Sales Pitches For Startup Founders

3 hours, 6 links


Updated August 22, 2022
Founding Sales

You’re reading an excerpt of Founding Sales: The Early-Stage Go-To-Market Handbook, a book by Pete Kazanjy. The most in-depth, tactical handbook ever written for early-stage B2B sales, it distills early sales first principles and teaches the skills required, from being a founder selling to being an early salesperson and a sales leader. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, commentary and future updates, and a high-quality PDF download.

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.

There is no way you will be able to maximize each of these terms in every deal. But if you focus on organizations with high levels of business pain, and do a good job ensuring comprehension, you may be able to surmount skepticism—as in, “Wow, based on what I see here, we can potentially save fifty thousand dollars a month by implementing this solution. Even if we only see half of that savings, that’s still awesome.”

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Keep this mental model front of mind, and it will help you push each of those levers higher in your pitching process.

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 doesn’t mean that you shouldn’t present to qualified accounts that you’re unable to reach in person. If an amazing opportunity shows up in your inbound demo request form, by all means, engage that opportunity digitally (no, don’t fly there, necessarily) as you would any qualified opportunity. It simply means that from a prioritization standpoint, you should be targeting accounts close to home, to enjoy the benefits of on-site presentation.

On the topic of travel, while you’ll generally want to stay local or use digital presentation tools, there may be situations, likely after you’ve booked your first few customers, where it makes sense to fly to a prospect’s location and execute an on-site sales presentation. This is usually best done in batches, so if you’re traveling somewhere, line up meetings with other prime targets in the city in question. Typically, these meetings become an initial opportunity to put a face to a name, and incremental presentations and meetings happen digitally, building off the comprehension and trust built in that first face-to-face exercise.

Later on, when you get to scale, it may be totally appropriate for all of your sales to be done inside, via telepresence. Once you’ve nailed your pitch and materials—and you’re sure your team can do an amazing job of communicating value, backed by ROI studies and existing customers that make those claims believable—you can take advantage of the efficiency of digitally hosting five, six, or more meetings a day. Or, it may turn out that your solution is sufficiently complex, with a sufficiently high price tag, that most sales will be done on-site. Or you may have a blend, where smaller customers are addressed via telepresence, in light of their lower deal sizes, while larger customers, with larger potential sales, are handled on-site. But to start, aim for pitching on-site.

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

The best way to make sure you don’t skip pre-call planning is to put it on the calendar. When you send a meeting invite to a prospect for the presentation, put an additional 15-minute block on your own calendar just ahead of the meeting. This way you won’t accidentally put another meeting back to back with your presentation, jamming future-you up, and you’ll have a calendar reminder to make sure you do your pre-call planning.

importantIf you’re doing outside sales, you’ll typically need to block that time on your calendar for travel time, as well. You want to book the travel time to precede your pre-call planning. Whatever the travel time will be, book that on your calendar so that you arrive 30 minutes ahead of your designated appointment. It will most certainly take 5–10 minutes for you to check in with reception, reception to contact your prospect, and the prospect to pick you up at reception. Target checking in with reception 15 minutes before your appointment, and arrive at your destination 15 minutes before that to adequately prepare for your meeting so everything is fresh in your head.

The goal of pre-call planning is to ensure that you have readily accessible, ideally in your brain, all the relevant information that you sniffed out ahead of time, and a list of known unknowns for you to figure out during discovery, the first part of your presentation. Much of this information you’ll remember from your prospecting activities, like outward signifiers of demand, relevant points of contact and influencers, and so forth. The goal is to stack the information advantage in your favor, so you know which questions to ask and which to skip. And if the prospect tries to introduce information that isn’t 100% true, you’ll know. It’s your job to control the call, and more information makes that more achievable.

Take another look at Early Prospecting for greater detail on how to gather this information. To refresh your memory, those are the different types of details you’ll want to make sure you have front and center before you hop onto your demo.

Pain Points and the Size of the Prize

These are the outwardly identifiable characteristics that indicated that the prospect had a need for your solution. For TalentBin, this could be open technical hires. For Immediately, it could be the number of field sales reps needing a sales-centric mobile email and CRM client. And for Textio, it could be the number of open job postings that need to be optimized. Knowing these pain signifiers will help you with your proactive ROI understanding. If you’re HIRABL, the staffing agency revenue-acceleration company, and you know that your solutions on average add ~$10K per recruiter per year in added revenue, then knowing how many recruiters there are in the agency you’re going to talk to (30! 50! more!) will help you proactively position that benefit in your presentation.

You’ll also want to know how much you can potentially sell, known as “size of prize.” You won’t be trying to sell just one seat of your solution, or some other minimum amount. Rather, you need to know how much of your solution the organization could potentially consume. This might be correlated to the potential number of users (like number of sales reps or recruiters or support reps) or some other characteristic specific to your prospect.

This doesn’t mean you’re going to eat the whole apple in one bite. In fact, selling a young solution across an entire organization—like selling 100 seats of TalentBin to a recruiting organization when we were a ten-person company—can be a dicey proposition. However, knowing how much could be sold, so you can properly guide the conversation, is a benefit.

example“Well, I know you have ten recruiters, and from what I saw, Jeff, Suzy, and Julie are the ones that focus on technical hiring, so perhaps three seats would be appropriate.”

Having this information available can help you determine what would be a good outcome from a first-sale standpoint.

There’s 14 recruiters at New Relic. Maybe we can sell them five seats to start?

Figure: Using LinkedIn to Deduce Size of Prize

Source: LinkedIn

Complementary Products, Competitive Products, and Capacity to Pay

You’ll also want to go into your pitch knowing the sort of products the organization has in the mix. Take another look at Early Prospecting for how to use tools like Datanyze and BuiltWith to determine the technologies running on an organization’s website and for where else to look to determine whether they’re paying for premium services. By understanding this ahead of time, you’ll get a sense of how the organization currently solves the problem your solution addresses and if they pay money to do it. And if you are able to sniff out a directly competitive product, not only will you know that the organization cares enough about the problem to spend money on it, you’ll be prepared to explain why your solution is better, faster, and stronger than the one that they’re currently using.

Lastly, understanding an organization’s funding situation can help with the question of their capacity to pay. If an organization has raised ~$100M in funding in the last few months, that money was raised to execute—to hire engineers, buy advertising, or what have you. Same with public companies—if they’re growing their revenue and have a strong balance sheet, they will be more open to solutions that make the business better, compared to an organization that is not only loss-making, but perhaps in decline (as measured by revenue growth).

Potential Users

Use LinkedIn to make sure you know who the potential users of your solution would be. You’ll already have done this to determine size of prize, but it will also help if you are speaking with a decision-maker different from the end user. Knowing your potential users can help if you get into discussions about who would be the most relevant person to use or even evaluate the solution. TalentBin needed to be careful that an inattentive decision-maker didn’t ask a nontechnical recruiter to take a demo to evaluate our solution.

Stakeholders and Influencers

Ideally your demo is with the relevant decision-maker, but that doesn’t mean there aren’t other stakeholders in the problem your solution solves—the decision-maker’s boss, for example, or her internal customers. Or if somehow you entered through one of those internal customers, you’ll want to know whom you ultimately need to talk to after that first meeting. Same is true if you are entering through a level below the decision-maker.

Not only will this allow you to demonstrate organizational mastery and diligence, but it provides a “credible threat” (not stated, but mildly implied) that you have awareness of other people in the organization and likely would not have any issue getting access to them. So, if you’re Immediately, and you’re talking to a Sales Operations decision-maker, it’s helpful to know who the VP of Sales is (say, Christina), as she’s ultimately on the hook for the organization’s revenue achievement and personally stands to make more money with increased revenues—as in, “And you can imagine how happy Christina will be knowing that the field reps you work with will be closing more business in less time because they’re not stuck in coffee shops updating Salesforce!”

Of course, this goes all the way up to the CEO, who has an interest in the downstream impacts of your solution. If you’re talking about a solution to assist with sales hiring, you know that private and public organizations are valued at a multiple of their revenues. So faster sales hiring, with better hires, and faster onboarding can get an organization to higher revenue levels faster—which could allow a private organization to raise their next round of funding at a higher valuation. Or if the organization is public with, say, a price-to-earnings ratio of 15, and your ROI analysis indicates that your solution will save them ~$1M a year, you’re looking at adding ~$15M of market capitalization to the organization through the implementation of your solution. Now, depending on the size of the company, this strategy may be more or less relevant. But at a medium or smaller organization, say 500 people or fewer, this is certainly something a CEO would be interested in. Knowing who that is, so you can demonstrate to your point of contact why they would care and how you could potentially deliver that message, will make your case stronger.

Same if you are entering the account a level below your intended decision-maker target. Characterizing to that staffer that you’re well aware of who the relevant decision-maker is changes his calculus when it comes to next steps. You can indicate that the staffer has an opportunity to be the bringer of innovation and excellence to his boss—or, if he chooses not to, that you’ll likely just engage directly with the decision-maker, potentially making the staffer look like someone who missed an opportunity.

example“You can imagine how excited Kieran will be knowing that she can save each of her recruiters ten hours a week. You’ll be a hero!”

In this case, your point of contact can help you with Kieran, or look to be behind the eight ball. It’s clear to me which one sounds better!

Customization Information

As we discussed in Early-Stage Sales Materials Basics, the ability to personalize your presentation and demo for the prospect is paramount. So if there is additional information that you need to gather in order to customize your presentation, do so.

exampleFor TalentBin, this could mean looking at the prospect’s careers site to see which technical openings you’d want to focus your demo on. So rather than asking, “What roles are you having a hard time filling?” the question is instead, “I saw you’re hiring for an iOS developer. That would be a good one for me to use to show you how TalentBin works. Does that work?” Better control.

Or if you’re LifeGuides and want to show how you can help with a problematic Glassdoor presence, you might want to take a screenshot of that Glassdoor page and some choice negative reviews. Or if you’re Affirm, use Google Chrome’s Developer Tools to drop a Pay with Affirm call to action into your e-commerce prospect’s product detail page.

Figure: Pay with Affirm Call to Action on Product Detail Page

Source: Affirm

Look how nice that financing call to action looks there. I bet it raises conversion rates!

Conversational Guides and Icebreakers

importantLastly, while business pain and stakeholder research is paramount from a nuts-and-bolts standpoint, you’ll want to take time to gather conversational guides, icebreakers, and rapport-building information for the first couple minutes of your call. If you think blathering about the weather is going to get this done, you’re really missing out. That’s the limp fallback of someone who doesn’t do his research ahead of time. This is especially important for phone sales. In face-to-face meetings, it’s somehow easier to establish rapport. You have to be intentional about it on the phone, though, so selecting a piece of information you’re going to key off of is all the more valuable.

LinkedIn is fantastic for a couple of reasons. First, you can see if you share any contacts with the prospect that you want to surface proactively. If it’s an existing customer of yours, excellent! You should certainly bring that up. “I saw on LinkedIn that you know Jeff from Dropbox. He’s a customer of ours. Great guy!” But this could be former colleagues or classmates of yours too—most shared contacts are a good opportunity to build rapport—unless the shared contact has a poor opinion of you. In that case, skip this! (Or be prepared for your words to get back to that contact!)

You can also see where else your prospect has worked. Perhaps you overlapped at a prior organization? And, of course, you can check out her educational background, which can be helpful if it’s college football season. Even if she’s not into that sort of thing, if you’re dealing with an Ohio State, Alabama, University of Texas, or USC alum, she’ll probably be at least secondarily aware, and it makes you look thoughtful. You can also check out geography to see where she’s based (not all points of contact are based in the same location as the organization’s headquarters). This can be helpful for local sports teams (“Wow, that Patriots-Steelers game was something, huh?”) or, at worst, local weather (“Wow, you have been hammered by that blizzard, huh?”).

Further, as LinkedIn has pushed users to surface personal interests on their profiles, you can often see if the prospect is into yoga, rock climbing, whatever. Sometimes she’ll have a concurrent role for a side project, like the small business she also owns or a non-profit organization on whose board she sits. All are potentially excellent topics for icebreaking. Beyond LinkedIn, many prospects will have active Twitter accounts, and they’re often a valuable source of recent interests. (Following your prospects on Twitter is a great strategy, in general, and we’ll talk about it more later.)

On the topic of rapport building, stay away from politics, religion, and so on. Even if the prospect is tweeting endlessly about this political candidate or that one, it’s just too dicey. You can find something else to establish rapport with if you try.

Known Unknowns

While you’ll be able to nail down a lot of great information about your prospect ahead of time with 15 minutes of work, you likely won’t be able to find everything you need. This is perfectly fine, as the first part of your sales presentation will be focused on discovery and surfacing this information. However, as you do your pre-call planning and research, you’ll want to note exactly what you weren’t able to find ahead of time, so you can make sure to ask the right questions during discovery.

As you do many of these presentations, your approach will evolve and you’ll eventually form a pre-call planning checklist, along with a discovery question checklist. When you do, capture this information in your CRM. You’ll be having dozens of these presentations, and when you go to follow up with the prospect, much of the pre-call research is reusable. Capturing it in its distilled form saves you time. Better yet, you’ll be creating a piece of tooling for the sales reps you eventually hire to scale your activities.

