email on day seven. By no means is this a cut-and-dried approach—you could decide to do calls with follow-up emails every other day, or some other permutation, if it works for you. To some extent, this will be related to how much content you have to share. If you have a lot of great things to say about your solution, and you have lots of video snippets you can add to consecutive emails, your cadence could potentially be longer and perhaps more frequent.

In addition to pure time-based cadencing, you can involve contextual data into this process as well. Part of your cadence could be reviewing the previous day’s opens and clicks and prioritizing those prospects for calls. Or it could mean breaking out of your cadence to immediately call a prospect who opened an email when you see the alert. Or it could mean sending an immediate follow-up email to a prospect who just opened one of your emails. All of this contextual activity can raise connect rates and appointment-close rates by focusing on prospects who are already thinking about your solution.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Referral Prospecting

With the advent of social networks like LinkedIn and Facebook, it has become far easier to understand who someone knows, and thus, could potentially refer you to, than ever before. This can be helpful for prospecting and reduce friction for getting your foot in the door to set an appointment.

Doing this at small scale can be a great way to initially supercharge your pipeline, but it will eventually run out of steam, in that you, your team, your investors, and so on will eventually run dry. So while it can’t be a long term solution necessarily, it can help early on.

Connection Discovery

First, note that referral prospecting is not about selling to anyone who will take a meeting because they know someone in your organization. Rather, it is about using relationships within your organization to more easily access accounts that you know are qualified and have the pain your solution solves. So just be clear on which direction the causality runs here.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Inbound Lead Capture and Response Preview

The last thing I want to cover on appointment setting is the basics of inbound lead capture and response. We’ll get into this in more depth in the following chapter, but I want to briefly touch on a number of key points.

As a result of your outbound appointment-setting activity, invariably you will generate what is known as inbound interest. People will read your emails and click on the links to your website to learn more. They’ll listen to your voicemail, open Google, and search for your solution. And if your website, along with your primary outreach materials, does a good job convincing them it’s worth engaging, you’ll want to make sure that you can take advantage of that and easily allow them to become inbound leads.

The basic requirement for capturing these leads is a means by which someone on your website can get in touch to express interest and engage with you. We’ll talk more about lead capture forms in the next chapter, but to start, this can be as simple as a big button that says “Request a demo,” with a mailto hyperlink to send an email to If you want to get more involved, maybe even utilize the subject and content tags to pre-fill some information like “Demo Request for product name,” so the prospect doesn’t have to write anything. The more advanced version can be a Google Form linked from that button. Seriously, this doesn’t need to be brain surgery to start. You want prospects to be on that page, say, “Huh, yeah, this does sound good. I would like to learn more. Click” and be on their way.

The next step is making sure you know someone’s trying to get in touch with you. An easy version of this is an email notification that is generated from whatever form or mailto setup you choose. The notifications should show up somewhere you know you’ll be able to check on a fairly frequent basis. I like email notifications that are automatically foldered, such that when I pop into my email, I can see if that folder has gone bold with a little unread number count next to it.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Early Inbound Lead Capture and Response24 minutes, 3 links

I don’t want to get too deep into inbound marketing, because when you’re very early in your go-to-market, it’s usually pretty unlikely that people will know who you are, what you do, or that they need you. This is the challenge with selling innovative solutions early on: if no one knows they have the problem you solve, or that there is a solution like yours that can solve that problem, they’re not going to be Googling for you or stumbling across your site.

Creating content, like blog posts, tweets, infographics, and such, and making sure that they are well SEO’d to engender inbound leads at scale, is what is known as “inbound marketing.” This is a more advanced form of lead generation that we’ll get into in a later chapter, as it’s typically not appropriate for a very early-stage go-to-market. (You’d be producing a bunch of content for people who aren’t looking for it…). There can be exceptions where you’re attacking an existing market for cheaper—kind of like Hubspot took the power of marketing automation like Marketo and Eloqua and brought it to the SMB and mid-market. But I find that these are often the exception, especially when we’re talking about acquiring your first 100 customers.

When you do get more advanced, there are lots of resources to assist with this, not least Mark Roberge’s book The Sales Acceleration Formula, chronicling analytics-driven sales powered by a robust inbound marketing machine. It’s no surprise that this comes from the former Chief Revenue Officer at Hubspot, the company that has done some of the most impressive work at popularizing inbound marketing as a practice.

However, at this early stage, even though you won’t be focused on manufacturing content for inbound marketing at scale, you will still need a minimum viable inbound-lead capture process to capitalize on your outbound appointment-setting activity. Why? Well, if your content and messaging are well executed, your outreach will actually end up driving people back to your website, where, if they are convinced by the messaging there, they could easily request a demo. I like to call this outbound inbound, and leads generated that way are some of the best inbound leads you can get—you know that you are only targeting qualified accounts, so inbound leads originating from your prospecting lists are bound to be strong.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Inbound Lead Qualification

As we discussed when we covered qualification in Early Prospecting, you want to be focused on potential customers that have all the characteristics required to have success with your solution—namely the business pain points that you solve and the staff who would use your solution. If they don’t meet those criteria, you don’t really want to spend your time talking to them. Even if they end up buying, they’re not going to have success and they’re not going to be happy—not with your solution, and not with you for selling it to them when you should have known better. Much better for you to instead funnel them away—giving them a good experience even when you’re saying, “We don’t make sense for you”—then spend your time giving relevant inbound leads a fantastic experience. Qualification is something you’ll want to keep in mind at every step, from how you set up your lead capture forms to the questions you ask once you get those leads on the phone.

Inbound Lead Capture Forms

First, you need a means by which to capture these inbound leads in a structured format. In the previous chapter, we talked about setting up a inbox as an early solution. And that can work to start—it’s definitely much better than nothing. But it also makes for a really difficult time of capturing the relevant demand signifiers in a helpful way. So as soon as you’re able, swap that email link out for a big fat Request Demo call to action on your homepage (ideally following the user down the page), and then point that button at some sort of form that lets you capture structured data. Don’t make it subtle. If someone shows up on your homepage and is eager to talk to you, make it damn easy.

Below are some examples of how to do this.

Figure: Demo Call to Action on HIRABL Website

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Inbound Lead Response

Once you have an inbound lead data-capture form in place, the next question is: what do you do with these leads as they come in?

importantFirst, the most important thing is to respond to inbound leads as quickly as possible. This is something that organizations botch constantly, thinking that because someone is asking to talk, they’re happy to do it now, later, tomorrow, next week. This is completely false. Instead, what you have is a prospect who passed the threshold of sufficient interest in your solution and has made herself available right now. The key thing to understand is the right now component—this can change because other priorities pop up, she finds another solution to her problem (how do you think she found you? She’s actively trying to solve this problem), or a myriad of other reasons.

The pace at which this interest falls off is incredibly rapid. As surfaced in research done by MIT Sloan and, there is a 100x drop-off in contact rates between leads that are contacted within five minutes of submitting a lead form and thirty minutes. And it’s a 10x drop-off just between five minutes and ten minutes. As you can tell, responding to a qualified lead quickly is pretty darn important.

Of course, the challenge here, if it’s just you, is that you’re probably doing other things that keep you from checking your email every five minutes! And even if you’re not, checking your email every five minutes sounds like a great way to get nothing else done (though later, you’ll have a market development rep who focuses just on this). That said, you should certainly make sure that your lead generation form provider can at a minimum send a new-lead notification to an email address of your choosing, including the information that was provided by the prospect—especially phone number, so you can call her right away from wherever you are!

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Lightweight Discovery

Ideally, because you called the inbound lead back so quickly (right?), you can get him on the phone. But although I know you’re excited about getting him on the calendar for a demo as quickly as possible, first you need to make sure he’s qualified. If you go back to your ideal customer profile, you’ll recall the demand signifiers that indicate a prospect has the pain points your solution solves. Now is the time to ensure that this inbound lead definitely has those characteristics. Of course, because you set up your inbound lead capture form in a way that captures these signifiers, this is more about verifying the information, and potentially digging in a bit more. Moreover, you need to be figuring out what other folks should be on a call. This is where size of prize comes into play—if the organization has many other potential users of your product, maybe you could get them all on a demo together? Or while you have this champion-to-be on the phone, figure out who would be involved in a purchasing decision—is he the person who would pull that trigger, or should you think about involving the boss in this case? These are all valid things to consider, which we’ll talk about more when we cover discovery in Sales Pitches for Startup Founders.

If, for whatever reason, it turns out that the individual and his organization aren’t qualified, it’s completely fine to let them know that this isn’t relevant to them. Of course, be sure to differentiate between a truly unqualified account and a qualified account for which this is simply an unqualified contact. Qualify the account, not the lead. By no means think that because someone came inbound you are obligated to do a demo for him. Rather, you are being respectful of his time and preventing him from having broken expectations at a later juncture when it finally surfaces that your solution isn’t a fit. Worst, of course, would be if he ended up buying your product under a mistaken understanding of what it does and proceeded to feel cheated, all while soaking up your support resources and complaining to his colleagues about it. Let’s avoid all that drama, okay? If you’re respectful and candid about not wasting prospects’ time, while making it clear who your solution would be relevant to, you have the chance to convert helpful brand ambassadors who will tell their colleagues about you.

exampleThis happened frequently at TalentBin, where our technical recruiting customers were so stoked on the product (and our delightfully designed swag!) that they often bragged to nontechnical recruiting colleagues about the solution—which is great. This is what you want. But those unqualified folks would then end up coming inbound as leads. As such it was very important that our inbound market development staff could qualify them. Rather than just putting a meeting on the calendar, they would pivot around the individual to figure out if she might simply be an unqualified contact at a qualified organization—and in that case, work with this contact to loop in more qualified contacts from that same organization. Or, alternatively, they would ascertain if the entire organization was unqualified. (For TalentBin, that means a company with no technical, healthcare, or finance hiring. For HIRABL, it’s a staffing agency that doesn’t do contingency recruiting. What’s your version?)

Follow Up on Inbound Leads

If, unfortunately, you weren’t able to connect the first time you called that inbound lead back, all is not lost. Just as with your pure outbound efforts, even inbound appointment setting takes persistence. In fact, the second thing that people screw up about inbound leads is giving up on them too soon. Again, our friends at and MIT Sloan figured out that each incremental attempt you make to reach out to an inbound lead adds another 15% chance of contacting them, falling off substantially after the sixth attempt. But after six attempts, you should have had roughly an aggregate 90% chance of making contact. So don’t give up! Remember, they asked for it, so you have nothing to fear.

While you’re trying to make contact, definitely make sure to leave voice mails and use your inbound lead response-email template to let the prospect know that you’re doing your best to reach him. But while persistence is good, you do need to move on after a half-dozen attempts or so. There are plenty of fish in the sea, and we need you spending your time fishing. Along the way, just make sure to log your activity in your CRM (or, if you’re still in that Google Sheet, the new row you created for this inbound lead) to keep track of who’s in process, and how many times you’ve attempted to contact them.

Lastly, not every inbound lead needs a call. If an inbound lead comes in, and the information that is provided makes it pretty darn clear it’s unlikely to be qualified, a better approach can be to send what’s known as a “hard qualifier” email. This would include who the product is intended for, and why you think it might not be relevant for that lead, plus an ask to clarify if your thinking is wrong.

exampleHi there!

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Sales Pitches For Startup Founders3 hours, 7 links

The Goal of Pitching

Your pitch is arguably the most critical aspect of all your sales efforts. Pitching is the process of persuasion, ideally ending in a sale. Up to this point, you were persuading the individual prospect that your solution could potentially help with her business pains. With pitching, you’re moving on to organizational persuasion. Pitching is about persuading your prospect, and other stakeholders in her organization, not only that they have this business pain but that it is of large enough magnitude that it must be solved, that your solution will indeed solve it, and that they get a return on investment by implementing your solution. To that end, pitching isn’t delivering a canned, pre-established speech—it’s a two-way conversation in which you’re discovering the organization’s needs, and customizing a persuasive case that you can meet those needs.

Moreover, pitching is about persuading the prospect that she needs to deal with this now rather than later, that the opportunity cost of holding off is too high to bear, and that notwithstanding the various pains facing her organization—and there are always many things that can be fixed—it’s worth the money and time to implement your solution ahead of all those other things.

This isn’t to say that it’ll be a one-shot deal, known as a one-call close. You might see those occasionally, but it’s pretty unlikely at the beginning of your process. And the more complicated your solution, the less likely they will happen. This exercise in organizational persuasion may take a number of steps, a number of meetings, likely involving multiple people within the target organization. But the goal is still the same: to get the ball, now in play, across the line. And there’s another related goal: if it is clear that the deal is not going to close, at least not this time around, you want to acknowledge that and stop spending time on something that won’t yield a return.

Like the topics we’ve covered before, it’s best to think of the process of selling as having distinct substages, each of which you’ll want to step through. Boil your sale down into those individual motions, and it won’t feel as monolithic and insurmountable. Rather, it’s just a case of going down a checklist, diligently checking things off as you go, and landing, at the end, in a big pile of revenue!

New Technology Sales Persuasion Formula

One way I like to think about sales persuasion is in terms of a formula: the potential value to the organization crossed with the level of value comprehension the prospect has achieved (did they get it?) crossed with the extent to which they believe they will achieve the promised value. Prospects will typically apply a risk discount—they’ll discount what they believe your solution is worth based on their incredulity that they’ll achieve all the promised value.

You can visualize the formula like this:

Your goal is to maximize all these terms. You can maximize the potential value to the organization by targeting those accounts that have the greatest need for your solution. You can maximize comprehension of that value through effective presentation, materials, and tooling. And you can maximize believability via proof points, demonstrations of the product, customization of those demos, and even proof of concept and pilots.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Inside or Outside Sales?

The decision to sell a solution in person, face-to-face with the decision-maker in a conference room, or over the phone with presentation and screen-sharing software is typically based on the complexity of the solution crossed with average deal size.

The number of meetings that you can have in person in a given day is far lower than the number of digital presentations you can do, just by virtue of transit times. A field sales rep getting two in-person presentations done in a day is pretty good, and three would be really pushing it. An inside sales rep who presents via phone and screen share, on the other hand, could easily do five or six 45-minute presentations a day and still have ample time for follow-up and pipeline maintenance.

Given that revenue is simply the number of opportunities attacked multiplied by your win rate (what proportion of opportunities result in a sale) multiplied by the average deal size, generally speaking, more opportunities attacked is a good thing. But that is often balanced by the higher win rate you can see from face-to-face interaction, as well as the increased comprehension, believability, and trust that it engenders. Also, some solutions are so involved and mission-critical that in-person is really the only way to go about it.

So for now, to begin with—and regardless of what you think the optimal approach to selling your solution would be at scale—it’s pretty much always going to be better to sell in person. Even if that means only one or two meetings a day to start, don’t worry about it. The increased fidelity of communication, the increased insights you’ll get from a lively face-to-face exchange, and the increased trust engendered will overwhelm the efficiency gained by digital presentation. This is why when we talked about prospecting early customers, we focused on those in your geographical vicinity.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Pre-Call Planning

Did you know your presentation starts before you even get on the call or show up at the prospect’s office? Just as professional athletes use scouting reports and watch previous game recordings to maximize their performance on game day, the best sales staff rigorously prep for their demos and presentations to ensure they make the most out of them.

If you consider the time and energy that went into putting the demo in question on the calendar, you might think, “How could you not prep for something like that?” Well, you’d be shocked by the preparation laziness demonstrated by a lot of sales staff. Don’t be that person. You or your market development rep helper spent hundreds of dollars of salary expense to get this demo on the calendar. Don’t set that work on fire. Further, this is about raising your win rate and making the most of this opportunity. What’s your average contract value? ~$20K? If proper preparation can raise your win rate from 15% to 25%, well, you just made ~$2K with 15 minutes of preparatory work. Pre-call planning is not optional.

Note that presentation preparation is not the same as prepping for cold calling—which is usually a waste of time. Because connect rates on cold calls are fairly low, spending five minutes to get all the context about an account into your head before you dial means that you’re just reducing the number of calls that you can make, for no particular benefit. However, because hold rates on demos should be 80% or higher, you know there’s at least an 80% chance you’re going to be having a serious commercial conversation that could result in ~$20K (or whatever your ACV is). It’s worth the time investment.

Calendar Management

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Pitch Materials and Concepts

Let’s talk about where the rubber meets the road—the actual pitch we’ve been diligently lining up and preparing for!

Tools and Materials

Depending on the location of your pitch, the tooling you’ll employ will change. However, just as you’ve been intentional with respect to your materials and preparations, so too you will be with your tooling.

If you’re pitching on-site, don’t assume that your prospect will have everything you need to present. Moreover, any hiccups will reflect poorly on you. The prospect will just remember an awkward, terrible meeting, even if it was his bad internet that caused the demo failure or his dysfunctional projector that kept blinking out. Things will invariably go wrong, so plan for it.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Pitch Introduction

Rapport Building and Opening Chitchat

Now’s the time when you deploy those nuggets of information you surfaced ahead of time and do some hypercharged rapport building. The goal of this part of the pitch is to form a bridge of shared experience that raises trust levels.

importantYou need to have a plan for transitioning things to getting down to business. There’s a certain amount of time, two or three minutes, that you can spend on this sort of thing before it starts to wear thin. Not to mention, you’re eating into the time that was budgeted for the rest of your pitch. A great way to do this is to move from less to more professional topics as you go. It’s nice to talk about the Red Sox if the prospect is from Boston, but you’ll want to switch it up to “How long have you been recruiting?” or remark on professional components of his role as a segue to the commercial discussion at hand. “Well that’s great. I’m glad we got to talk about that stuff! So…” And then begin.


This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Presentation, Demo, and Asking for the Sale

Once you’ve completed discovery, you’ll move from the part of the conversation where you are primarily consuming information to one where you are both consuming information and communicating it. Note that I didn’t say that you’ll be moving from listening to talking. If you are doing it right, you will still be consuming lots of information, asking lots of questions, and eliciting lots of feedback. However, you will be doing this while communicating your sales narrative, as documented in your slides, presentation, and demo scripting.

Before we talk about specific parts of your presentation and demo, here are some overarching guidelines on things that will make you successful in your approach (and which may be different than prior presentations you’ve likely done).


For many people, it’s a big change to adjust to the amount of repetition that goes on in sales presentations. As writers and communicators, we typically worry about saying the same thing more than once, for fear of being boring or insulting the intelligence of the audience. In a sales presentation, repetition is your friend. You need to appreciate how new the topic you’re covering is for your audience. You deal with the topic all the time, but they don’t. It’s critical to keep coming back to the key points that you want to get across, which typically correlate to the big messaging buckets in your sales narrative.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Handling Objections

In the grand majority of your sales interactions, it’s not going to be an immediate yes, nor will it be a cut-and-dried no. Instead, it will most commonly be, “No, because of this” or, “Well, what about this?” And all those equivocal responses come under the heading of objections that you need to handle before returning to the close.

Often first-time sales staff are afraid of objection handling, because it feels like you’re starting conflict with the prospect. Why am I arguing with the person I want to sign this proposal?!

importantThe reality is that handling objections is where some of the most valuable work in sales is done. If sales is about commercial persuasion, this is where the rubber hits the road. This is where you examine, one by one, the things that are blocking your prospect from proceeding and surmount them using business-based arguments and proof.

That’s not to say that this has to be contentious, but you will be best served by being direct. When a prospect surfaces an objection that runs counter to their business reality, it is your duty to address it head on. This general concept of respectful contentiousness has been popularized by Matthew Dixon and Brent Adamson in their book The Challenger Sale. It’s all the more important in innovative technology sales, where you must change minds to popularize a new approach to a business problem—which typically requires challenging existing mindsets.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Demo Follow Up and Further Meetings

Depending on the cost and complexity of your solution, your prospects probably won’t be purchasing directly from you at the point of demo, or immediately thereafter. There will likely be some sort of follow-up required. In the best-case scenario, that might be sending the prospect a contract that she can e-sign immediately. Fantastic! It might be sending a proposal with pricing options as discussed in your demo. It might be the delivery of some key information to help with the decision-making process and to address objections that arose in the demo, like ROI proofs, and so on. Or it might be a further demo or meeting with another stakeholder whose agreement is required to progress to a sale. There are many permutations.