Stated Pitch Goal

Once you have all of this information, you should be able to form a plan and establish your goal for the call. If you’re talking to the right decision-maker, and it’s clear that the account has tons of need for your solution and spends lots of money on analogous products, maybe that goal is to win consideration of a purchase. If you’re talking to someone who is likely not the end practitioner, but is an internal customer and potential sponsor, perhaps the goal is to convince him of the benefit of your solution and partner with him to drive to a second call with the ultimate decision-maker. If you’re coming in below the decision-maker level, maybe it’s to drive to a secondary call with the decision-maker and the rest of the staffer’s team. Whatever the goal, make sure you know what it is. Don’t worry, your call will certainly diverge from plan! But identifying your polestar will help you drive toward it, even as things go sideways.

Pre-Call Attitude

Beyond gathering information and establishing your goal for the call, there’s also the matter of just getting in the zone. A large part of selling is projecting confidence in your solution and your recommendations to the prospect. So prepare yourself accordingly. Stand, walk around, do jumping jacks (probably not in the prospect’s lobby, if you’re on-site!), and get yourself in a positive, and active, frame of mind. I have a standing desk, but even if you don’t, take sales calls standing. You will project more authority and be quicker on your feet.

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.

It sounds obvious, but you’ll want to make sure you have a laptop, loaded with your sales deck and demo materials, with which to present, and all the relevant connectors needed to connect your laptop to a projector. (This is another reason why showing up early is great. Projectors seem to be designed to derail the beginning of pitches!) I like to keep them in a little mesh bag in my backpack so there’s no frantic digging required. Or, if it’s just you and a prospect, present off your laptop screen, with the two of you looking at it side by side. Less risk, more intimate.

Recently, it’s become fashionable to connect to large flat-panel displays via Apple’s AirPlay. As far as I know, unless you download extra software to your Windows machine, you need an Apple laptop to AirPlay to one of these screens. So if you have an Apple machine, figure out AirPlay. And if you don’t, think about adding that third-party software. Beyond knowing how to use existing projectors, bringing your own mini projector can be excellent as well. It isn’t very costly, and you’ll be 100% confident that you can project at a moment’s notice.

Bringing your own source of internet access can shortcut issues associated with office Wi-Fi access—you’d be amazed how hard it can be to track those passwords down, eating 15 minutes of your demo time. Just flip on your personal hotspot or pair your phone, and you’re on your way. All of this makes you look super prepared and awesome, like the kind of person the prospect would like to be in business with. Lastly, make sure you have a lab notebook to take notes in. (Perhaps you already have your pre-call planning results in it for reference!) You’ll be using your machine to present, so you won’t be able to take notes with it. And you’ll want to make sure you’re diligently recording everything you cover in the discovery part of your conversation.

If you’re presenting digitally, tooling is more straightforward. First, you need software that allows you to share your screen so you can show your slides and demo. One great, cheap option is Showpad is a little more involved and expensive, but integrates well with Salesforce. DocSend is a lightweight screen-share and document-sharing system that is a happy medium. All of these allow prospects to immediately see your screen without having to download any software—something that was always a huge pain with WebEx and GoToMeeting. If you use those last two, prospects invariably won’t have the most recent version, or won’t have the ability to administer and install software on their machine, and you’ll spend the first ten minutes of your call trying to get the software installed. It’s just a total disaster. I haven’t personally used Google Hangouts or Skype for face-to-face digital sales communication, which is something I find potentially interesting from a rapport-building standpoint. Whatever software you choose, you want to optimize for ease of use, so the prospect can just hit the hyperlink that was included in the meeting invite and reminder email you sent them and, poof, be seeing your screen and hearing your voice.

You’ll also want some sort of earbuds or headset for your phone. You’ll be using your hands to mouse, type, or take notes, so occupying one with a handset is silly. And speakerphone makes for a poor user experience for the prospect, so don’t do that. You’re going to be on the phone a lot—I like to buy a half dozen Apple earbuds so I know I’ll have one in a pinch, even as I lose them. (You will.) As with on-site pitches, you’ll want your lab notebook with your pre-call planning notes, ready to record the information (typing it while on the phone never seems to work for me).

We covered the construction of your sales materials in a prior chapter, but the primary materials you’ll need for your pitch are your sales deck and your demo script (which you already memorized, in broad strokes!). Make sure you have an offline proof version of your demo—pre-populate your browser (assuming that’s where the demo takes place) with the key screens that would allow you to give a good demo, even if something happened to your internet connectivity.

Pitch Format

importantI find that the best pitches follow a consistent format. Specifically, they start with quick pleasantries, move into discovery, feature a slide-based presentation followed by a live demo, touch on success proof points, and conclude with pricing and commercial discussion. This format allows you to build the best case for your solution. You start with pleasantries to build rapport and set the tone for the prospect to share information with you and be receptive to your arguments. Discovery gives you the information you need to make an ROI argument to the prospect. (Or, if it turns out that she doesn’t have the pain point that your organization solves, you can end the call and save both of you time!) Next, you use slides and visuals to make sure the prospect has the proper mental model for understanding the sales narrative you’re delivering, and to prepare her to understand the features you demo—all of which builds up to a compelling argument for spending money on the solution.

One of the biggest things you’ll converge on as you start selling is whether you’ll be able to do discovery and presentation together or have to separate them. As you increase your volume of demos, one way to be more efficient with your time is to split your full presentation and demo from initial discovery by having a dedicated discovery call, often known as a “disco call” (what a delightful abbreviation!). The benefit of this approach is that it is often easier to get someone to agree to an initial 15-minute phone call than a 30-, 45-, or even 60-minute presentation and demo. In this mode, your discovery call helps you get better information about the prospect, but also lets you sell the full demo, as appropriate. Further, if your discovery questions reveal that the prospect is unqualified, you can conclude the call quickly. There isn’t an onus to make it worth their time because you had them block 30 or 60 minutes.

The necessity of splitting your pitch often depends on how long your demo needs to be to characterize the solution’s important functionality. If your solution is straight to the point, and can be demo’d in ten minutes, then the coordination costs of a ten-minute discovery call at one point in time and another ten-minute demo aren’t worth it. You’ll be adding fragility to your appointment setting, as there’s about a 10–20% chance that each meeting will be missed and thus rescheduled. So do them together. Moreover, as discussed in Early Prospecting, if the signifiers of a qualified customer are readily discoverable ahead of time via online research, you dramatically reduce the amount of time needed for discovery, as you can be more sure that the prospect is qualified.

As you start, even if your solution is complex, it’s probably best not to separate your pitch into two meetings. At least for your first few dozen demos, having more time to have a richer conversation is better, plus you’re ideally on-site anyway.

Who Are You Talking To?

When you’re approaching your pitch, you need to be mindful of who you’re talking to and, as such, what you will be emphasizing. We talked about this a bit regarding the stated goal of pre-call planning—different types of people are going to be more receptive to different messages.

A friend of mine, Skip Miller, author of a number of sales books, crystallized this in three distinct personas set out for his sales reps. He even gave them national names to help differentiate them and to remind reps to speak the right language when engaging. Each persona—individual users, first-line managers, and second-line/CXO managers—will speak quite differently. Your job is to learn, and develop messages in, all three languages.

First up are end users. They are going to care about making their jobs easier, pleasing their internal customers, making themselves look good to their managers, and setting themselves up for career progress. These contacts will be less concerned about ROI arguments, because it’s not really their money. Some may care, but they’ll be more focused on how your solution impacts them. Maybe your product helps them get a promotion or a better job somewhere else, for example. So when it comes to an email-automation solution for sales, sales development reps are going to care about how it removes annoying repetitive email activity for them, helps them set more demos (because that makes them more money!), and maybe gives them a shiny new toy that they can brag about to their friends. They’ll probably care less about how it accelerates top-line revenue for the organization.

Next you have first-line managers. They’re going to be more interested in the ROI arguments you bring to the table. They’ll be mindful of the impact your solution has on their commitments to internal customers. They’ll probably also be responsible for a budget, including payroll for their team, so they’ll be more attuned to arguments about making staff more efficient, producing more value for their internal customers, and facilitating staff adoption. While they’re likely former individual contributors, and thus will probably enjoy understanding how various features work, they’re going to care more about the business impact of your solution.

exampleTalentBin’s email automation functionality helps recruiters send drip-marketing emails to candidates, raising response rates and the number of phone screens a given recruiter can set in a given time interval. So the manager will care most about the fact that this means he can reduce his spending on candidate flow, he won’t have to hire another sourcer at ~$65K a year just yet, his existing staff will be happy to lose some of their job’s drudgery, and the VP of Engineering will be happy with the increased candidate volume.

Lastly, there’s the second-level managers or CXOs. They’re going to be responsive to arguments that drive top-line business value for the entire organization. If your solution speeds onboarding of new salespeople, so they can become fully productive quickly, the CEO will care because more salespeople adding more revenue literally raises the value of the company. And that’s the CEO’s job. The CFO, who’s concerned about cash flow, will care that this reduces the salary expense new sales hires consume before they become productive, thereby helping the cash position of the company. These are not things a line recruiter or sales rep or data scientist will likely care about; they’re not even things a first-line manager will frequently consider. But they’re definitely things that a CXO/VP thinks about.

This isn’t to say that a single argument will be sufficient. You will very likely have multiple meetings with each of these different types of folks, so make sure you’re speaking the right language each time. Even more fun is when you have people who speak different value languages in the same meeting. That’s some serious advanced action right there. But as long as you understand what each person cares about, and have that in mind when explaining features and benefits, you’ll do well.

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.


cautionDiscovery is where you take the time to ask questions of prospects to both qualify them and set yourself up for a more productive pitch. It’s also the thing that first-time salespeople bungle the worst. Eager to hop into their pitch, instead of digging into the prospect’s business realities, they just start firing from the hip—and miss a huge opportunity to tailor the conversation to the prospect’s pains. Or, worse, they waste time and energy presenting to someone who isn’t even qualified. Discovery is an extremely important part of the pitching process, and you should allocate the first five or ten minutes of your presentation to it (depending on the total time your presentation and demo take).

It’s best to set this up at the beginning of your pitch and characterize it as a benefit to the prospect. Something like, “I like to start with some questions so I have a better idea of how your team goes about its day-to-day, and so I can do a better job of focusing on things you’ll get more value out of.”

There are a variety of qualification frameworks that sales folks will often refer to, each with its own helpful acronym. There’s the classic BANT, which stands for “budget, authority, need, timeline”—as in, the prospect isn’t qualified unless he has those four things: budget to pay for a solution, authority to command that budget, need for the solution, and a timeline as to when he wants to solve this pain. ANUM is another one I like, standing for “authority, need, urgency, money.” And I recently came across ChAMP, or “challenges, authority, money, prioritization.”

You’re probably seeing a pattern here. During the discovery process, you want to make sure that the prospect has the problem you’re solving, but that’s not necessarily sufficient. You also want to know that he does indeed have a process by which he considers and purchases technology to solve problems. You want to know who the person, or group of people, is who makes these purchasing decisions. And you want to know the level of urgency with which they want to solve this problem. Discovery is how you figure this out (to start).

The problem with strict letter of the law qualification when you’re selling an early-stage product is that, oftentimes, you’re having a conversation with someone who had no idea that this solution existed. If he didn’t even know that it existed, it’s probably pretty hard to have a set budget for it, right? And probably pretty hard to have a timeline. This is why some of the other qualification frameworks I mentioned focus on how big the problem is and how much urgency there is around solving it (even though our early prospects didn’t know that internet talent search engines like TalentBin existed, they certainly knew that technical hiring was a big challenge for them, and one that they were eager to solve).

In Early Prospecting we discussed how, thanks to the magic of the internet, you can often uncover discovery information ahead of interacting with prospects, and even use that information to engage them. Depending on how much of this information you are able to gather for a particular prospect, you could be pretty well informed ahead of your pitch. But you’ll still want to validate that information to make sure that it’s accurate and also, importantly, to ensure that the prospect knows that you know it. You’re diligent and have done your homework, so set the tone for the conversation: you have good informational backing for the argument that your solution is likely a fit.

Moreover, because you have this information, you’ll be able to position your discovery questions in a leading way, focusing on the part of the prospect’s business pain that is aligned with your solution.

exampleIf you’re from LifeGuides, makers of recruiting brand software, and you’re talking to someone whose company has a 2.5-star Glassdoor rating, rather than asking, “Are you familiar with Glassdoor?” the question would be, “You’re probably aware that your company has a 2.5-star rating on Glassdoor. Do you find it frustrating that negative employee content is crowding out the employer story you’d like to tell?” Or you might try, “When I Googled ‘working at ____,’ that Glassdoor page was the top result. Do you find it frustrating that they own that top result and hijack candidates who are looking for you?”

exampleOr if you’re Immediately, makers of an awesome sales-centric mobile email and CRM client, and you’ve determined that the prospect likely has primarily outside-based sales reps (based on the geographic distribution of their sales reps’ LinkedIn profiles), instead of asking, “Do you have outside sales reps?” you might instead say, “Based on what I saw on LinkedIn, you have sales reps in the Bay Area, Chicago, New York, and Dallas. That’s quite the outside team! Do you find that, like with most outside sales teams, they have a tendency to do a poor job of logging meetings and activities in the CRM because they’re not at a desk?”