However, regardless of which variety of follow-up item is required, the approach to executing them all is largely the same. Firstly, you must directly and concretely state what the next action is. Remember our discussion above about contracting for each next step? This is where it becomes very important to guard against spending your time on useless opportunities and to hold your prospect accountable with those micro-contracts. Don’t resort to, “Well, I’ll send you some information. Let me know what you think!” Instead, you should concretely articulate the state of the deal, what you will do, and what the prospect will do in return.

example“Based on our agreement that this solution makes sense for your organization, and your desire to spend budget on it, after we get off this call, I am going to send you a contract for one seat using our e-sign system, and you will be able to execute that today. Is that correct?” Or, “You would like to purchase three seats of our software, provided I supply you with the ROI study that we discussed in our call. I will provide that after I get off the phone, and then we will reconvene to discuss your analysis of that ROI study and whether it has resolved your concerns.” And so forth.

If there is a further meeting required, calendar it. If another decision-maker needs to be involved, propose getting a meeting on the calendar with all three of you. If your prospect is going to consume some information that you have delivered or discuss the solution with his team or simply consider the information you’ve shared, that’s fine. But set a specific follow-up appointment to discuss the outcome of those actions. By doing this, you’re making it clear that you won’t be chasing him around via unresponded-to emails or phone calls, and that if he’s going to promise to do it, you’re going to hold him accountable. Partly this is to dissuade him from faking interest. If he’s not actually interested, or only partially so, putting a call on the calendar where you will jointly review follow-up materials will make him think twice about asking for a proposal just so he doesn’t have to say no. So if you get, “Let’s touch base in a month or so,” the response to that is, “Fantastic, let’s get that calendared right now and set the agenda that we’ll be reviewing—namely, what’s keeping us from progressing right now, and whether it has changed.”

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Practice and Iteration

There’s nothing like “live fire” drills with actual prospects to hone your skills. That said, doing a series of practice demos, complete with objection handling, can really help get you warmed up and ready for the real deal. You might even continuously mix those in when your calendar is light. If any of your prior interviewees from your customer development research would be willing to do these drills with you, fantastic. But even if it’s people on your team who are not revenue-facing (forcing them to ask questions like a prospect is probably good for them too!), your significant other, or otherwise, any practice is helpful.

importantAlso, recognize that your pitch, demo, and objection responses will never be set in stone; you need to be seeking to improve them as you go. Did you realize that, yes, just like Pete said, offering trials to people is a terrible idea with your current product, and you would be better off just cutting that out of your pitch? Great! Cut it out! If that one slide in your deck isn’t helping, or is constantly causing confusion, drop it. Don’t slavishly adhere to something that doesn’t work. You should view your pitch and down-funnel protocol as a product that you are constantly iterating.

With that said, nothing drives success like raw activity. So get out there and go!

Further Reading on Discovery, Pitching, and Demos

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Down Funnel Sellingan hour, 6 links

In the last chapter, we covered how to prepare for and execute customer-facing pitches. While you would prefer that pitches and deals proceed in a linear process from beginning to end, that’s far from the reality. In this chapter, we’ll cover some of the more squirrelly bits of dealing with opportunities that are in a down-funnel state, from negotiation, driving urgency, and closing (whether winning or losing—both important), all the way to guidance on how to deal with a pipeline of a dozen, two dozen, or maybe more of these concurrent opportunities.


The more costly and complicated your solution is, the more likely there will be negotiation at the end of the purchasing process. This shouldn’t be viewed as a negative and something to avoid, but simply another signpost on the way to a successfully acquired new customer. And this is different than the pricing objections we’ve discussed previously. When you get to negotiation, the prospect is convinced that there is value in your solution—it’s a question of whether he’s going to pay rack rate or 30% below that. Regardless, my goal isn’t to make you a master negotiator; there are plenty of books on that already. It’s to give you a general framework for how to think about negotiation and getting these deals across the line.

Firstly, whenever you are selling to people who have purchased enterprise software before, and especially if they do it frequently, there is going to be a baked-in expectation of negotiation and discounting. We touched on this in Pricing and Early-Stage Sales Materials Basics, but don’t be surprised when your prospect views your first proposal as a jumping-off point to negotiate you down. As such, you should factor this into not only your sticker pricing, but also any initial proposals you prepare. Start with inflated pricing in anticipation of being negotiated down, so that wherever you end up still provides an economically viable deal for you. If the prospect simply takes the price, fantastic, lucky you. And if she wants to negotiate, great, you’ve provided yourself room. And in the event you have to deal with a procurement department, you’ll be really glad you built in that room; they’re likely going to attempt to wrangle another discount on top of whatever you agreed to with your direct decision-maker. (Now, if you’re selling to “deer” like we discussed in Early Prospecting, it’s unlikely that they’ll have a procurement function. But it’s something to be aware of.)

When approaching these negotiations, you want to be clear on what is valuable to you—what you want to preserve—and what may be valuable to your prospect. Then look for opportunities for trades, where you can give the prospect something he wants (which is less valuable to you) in exchange for something that you want. The big levers at your disposal will be price (per seat, per unit), amount, duration of contract (a year? two years? six months? month-by-month?), payment terms (total contract value paid up front? biannually? monthly?), and then terms like automatic renewal and opt-outs. As far as you’re concerned, you would like a long contract, the entire value of which is paid up front, that automatically renews.

So what should you value the most? Cash is king for early-stage companies, and you should always prioritize getting more money in the door up front. You never know what could happen with accounts receivable. The customer could go out of business, have a new purchaser who comes in and holds payments hostage, and so on. Yuck. Get the cash in your bank account. Secondarily, you should value length of contract, in that longer terms reduce the risk that your customer will churn out. In the context of your negotiations, you’ll want to maximize these variables where you can (and later, when you’re training and compensating sales reps, you’ll want to incentivize these variables as well) and, if you have to give things up, give them up last.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.


importantWhile hearing the prospect say yes is definitely super exciting, that doesn’t mean your work here is done. Don’t stop to do a happy dance and risk your deal. You have to run all the way until the money’s in the bank, and then run to make sure that the new customer is up and running and getting value out of your solution. We glorify the closing bit of selling, but it’s just another step to nail, of many before and more after.

Order Forms and Contracts

Once you’ve agreed to a price, you need to act as quickly as possible to execute the contract. You don’t want to leave any room for second thoughts to creep in—get the contract signed and the client on their way to your customer success team for implementation and training.

An important part of your toolkit will be your order form, associated contract, and e-signature software. Different from your proposal, which is more a piece of marketing collateral than anything else, your order form is simply there to memorialize the key terms that were already agreed verbally and allow for signature by the purchaser. The goal is easy, friction-free execution. We used this TalentBin order form all the way through acquisition. At the very beginning, I would manually enter the relevant terms and then upload the document to e-signing software—initially I used HelloSign, but then moved to Adobe eSign because of its integration with Salesforce—to send to the prospect. Later we used Adobe eSign’s integration with Salesforce to automate the population of terms. But the key was that we kept it simple.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.


While we’d love to win every deal that comes through our pipelines, it’s just not going to happen. In fact, if you’re winning all your deals, you could even make the argument that A) you don’t have enough deals in your pipeline (Are you doing just one demo a week, and bird-dogging that one like crazy?), or B) you’re not talking to enough customers who are lightly qualified (you’re cherry picking only the best ones, but not taking enough shots on goal). If you’re fully utilized (ten demos a week or more), and you’re winning all of them, OK, something you’re doing is magic, and I’d like to talk to you. But with a new solution—or even worse, in a newly forming market—win rates in the 10% or 20% range will be more typical. If you hit 30%, you’re doing pretty great.

And this isn’t something to be ashamed of. Think about all the reasons why a deal might not happen: it turns out that there really isn’t budget available right now (but maybe in four months!), priorities shift away from the problem that your solution addresses (don’t worry—they’ll likely shift back!), or the person you’re selling to leaves the company. There are myriad reasons why this time may not be the right time for that deal. So closing out an opportunity as “closed-lost” is totally okay, and certainly better than spending your emailing and calling time on a deal that’s never actually going to come to fruition. Remember, your time is your most valuable asset in enterprise selling. So being dishonest with yourself about the likelihood of a deal closing, and letting it take up time and space in your pipeline, is actually far worse than closing something out.

When to Close-Lost Something

When should you close something out? Well, the easiest is when you’ve tried to handle the prospect’s various objections and she still gives you a direct answer to a direct question that she’s not going to move forward right now. This is almost the best-case scenario (aside from a win!), because you have a clear understanding of where you stand and the opportunity to ask specific questions about why she didn’t want to progress. Was it competition? Was she not convinced of value or that she actually had the need? If that’s the case, then it’s probably low likelihood that you’ll be able to get her later. The more likely scenarios, though, will be the prospect not having the budget to purchase, or the prospect largely going dark—which is usually indicative of some sort of issue with priorities changing, an unstated lack of budget, or an unwillingness to go to bat to purchase the solution. This case is actually not bad, because presumably the prospect still has the need for your solution. It’s not a “no,” but a “not now.”

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Pipeline Management

Now that we’ve talked about what a trip through the funnel looks like for any given opportunity, how do you manage a few dozen of them at once? Depending on the length of your deal cycle, and your average contract value, you can imagine working between a dozen, 50, even up to 100 deals concurrently, each spanning 30, 45, 60, or maybe even 180 days from beginning to end. This goes back to one of the most jarring things about selling for the first time: trying to manage that many concurrent threads, and herd those cats toward a finish line, is a shockingly large adjustment from non-sales work.

And while a holistic rundown of how best to manage a pipeline could be a chapter unto itself, these are some general guidelines.

Pipeline Staging

One of the most important things in enterprise sales is having control of the deal and knowing, truthfully, the state of the opp. The first step here is obtaining the information by asking good, direct questions, whether at the top of the funnel in qualification, or further down the funnel as you’re pushing an opportunity toward completion. But the second step is ensuring that you’ve recorded that information in a way that lets you easily report and act on it. One of the most important parts of pipeline management is deal stages—making sure each opportunity is tagged with the specific step it’s currently in. That will signify to you how far a deal is from the finish line and, relatedly, how likely it is to get across it.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Part III: Customer Success

Customer Success Basics9 minutes

You’ve just closed a new deal. You’re pumped up, having gotten a customer across the line and booked the revenue, with the check in the mail. You’re ready to repeat your success and get another contract signed. In fact, you’re starting to forget about the customer you just sold and turn all your attention to the next prospect.

Don’t give in to that temptation! In a SaaS world, the reality is that the moment you close a new customer, it’s a countdown to when they will be renewing, or not renewing, their contract. And if you don’t ensure their success with your solution, they won’t be renewing. But that’s not the worst of it. Even before renewal comes up, they certainly won’t be buying more seats or units of your solution. And while they’re not buying more, they certainly won’t be telling their friends and colleagues nice things about your solution. They won’t be providing you with delightful marketing-ready testimonial quotes and videos. Worse, if a new leader comes into the organization and does a tool review to see what is being used (and what isn’t), she could easily decide to break your contract—and not pay the remaining installments. Yikes!

Why Customer Success Matters

While losing out on a renewal is a big problem for your business, unsuccessful customers present all sorts of other problems ahead of that. And you don’t necessarily have a year to fix them. While we talked in prior chapters about the benefits of longer contracts—they give you more time to get a customer to success—that doesn’t mean you can get away with skimping on customer success and then save the contract in a last-minute scramble. There’s actually only a short window in which you have a customer’s attention and faith and can work with them to invest their time and attention in adopting your solution. It’s far easier to get a customer up and running as an extension of the sale process, with all the associated excitement, novelty, and executive buy-in, than to resurrect something that has fallen by the wayside and been deemed a failed purchase.

Now contrast this to a happy customer getting value from your solution. In their first couple weeks using the product, following a successful implementation, they already have some massive wins. And those wins are exactly in line with promises that were made during the sales process, demonstrating that they’re well on their way to achieving the expected ROI. So they decide that more team members should have licenses and ask to double the size of the contract. All the while, because they’re so proud of themselves for being smart purchasers of a new solution, they’re happy to take customer reference calls. In fact, they’ve already recorded a nifty little webcam video raving about your solution, which you’ve embedded into your sales deck. When the decision-maker who purchased your solution gives his talk at the fancy new-technology conference, he cites you as being core to his company’s success. And when one of their users leaves for a new role halfway through the year, her first call is to you to get a license for her new company.

That’s the virtuous cycle you want to be a part of.

Do customer success wrong, and bad things happen. Do it right, and great things happen. How great and how bad? Check out this chart detailing the monthly recurring revenue for three versions of the same hypothetical businesses.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

What Is Good Customer Success?

Above all else, customer success is about fulfilling the promises that were made during the sales process. The customer handed you money in exchange for a promise of value, and now you’re going to deliver that value.

What does that value look like? Conveniently, it’s documented in your sales narrative. Those KPIs (key performance indicators) that you said you were going to raise or lower for the customer? That’s customer success. So if we were TalentBin, this would be all about driving more engineering talent into the top of the customer’s hiring funnel. And if we were Textio, it would be about optimizing job postings such that more applicants would apply per post and posts would attract more diverse applicants. Customer success is about delivering on your ROI promises, and doing so for each of the involved stakeholders. Was there a certain set of value propositions for the manager, but others for the individual? Well, you’re going to want to check both of those boxes, and make both of those customers successful.

You methodically, and in a stepwise fashion, engage with prospects and drive them down the sales pipeline toward being a customer. Now, the same approach will ensure that you deliver the success you promised those customers and find yourself on the happier versions of those revenue graphs above. It’s methodical, in that it will be rigorous the same way your discovery, presentation, demo, and pipeline management was, and stepwise, in that it’s not a question of getting a customer implemented, handing them the keys, and forgetting about them. Rather, after implementation, customer success turns to cadenced check-ins, instrumentation of success markers, and documentation of ROI achieved, all aimed at supporting an airtight case for renewal at the end of the contract.

Mechanisms for Customer Successan hour, 2 links

When it comes to customer success, there are a broad array of tools to get the job done. That said, don’t think that you need to employ all of the approaches we’ll touch on. They are presented in order of most integral to more optional. All will deliver value, but depending on your bandwidth, you may need to pick and choose until you have dedicated customer success staffing. Regardless, they’re all good to have in the back of your head.


The broad bucket of implementation is the set of steps that you take after a customer has signed to get them quickly up and running, and can include technical implementation steps, user training, and more. Depending on the complexity of your solution, this could be as simple as a 30-minute call and guided tour, or as complicated as a multi-month, full-blown professional services engagement. In either case, though, implementation is the first step on the road to customer success, without which you’re putting yourself at a substantial disadvantage. Invest in it accordingly.

The goal of implementation is to execute all the preconditions needed for your customer to have success with your solution. So the first step is to understand what those first steps are. This ranges from the completely mundane, like securing credentials for a user, to the more involved, like integrating with existing systems, migrating data over from legacy systems that your solution is complementing or supplanting, and so on. It also includes user training for all archetypes of users: individual contributors, managers, and beyond.

exampleFor a company like Textio, makers of job posting optimization software, implementation would start with securing credentials for all the recruiters who would be using the solution. Next, they’d hold training sessions with those users to understand how best to use the system, and with their management to help them understand that the system is being properly used and creating the promised value for the organization. And it would keep going all the way to securing proper integration with the customer’s existing applicant tracking system to ensure that Textio could start learning from the organization’s prior job postings (and the applicants and eventual hires that came from them).

importantOnce you understand how many of these steps need to be taken, and have a sense of how much time that should take, you’ll start to see how involved this might be. This will indicate whether your implementation process can be as simple as a one-and-done call and screen share with the primary user of your product (or even a self-guided onboarding tour, for extremely inexpensive, uncomplicated solutions), or if it will require a series of meetings with various stakeholders, project managed to completion.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Inbound Response and Support Tickets

Once you’ve completed implementation, it’s time to drive your users to a return on their investment as quickly as possible. Let’s talk about the tooling you’ll need to achieve that.

The first bucket of tools allows users to easily contact you when they hit snags and need help. We’ll talk later about proactively identifying users who are having issues and engaging them before they even reach out. But the first step is having a means by which users can get in touch with you when they have issues.

You’ll recognize a lot of the same tenets from Early Inbound Lead Capture and Response, in that support is rather similar—it just happens to be for existing customers rather than prospects.

Inbound Support Request Capture

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Proactive Customer Monitoring

While low-friction inbound support and rapid response is fantastic, there’s a step beyond: proactive, preventative customer support. One of the beautiful things about modern software, particularly SaaS solutions, is that the customer actually uses it on your servers, or at very least, in a way that allows you to instrument their usage. This is in stark contrast to how things worked back in the day, with on-premises enterprise software that was installed on customers’ servers that were racked in their data centers. Then, you might have had no idea whether the software was being used and value was being provided to customers.

Now, SaaS delivery means you see what sort of usage customers and users are engaging in. And that’s crucial to your business. Because users are subscribed (and didn’t purchase a perpetual license of the software), they can just stop subscribing if they aren’t using the tooling (and deriving the promised value). The logical implication of that turns out to be: pay attention to whether customers are using the tooling the way they’re supposed to! This notion of customer success monitoring has really taken off only in the last few years, and the associated tooling is still being developed. However, there are fairly basic ways that you can accomplish this now.


It’s fairly common to architect your application such that a customer success manager can log in as the user to see what’s going on. This is helpful when troubleshooting but can also be great for customer success, as you can dip into customers’ accounts to check for the telltale signs of proper usage. You would be looking for those value precursors and value outcomes discussed above—the actions and outcomes that lead to the value you’ve promised.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Success Outcome Capture

In addition to monitoring usage to get ahead of any problems, a successful customer success function needs to understand and quantify users’ success—and then make sure to tell them about it! In business speak, this evidence of success is often known as outcomes.

In the sales process, you promised certain kinds of business value to your customer. Instrumenting the achievement of that value is important for a variety of reasons. When customers can see that they are achieving the desired business value, they’re more likely to stay customers. Moreover, by documenting and capturing success outcomes, you’ll be able to use that information in go-to-market materials, like sales decks, customer success stories, and so forth—more on that later in the chapter. There are a couple of ways to go about this.

In-Product Capture

If you can design your product in a way that captures outcome value, all the better. At TalentBin, we had a concept of stages associated with candidate profiles, and one of those stages was Hired. If people were buying TalentBin to help them hire hard-to-find engineering talent, chronicling when that happened was one of the most direct ways of proving its value.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Quarterly Business Reviews

There are all kinds of benefits to instrumenting and capturing success signifiers. But you can’t forget to reflect this customer success information back to the customers themselves. That might sound a little weird—if they’re having success, you’d think they’d know, right? No! Customers are super busy, use dozens of tools, and have all kinds of competing vendors whispering in their ears that their software would provide a better, faster, smarter solution than yours. You need to do a good job of documenting and reflecting back the success your customers are having, so it’s super clear that they’re getting that all-important ROI.

If you’re proactive about sharing this ROI information, great things happen. You’ll be top of mind with users and decision-makers, who will understand why this was a great investment of their time and budget. And if there are other potential users of your solution in the organization, it’ll be that much easier for you to sell more seats. These decision-makers and users also interact with friends and colleagues that share their business challenges. Making sure your ROI proof is readily available will arm them to be great promoters to others. And it helps cement their existing commitment bias ( aren’t they smart for choosing you?), which is very helpful if competitors and alternative solutions show up in their inboxes. Why would you open an email about a competing solution when you know that you’re getting great value from the one you’re using?

cautionIf you don’t do a good job reminding customers of their successes, the opposite can happen. You’ll miss out on upsell opportunities, as no one is clear on why your solution is a great investment. You’ll miss out on word of mouth because your decision-makers and users aren’t armed to advance those arguments for you. And you’ll leave yourself wide open for competitors to come in, making a case that their solutions can provide more value. Not good.