Lastly, as with your other sales materials, your discovery questions will be a work in progress. But even while in progress, they should be documented. Make sure they are saved as a living list in a Google Doc that you can refer to (and, later, hand to reps that you hire).

The goal of all of this is to have the information you need for a productive pitch and down-funnel process. Or, if the account lacks important qualification criteria (like no pain, little urgency, or no ability to pay), discovery enables you to helpfully truncate the conversation, respecting the time of the prospect and, most importantly, keeping you from burning your time on something that will never turn into a sale.

Pain and Urgency

importantThe critical thing to converge on is whether the prospect has the actual business pain that your solution is seeking to solve. If she doesn’t, this is going to be a useless conversation. Having done that, you can seek to discover the magnitude of that pain and if she has tried to solve it previously, along with how successful those attempts have been. All of this will give you a nuanced understanding of the prospect’s business situation as relates to your solution.

exampleTake TalentBin’s discovery process. We would start by asking what sort of technical roles an organization was hiring for, and how many. So this might have been something like, “I saw a few technical roles on your careers site, but over the next twelve months, what software engineering headcount do you think you’ll be hiring for? And what proportion of your hires do you think this will be?” Once we had an answer, we’d get into pain associated with the organization’s current means of solving this problem, as in, “When you think about how you currently do technical hiring, would you consider it easy?” (A leading question. No one is going to call his or her job easy!) Once the prospect had responded to that, we would then cascade further: “Do you find job postings insufficient to get the sort of software engineer applicant flow that you want? Have you had to do passive-candidate recruiting and outreach, for instance via LinkedIn?” If she answered no to this, then we knew the organization may not even have the pain we solved, and we’d have an uphill battle. If she answered yes, we’d cascade further, into problems that we knew many prospects were likely to have. For instance, “Interesting. Are you like most of the folks I talk to, struggling to get the level of responsiveness to LinkedIn outreach that you’d like? Is it a lot of time for not a lot of response? Right, well, many folks don’t check their LinkedIn messages. Do you try to fix this by searching out personal email addresses so you can have a direct messaging path with better responsiveness? Yeah, I don’t blame you. Who has the time?” or, “Very nice. Yeah, it’s kind of a lot of time, huh? But it can be worth it, because the response rates are so much higher.” The idea is to keep cascading down the prospect’s pain—its size and urgency, how it’s currently solved, and the downsides of those approaches (sounds like your sales narrative, right?!)—all while recording this information in your handy dandy lab notebook.

You’ll also want to touch on the downstream business implications of not solving this pain point.

exampleIf you’re Textio, the service for job-posting text optimization that is particularly helpful for raising the number of female and people-of-color applicants, it might be something like, “Why is diversity hiring so important to you? What will happen if you aren’t able to hit your diversity hiring goals?” To which the answer might be, “Well, the CEO has publicly committed to these goals, so I’ll kinda be in a lot of trouble nervous chuckle]!”

Lastly, you’ll want to try to tie your discovery questions to the features you’ve built to solve those pain points.

exampleFor LifeGuides, not only would that be asking questions about Google search results and Glassdoor average ratings, but it might also be things like “It seems you’re concerned about getting your employer branding story told. Have you thought about interviewing or recording video of your employees talking about their jobs? Yeah, it is a lot of work. It’s no wonder you haven’t gotten around to it.” LifeGuides makes it extremely easy for employees to use their laptop webcams to record testimonials about what it’s like working at a company, so they remove that time cost. Or, “I saw that you have a careers Twitter handle and a premium LinkedIn company page—that’s great, it shows that you’re ahead of the pack! How do you find content to distribute on there? Yeah, it is a struggle to constantly find new things to publish that present the recruiting brand voice. I get it.” LifeGuides makes recruiting brand content production easy, and high volume, so you’re teasing out the pain associated with needing large amounts of recruiting brand content to share.

Think about doing the same with the features your team has built, by targeting discovery questions to validate the existence of the business pain those features intend to solve.

Team, Authority, and Commercials

Assuming that your discovery questions about business pain and urgency point to a worthwhile opportunity, next you need to understand the ins and outs of how this particular organization goes about purchasing things to solve business pain. Start with the people who would be using your solution. Do they exist in the organization? If not, it’s going to be hard for your solution to get used! How many are there? Do people on the team have particular specialties?

Then it comes down to authority and commercials. Who is the person or group of people that makes decisions about buying solutions for the organization or this particular slice of it? Have they done it before? Do they know what this process is? Is there a formal evaluation period for this sort of thing (“We buy all our tools in November and December for the year ahead.”)? Or is there discretionary budget that can be utilized outside of typical budget cycles? This is why it’s particularly good to cover other common solutions in the pain and urgency section of your pitch—if a prospect has spent money on solving this problem before, they clearly have a process for doing so.

importantThough it may feel weird to directly ask about this sort of thing, it’s very important to do. It’s great if an organization has business pain, but if they are unable to spend money on anything, let alone your solution, you’re wasting your time. And if your point of contact can’t make purchasing decisions, that’s fine—but you need to sort out who can, so you can make the case to the person with decision-making authority.

While the main goal of discovery is to qualify the prospect, you’ll find yourself uncovering other valuable information. You’ll start to get a sense of the general maturity level of the organization and their ability to solve the problems your solution addresses. You’ll understand how forthcoming your point of contact is and how readily he shares information. You’ll even start settling into a better back-and-forth communication pattern, which is what you want the rest of your presentation, and the rest of your pipeline journey, to look like. And beyond all that, you’ll benefit from demonstrating your commitment to making the conversation about the prospect’s needs and business realities.

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.

You can see what I mean in the TalentBin demo script we’ve already looked at. In brief, the key is that repeating the major points you want your prospects to take away—and constantly connecting various parts of your pitch, including pain point slides, solution slides, proof-of-value slides, and demonstrated features, back to those key points—will ensure that they stick.

Validation of Attention and Understanding

importantIf the goal of the presentation is the communication of information that drives a prospect toward a commercial transaction, it’s probably pretty important to know that the information is being consumed! How do you do this? Validate that your prospects are paying attention, and validate that they’re understanding.

How do you validate attention? If you’re face-to-face, look! Is your prospect looking at you or what you’re projecting? Or is she on her phone or her laptop? If the latter, you have to get her attention before you proceed, because otherwise you’ll just be talking past her. On the phone this can be more of a challenge, in that you can’t see what the prospect is doing. Tools like ClearSlide can tell you if the browser tab showing your presentation on prospects’ computers is front-most, but even that’s kind of weak. Instead, you have to ask things like, “Can you see this right here on this slide?” to validate that they’re following along.

Across the board, the best way to confirm that someone is paying attention, to regain attention if you’ve lost it, and to validate understanding is to ask questions. So after you make a point, ask something to make sure that the prospect has comprehended it—that will confirm whether she was paying attention and whether she actually got it. The most basic question is, “Does that make sense?” But the problem there is that prospects don’t want to look dumb, so this often invites a standard “uh-huh” response, regardless of whether they are following along.

This is a bad outcome. You desperately want prospects to tell you if they’re not following along so you can fix it quickly! One approach I use is proactively giving permission to say, “I’m not understanding.”

exampleWhen presenting a slide for TalentBin on the growth of new specialty social networks like GitHub, Stack Overflow, Meetup, Behance, and so forth, I would ask, “Have you heard of some of these before?” to validate understanding. But to prevent prospects from saying yes even if they hadn’t, I would say something like, “It’s okay if you haven’t. Many are fairly new, and I didn’t even know about them before we started TalentBin!” or, “It’s okay if you haven’t. These are pretty obscure specialty sites!” By doing this, you give prospects permission to not know and ensure that they aren’t too embarrassed to communicate their lack of understanding to you.

Another approach is to ask a specific question that requires a specific answer, ideally correlated to the pain point, solution, proof point, or feature being discussed.

exampleIf you were Immediately, and discussing the challenges of field sales reps documenting customer-facing interactions, rather than saying, “Does that make sense?” the better approach would be something like, “Do you find your field reps have this same issue?” Or if you were pitching TalentBin, and demonstrating a feature that showcases the benefits of automated email follow-up and drip marketing, you might ask, “Can you see how this sort of automation would reduce the amount of manual follow-up required to increase candidate response rates?” In this case, you can see that I am killing two birds with one stone: I am both trying to validate understanding of the feature and, by asking a leading question, seeking to elicit the prospect’s agreement with one of my core points about TalentBin (another example of repetition).

Lastly, you can do open-ended questions as well, like, “Do you have any questions for me so far?” allowing the prospect to bring up anything that has been bothering her. By giving permission to do so, without judgment, you allow her to surface potential objections or concerns. Sometimes it takes real work to validate understanding, especially if you’re selling over the phone and not face-to-face. But you absolutely must do it. Otherwise you might as well be talking into an empty room.

Rolling Discovery

One thing you may have noticed in the preceding section is that the questions used to validate attention and comprehension often sound a bit like discovery questions—or at least shortened versions of them. This is not a coincidence. In fact, as you proceed along your presentation, you can implement a form of rolling discovery, where you learn more and more about the prospect’s pain points, existing solutions, and so on, right at the moment that you’re talking about a particular topic. If you’re presenting pain point slides, you might ask if the prospect encounters those challenges.

exampleAt TalentBin, when we were talking about poor LinkedIn InMail response rates, we’d ask, “Do you find your response rates aren’t as good as you’d like?” and, “Have you ever tried to find personal email addresses to help fix that?” Of course, if you already asked and got the answers to these questions in discovery, don’t re-ask the question—take the opportunity to cite the prospect’s response (repetition!). “As you said earlier, you folks have the common issue of poor LinkedIn InMail response rates.”

This sort of rolling discovery lets you get into discovery questions that are correlated to the specific pain point, solution statement, or feature that you’re covering right there, which helps with comprehension. It also helps you out if you forgot a question in your discovery section. And if you have a lot of discovery questions you’d like to ask, this lets you distribute them, rather than stacking up a ten-minute interrogation at the beginning of the call!

Relatedly, you want to make sure that you’re making use of the information that you surfaced through your discovery questions. This will allow you to make your pitch more impactful by correlating the things you are talking about to business realities at the prospect’s organization.

exampleSay we’re pitching TalentBin, and the prospect tells us she’d love to send recruiting outreach to personal email addresses but doesn’t have the time to find those addresses. When we get to the part of the demo where we are showing off that TalentBin has millions of personal email addresses tied to candidate profiles, we’ll relate that to the prospect’s own words. By making good use of discovery information, we can demonstrate how our solution fixes a problem the prospect said she has, via a solution she already told us she knows is the right one. Twofer!

Building Agreement

Extending from repetition and comprehension is the notion of building agreement. At every opportunity, you want to elicit agreement from your prospect that his worldview is aligning with the one that you’re espousing. If you do this well all along, at the conclusion of your pitch the sale should be a no-brainer! At that point, the prospect has agreed with you the whole time about the pains he feels, the fact that existing solutions are not getting the job done, that it’s important to solve this problem now, and that the solution you’re proposing definitely does so. Now let’s just sign a contract!

How do you achieve this consensus? As with validating comprehension, the best strategy is to ask for agreement at every point where it makes sense—to score points. You can do this with leading questions that get the prospect to surface his agreement, or, just as important, his disagreement. Every time you can get the prospect to say that yes, he shares that pain point; that yes, it is substantial across his organization; that yes, he’s tried that other approach to fix it; and that yes, this specific feature looks like it fits that specific pain point well, you’re building agreement. You’re building a groundswell of alignment that leads inexorably to the prospect purchasing your solution.

Pacing and Pausing

By the time you’ve done a dozen or so of these pitches, you’re going to have it pretty nailed. And when you know something well, you have a tendency to speed up your delivery. Even before that point, nervousness also tends to compel faster delivery.

importantResist this. In pursuit of comprehension and agreement, you need to make sure that your delivery is methodical. Deliberate pacing will ensure that words aren’t missed and that your prospect has the best chance to comprehend what you’re saying and how it relates to what’s on the screen or projector. Further, pausing here and there to allow for questions, and to proactively test for comprehension, ensures that there are opportunities for the prospect to catch her breath and clarify, if needed.

This becomes all the more important if you are delivering the pitch via phone. Because the prospect doesn’t have the benefit of facial and gesture-based information, enunciation and conservative pacing will be all the more important. But even face-to-face, you want to make sure your presentation pacing is deliberate and includes frequent breaks.

Customization and Curation

We’ve discussed personalization of your pitch at length in Early-Stage Sales Materials Basics, and in Pre-Call Planning, but now is when you put it to use. Because of your diligent prospecting, planning, and discovery, you are at peak understanding of the account’s business context. So use it! The worst thing possible would be running through a canned presentation despite all that additional information—instead, put it to work for you.