The best way to achieve scenario A, and to effectively share success data with your customers, is to implement quarterly business reviews (QBRs). Oddly named—probably better to call them something like success reviews—these are formal quarterly checkpoints between a vendor and a client to document progress against joint business goals. This is the means by which a vendor can present formally the value that has been delivered to the client so the customer can say, “Wow. This is great. I’m so glad that I’m doing business with you. I’m totally going to renew when the time comes around. In the meantime, I’m going to think about how I can maybe reallocate some budget from the other solutions I’m using, since clearly yours is working so well. Oh, while I’m at it, I’ll tell all my peers at different organizations about this next time we have cocktails.” At least, that’s the best-case scenario!

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Support Sites and Asynchronous Support Materials21 minutes, 1 link

While most of the things we’ve discussed have been one-off actions that are either proactive or reactive in nature, asynchronous support materials are also a powerful way to drive more and better success with your customers. Much like we look for places where we can templatize and collateralize our sales message—with email templates, slides, videos, PDFs, and so forth—we can do the same in customer success.

And the benefits are the same: you can make sure that the information that you’re providing is correct, since you wrote it once and double- and triple-checked it. But even more importantly, customers usually just want to solve their problem and get on their merry way. If they can do that by reading a success note or watching a quick video, that can often be more satisfying than having to file a support request or engage in a chat conversation with an agent—not to mention that by letting customers answer their own questions, when appropriate, your success staff can spend their time on implementations, QBRs, and thornier support issues.

The traditional way to do this is via a support site. Most support software like Zendesk, Desk, Freshdesk, and so forth have lightweight content management systems that allow you to create a dedicated page for a given topic (usually in the form of a how-to answer) with text, embedded images and screenshots, and even videos, that lives on a hyperlink. Moreover, they typically let you embed links to these pages in support response macros/canned responses to let support staff quickly respond to inbound requests with the relevant answers.

Most support software also provides functionality that allows users to search across the support articles, or suggests support articles that match the initial input a user puts into a form. Lastly, they provide analytics on these documents to show how frequently users are reading them, which helps you understand the benefits they’re providing and also where there might be confusion about the product.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

New Release Communications and Ongoing Training

It sounds obvious, but one of the biggest missed opportunities in early-stage customer success is insufficient investment in the documentation, announcement, and adoption of new features. In early-stage software, the reality is that you’re likely iterating your product pretty substantially as you go, adding new features and extending existing ones. The funny thing is that while new features get incorporated fairly regularly into prospect-facing materials—like demos, slide decks, and so on—folks forget about the customers who have already bought a version of the product that didn’t yet have these magical enhancements.

That’s a problem. If your customers are not being kept up-to-date on your advancements, but are being wooed with the latest and greatest versions of your competitors’ products, you’re missing out. And if your evolved features are addressing pain points that were surfaced via support channels, well, all your customers likely have those pain points. If you aren’t communicating that they’ve been solved, they’re likely still being frustrated by them. Further, while customers primarily buy your solution, as is, to solve an immediate problem, there’s a part of them that is buying into the belief that you will continue to get better at solving this problem for them, with better and better technology. If you are indeed iterating your product and shipping new features, you need to show it to your customers and get credit for that momentum. You want them to say to themselves, “You know, it was a really great idea that I bet on these folks. They’re always coming out with great new things for us.” Lastly, appropriate communication of new features and functionality is a fantastic way to re-engage disengaged customers who are at risk of churning.


What materials should you use for this? Well, as noted above, creating a support site note as part of your release process will help ensure that you at least have the key information readily available: what the goal of the feature is, why it’s helpful, and how to use it.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.


It bears repeating: the goal of customer success is to ensure that customers get the value they were promised when purchasing, so they will continue to be customers. In a SaaS world, if they don’t get value, they won’t renew. Everything we’ve covered has been in support of that goal. So by the time a year has passed (the typical length of a SaaS contract), it should be just an absolute no-brainer for the customer to renew. After all, you’ve done such a good job helping them capture tons of business value from your solution, in a way that was fully documented. So first things first: to ensure renewals, make sure that folks get to value.

But even if you’ve done all those things right, you still need to capitalize on it by executing a good renewal process. These are some ways to do that.

Automatic Renewals

First, in your order form and master service agreement, you need to have an automatic renewal clause. Customers may seek to negotiate it out, but most will never consider it, and this way, your solution just default renews. When the time to renew comes around, you just run the credit card on file using something like Recurly, Zuora, or Aria Systems. With automatic renewals, it can also be nice to provide a courtesy email note a month or so out. This doesn’t mean that you can skimp on getting customers to success, but it can help in some edge-case scenarios where implementations have taken far longer than they should, stakeholders have left a company (resulting in a new sales cycle simply to get adoption of what has already been paid for), and so on. Further, automatic renewal at existing pricing can be a boon to a customer if you raise your pricing as you add new functionality and the product gets more robust.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Learning From Your Customer Success Team4 minutes

While all of the above activities are key to getting customers to success, and eventually renewing their contracts, an effective customer success function can and should play a larger role in your organization. Because it’s uniquely positioned to have meaningful, ongoing interactions with your customers, customer success can often pass on a wealth of information to sales and marketing, product development, and other key functions.

Product Development Insights

An outcome of all of your customer success activities—rigorous onboarding, inbound support request capture, and proactive monitoring—will be a wealth of information on what customers like about the product, and what they don’t. Customer success uses this information to resolve issues and enable success, but it’s also important to feed this intelligence back to the product development organization. If certain features are hard to use, and create a large amount of inbound support requests, product and engineering can prioritize refactoring those features. That will in turn not only reduce the support resources needed to paper over that issue, but will ideally enable more success, creating happier customers who are less likely to churn (and more likely to generate positive word of mouth).

Sales Insights

Your customer success team will also be the first people to know that a user or decision-maker is departing from one organization to join another. This is a prime opportunity to follow them to the next company as well, as typically the settling-in period in a new role is accompanied by setting up new tooling. Handing this information off to sales to execute on in a timely fashion is paramount.

Customer success can also be extremely helpful in surfacing customers willing to do customer reference calls with prospects. Connecting prospects with customers who are rabid fans due to their success is a great way to get deals across the line, and your customer success staff can help you achieve that.

Marketing and PR Insights

As your company matures, your pitch should too. You no longer have to speak about hypothetical success—now you can point to real-world examples of how your solution is changing how your users do business. Customer success plays a key role in finding valuable usage data and product evangelists and passing that information back into your marketing and media outreach.

Proof of Success

Earlier in the chapter, we talked about the importance of capturing successful outcomes in your CRM so you can report that information back to the client. Equally important, though, is having the ability to report those outcomes across all users, or particular subsets of accounts. As customers reach their goals, customer success can harvest this information and provide it to marketing for use in proof of success collateral like slides, videos, and so on, as discussed in Early-Stage Sales Materials Basics.

Events and Customer Advisory

Customer success will be best positioned to identify cheerleaders and advocates who can be helpful in the context of conferences, speaking opportunities, and customer feedback on new products.

If customer success is going to help all these other parts of the organization, the first step is to make them aware that these are activities that they should be engaging in. The second, more advanced, step, especially as you start establishing a specialized customer success function, is to provide compensation inducements to them. Offer a ~$50 bonus for each upsell or new opportunity (again, contingent on the size of your typical deals) identified by customer success that ends up getting sold.

Customer Success Role Specialization8 minutes

As discussed in the previous chapter, as you start to have more responsibilities that occupy your time—but before you bring on staff to hand those off to—you’ll have to be mindful of splitting your calendar to achieve them.

Previously, you had to find time for prospecting, initial pitches, and down-funnel follow-up meetings; now, you’re adding implementation meetings, monitoring success KPIs, QBRs, and renewals! It’s a lot, so it’s vital that you be vigilant about blocking segments of time on your calendar, or those activities won’t get done.

The first step is to make sure that meetings for customer success activities—implementation calls, kickoffs, check-ins, and QBRs—get on the calendar as soon as deals are closed, so your future time is burdened appropriately. The second step is to start tracking these activities in your CRM. The same way you may have a Demo event activity or Follow Up meeting activity, you should track Implementation Meetings and QBRs such that, with a simple report, you can see, for example, all accounts that have a closed-won opportunity but have not yet had an implementation meeting.

After you have onboarded a dozen or so customers (depending on the size of your deals), you should start to think about how you could hire someone to take this responsibility off of your plate. Importantly, because of your experience onboarding, getting to success, and doing QBRs for that initial set of customers, you should have the beginnings of a customer success playbook. Codify it in documentation and process (again, to be tracked in the CRM), such that you can hire that first CS specialist, get him to success, and then start the process of stamping out more of him.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Responsibility Specialization and Compensation

importantThe compensation of customer success staff is heavily influenced by the responsibilities they bear. Firstly, as an aside, as of the mid–late 2010s, the compensation models of customer success staff have not yet seemed to wake up to the realities of the importance of customer success in a renewals-based world. If you refer to the revenue growth chart in the introduction of this chapter, and look at the scenarios with differing churn numbers, you can see the deep importance of customer success. That should be reflected in the level of talent you are willing to pay for and the compensation requirements that flow from that. Historically organizations have viewed support and customer success as a cost center to be minimized, rather than considering the opportunity cost of under investment in the function: higher churn rates, lower lifetime customer value, and reduced opportunities for upsell and positive word of mouth.

That said, one of the most important determinants of how you compensate your customer success staff is their commercial responsibility, or its absence. Will your customer success staff be responsible for renewals? Or will an account management staff or even the primary account executive staff be responsible for these? Generally, focusing account executives on new business is the right approach; focusing efforts and not splitting attention is typically the best way to assure that things are done right. AEs that are responsible for renewals often follow the same pattern, showing back up to an opportunity 60 days from renewal—270+ days from the last time they exchanged emails with the client. Approaching a client with the attitude of, “Okay, so catch me up!” is not a recipe for a functional success and renewal motion. The best organizations specialize this responsibility.

Who, then, should be responsible for renewals? There are typically two approaches. Customer Success staff can be responsible for renewals; you might even base part of their compensation, in a variable fashion, on renewals and upsells. The other approach is one wherein responsibilities are split, and Customer Success is responsible purely for customer success activities, like implementations, ongoing support, quarterly business reviews, and so on, but another commercial account manager is responsible for seeking out upsell opportunities and ultimately renewing the business. This latter approach offers the benefit of specialization and eliminates the concern (oft stated but dubious, in my opinion) that success staff can’t “close.”

My take on this is that early on, when there are fewer customers, that level of specialization creates unnecessary overhead. Creating specialization between account executives who are hunting new business and Success and Account Management staff who are farming existing business certainly makes sense—the behaviors and operational tempo of a new-business hunter are very, very different than those of an existing-business farmer. But at the very early stage, specialization between Customer Success staff and Account Management staff creates more complexity and overhead than benefit. Having a class of customer success person that’s responsible for the implementation, ongoing support, quarterly business reviewing, and eventual renewing of customers seems to be the best balance. You get both specialization and the benefit of a rep who’s deeply familiar with the 100, 200, 300 accounts that he is responsible for.

Later Customer Success Role Specialization

As your customer base grows into the hundreds or thousands, more substantial specialization of success and support roles may make sense. For example, you might split out inbound response support versus implementation versus ongoing success versus account management and renewals. The benefit of this is that you can get efficiencies of specialization and scale. You can provide a better level of service to folks who are chatting on your support chat widget or sending in tickets if people are staffed purely to deal with those; otherwise, they’ll be left waiting until a customer success manager gets off an implementation call and can turn her attention to tickets. Or you can have more senior, more skilled, and thus more expensive customer success staff focused purely on implementation, quarterly business reviews, and project management of success activities, while more junior (and less expensive) staff focus on first-line ticket response—not dissimilar from the specialization of SDRs and AEs in a pre-sales environment.

Regardless of how deep you get into customer success in your company’s earliest days, the most important thing is to think about it at all. The biggest error founders and other first-time revenue leaders make, aside from the inability to sell at all, is insufficiently investing in the success of customers once they have been sold.

If at very minimum you have a success mindset, and choose from the approaches above, you will already be far ahead of the game.

Part IV: Scaling Sales at Your Startup

Early Sales Management and Scaling Concepts2 hours, 12 links

What the hell is scaling? People use the term all the time, but I find that about 80% of the time someone talking about scaling has no idea what they’re talking about!

importantIn B2B sales organizations, scaling is when you take something that has been proven to work at the unit level—one sales rep, one sales pod (an SDR, two AEs, and a CS rep)—and you start adding more of them, in order to parallelize your go-to-market. This is an important thing to realize—the way that most B2B organizations scale their revenue acquisition is not through magically selling more deals through your existing reps, but rather by adding more reps.

At a certain point, your sales reps only have so many hours in the week, and executing discovery calls, demos, follow up meetings, email, and closing calls with prospects takes time. So the way you scale revenue is by adding more people to do these actions.

And now that you’ve proven that you can reliably sell your solution yourself, your job now becomes proving that you can take that ability—that sales and success motion that you’ve developed across dozens and dozens of demos, closed deals, and onboarding and successful customers—and instill it in other sales and success professionals that you hire. You are moving from creating the approach to selling to starting to build an organization that implements that approach in a repeated, scalable way. This is the beginning of scaling, which, in turn, requires management.

Scaling Anti-Patterns

There are a couple anti-patterns related to scaling that I’d like to discuss before we talk about sales management basics, namely premature scaling and lagged scaling. Both are problematic in different ways.

Premature Scaling

Premature scaling involves adding sales staff (or adding many more sales staff) before you have proven that the sales motion actually works. This approach typically results in an inefficient or aborted go-to-market effort that destroys cash and enterprise value, and often leads to layoffs of those sales staff, and maybe others, and an injured fundraising position. This can happen a few different ways.

cautionThe most common way is for a founder to try to avoid having to figure out the sales and success motion himself, and instead try to “sprinkle some sales on it” by hiring a sales leader or a bunch of sales reps to figure it out. Usually what happens in this scenario is a sales leader who follows the playbooks that he’s previously seen to work at organizations where the sales motion has already been cemented, typically by throwing bodies at the problem. The result will frequently be very inefficient reps and often customer success problems, leading to low customer satisfaction, churn, and eventually the laying off of that sales staff. I would give some examples of companies where this has happened, but you likely won’t recognize them because typically it kills the company—they’re not around anymore, so you won’t recognize the names.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

When Is the Right Time to Scale Sales?

So if this is indeed a Goldilocks situation where we don’t want to scale too soon, and don’t want to wait too long, then how do you know when you’re ready to go?

First, it’s less of a binary “now you’re not ready, poof, now you are” situation, but instead it’s typically better to treat this like making your way into a hot jacuzzi, a bit at a time, validating that things are working as you go, but always making constant progress.

How do you know the time is right for you to take that first step of bringing on another sales rep, or two, to prove that someone other than you can sell the solution? Usually the answer can be found in the math of your sales metrics. A good B2B sales win rate is typically anywhere between 15% and 30%. Of all demos or first meetings you do, eventually 15–30% turn into closed-won deals (while the others either closed-lost or fizzle out into nothingness). If you find yourself in this range reliably, then it’s probably time to bring on other reps and prove that you can get them to close at a similar pace. If your win rate is substantially above that—well maybe consider raising your pricing, but certainly get a move on on abstracting and scaling your sales function! If your win rate is below that, then it probably makes more sense for you to figure out why only, say, 10% of your initial engagements are turning into customers before you turn to scale up customer engagements. Whether it’s the result of your messaging, product feature deficit, or pricing, sort that out first before scaling up.

The motivation behind these efficiency metrics is that to have an efficient sales organIzation, the total cost of your AE and SDR and sales engineer costs ( if you have a very technical sale and have sales engineers) should not add up to more than 20% or 25% of the amount of revenue they close, as a rule of thumb. So if your sales motion seems to require a single sales reps who set his own appointments, does demos, and closes deals, and he costs ~$100K a year, you’ll want to see him booking around ~$500K of revenue a year—because after you pay him out of that kitty, you want there to be plenty of other money leftover to pay for engineering, customer success, and so on. This is what is known as cost of sales, and you want it to be 20–30% (at the highest.) As a result, that rep needs to be able to close deals reliably, based on a good win rate, or else that ~$100K rep might only be able to bring in ~$300K of bookings, resulting in a really inefficient sales motion and difficulty scaling up.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Abstraction and Specialization of Sales Roles

We talked about the basics of role specialization earlier when discussing how hiring an SDR rep early on can be a force multiplier when you’re running through your first few dozen sales cycles. Whereas that goal was to help you free up your time to do more selling meetings (demos and follow-up meetings) and do customer success activities, now the business of specialization is about preparing your sales team for scale up—we are proving that AEs other than you can successfully sell the solution, and that CS staff, again, other than you, can successfully implement, monitor, and drive success of customers. Doing so prepares you for hiring and managing many of these successfully, which allows you to ramp your organization’s revenue.

Full-Blown Role Specialization

importantEven as you abstract the selling behavior into other staff, you’ll also be working on specialization of those staff as well. This will likely happen in a stepwise fashion, as discussed in the maturity model to follow, but ultimately specialization of sales and success staff is a very powerful modern way of selling.

The benefits of specialization are an extension of what you found when you hired an SDR to help set appointments for your calendar. Not only does specialization lead to individuals being better at the thing they are specializing in, due to doing more of it (~AEs doing demos and closing calls constantly versus Account Managers doing QBRs versus SDRs cold calling and emailing), but you also remove the cost of context switching between different roles that would otherwise be present within a single person. And of course this has all been enabled by the trusty CRM, which acts as a repository of truth with respect to the state of a prospect, from lead to opportunity to customer to renewal.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Early Sales Management

Sales management is the practice of enabling, coaching, inspecting, correcting, celebrating, and, generally, managing groups of salespeople in the pursuit of taking your product to market. And understanding what drives the success of a B2B go-to-market is instructive in how to think about your role as an early sales manager.

Ultimately what drives sales and customer success performance is a high quantity of high-quality customer-facing selling activity. We can improve the output of this formula through raising either the quantity of sales activity, the quality, or both. We can raise the quantity of this activity by improving focus and effort through better management of staff in their execution of these activities—like helping staff focus on customer-facing activities rather than internal-facing communications or other non-work distractions. We can further raise the quantity of activity, through the specialization or automation of tasks that are automatable—like by doing mass prospecting and filling the CRM with accounts and contacts for reps to target rather than them splitting their attention to do so themselves. And of course we can also raise the raw quantity of this customer-facing activity by simply adding more sales people doing this selling activity—this of course being the crux of scale out in a modern B2B sales org. Adding more cylinders to an engine adds horsepower and makes it go faster.

The quality of customer-facing activity also matters—the discovery, presentation, pitching, demoing, and deal running. This can be raised through better training and messaging—by ensuring that reps understand the pain points that the product solves, the conditions in which those pain points exist in a prospect’s business, and being able to effectively discuss these points. Quality of customer-facing activity can also be improved through better process—by preventing reps from losing track of their opportunities, being diligent in their follow up, and generally running a good sales process across their opportunities. You can think of this as ensuring that these cylinders in the engine are burning cleanly and not leaking.

Sales management is adding those cylinders, getting them properly hooked up to the fuel system and exhaust system, and ensuring that they’re pulling their own weight in an effective fashion, and continuing to do so on an ongoing basis.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

High-Impact Sales Hiring2 hours, 12 links

Now that you know that your initial go-to-market strategy is working, based on the metrics we covered in prior sections, it’s time to scale by adding more people.

For good and for bad, the way that traditional SaaS sales organizations scale is by incrementally adding humans to execute the sales work—calls, emails, demos, negotiation, closing—that leads to revenue.