You can feel empowered to completely drop whole slides out of your presentation or to skip over features in your demo that you don’t think will appeal to the audience. You only have a certain amount of time in which to make your case—you want to be spending those minutes on the topics that have the highest chance to resonate. This also means doubling down on pain points, value propositions, and features that will be particularly meaningful to the prospect.

exampleIf you were pitching TalentBin to someone who was already very well aware of GitHub and Stack Overflow, and had previously used a competing talent search tool but canceled it, you would focus on substantially different things than if you were pitching to a prospect who was completely new to internet talent search. You would probably quickly gloss over the, “Here’s how the internet has changed to allow for finding technical talent” section, because the prospect knows the landscape already. And you’d probably speed through how TalentBin aggregates social network web profiles, since, again, he likely already knows that from prior experience. However, you would likely focus more on the differentiators between the former solution they were using and TalentBin. You would change your pitch to focus on the things that were likely to matter.

Micro-Contract Creation and Execution

importantIt’s crucial during the pitching and down-funnel process that you have a good handle on where things stand. Is this deal still heading toward success? Has a potential block arisen that needs to be handled? Or has the prospect decided that there’s no way he’s moving forward? The reason knowing where you stand is so important is so you don’t spend time on opportunities that are dead in the water. As we’ve previously discussed, your most important resource in sales is your time. There are likely thousands and thousands of potential prospects for your solution, but you only have 40 (or 60!) hours in your week.

A great way to facilitate being on the same page is what are known as micro-contracts between you and the prospect. Before you do something with the prospect (for example, ask discovery questions, present slides, demo), you articulate what you want to do and why and ask if she is in agreement that it is the correct next step. This is a tool espoused in the Sandler Sales Methodology, called upfront contracts. You likely used it when setting the appointment, when you characterized the agenda and gained the prospect’s agreement to attend, but it extends to the pitch, and even beyond. As you progress through your pitch and your demo, and through incremental demos, negotiations, and implementation, setting clear expectations with the prospect will help keep things moving and prevent getting stuck.

exampleIf after your initial demo it appears that the solution is a good fit but there is a need to involve another decision-maker, then you should contract for that next meeting. “It seems to me that you believe this solution can help your organization solve the problem that you’re focused on] and that you believe it would be a good fit. But in order to progress, we need to involve Jeff so he can validate the conclusion we have come to. Is that right? If so, let’s get another presentation on the calendar for you, him, and me. Do you have your calendar and his available to you?”

If the prospect was genuinely interested in proceeding, then great—you get that meeting on the calendar right then and there. If for whatever reason the prospect was fudging a little bit, and there is another wrinkle (as in, they have no budget), it will surface. And that will be a huge benefit to you. The contract that the prospect wouldn’t make keeps you from wasting your time chasing Jeff around. It gives you clarity.

If you do make the contract, restate it at the start of that next meeting to establish continuity of the deal in flight:

example“Jeff, Susan and I met last week to discuss ____’s challenges in ____. Based on the outcome of our conversation, Susan and I believe that this is a very worthwhile investment for your organization and stands to provide a lot of value. But it is my understanding that we need to share this case with you, so you can validate our conclusion, before we progress to a commercial agreement. And that is the purpose of this call today. Does that align with your expectations?”

At any point in the sales process, if you uphold your side of one of these micro-contracts, but the prospect diverges from his commitment, it is an early warning system. And you’ll be justified in stating your concern:

example“I’m confused. We agreed that you believed this solution made sense for your organization and is well positioned to help you save ~$X per year. Our next step was to meet with your CFO to help him validate your conclusion. But two of those meetings have been canceled at the last minute. Can you confirm for me that this is something that is a priority and that you believe is important for your organization?”

Through continual creation and execution of micro-contracts, you can make sure that you’re effective with your time and always on the same page with the prospect.


Now that we’ve covered some overarching principles for your pitch, let’s talk about its chronology. Some people think that a pitch should only be done in-product and jump straight to that. I feel it’s important to set the correct mental model, so that prospects are well primed to get the most out of the conversation. I like to start by getting them into the mindset of the problem that we solve, and how our solution is poised to help, and only then move into showing how the product actually works.

cautionWhat we are not doing is running through a slew of features and screenshots, where the prospect sits back and just listens. A show and tell presentation (or sometimes, “show up and throw up”), and later demo, is a recipe for an unengaged prospect who is not actively considering your commercial argument nor seriously thinking about business pain and how your solution solves it. Instead of reeling off feature after feature in a one-way information deluge, you want to use the tone you set in your discovery conversation and cultivate rich back-and-forth with the prospect.

The best way to make sure that this happens, again, is to be explicit about it.

example“Okay! Thank you so much for sharing all that great information with me. It’s really going to make this a productive conversation. So, based on what you’ve shared with me, I think that what we’re up to is definitely relevant to what you folks at ____ are doing as related to ____. What I’d like to do next is share some slides that help set the tone on what we do, before we get into the product live demo. Does that work for you?” This helps the prospect understand what’s coming and continues the process of building agreement.


Of course, this is also the point in time where you can offramp a prospect that isn’t qualified. If the organization doesn’t have the pain points that you seek to solve, or it is clear that it has no ability to pay for solutions to solve the problem, then you should seek to conclude the conversation on great terms. (Remember, though, that if it’s simply your contact who doesn’t have authority to expend budget, but the organization does have the pain points you solve, you can partner with him to get to the right decision-maker.)

The best way to close out the conversation is to frame it in terms of respect for the prospect’s time.

example“You know what, ____, based on everything we just talked about, I don’t think that what we’re up to is going to be super helpful in your efforts. We mainly help out people and organizations that ____. I know you’re a busy person and don’t want to waste your time on something that isn’t helpful. I’m happy to send you some slides or demo videos, but I would propose that we just go ahead and conclude this call, and I can give you back thirty minutes of your time. What do you say?”

You win credibility with prospects this way, and you make it clear who you’re relevant to (so they can refer their friends who do have the pain point in question). Ideally this doesn’t happen too much, especially if you’ve done a good job of using externally available information to prequalify prospects, and if your appointment-setting process is honed to put only valid opportunities on the calendar. But in the rare case it happens, close it out.

Introducing Your Narrative

If the account is qualified, there is a set of goals that you want to achieve during the presentation before you get into the actual product demonstration. First and foremost, you need to convey the parts of your sales narrative that are better communicated with slides than with a demo—things like pain points, the failures of current solutions, how your solution works (the conceptual framing), and qualitative and quantitative proof of why it is a better way to solve the business issue. As discussed in Early-Stage Sales Materials Basics, the visual nature of slides allows for much richer communication of these parts of your narrative than simply speaking to them in the abstract. Communicating your product’s features and how they work is typically better done in a demonstration, but for the other parts of your sales narrative, this is the exact reason you invested in building a sales deck.

While product features and their value proofs may be documented in your presentation, you generally should avoid getting into them ahead of your demo. Those slides are typically better used as offline reminders of the features you’ve demonstrated live. Think of them as something for your prospect and her colleagues to refer to after you’ve blown their socks off. The exception here is cases where, for whatever reason, a live demonstration of your software is not possible. Nowadays this scenario is pretty rare, and I would recommend figuring out a way to avoid it—even if you need to do a demo loaded with dummy data.

For your presentation, you’ll want to have your master deck, or the personalized variant of it, ready and loaded into Showpad or DocSend, or ready to project on your machine. As you progress in your presentation, especially if you’re doing a good job of facilitating a rich back-and-forth, invariably topics or questions will pop up that may make you hop out of order. That’s perfectly okay, and should be welcomed. You want to use all the materials you have at your disposal to achieve the goal set out above, and if that means backtracking to an earlier part of the presentation because one of your comprehension checks fails, or skipping to an appendix slide based on a question that surfaces, then do so. Don’t think you have to slavishly progress slide by slide, on a death march through your presentation, as that will trip you up in your pursuit of a rich consultative conversation. Moreover, if it becomes abundantly clear that the goal of your presentation (comprehension of the parts of your sales narrative not covered by your demo) has already been achieved, and the prospect is ready and eager to progress to the demo, by all means, skip ahead!

You can come back to slides after the demo too. In fact, this is a fairly typical pattern. Jumping from the live demo back to a slide that talks about the benefits and ROI of the feature you just highlighted is a great way to connect the live product to the value the prospect will get out of it.


We talked about your demo script earlier, so you should be familiar with what you want to talk through in your demo. However, to reiterate, the difference between your sales presentation and your demo is that your presentation is about setting the correct mental model, and the demo is about demonstrating how the actual product delivers on the promises you’ve made. It’s also an opportunity to do so in a way that makes maximum use of the fact that you and the prospect are synchronously looking at the same thing and can have a rich discussion (whereas slides can be consumed asynchronously at a later date).


One of the biggest differences between the sales presentation and the demo is that while the sales presentation slides will frequently be the same from prospect to prospect (with perhaps some light customization as discussed in Early-Stage Sales Materials Basics, the demo is far more likely to be heavily tailored to the prospect’s needs.

The best option is using actual data or materials from the prospect in your demo.

exampleThere’s a great old story about how Postini, a spam filter company long since purchased by Google, would have the CIO they were selling to point email traffic at a Postini server, which would immediately start filtering out spam that the CIO’s existing filters were failing to catch—a great demo to be sure! At that point, the rep could say, “Pretty great, right? Shall I draw up a proposal? Or would you like your spam back?”

It’s a bit flippant, but it really gets the point across. The demo had proven that the solution did what was promised in the sales presentation, and did so with the prospect’s actual work environment.

If your product has a partial freemium component, and some employees of the target organization are already using it in some regard, a good approach may be to use that particular instance, perhaps alongside one set up for a demo.

example“You can see what Fred, Jane, and Ian from your team are doing here. In fact, here’s the reporting interface that you would get access to as a paid customer, and you can see their level of usage.”

Not every product is going to be easy to use with real customer data in a demo. But as you’re thinking about your product and its features, you’ll be well served to consider how they can best be demonstrated, not just how they work in the abstract. Remember, too, that you’re customizing your demo not just for the account in question but for the type of stakeholder you’re talking to.

Demo-Ready Data

If you can’t use your prospect’s real data, you can use the next best thing: data that supports all the use cases and proofs you want to demonstrate.

You’d be amazed how many demos I’ve watched where the data being used made it nigh impossible to get the point across. That’s not just a huge lost opportunity, it’s also an ugly turnoff. You have total control of the demo instance, so definitely be sure to get it into a state that easily demonstrates the value of your solution. Don’t take shortcuts. They will not instill a lot of confidence. Any time you find yourself saying things like, “Well, ignore that” or, “Imagine if XYZ,” you probably have a data problem.

This doesn’t necessarily mean that you need product investment or engineering assistance to fix the problem, but you do have to do the work to get yourself properly set up—which likely isn’t all that challenging. But if, for whatever reason, you can’t manually get the data in your product into a state that lets you demonstrate effectively, well, then you might need to have a conversation with engineering and product. You’re going to be doing a lot of these demos, and later, if you’re successful, there will be many sales reps joining you. (Not to mention that having example data in your product for new customers is often helpful and makes for more compelling first-user experiences.)

importantThink about this every time a feature ships. You likely add a slide to your sales deck breaking down a new feature, so what do you have to do to your demo to make sure that you can showcase this new feature and its implications in a high-impact fashion? If you’re spending those expensive engineering resources on building something, you certainly want to make sure it’s nice and sales-ready, with all the associated sales materials.

Focusing on Features That Matter

As with your sales presentation, you should think about which specific features you want to focus on to make your demo most effective. You probably only have 15–30 minutes of time to do actual product demonstration, so make sure to prioritize the features that will be most compelling to your prospect. Now’s the time to put to use all that excellent prospecting, planning, and discovery you did, and to remember to speak the language”of your prospect.

exampleIf you were selling Textio and learned in discovery that the prospect was frustrated with what a mess job-description management is for hiring managers and recruiters, you would take special care to demo the templating and management features of your product. Or if you were LifeGuides, and you knew that your prospect was very much into making sure their careers Twitter feed was well stocked with compelling content, you would focus on how LifeGuides makes it extremely easy to produce dozens and dozens of lightweight employee video testimonials that are perfect for stocking an employment-focused social media feed.

Obviously there are going to be parts of your demo that you’re very excited to share across prospects and core use cases you’ll include to make sure your point comes across. (We discussed this earlier in Demo Scripts.) But make sure you know what parts are optional and can be cut out so that you can spend more time on high-priority features.

Proof Demonstration

The demo isn’t the conclusion of the sales call; it actually sits in the middle. Once you’ve completed discovery to arm yourself for the call, the slide presentation to set the right mental model, and the demo to show off the actual goods, it’s time for the next step: “Why we know this works and why this is a great investment.”

This is where I like to switch back to slides, where all of these proof points are laid out. As with the pre-demo sales presentation, the visual nature of slides makes for better communication of quantitative and qualitative material. If you talk about ROI and other proof points while the prospect is looking at features, he’s not going to retain anything. Use visual exhibits.