On the one hand, this can be challenging, because humans are complicated; it’s difficult to make judgments about an unfamiliar person when hiring and, later on, when managing. On the other hand, if you get the right folks in-house—professionals who are hungry, intelligent, self-directed, and results oriented—it can be magical, and not just for individual execution of calls, demos, and so forth. There’s a rich-get-richer flywheel mechanism to sales hiring: high-quality folks produce high-quality work, leading to high-quality business outcomes, leading to a more engaging, rewarding work environment, leading to more high-quality employees and recruits. And the cycle reverberates throughout the company. Let’s make sure this scenario applies to you.

importantIt’s hard to overstate the importance of high-quality hiring in early-stage sales organizations that have hit the point of scaling. When you’re taking a new solution to market, your biggest cost is opportunity cost. In a greenfield market, it’s generally a land grab. Every week you don’t have that next market development rep calling against qualified accounts is a week your competitors have an advantage. And every week you don’t have that new account executive doing demos and closing business is a week that your competitors are doing their darnedest to lock those customers in for good. Not to mention, if your startup is not yet profitable, it’s a race against time before you run out of money; you need to quickly demonstrate sufficiently attractive metrics to raise funding.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Scaling by Specialization

As I’ve noted previously, a hallmark of a modern sales organization is specialization, which ultimately fosters greater expertise and efficiency in executing each step of the sales process.

As you start to hire, then, you should be thinking about what part of your sales process you’re hiring to support. Generally speaking—given that a founder or product manager starts out doing both the market development activities of calling accounts and setting appointments with decision-makers, alongside account executive activities like sales presentation, demo, negotiation, and closing—the first thing you’ll need is market development help to load your calendar with appointments. Then, once your lead-generation function is sufficiently ramped that your individual calendar is overloaded (when you don’t have enough time for sufficient down-funnel follow-up and closing conversations), it’s time to add more account executives. Later, when you have enough customers approaching renewals, it’s time to add account management functionality.

Depending on the role(s) that you’re hiring for, your approach may change at the margins, typically with more involved hiring processes for more senior roles. But the kernel will be largely the same.

We’ll start with the most general components, then move to the specifics of hiring for certain key roles.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Articulating and Documenting Your Hiring Profile

When you’re getting started, it can be helpful to consider how other successful SaaS sales organizations approach their hiring profiles.

exampleTalentBin: At TalentBin we targeted new grads out of high-quality universities, like Stanford, Cal, other UC schools, and so on, with a history of achievement in both taking initiative and building things. We also looked for indicators of success in team endeavors and athletic excellence (particularly in those unpleasant grinder sports). Alternatively, we targeted existing market development staff from LinkedIn—an industry bellwether in the recruiting market—with the promise that those market development reps (SDRs) would have a faster path toward becoming account executives at a fast-growing organization like TalentBin, compared to a slower-moving, larger organization like LinkedIn. We also hired former technical recruiters who had high subject-matter expertise but also the high-activity execution characteristics needed to sell software. We specifically did not pull account executives out of LinkedIn, or legacy sales organizations like Monster or CareerBuilder; these more senior staff were typically inured to selling existing solutions that the market is well aware of (job postings, resume search, and LinkedIn Recruiter) and thus were less suited to presenting a new, innovative product that substantially departed from legacy solutions. They were also typically more focused on maintaining and renewing existing contracts than on acquiring new customers, and relying on an established brand for making contact with customers rather than being a tip of the spear and penetrating and proliferating within accounts.

exampleMeraki: A highly successful hardware sales company, Meraki adopted the strategy of pulling high-impact sales staff out of IT value-added reseller (VAR) shops. In those small IT consulting shops, which are largely undifferentiated from each other, sales professionals need to hustle hard in order to beat others out for business. Moreover, because they are dealing with organizations that typically are without IT leadership (CIO, VP of IT), reps are serving in a very consultative role. IT resellers constantly see new technologies come across their shelves, so the ability to understand customer pain and then identify new technologies to solve those problems was paramount for these folks. Lastly, there is a high level of inside-sales execution on the part of these VARs, in order to keep their efficiencies high and cost of sales low in a low-margin business. All of these characteristics aligned with Meraki’s needs and drove sales excellence in the organization.

exampleYelp and Groupon: Yelp and Groupon would be examples in the other direction. Because of low average contract values, a massive market of hundreds of thousands of small to midsize accounts, and a relatively uncomplicated value proposition, their sales teams are architected for extremely high activity in support of a fairly transactional sales cycle. This means lots of junior go-getters—fresh out of college and willing to make hundreds of calls a day—looping across thousands of accounts. And while having intimacy with the local merchant’s business pains is helpful, because of the fairly straightforward sales being proposed, reps aren’t required to have a high level of selling expertise or technical acumen (unlike a Meraki, LinkedIn, or TalentBin). Thus the hiring profile is one of scale and cost reduction; junior staff straight out of college are less costly than more senior staff. When you look at the talent pools that both Yelp and Groupon have tapped into, it’s recent grads out of second-tier regional colleges with lots of graduate volume, particularly in humanities, communications, and business majors. In the case of Yelp, for their Tempe call center, that’s Arizona State University, or for their San Francisco sales center, it’s San Francisco State, San Jose State, UCSB, and so on. In the case of Groupon, much of their talent comes from Indiana University, De Paul, Ohio State, and other schools surrounding the Chicagoland area. Both companies found high volumes of charismatic, articulate, nontechnical staff to mop up thousands and thousands of ~$1K contracts here and there.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Hiring Sources

Now that we’ve discussed the profile that you’d like to see on your sales team, we can talk about where to go to find it—or how to get it to come find you.

It’s important to realize that not all sources of hire will require the same approach or be appropriate at every stage of your growth. Some sources make more sense earlier on, but become less relevant as you grow. And some sources make it easy to home in on higher quality from the get go, while others will require more screening. These are the various sources to consider early on.

Staffing Agencies

When you’re hiring your very first real sales staffer, agencies can be a great source of hire. Staffing agencies are set up to provide you with ready-to-go, qualified candidates who are seeking new roles, and for this, they typically take a fee of 20–30% of that candidate’s first-year salary. While 25% of a ~$60K base salary for an account executive is substantially more costly than a job-board posting or even a staff-referral fee, there are a variety of benefits to this approach.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Screening, Interviewing, and Closing a New Hire

While sourcing for the top of your hiring funnel can stock your pipeline with higher-probability candidates, your screening, interviewing, and closing process is what will maximize your conversion of these potential hires.

I find that a lot of organizations don’t know what they’re looking to achieve in the screening and interviewing part of the hiring funnel. I boil it down as this: the screening and interviewing process exists to authenticate that would-be candidates have the characteristics required for success in your sales org. Authentication is the key. While experience at a prestigious organization, a degree from a compelling school, or a shiny-looking resume may be potential leading indicators of success at your organization, the goal of the screening and interviewing process is to prove it, and once proved, to close the candidate on working at your organization. All the steps in your screening and interviewing process should support that goal.


Hiring, while of extreme importance, can be a large time suck of inefficiency if you aren’t mindful. This is why I am a big proponent of the use of asynchronous screening approaches earlier in the hiring process—it puts the time cost onto the candidate, while at the same time creating rich “interviewing artifacts” that are better reflections of a candidate’s abilities than a resume or personal statement that has been polished to perfection. This can be all the more important when working with staffing agencies whose incentives are to shove someone, anyone, in a seat. Having a strong screening mechanism in place that doesn’t consume all of your time, and gives you a high-signal outcome on which to base judgment, is all the more important when working with recruiting agencies.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

High-Impact Sales Onboarding and Trainingan hour, 8 links

Now that you’ve gone and invested all this time and energy in hiring sales staff, the next step is to get the most out of your investment. You want to get new hires up to speed—selling and closing business—in the shortest amount of time possible.

Why Onboarding Matters

In early-stage B2B sales, once you’ve hit product/market fit, your biggest cost is the opportunity cost from missed, or even just delayed, sales. This is especially true in greenfield markets, where the competitive landscape is only just forming and it’s a true landgrab. The salesperson you haven’t hired yet, and haven’t gotten productive yet, isn’t generating the ~$50K, ~$100K, ~$200K a month in sales they could be. Consider the future value of those customers as they recur, proliferate, and refer other customers, and that lost revenue looks even more troubling.

Moreover, if you are losing 30–50% of each sales hiring class to flameouts, in part due to faulty onboarding, you are eating this terrible opportunity cost again and again—not to mention the pure cost of the time, treasure, and energy put into recruiting those flamed-out reps.

This is why the lack of rigor around sales onboarding in so many organizations astounds me. You’ve ideally done an excellent job (and presumably spent a lot of time) screening and interviewing your new hires. Why would you then half-ass their liftoff? Why spend the time and money to get a great race car, but not tune it up, fill it with premium, and top off the tires? Why risk a failure to launch?

Yes, there is a temptation to get new hires facing customers as quickly as possible. See previous comment about opportunity cost of lost and delayed sales. This is a false economy. You will simply be burning good leads and injuring new reps’ confidence and, ultimately, their chance for success. Mitch and Murray paid good money for those Glengarry leads, and they would be wasted on your poorly onboarded staff.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Sales Onboarding 101

So what should your boot camp look like? I prefer a university-style onboarding for new hires, with a singular focus on imparting the knowledge required for high-impact selling conversations. You will be hiring smart; now the goal is to fill those brains with the necessary information, and then run them through enough repetitions that muscle memory takes hold and your hires’ confidence grows.

Remember, like a university, you want to be conducting this training with cohorts and classes. The traditional thinking in sales management is that you’ll lose 30–50% of each class within six months of hiring them. That statistic is frightening; I believe that with proper screening and onboarding, you can have a much higher yield. However, even if you’re amazing at hiring, it’s a similar amount of work to onboard four salespeople as it is to onboard one. They’re all sitting there, listening to the same instructor (you), so why not force multiply? You can even give them team names and use training cohorts as a chance to foster a sense of shared identity. TalentBin classes included Gryffindor and The Three Amigos, underscoring a notion of shared identity. Onboarding a class creates a sense of both competition and camaraderie that pays off: one person may miss something, but his teammate didn’t, and they can help each other out. And when it comes time for sales drills, you have natural sparring partners. Hire in classes and run your onboarding as classes too.

As for your curriculum, obviously as your go-to-market strategy evolves—and you learn as you go—you’ll fine-tune it. When you start out, it could simply be a really big Google Doc that you fork with each new class, highlighting sections in green as you cover them. That may eventually turn into a series of Google Docs, each linked to a Google Spreadsheet checklist to track the execution of each class. We started this way, and after a couple iterations our sales ops lead, Manny Ortega, codified a pretty curriculum in Google Docs. From there, you can go all the way up to onboarding software, like Parklet or Kin, that tracks (in a much fancier way than a spreadsheet) the execution of each step. The important thing is to have a holistic set of topics to cover, and to work your way—exhaustively—through them each time, adding and removing as you go.

These are the general buckets that I have included in each iteration of my onboarding curriculum.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Tools and Process Onboarding

While cultural, market, business driver, and product expertise onboarding lays the foundation for sales rep success, it’s important to not underestimate the importance of training in the nuts and bolts of tools and processes.

The modern sales rep ought to be a software-enabled, highly levered professional. An average day will include office basics like email and calendaring and sales standards like, all the way to more advanced software like email open and click tracking and presentation software like Showpad. If you simply assume your staff understands how to use the tools you provide, and use them well, you run the risk of setting them up to underperform.

Provisioning and Configuration

An often-overlooked part of onboarding is simply provisioning the proper tools for success. You might be chuckling to yourself, wondering how that could possibly be overlooked, but you’d be surprised how often it happens.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Drilling, Repetitions, and Shadowing

One of the things that I have seen sales organizations really drop the ball on when it comes to onboarding and training is the repetition and practice of key actions. The irony of this, of course, is that sales teams are usually full of former athletes and often analogize themselves to sports teams. But somehow they forget that practice is as important—often more important—than the actual games. Presenting information from slides, even with testing, is not sufficient. No way. Drilling and repetitions, paired sparring, and shadowing are all critical to ensure your reps develop muscle memory before they go live.

Group Drilling and Repetitions

The biggest thing your reps are going to need to drill is their demo and presentation. They can (and will) learn on the job, but there’s no reason to burn through actual, valid opportunities as they do so.

During your presentation and demo onboarding, you went through each chapter of the presentation and demo, step by step. Now, have each rep do the same thing. I prefer to do this in the class setting, with each person presenting each chapter of the presentation or demo, and then stopping to get feedback from the instructor (you) and the rest of the team. It’s a slow process—that’s why you only do it once—but it really drills the heck out of the material.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Ongoing Learning and Development

One thing about onboarding is that it can feel like when you’re done with it, and a rep or class of reps is up and running and successful, you’re done with the learning and training. While onboarding is the most intensive period of learning and development, ignore ongoing investment in that at your peril. Not only can reps continue to get better with better coaching, it’s key for professional development, retention, and promotion. Further, it’s unlikely that your product and the market will remain static. As your product changes, and the market in which it operates changes, your reps will need to be updated and then tested on this new information, so they can be just as sharp as when they exited onboarding, however many months or years ago.

Cadence for Coaching and Professional Development

Just like you had a structured calendar for onboarding reps, whether SDRs, AEs, or AMs, you’ll want to do the same for ongoing learning and development. At TalentBin, we had an hour blocked at the end of the day on Friday that was specifically for this. SDRs took the time to do drilling with their management and each other to work on objection handling, messaging review, or demo practice (which wasn’t something that was important for their day-to-day, but was part of professional development, and had the added benefit of making them more confident and competent in their prospect-facing interactions, regardless). AEs would use this time to work with their managers and teammates on different parts of their sales motions, whether it was discovery, presentation, objection handling, negotiation, and so on. But the important part was that the time was on the calendar, and as such, would be prioritized.

Ensuring that this time is well used is particularly important for SDRs. The ability to hire, onboard, and train up SDRs to the point where they can be revenue-generating AEs is an extremely valuable skill for an organization to have. It’s a sort of enterprise value sales alchemy, where through smart recruiting, onboarding, and training, you can turn copper into silver into gold. This also keeps your cost of hire and sales down, in that you’ll have a machine manufacturing fully functional junior reps, rather than having to bid at existing reps at benchmark organizations. And your investment in SDR professional development will pay dividends.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

Conclusion: Where Do You Go From Here?10 minutes, 11 links

At the beginning of this book, I told you that your go-to-market would have two stages: First, you would need to figure out how to sell your offering (the approaches for which were discussed in the first two-thirds of the book). Then, you’d begin to scale that up (which is what the last part of the book was about).

If you are now successfully scaling up, then congratulations! You’ve moved beyond the province of this book. You are now a bona fide sales professional. And if you have a set of sellers reporting to you—successfully closing business—then guess what? You are now a sales leader. Way to go!

Are You Ready to Hire a Sales Leader?

At this point, it’s usually a good idea to hire someone to handle the day-to-day work of managing the sales team so you can move on to other parts of the organization that need your assistance.

However, before you progress to professionalizing your sales organization, it’s key that you’re ready to do so, and that you’ve met the exit criteria for moving to the next stage of your company. Remember how the exit criteria for knowing that it was time to hire dedicated sales staff was that you had successfully sold to a statistically significant number of customers? Well, the exit criteria for knowing that you’re ready to hand the reins off to a dedicated sales leader is that you have a set of sellers who are successfully selling your solution at least as well as you were.

This isn’t to say everything will be humming like a fine-tuned machine, because startups are chaos and that will likely never be the case. However you will want to know that you have successfully gotten one, two, or three sellers to the point of repeatability. If you have, you should definitely congratulate yourself. That’s a very powerful thing. SaaS sales orgs “scale up via scale out,” which is to say that revenue growth comes from more sellers selling more deals—not from a small number of sellers magically selling bigger and bigger deals more quickly. So proving that you can bring new salespeople into your organization, and that they can generate ~$30k, ~$50k, ~$100k, and up in revenue a month, is a momentous occasion in the development of your company. It’s also something that investors will likely be very excited by. You’ve now proven that you can take the money an investor gives you and turn it into salespeople who, just a few months out, will start bringing cash into the organization. That’s a good return on investment!

If you haven’t proven this quite yet, well then you’re probably not ready to move on to professionalized sales management. While it’s tempting to make it someone else’s responsibility to own the management and enablement of your small band of experimental sellers, it’s a rather dangerous exercise. Having proven the ability to sell this repeatedly yourself, you are now the most expert person in the world at selling your solution. You’re the one who cracked the code, so you’re also the best-positioned person to teach others how to sell your solution. Having someone else do it would be engaging in a high-risk game of telephone—with you teaching the new leader, who would then teach the reps—and that’s a situation that your company likely doesn’t have time for. So this is your warning that prematurely adding a sales leader before you’ve systematized your sales process is likely a losing proposition in all but the rarest of cases.

Who Should You Hire?

If you have indeed met the exit criteria for professionalizing your sales leadership, the next question of course is what type of person should you be looking for?

Just as it was when you were converging on a hiring profile for your reps, it’s important to understand the difference between varying candidate characteristics, and what is stage-appropriate for your organization. People throw around the term “VP of Sales” quite a bit (and boy, people LOVE to spill it all over LinkedIn profiles), but please be clear about what you’re actually hiring for.

For the most part, assuming that you’re hiring a sales leader to slide in on top of a handful of AEs and SDRs to stabilize that team—and then likely double it in the short term, and maybe even double it again shortly thereafter—what you’re looking for is a hands-on tactical sales leader. That person is currently probably running a single sales team (for example6 AEs), or perhaps a director who sits on top of a handful of teams (such as an 8-person SMB AE team, a 4-person mid-market AE team, and a 6-person SDR team). And this tactical sales leader is probably working at a similar organization to the ones we used to target our AE candidate profile: a scaled startup that’s in your space, or a tangential space, with a similar sales motion and average selling price, and that’s scaled up to dozens or maybe low hundreds of sellers but isn’t a doddering dinosaur. If you’re a new business intelligence (BI) company, hiring a sales manager or director from Looker, Mode, Domo, etc., is the better bet than hiring one from Tableau, SAP, or Oracle. If you’re a new recruiting solution, it’s the better bet to hire from Greenhouse, Lever, Workable, etc. than from, say, Oracle, Taleo, SAP, or SuccessFactors. Whatever your space, you should be able to figure out the set of companies to consider.

I won’t get much more into this, as this is something that I haven’t done enough times to speak authoritatively on (whereas the stuff earlier in the book I’ve done the hell out of). Suffice it to say, this is an extremely critical hire, and the key is to reference, and back-channel reference, the heck out of any candidates who get down to the finish line. Once they’re on board, your job is to help this new sales leader ingest your well-documented sales process and quickly get up to speed successfully managing the team. Congratulations! You are no longer the Sales Manager. You are now the manager of the Sales Manager.

In Conclusion

That was quite a journey, eh? For those of you who are reading the end of this book because you’ve advanced your organization through all the steps described in previous chapters: Congratulations! You’re at a stage that very few get to, and should be very proud of your work. And for those of you who are reading this conclusion while still partway through the journey: Keep at it. While acquiring knowledge is important, having the perseverance and grit to put it to work is paramount. This book is set up to be a constant companion for you as you go from step to step. It’s less a one-time read, and more a handy desk reference that’s here for you as you hit challenges along the way. And you will.

Either way, acquiring the skills of selling is an important arrow in your professional quiver. Far too many startups have floundered for want of being good at sales, and the same is true of individual startup executives and operators. Deciding to get good at sales is the first step, the next step is learning about it (this book!), and the step after that is honing your craft through ongoing effort. Having internalized what’s presented in this book, you’re well on your way.

Further Reading

Founding Sales was written because there wasn’t yet a tactical textbook for early-stage sales written specifically for founders and other non-sellers. But there’s a whole constellation of high-quality sales books for sales professionals. I’ve listed my favorites below. I highly recommend you check them out to help further your sales education.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.