You can refer to the previous section on proof points slides for your sales deck to refresh yourself, but the point here is that you’re now talking about why everything you’ve presented so far is a great investment. And you’re backing it up with proof. Whether that means feature-by-feature ROI studies, aggregated customer ROI information, customer-by-customer ROI examples, or qualitative proof—or a combination of all of that—you’re progressing to the “Why this is a no-brainer” part of the presentation. Don’t skip this important step before attempting to close the sale.

Pricing and Asking for the Sale

cautionThis is typically the concluding part of the pitch, although you may not get to it if you haven’t done all the preceding steps correctly. If you have, it is critical to not skip this step. For founders and first-time salespeople, presenting pricing and affirmatively asking for the sale is often where the most mistakes are made—largely because they don’t do it. After going to all this trouble to find the prospect, make an appointment, and then present the value of their solution, they drop the ball short of full execution.

It’s an understandable error. This is where you can feel the most exposed to rejection. It’s akin to another common founder error, selling to people they know versus qualified accounts because acquaintances are less likely to reject them. But we’re going to surmount this! And we’re going to get good at it. Part of the trick here is convincing yourself that your solution is worth it. And if your pitch is well formed, with great proof points and a rational pricing scheme based on market comps or proven ROI, you should have zero fear. Your engineers cost money, and you need to pay them. Your solution will put money in the customer’s pocket—either through reduced costs or increased revenue—so you are completely justified in taking part of that created value for yourself. Let’s ask for it!

First, prospects often ask for pricing on their own. If you’ve followed the flow we just walked through—discovery, presentation, demo, proof—and done so with a prospect who has your pain points, validating along the way that he is qualified, you’ll be amazed how frequently prospects ask for pricing information at this stage. Don’t be surprised! They’ve been in commercial conversations like this before; that’s part of what makes them qualified prospects. Particularly if a prospect is already using inferior existing solutions—paying money to solve the specific problem your solution solves—the revelation of your magical new solution to their now-validated pain points will of course lead to the logical next question: “Wow, this is all really great. What’s pricing?”

If a prospect does indeed ask for pricing, you should be happy. People typically only ask if they’re interested in buying, and you just captured a valuable piece of information: this prospect likely thinks your solution makes sense, provided the price is right. This is when it is helpful to have that pricing slide that you can flip to quickly. Also, this is why, when we covered appointment setting, I encouraged you to forestall discussion of pricing until you could help frame the conversation with the prospect. Telling someone, “Yeah, it’s ten thousand per recruiter per year” in a vacuum could result in a lot of sticker shock. However, once you’ve presented the problem, how you solve it, why this is better, and all the proof points associated with that—well, ~$10K might be a screaming deal.

If a prospect doesn’t ask for pricing unprompted, I like to use this as an opportunity for a trial close, rather than just driving ahead to a pricing slide. I gather more information about his mindset, post-presentation—something along the lines of, “Given all we’ve covered, is this something that you see being useful in solving your challenges?” If the answer is no, that’s potentially very concerning, since they’re articulating lack of interest without even knowing the price. Yikes. It will be all the more important, in that case, to dig into the prospect’s objections, because this may be indicative of an issue with your prospecting, discovery, presentation, and demo process. More on handling these sorts of objections below.

If the answer is yes, the prospect has just given you an interesting piece of information: he’s excited about paying for your product, even though he hasn’t heard pricing yet. This seems like a pretty good sign for you, given that he certainly knows your product will cost something. In fact, in the back of his mind, he likely indexed off of an existing solution that he’s already paying for.

exampleIn TalentBin’s case, the thought running through the prospect’s head was typically, “This probably costs the same as a LinkedIn Recruiter or Monster Resume Search seat. I’d pay that for this.” So, in effect, the prospect has signaled not only his interest, but also, perhaps, a price floor. If the answer is, “Well, that depends on what it costs,” that’s also fine. Just progress to discussing pricing as if the prospect had asked you directly.

Presenting Pricing

Depending on your model, the pricing you present will often be just a straw man of what you eventually put together in an honest-to-goodness proposal (more on this in a second). If you sell on a per-seat basis, you would likely present the list price for a single seat to gauge reaction. Or if you sell on some other per-each basis, the same would be true. If you sell based on some other constraint, like size of an organization, it’s going to be fairly obvious what pricing will be, so you’ll want to jump to that. When presenting pricing, it’s great to frame it in the context of existing solutions, best alternatives, or opportunity costs that you’ve already touched on in discovery and your presentation.

exampleIf you’re Immediately, and your pricing is, say, ~$30 per month per sales rep, you might frame it as, “It’s thirty dollars per rep per month. So if you consider that your average rep is making a hundred fifty thousand, it’s fifteen minutes of salary expense per rep. Of course, Immediately will save them hours and hours per week.”

exampleIf you’re LifeGuides, and you know that the customer is paying for a ~$20K-a-year LinkedIn Premium company profile, you might present your pricing in relation to that.

exampleOr if you’re HIRABL, you might present it in the context of projected ROI based on existing experience, like, “Typically we charge one dollar per monitored submission per year, so based on your organization’s submission volume, that would be around ten thousand dollars. We would anticipate finding between ten to twenty missed fees over the course of a year, representing between one hundred twenty-five and two hundred fifty thousand in recovered fees for you. Not a bad deal, right?”

Eventually you may do this more formally, using text and visuals, in a follow-up proposal, but doing so verbally is the first step.

importantWhen you’re verbally presenting pricing, you’ll want to start at the most extreme case, knowing that you’ll probably end up being negotiated down. This is why presenting just a single unit of pricing (for example, one seat, one discrete unit of use) is helpful, because when you then roll that up to the 50 seats that the prospect needs, you’ll have baked in wiggle room for yourself. Don’t back yourself into a corner and start negotiating against yourself at the start, like, “It’s ten thousand dollars per seat, but don’t worry, I can get you a deal.” Just state the pricing and the rationale that backs it, shut the hell up, and see what the reaction is. This is often one of the hardest things to do, sitting in silence waiting for the reaction. But you have to do it.

From there, you can take a variety of paths. If the reaction is positive—along the lines of, “Well, that’s not bad” or, “That makes sense”—you should move on to asking for the sale and closing. We’ll have more on this below. If the reaction is negative—like, “Wow, that’s really expensive” or, “There’s no way we could pay that”—you’ll have to get into handling that objection. And if it’s in the middle—like, “Well, that’s a lot, but I see where you’re coming from”—you’ll progress along the same lines as the positive case and ask for the sale.

Asking for the Sale

When you have leading indicators of interest, it’s time to proactively ask for the sale—no “So, what do you think?” wishy-washy stuff. Forthrightly ask for the business.

example“Based on what we’ve discussed, this sounds like a great fit. Is this something that you would want to progress with?” or, “Is there anything that is preventing us from getting you started as a customer?”

As noted before, so much of business-to-business selling is simply understanding where you stand with your prospect and taking the next appropriate action. Nothing quite cuts to the chase like asking the prospect whether she wants to make a deal.

There are a variety of other skillful closing techniques, but all are really just versions of asking for the sale. There’s the waffles or pancakes approach of, “Would you prefer one seat or two?” And the timing-centric, “We have a number of openings with our customer success organization for implementation calls next week. Would you like to schedule one?” and so on. You can Google around to see other approaches. But the point is, directly asking for the sale (compared to beating around the bush, or avoiding it because you’re afraid of rejection) is 90% of the battle.

If the answer is yes, fantastic! You’re closer to the goal. The next step would typically be to put together a proposal with a couple options for them to choose from, assuming there are different options.

exampleSay you’re TalentBin, selling to an organization with 20 recruiters. If there was discussion as to whether the prospect might start with just one seat, or seats for all 20, you’d want an opportunity to craft a proposal that potentially leads the prospect to a higher initial purchase. You can present along the lines of, “Excellent! Would you like me to put together a proposal that covers some options that you could go with?”

If there’s no reason to present a proposal with varied options—it’s clear there is really only one path to a purchase for the prospect—it’s better to just skip to the contract.

example“That’s fantastic. If you’d like, I can send over an order form that you can execute via digital signature, and we can get started today.”

Again, you would only do this if the customer is qualified, she has articulated that she wants to execute on this, and you believe she has the authority to do so. Conveniently, all of this was covered back in discovery, setting you up for this very moment. Now you can see why we do this!

If the answer is no, welcome to the most common response. But instead of meaning, “No, never” or, “No, no way,” this is typically, “I’m not sure” masked in a no. Your job is simply to uncover the objections that are blocking you from progressing, handle them, and then loop back to, “Okay, now will you buy?” We’ll explore this further below.

Proposals vs. Contracts

A proposal is a helpful way of framing a couple different options to a customer who has articulated a desire to buy.

That stated interest is crucial—you definitely don’t want to be in the business of sending proposals willy-nilly to prospects who haven’t asked for them. Do that, and you’ll be losing out on a key signpost on the progression from prospect to customer. Proposals should be reserved for prospects that have said they want to buy.

Why a proposal and not just a contract? Well, an order form/contract is probably the most basic proposal that you can produce, and shouldn’t be disparaged at all. It has the added benefit of being executable (assuming you send it via digital signature method, like DocuSign, HelloSign, or Adobe eSign). The downside with sending a contract is that a contract is typically just for a single offering—like one seat of your solution. So if you want to show a couple options, you’re stuck. Moreover, a contract or order form is more about documenting the price that someone is going to pay for a set of services. It’s not a piece of marketing collateral, and to the extent that your deal isn’t closed yet, you would like to use all the tooling available to get that deal slammed shut.

A lightweight proposal can help with these downsides. First, it lets you present a couple of options whereby you can direct the prospect toward an outcome that is more beneficial for you. By presenting options, you’re removing cognitive overhead, so the prospect doesn’t need to compose his own option. At the same time, you’re making it clear that this isn’t about whether he’s going to buy—it’s just a question of which option!

At the earliest stages, bigger purchases are better—within reason—provided they don’t overwhelm your customer success resources. The marginal cost of adding another seat of software to an account is typically pretty near zero; this is the magic of software. Yes, there may be more support costs, but even those are usually added on a per-account basis. Selling three seats to a given account will not cost three times the support as one seat to the same account. So if you can figure out how to get marginal revenue out of a given opportunity, you should try to jump for it.

One strategy for maximizing a sale is to present three options in your proposal, where the middle option is your target (and the highest option is still a realistic reach).

exampleLet’s say you’re TalentBin, selling to an organization with ten recruiters, only five of whom would get maximal use out of the solution (five are technical recruiters, and the others are generalist recruiters who might only occasionally dip into the product). You might still present pricing for three, five, and ten seats. But where the three-seat option is nearest to list price ~$6K x 3 = ~$18K), the five-seat option seems like a pretty compelling discount (maybe 5 for the price of 4.25). The ten-seat option—again, taking into account that those incremental five users are pretty unlikely to use TalentBin except cursorily—might be ten seats for the price of seven. So, for those incremental 5 seats, you’ll only charge the cost of 2.75 extra seats, recognizing that the value they provide might be lower (but still significant on the occasions the product proves useful to the casual user).

Ideally the various options land at helpful price points, just below potential psychological thresholds (~$10K, ~$19.5K, and ~$24K, as an example). You can take this approach, as well, when you know there’s a certain amount of budget available. You might price your middle option for that known good budget, your bottom option below that (but very costly on a per-each basis), and the highest option as a stretch goal that is a screaming deal on a per-unit basis.

If you know that the maximum budget could potentially be in play, then you certainly want to not only present a proposal for it, but guide the prospect toward that best deal via pricing inducements. Many corporate purchasers are used to taking the gold-plated option, so having something at the top end, while also providing some air cover by making it look like a deal, makes it more likely they can jump on it. Plus, if it’s not there, they can’t even consider it. So include it! Even if they don’t end up going for that high end, by presenting it you make it that much more likely the prospect goes with an option above the very bottom one. Going back to our TalentBin example above, if you only presented pricing for three and five seats, the five-seat option would be the “expensive” one, potentially impacting the prospect’s perception of its viability.

There’s definitely an art to these sorts of things, requiring an understanding of how much potential demand there is in the prospect organization, how much budget is available, and how much pain is present. You don’t want to overthink it and get too complicated. And if the prospect pushes back and decides to go with a lower-tier option that wasn’t presented, that’s fine; send over an order form and call it a day. But there is a lot of potential upside associated with presenting options that are above and beyond just trying to sell the base-level deal and running on to the next one.

A note on cannibalization. At a later stage, you might be worried about cannibalizing potential demand via discounting what you could sell for full price. If you have confidence that your solution will spread within an organization, you might be concerned that you were taking ~$16.5K (5 seats for the price of 2.75 x ~$6K per seat) for seats that could eventually earn you another ~$30K at full price. Early on, don’t worry too much about it. Instead, strive for that incremental cash that will turn up in your bank account right now.

Another thing that proposals can be nice for is framing the projected ROI associated with those different options. This goes to the concept that a proposal is a piece of marketing collateral, helping to sell for you even when you’re not engaging directly with the prospect. They can also help your champion play Show and Tell with the ultimate decision-maker, if necessary. If it’s just your contact who needs to make the decision, then having this information nicely presented for her is helpful. However, if there is a CFO or some other back-check authority, having all of this bundled up in a nice tight package, ideally including your logo and the prospect’s, will do wonders for the credibility afforded you, and your champion. You make her look like she’s done her homework and is bringing a well-reasoned proposal (ha!) to the table, reducing potential skepticism by her internal back-check counterpart.

When it comes to delivering a proposal, it doesn’t have to be too fancy. To start with, you can do it manually. I’m a fan of a templated PowerPoint presentation where you can drop in the relevant options, the prospect’s logo, and any sort of ROI projections. Later, you can get more involved and tie information from your CRM Opportunity object into a programmatically generated proposal using something like Conga Composer, Drawloop, or Octiv. Not only do these save you the time of manually putting the relevant information into a proposal, but often they will have their own e-signing functionality or let you integrate with DocuSign or Adobe eSign. That way, when the prospect chooses which option she wants, she can just click through and sign, rather than having to tell you her selection. Anything that can remove a step of friction and back-and-forth is beneficial.

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.

We touched on this briefly when talking about objection handling in Prospect Outreach and Demo Appointment Setting. Now, instead of surmounting objections to taking a meeting, you’re surmounting objections to proceeding with the purchase. Further, you have far more information about the prospect’s internal situation, thanks to all the discovery you executed, so you can handle these objections with very concrete examples that are rooted in his business realities. Moreover, you are on the far side of your presentation and demo, in which you made the case for why your solution is a solid fit for the organization, building agreement with the prospect as you went. So objections should be nothing to fear, given your position of strength.

As with the objections you were handling when setting appointments, objections to a sale are a good thing! You know the prospect is actively engaging with you and considering the sale, rather than going silent or just saying something abstract and content-free like, “No, I don’t think it’s a fit.” A great way to elicit specific objections when a prospect is being vague is with a line like, “What specifically is blocking us from progressing right now?” That puts it to her to surface one, or many, concrete objections.

The objections that you run into will be both generic and specific to your solution. The generic ones will be similar to those we covered in Prospect Outreach and Demo Appointment Setting around timing, budget, authority, need, and price. Then there will be those that are specific to your solution, which may be versions of those generic ones or specifically address feature and functionality concerns or competition. We’ll talk about the generic ones first, then move on to the solution-specific ones.

Generic Objections

Generic objections can generally be divided into the following categories—lack of decision-making authority, lack of need, fear of change, timing, price, budgeting challenges, and reluctance. We’ll discuss how to resolve each of these issues below.

Lack of Decision-Making Authority

If the objection is around authority, this is an easy one to resolve. During discovery (see how it all comes back to discovery!?), you were supposed to figure out what the organization’s process is for making judgments about tooling and who makes final decisions. Well, now you just come back to that.

importantUnderstand whether this is the true blocker. Is the prospect sold on the solution and honestly telling you that he doesn’t have the authority to commit to purchasing? Handling this objection is going to involve assisting the prospect in navigating his organization with your help—you will essentially be partnering with the prospect to sell the next decision-maker in the org. And because this can be a squirrelly exercise, you want to make sure that he is fully bought-in as a champion of your solution.

You can validate that with something like, “Is the authority to make this decision the only thing that is blocking us from getting you started?” This helps you understand if there is anything else lurking or if you can point your efforts toward this issue. If questioning elicits other objections—like price or budget or feature deficit—great, handle those first. But you don’t want to get into a situation where you and your champion are sitting on a call with his boss or the CFO and something else bubbles up. Yuck.

Assuming that yes, your prospect is indeed bought-in, it’s now just a question of project-managing the next step of the sale to engage, with the help of your prospect, the ultimate decision-maker or set of decision-makers. Ideally you would have been engaged with them from the get-go, but often the budget-holder and decision-maker are removed from the person who would understand and appreciate your solution. Sometimes organizations will run purchasing decisions through a finance staffer, like a controller or CFO, to make sure that there are strong ROI arguments and efficiencies deriving from the purchase. Or other times, it may be the manager of the prospect that you’re engaged with, who is removed from the pain point that your solution addresses. Whoever it is, you need to elicit that information from your prospect and then offer to run point on engaging the decision-maker to get the ball across the line.

Typically I prefer to not give the prospect the ball to run with here and, instead, like to put the onus on myself to manage that process, under the guise of being helpful. Of course, the goal is to ensure that I have control over moving the conversation forward and am not gated by the prospect dropping the ball. Because while your contact may be excited about your solution, advocating for it is not his day job. It’s yours. Also, he likely will not be as good at it as you. So you need to be the one running point on setting up incremental meetings with other decision-makers. Just treat it as another demo that will likely be foreshortened.

How to do this? Well, first, eliciting the names of the decision-makers can be dicey this late in the conversation, because the prospect may be concerned that you’ll just run ahead and engage them, leaving him out of the loop—or making it look like he just dropped a rabid sales rep in their laps! Again, that’s why getting this information via discovery at the beginning of the conversation is so much better, or even before that in pre-call planning, when you figured out who the potential decision-maker could be (boss, boss’s boss, and so on). The closing conversation is so far from prospects’ minds at that point, they’re less guarded with this information. But regardless, you can use the same gambit as before, using LinkedIn to sniff out who your contact’s likely boss or likely decision-maker is and surfacing that.

An easy approach here is something like:

example“Fantastic, I am very excited to work with you to help understand how helpful this will be for ____. I know you’re busy, so I would love to take point on setting an appointment so we can both present this to her. Is her calendar available to you? If so, we can get fifteen minutes scheduled right now, and keep this ball rolling!”

If the relevant person’s calendar isn’t available, you can volunteer to start an email thread including your champion and the target decision-maker wherein that scheduling takes place. (Ideally you should just assumptively propose some times, the way you would in an appointment-setting context.)

Once a meeting is calendared, you would just approach it as a second demo, with all the associated pre-calling planning, a stated goal, and customization for the type of person that you’re selling. In this case, you’re selling the decision-maker on the fact that her deputy is bought-in to this solution; you just need to make it clear that this is a good expenditure of budget. Often you’ll find that the decision-maker in question is just back-checking the judgment of the deputy and that it’s a rubber stamp situation. However, this goes back to the importance of having good ROI documentation in your slides and proposal. These higher-level managers are not going to care as much about individual bells and whistles as business outcome proof.

We Don’t Have a Need

importantOf all the generic objections you’ll get, “We don’t have the need” is the most concerning. As touched on above, if the prospect doesn’t think your solution is a fit, there’s something problematic going on. It goes back to the persuasion formula we talked about at the beginning of the chapter. Does the prospect really not have the need, and you just did a poor job on prospecting and discovery? Then you probably shouldn’t be selling to him. Or does he actually have the need but is not grasping the potential value? Or does he not believe that his organization would capture it? You need to figure out the issue.

On the first point—validating actual need—this is why understanding objective external signifiers of demand, and making sure to do good discovery, is key. Because if those signifiers of need are absent, you wouldn’t want to be pitching that prospect anyway. But if they’re present, it puts you in a much better position to get to the bottom of things.

Despite all your best intentions and efforts, sometimes through crossed wires you can get to the far side of a pitch and discover something that contradicts those previous signals of need. So your first job is to re-verify that need.

exampleFor Immediately, this might be something like, “I’m confused. Based on our discussion at the beginning of this call and my research on LinkedIn, your company has fifty outside sales reps. And from what we talked about earlier, your sales management struggles with getting those reps to log meetings, emails, and contact information in the CRM because they’re mobile all day long. Is this not the case?”

Note that the sentence includes all of the need signifiers, so you are sure that they have an opportunity to address where the shortfall is. Is it with the number of reps? Are they not actually outside sales reps? Or are they actually quite good about logging activity in the CRM? What are you missing? Again, this is not about calling someone out as a fibber, but instead about getting clarity of information, so do not be squeamish. If in response to this inquiry, your prospect surfaces a piece of information that makes it clear that, after all, they don’t have the need for your product, then next time you need to be better at discovery! This would have to be something specific that contradicts the prior indicators of need, though, like, “Oh, well, we do have fifty reps, but only five are actually outside sales reps.” That would be a specific data point, and you should take it seriously. However, if the response is squishy, like, “Well, I just don’t think we need it,” that’s code for something else, and you need to get to the bottom of it.

It can be harder to contend with a prospect who continues to claim that he doesn’t have the need after all, even though you know that he does (either from external information, things that he or his colleagues have already said, or just a general squishiness in his response to your inquiries). In that event, it’s likely that he’s using this generic objection as a cover for the real objection (whether budget, authority, priority, or something else). You want to get clarity on that by helping him understand that he can be straight with you. This can be delicate, because you don’t want him to feel that you’re calling him out, so frame it in a way that makes it seem like perhaps he was just sparing your feelings before. You can do that by adding something to the above question, like, “Well, from everything I can see, it appears to me that your organization definitely has the need for this, but perhaps there is something else blocking us from progressing that we haven’t discussed yet? You can be straight with me, I can take it!”

The goal here is to get down to the actual reason, so you can handle that objection on its merits. You’re trying to get the prospect to surface a more specific issue, like, “I’m concerned that I won’t have time to use the product” or, “I don’t think it will be as useful as ____” or something like that—something that is specific and can be addressed on its own.

We’re Happy with How We Do It Right Now/Fear of Change

Often when prospects articulate that they “don’t see the need” or “don’t think it’s a fit,” they’re actually making this objection, in disguise. The prospect validates that she does indeed have the need in question but articulates to you that she is unwilling to make a change to her way of doing things. This is actually a much better place to be than her saying, “We don’t have the need,” because you have gained agreement that she does indeed have the need. Now you’re just having a discussion about why she should grasp the opportunity to adopt a new way of attacking this need.

The best way to approach these objections is to take the hidden cost of continuing to do things business as usual, whether true cost or opportunity cost, and make it visible. You may recognize some of this language from the proof of a better solution section. That’s no coincidence—this is the point at which you should bring out your quantitative and qualitative proof of a better solution. Do the actual math for the prospect on what she’d be missing out on.

exampleIf we were Textio, the makers of job-posting text-optimization software, and we were selling to someone who wasn’t sure if she wanted to Textio-optimize her job postings, we would compare the projected outcomes for the following 12 months using her status quo with what it would look like with our approach. In this case, we would go back to those key metrics that we know our prospect cares about: click-through rates for candidates that see postings on job boards and our career site, applicant-to-screen ratios, and such. If we knew that the prospect spent ~$100K a year on job postings on Monster and sponsored clicks on Indeed, and we have shown that we can reduce posting spend by 15–40%, we could say, “By continuing your current approach, you’re wasting fifteen to forty thousand dollars a year. That’s half a Recruiting Coordinator salary. Saving that from your budget would make you a hero to your CEO and your VP of Engineering.” Note that you’re not just making it clear to the decision-maker that this decision is something that impacts her, you’re bringing in her internal stakeholders too—who would likely be evaluating this decision with a more dollars-and-cents mindset. That hint of a stick, to go along with lots of carrots, can sometimes help focus minds.

This is a great time to flip back to the materials (like your slides you put together to crystallize your proof points. Objection handling is another reason it’s important to have sales materials other than just a demo.

exampleWe had some slides from TalentBin’s sales deck that demonstrated the time savings associated with adopting a talent search and automation solution. In this case, we made it simple and said, “TalentBin will save you one thousand dollars of recruiter time per week,” with the model to back it up. If we ran into fear-of-change objections, we could use the discovery information we’d gathered (how many recruiters the prospect had in house) to crystallize that opportunity cost. If the company had ten recruiters, we’d make it clear that they’d be wasting ~$10K of recruiter time every week.

Figure: Using a Demo Slide for Handling Objections

Source: TalentBin

Figure: Additional Demo Slide for Handling Fear of Change Objections

Source: TalentBin

Beyond the pure quantitative arguments, you will use qualitative approaches as well. You can use all those arguments about how your solution is the emerging industry standard, along with other types of fear of missing out arguments—including which of the prospect’s competitors are likely using the solution. (It’s kind of like a “No one got fired for buying IBM” argument, but more like, “People who bought IBM early looked brilliant!”) These approaches are useful in dealing with other objections as well. Frame the purchase as inevitable and the next logical thing—and subtly suggest that the prospect will be kicking himself in a year when all his colleagues and competitors have implemented these sorts of solutions and he looks like a caveman. In fact, this is an opportunity for him to look advanced, and to advance his career!

Lastly, there’s the fear-of-change aspect. Your prospect believes that she has the problem, and she believes that your solution is the right one to address it—that it’s quantitatively and qualitatively better than what she has in place. But she’s afraid that it won’t actually end up that way for some unknown reason—a generic boogeyman. This goes back to our persuasion formula—in this case, the belief term is where we need help. The best way to address this is with your arguments around “How we will make this easy for you,” as that’s often where the concern flows from. Existing proofs of success, using real customer success stories, may also help. But mainly this is a nonspecific concern—while this all sounds great, and makes sense in theory, the prospect simply isn’t sure it will come to pass in practice. And the best way to handle that is to say, “Here are all the resources we have in place to ensure that you capture the value we both agree is on the table for you. We will make you successful.”

Timing Is Bad or We Have Higher Priorities

This is a variant of, “We’re happy with how we do it now,” but a slightly better version. The prospect agrees that his organization has the need, that the solution addresses it better than what they have in place right now, and that they will get value out of progressing with the purchase. And given that he hasn’t just jumped to the king of objections—no budget—it would seem that he knows they can pay for it. The sticky part is that they have other things that are higher priority right now. This objection may also appear as its cousin, “The timing is bad.”

The reality is that your prospect always has a bunch of competing priorities, including day-to-day execution of his role, so the key to addressing this objection is to reduce the perception that implementing your solution will be a lot of work. The implication here is that he only has so much time to roll out a new solution and that that time is already spoken for. Once again, a great way to address this is with your arguments around how easy you will make it. Make it clear that all he has to do is say yes, and poof, it will be done without any more involvement from him, short of providing authority and names for users.

example“The timing is bad because I am in the middle of rolling out a new applicant tracking system” could be addressed by a Textio salesperson with, “That’s actually a great time to start using Textio, because you’re already going to be changing business process around how your job postings are written and deployed. It’s a great time to cement new, better habits. And the good news is, we have six customer success specialists on staff who can run daily webinars for your team on how to get the best use out of Textio, and ensure that all your hiring managers have attended and passed out of the training. This is fantastic, because as you roll out your new ATS, you’ll see even better ROI from it by mixing the two solutions.”

Another approach is to help characterize why working on your solution should actually be a higher priority, even assuming scarce time resources. In this course of argument, you’ll now need to do some more discovery around what other programs they are considering implementing. For example, you’ve just discovered a new type of competition, which isn’t pure competition—it’s just something else competing for the headspace and time of your prospect. This can be dicey if the prospect has already committed to that course of action (commitment bias is a two-edged sword!). But you can certainly sniff out what those alternative programs are, and their perceived ROI, to position your solution as a higher-priority project—again, using numerical and qualitative arguments that compare the opportunity cost of not adopting your solution to the opportunity cost of not adopting that other product. This is where being a student of your market is important, because you’ll have to make the other solution’s ROI argument for it (in a way where your solution wins!) in a credible way. But it certainly can be done, because often prospects haven’t been super rigorous in their analysis of whether to spend their scarce time and budgetary resources on this project versus that. So now you get to help them do that, with a preference for your solution!

These have been examples of how to actually change minds. But you can use sleight of hand without challenging the underlying objection—“This is not a priority right now” or, “The timing is off”—and still get the deal done. You can capitalize on the fact that you have the prospect’s attention and buy-in right now and that they agree that this is a project that is worthwhile. When will be the right time? In a couple weeks? In a month? In that case, let’s just get this deal done now and make sure that it gets on the prospect’s dance card for when he does have time. Why would he jump at doing that now? Well, you can take a couple of approaches.

exampleYou can create a pricing inducement, like “If you buy now, I can give you fourteen months of service for the cost of twelve” or, “It’s likely our pricing will go up in the new year.” You could use both of those together. Or you could try, “You can buy now, and I’ll start the contract in a month.” These various approaches can be especially helpful at the end of the year, or of an organization’s fiscal year, when they are making budget allocation decisions for the year ahead, even if they don’t intend to take the associated actions for a couple months.

The upshot on this bucket of objections is this: if you’ve got the momentum of a prospect agreeing that your solution should be implemented, it’s just a question of when—take appropriate actions to make that “When?” be now.

Price or Value

An objection around price is actually a great place to be—it would appear that the prospect is convinced and wants to do this. Now you’re just haggling over the price.

importantPricing objections can mean a couple different things, and it’s important to precisely nail down what the prospect is actually objecting to. Sometimes vague price objections amount to posturing for a discount. In that case, you need to just get down to pricing negotiation rather than a deeper conversation around value provided compared to price. We’ll talk about pricing negotiation in a section a bit further on, but the important thing here is to figure out which conversation you’re having: one about value, or one that’s just about discounting.

A great way to do that is to specifically ask, using language like, “I’m happy to talk about the value that the product provides, and we believe that our pricing is a fair split of the value created. But could you help me understand what you think would be a fair price?” or, “Are we far apart here? How far would you say?” If they come back with something that is, say, 10% below the price you quoted, this is clearly just a discounting conversation, and you don’t need to make it any more complicated than that. We’ll talk about how to handle that when we get to negotiation.

But if the response that comes back is something more like, “Well, I couldn’t pay more than [50% of your quoted price] for this,” then you’re not really talking discounts. You’re talking about your prospect’s understanding of the potential value your offering provides. The best way to approach that is to walk her through the way the offering will create value, piece by piece, along with the projected ROI associated with it, or the relevant market comparables. Essentially, you’re going to be justifying the decisions that you made when concocting your pricing, something we touched on in Pricing.

exampleIn the case of something like HIRABL, the response might be, “Based on your submission volume and recruiter counts, we quoted you a price of forty thousand for the year. From the hundreds of customers we’ve serviced, and hundreds of thousands of candidate submissions we’ve tracked, we know that over the ensuing twelve months, we will most likely catch twenty missed fees for your organization—not to mention the ones that we will identify from the last eighteen months of submission data. And given that you make an average fee of thirty thousand dollars, we anticipate that HIRABL will drive an incremental six hundred thousand dollars of revenue to your organization that you would otherwise miss out on. Given that, we feel that forty thousand is a very fair price and will be nearly paid for by your first collected fee. Can you help me understand where my analysis is falling down?”

exampleOr in the case where your pricing is based on comps, like TalentBin pricing just below LinkedIn Recruiter, it might be something like, “Well, currently you pay nine thousand dollars per year for a seat of LinkedIn Recruiter for each of your technical recruiters. TalentBin, meanwhile, only costs seven thousand per year per seat. Not only does TalentBin have 3–10x the number of potential candidates for certain technical skill profiles in the geographies you recruit for, but we also provide personal email addresses for candidates—something that can double or triple response rates to recruiting outreach. Moreover, we don’t cap your outreach activities. Whereas each of those LinkedIn Recruiter seats only gets one hundred fifty InMails a month, you can send as many emails as you’d like through TalentBin. And those emails are open- and click-tracked, unlike LinkedIn InMails. Lastly, TalentBin offers automation functionality, like drip-marketing campaigns, that not only raise response rates, but save your recruiters tons of time for sourcing. Given all that, can you help me understand how this isn’t a fair price for the value TalentBin will offer your technical recruiters?”

In both of these cases, what you’re doing is laying out the ROI argument and providing an opportunity for the prospect to object to something in the analysis. If there isn’t a distinct justification for her price/value objection, then you’ll quickly find yourself converging back on a different objection (likely the true objection)—maybe she only has ~$5K in budget, which is why she was saying she would only pay ~$5K. Or you’ll find yourself having a discounting conversation, but closer to your proposed pricing.

However, if there is a legitimate rationale for the objection, this can also be an opportunity to understand why your pricing model may actually not be set up in a way that aligns with the value that is being provided to the user. Take the HIRABL example. Perhaps the prospect would point out that her average fees are actually more like ~$15K (instead of the ~$30K you cited) and could prove that to you. Well, if that is indeed true, and your pricing targets a 15x ROI, then she might have a point, and you might consider making an exception here. Moreover, you might consider modifying your pricing model to accommodate this sort of thing if you think it’s going to be a more common case.

Another legitimate rationale might be that the prospect only intends to use a portion of your solution’s functionality.

exampleTake TalentBin’s pricing argument above. Imagine a situation where the customer already has a marketing automation solution like Marketo or that they intend to use for recruiting purposes, using TalentBin’s profile and email addresses simply as leads to import into that system. All of a sudden the bundle that is TalentBin’s search, qualification, contact information, and recruitment marketing automation becomes less valuable to them, because they’ve already got the automation part handled and paid for. Again, in a case like this, you might want to consider some sort of exception, and if the exception ends up being common, this could be an opportunity to segment your solution.

Lastly, you might encounter a situation where a prospect’s best alternative is substantially different than most of your prospects’. They may already be addressing the problem your product solves, but with a bailing wire and duct tape solution—still, a solution nonetheless.

exampleTake HIRABL again. The prospect might already be doing backdoor reference checking, but doing so in a manual fashion, using existing staff. Perhaps twice a year, they have some of their clerical staff take all the submissions from the last six months, sort them by the most valuable fees (perhaps cutting off those below ~$10K in value), and then manually go through LinkedIn profiles to see if those candidates ended up at places they were submitted by the recruiting agency. In this case, the marginal value that HIRABL provides isn’t the same as what it provides to a prospect who isn’t doing any of this at all. Rather, HIRABL’s ROI argument here might be that their solution does all of this automatically, so those clerical workers who take a whole week to do this manually, at a cost of ~$20K in salary expense, could be redirected to more valuable activities—like recruiting and business development activities. Or that now they can track all their submittals, not just those above ~$10K. Or that rather than doing this twice a year, monitoring happens on a continual basis, which aids in collections efforts. With all that said, it is certainly the case that HIRABL would bring less value to this prospect than to the same prospect with no backdoor hire checks in place at all. So HIRABL might consider making an exception case here.

importantIn general, these deeper discussions around price and value (assuming they are about that, and not discounting conversations in disguise) are a great opportunity to learn what parts of your product are valuable for what customers. When you are early-stage, I suggest getting a deal done rather than drawing a fixed line in the sand. As long as the prospect meets your ideal customer profile, and will actually get value from the solution, usually it’s better to have them onboard, even if it’s at half of your list price.

If you do engage in this sort of pricing modification (I don’t want to call it discounting per se, because it’s really a reimagining of your pricing model to accommodate a previously unaddressed scenario), you need to clearly document the rationale, ideally in the contract, for a couple of reasons. Firstly, when the renewal comes around, and the scenario has changed (for example, in HIRABL’s case, the customer’s average fee is now ~$25K, not ~$15K), you have it documented and can remove that concession. Secondly, you don’t want this pricing concession to be construed by a third party as standard. We wouldn’t want someone paying ~$5K for a “no marketing automation” seat of TalentBin to tell his buddy who doesn’t have a marketing automation solution in-house that the product costs ~$5K a seat—because that buddy is more than likely going to want to use the TalentBin recruitment marketing automation.

cautionThis does not mean that you should be selling to folks who won’t get value out of your solution just because it’s cheap. If someone is saying he won’t pay more than X because of the low amount of value the tool would provide him, and he’s right (that the solution actually doesn’t provide a lot of value), then you need to pass on the conversation. Moreover, it’s better to have learned this earlier in your sales cycle during discovery and qualification. Don’t sell to people who will get minimal value. They will only use up your customer success resources, churn out, and generally fail to provide you enough revenue to surmount their cost. It’s also a distraction. Avoid it.

We Don’t Have the Budget For This

Not having budget is often a failure of imagination on the part of the prospect, and it’s just a question of you helping them find that budget (unless it’s being used as a red herring for another objection, in which case you still need to get to the real issue). In Discovery, we talked about qualification using frameworks like BANT and ANUM (where B is budget and M is money), and how the challenge with new-technology sales is that there often isn’t an already-existing budget that addresses the solution you’re selling. This challenge will also show up in closing conversations as an objection to be handled.

In discovery and qualification, did you validate that the organization does actually purchase tools for solving business pains, and that the decision-maker that you’re working with has done this before, or knows that it can be done? If no, that was a big boo-boo back then, because they really may have no budget, in the sense that they don’t have a process by which to spend money on products to help their business. Yikes. So we’re not going to address that as an objection, as it is really a disqualifier—if the organization doesn’t have a notion of spending money to make money, well, we’re not in the business of teaching market capitalism, per se.

If yes, then great. Now you just need to make it clear that this solution is worth spending money on in much the same way that the organization has done before. A great first step there is to sort out what the current budget is for solving the problem you address, and if it is recurring in nature or already fully committed. While there may not be budget currently available and earmarked for your exact solution, there could well be budget dedicated to addressing the problem.

exampleIn the case of TalentBin, prospects typically spent a goodly amount of budget to solve the problem of needing to hire engineers to build their product. Purchasing our product was a question of digging into that budget to see what was already spent and what could be shifted. One of the ways that organizations hire software engineers is to spend money on recruiting agencies that typically charge 20–30% of a first year’s salary as their fee. Well, when an organization was budgeting for its year, they may have budgeted for one or two fees per quarter. Presto! We found our budget. Another way to do budgetary horse trading like this is to sort out if there is any existing source of budget that is coming up for renewal soon. If there were ten seats of LinkedIn Recruiter coming up for renewal, then we could propose that three seats’ worth of that budget be allocated to this new, better solution and bridge the time gap with free months.

A more complicated version of this fiscal maneuvering is when budget is transferred from one substantially separate bucket into another, like from payroll expense to tooling.

exampleImagine you’re selling support-ticketing software like Zendesk. The prospect’s current means of addressing inbound support ticketing is a shared email inbox with very little automation, business rules, or templating support. The company’s support organization is growing to accommodate a growing customer base, at a ratio of, say, one new support agent per 200 customers added. In that environment, the adoption of a mature support system like Zendesk, with all of its automation functionality, could raise that ratio to something more like one support agent per 300 customers added. That means that if the organization’s plan is to add 1K customers in the coming year, the adoption of something like Zendesk would mean hiring three new agents in the coming year, versus five under the current staffing plan. Assuming CSRs cost ~$50K a year, fully loaded, we’re talking a cost reduction of ~$100K—money that was already allocated for the year when the support organization signed up to support 1K new customers. Poof! There’s our budget.

Of course, this sort of cross-bucket budgetary horse trading often involves more than just the budget holder you’ve been engaging, like the head of support, head of recruiting, or what have you. It may require looping in a finance staffer like a controller or CFO, or another CXO type. And while that’s another moving part, it’s actually a good thing, in that those staff are more used to looking at the big picture.

Beyond budgetary transfers, there’s also discretionary budget, and one-off budgetary justification. While the individual you’re interacting with—the VP of Recruiting, VP of Customer Success, VP of Engineering, and so on—may have already exhausted her allocated budget, that doesn’t mean that she, or especially the CFO, doesn’t have a hidden kitty of money. You just have to make sure to ask for it. And moreover, if your decision-maker hasn’t considered this, you need to work with her to go together to the CFO, or other budgetary controller, to see what may be squirreled away. This is where having a solid ROI argument is key—because since this discretionary budget is being held aside for exactly this sort of thing, but also for other unexpected opportunities, you’re essentially competing with those potential projects. So you need to bring your A game.

Typically these pools of budget are specifically earmarked for experiments, and whoever disburses the money will be looking at your solution as exactly that. So just be aware that it’ll probably be a purchase at the small end of what you do—whether a single seat, a constrained time period, or what have you—and you’ll have to work to make sure it sticks. This is the sort of budget that land and expand solutions are often depending on. This doesn’t mean it’s a bad idea to try to access discretionary budget if you can, it just means that you need to weigh that reality compared to your other options (for example, financing, pricing inducements, and so forth).

The bigger version of this approach is a one-off budgetary justification. In other words, don’t go after discretionary budget that already was sitting there—create your own new bucket of discretionary budget. Doing this usually means working with your prospect to advance a one-off justification to the part of the organization that makes these decisions—again, usually finance. While this adds complexity, it can be a fantastic opportunity to grow the deal. First, your decision-maker is now going to be having a strategic discussion with the CFO, COO, or what have you to address a deeper question in their organization. It’s less a case of, “Are we going to buy a single seat of TalentBin” and more a question of, “Should we reduce our reliance on recruiting agencies, in general?” And if the ROI justifications to embrace this change at an organizational level exist, then this is exactly what the CFO and COO are there to do: make capital-returning judgments. Moreover, given the time cost associated with meetings, and the collaborative partnering between you and the decision-maker, you have an opportunity to enlarge the deal size—the difference between ~$40K of incremental spend versus ~$20K of incremental spend may not be a meaningful one.

Outside of budgetary horse trading, discretionary spend, and off-cycle budget justification, there are a number of clever moves that can be made to paper over a lack of budget. If it’s a case of timing before the next budget cycle, then you can often place a marker on that budget in the future by getting the deal done now and simply starting it later, or providing free months to bridge the gap. This is akin to the timing objection above, but this is the budgetary version thereof.

If the organization is simply cash poor (or thinks it is), then you can potentially help with financing. This isn’t to say that your organization is going to offer financing to your customer—but through pricing inducements, you can help them think about existing financing instruments they could potentially access. If you traditionally charge ~$9K up front for a seat of your solution for a 12-month contract, but the customer states they don’t have the budget to swing that, you can offer monthly pricing of ~$999 for a 12-month contract. Monthly payments are undesirable to you, in that they can become a collections issue, and typically you would love to have that cash in hand to cover payroll.

However, offering this option can help get a deal done in a couple of ways. Over the course of a year, that would amount to ~$12K, 33% more than the organization would otherwise pay. Once the opportunity cost of taking that approach becomes clear, the organization can figure out how to rustle up that ~$9K and save itself ~$3K over 12 months.

A hybrid approach is to start with monthly payments (at the rate that is higher than the up-front price), but offer the customer the ability to pre-pay the rest of their tab at any given point of time. This can work particularly well when your solution drives a cash-centric ROI.

exampleIn addition to finding missed fees, HIRABL’s solutions help staffing agencies sniff out new business opportunities when candidates they’ve previously placed moved to new organizations, or hiring managers they currently work with move to new organizations. All of those things represent new revenue for a staffing agency using HIRABL. The challenge can be that that ~$30K missed fee or fee from a new client might not show up for a month or two after the organization starts using HIRABL. No problem! What would have been a ~$20K license for 20 recruiters for the year can be broken down to ~$2.2K a month. And then when that first ~$30K missed fee comes in, the client can decide to buy out the rest of that contract and save himself the 33% on whatever remains on the term. Win, win!

I Need a Trial or a Reference

cautionThis is one that will show up frequently, and you need to be careful. The concept of a trial is not a bad one. In fact, a demo that is well tailored to the prospect, ideally including his organization’s data, is pretty darn close to a trial. And the notion of a customer reference is a good one too; it is an example of a powerful piece of proof data. But you need to use caution here for two reasons: One, the prospect may be using this as a way to avoid saying no or surfacing the actual underlying objection, and simply putting off a decision. And two, you don’t want to lose control of the deal or add unnecessary time and complication to it. When someone asks for a trial, and you just flip him a set of credentials with no structure, you’re simply asking for him to come back at the end of the week and say, “Wow, yeah, I didn’t get to this. Can I have another week?” Make sure this doesn’t happen to you, as it wastes your time, hurts deal momentum, and plants the seed in the user’s head that he may not end up using the product after he buys it (he isn’t using it right now, right?).

When the prospect says, “I need a trial,” really what she is saying is, “I’m not sure I believe this, and I need more proof points, ideally ones that I can hold in my hand/see in my browser.” Her proposed solution to that is a trial (vague, abstract, but something she feels would help achieve this goal of seeing it with her own eyes). You can often address this very easily by asking what she would want to see to help address her concern.

example“I’m happy to help you get more comfortable with the value the solution provides. What sort of further proof would you be looking for?”

You will be amazed how many times this turns out to be something as simple as, “Well, I’d like to see some proof of prior success.” That can take the form of marketing collateral focused on qualitative and quantitative proof of a better solution, like customer success stories, ROI studies, or customer references. Conveniently, you should already have a bunch of this documentation in hand—in your deck appendix, for instance. In fact, she may have already seen it and now just needs to be reminded. So great! Use that as your means by which to surmount this issue without adding more time and complication to the deal.

But if instead the prospect is eager to see what the tooling looks like in her own hands or the hands of her team, and won’t be satisfied with collateral, that’s fine as well. When a decision-maker wants to have the team look at something, often they’ll use the term trial when what they really want is another demo for the larger group—in which case, great! That will be a good opportunity for you to do value selling in a presentation and demo to this new group of stakeholders. Offer to do just that:

example“Showing this to your team sounds like a great idea! I would love to give them a guided tour, and let them get their hands dirty with my help.”

If the goal is further understanding of how the UI works, or the usability of certain features, you can achieve that with a guided walk-through or ride-along. Schedule another meeting specifically to walk through all the pieces of the product that the prospect might want to investigate, and let her control the mouse and screen so she can see how things work and satisfy her curiosity.

exampleAt TalentBin our sales reps would often schedule a follow-up hour after the initial demo to do just this, and let the prospect click around and make sure that the demo she saw wasn’t smoke and mirrors—and that when she controlled the mouse, the profile volume and quality was just the same.

Of course, you’re there the whole time, to support prospects if they get sidetracked, add commentary about the value of the various features they’re using, and, most importantly, make sure the product actually gets used.

cautionIf your product is not set up for freemium usage, or unattended trial, just handing users the keys to the car and assuming they’re going to know how to use it as well as you or one of your customer success staff, is a terrible idea. They’re not going to be experiencing the product the way they would after they’ve been fully trained and gone through an implementation process. Now, if your product management and engineering staff has invested in features that help users get to value quickly, by all means, you should leverage that (and you probably already are for the purposes of lead generation). But if that investment hasn’t taken place, do not assume that your prospects will just magically get it if you let them have an unattended trial. Rather, if they actually end up using their trials (a big if), they will likely run into small issues here and there that stop them in their tracks and lead them to blame the tool. And that’s hard on your deal.

While the grand majority of trial requests can be handled in the ways outlined above, more mature buyers with better process may seek to do a formal pilot—a time-bounded experiment where they go through certain key actions in the product to see examples of the promised ROI.

exampleWith something like Textio, prospective buyers might want to optimize a single job posting, and set it live on Monster to see how it performs compared to their existing postings. Or with TalentBin, they might use the tool for a week to execute outreach to candidates and gauge responsiveness.

importantIn all of these cases, frame the pilot in a way that makes it clear how success will be defined, and for prospective buyers to be held accountable for participating in training sessions and check-in meetings and acting on defined activities, which they know will be instrumented and reportable. To the extent that you can remove the risk of non-execution on their part, you should seek to do so, because the biggest issue in trials is always non-usage.

As you can see, all of sudden it becomes clear that you only want to be doing this for the largest deals, where there is a lot of revenue opportunity. It can be worth it, but you need to be realistic about the associated time costs (you could be doing demos for new, potential slam-dunk prospects who don’t need a structured pilot to prove things out). Include that time cost in calculating whether you want to offer a structured pilot.

The alternative is not an unstructured pilot, as that will simply blow up your deal. So for small customers who may not be worth the time associated with a structured trial, you can draw the line in the sand and say:

example“We don’t do this because people don’t use it and don’t have success, and that’s not fair to them, nor to me. I am committed to helping you get comfortable with this solution ahead of purchase, so we can do an hour-long guided session where you have control. But I can’t do an unguided trial.”

If this comes up enough, you can decide to prioritize product and engineering resources to make unstructured pilots and self-serve usage an easier process. Raised close rates and faster deal times may justify the investment, much the same way you can build in features that make demos better and more tailored to prospects. But just tossing the keys to a prospect is usually a losing proposition.

Solution-Specific Objections

We’ve looked at the major buckets of objections that show up regularly, regardless of the specifics of your solution. But that doesn’t mean those are the only ones you’ll run into. Undoubtedly, a number of objections that are specific to your market and your solution will pop up again and again. This is to be expected, and like the generic objections above, should be viewed as a positive—it’s a signal of an engaged prospect who’s actually thinking about how your solution could potentially impact her business. So you should be ready to knock those objections out of the park.

Because I don’t know what those specific objections will be for your solution, I’ll just talk to a generic framework for handling them, and then you can apply it as appropriate. Solution-specific objections will usually involve questions about whether this is actually a better way to solve the problem your solution addresses. So the best way to tackle those is using the same approach you did in your core narrative: with quantitative and qualitative proof—ideally documented in the form of a slide!

exampleSay that you’re HIRABL, selling software to help catch missed contingency recruiting fees. A prospect might believe everything you’ve discussed, but might be concerned that even if you surface these backdoor hires to them, they won’t be able to collect on the fees that they’re owed. So how would you address this objection? Well, you might point out your clients’ aggregate collection rate to give them comfort. Or you might talk about how catching backdoor hires quickly, within a few weeks of the hire, makes collection many times more likely to happen because it’s still in the “Whoops, that was an accident!” phase. Or you might talk about how your customer success staff has all sorts of tools to help broach those topics with clients, so the prospect need not worry about angering them. Or you might do a combination of all of the above!

As touched on in the section on sales decks, I recommend that if you hear an objection a couple of times, you might as well build a slide to address it and put it in the appendix of your deck. This has the benefit of making you look like you’re super prepared and expert in all things regarding your solution. It also acts as a handy little script so you can nail all the points you want to make when handling that objection. Beyond this, you should also just keep a running list of objections in a living document, like a Google Doc, so that you can refer to them as necessary. Moreover, when you start hiring reps to help you scale your efforts, all of those objections, and their associated responses, will already be ready for them!

If an objection gets to the point where it shows up very frequently, you can make the call to actually include it in the main part of your pitch and narrative. This can be a two-edged sword, because you’re now proactively bringing up a potential concern that the prospect may not have thought of on her own. But if it’s such a common objection, it’s often better to just bring it up, and demolish it, proactively. Otherwise, the prospect may not think of it until later, when you’re not present, and have to reason through it on her own without your help.

exampleWith TalentBin, this might have been something like “Now, I know what you’re thinking. ‘Do candidates get weirded out by the fact that you know everything about their activity on GitHub, Stack Overflow, Twitter, Meetup, and so on?’ It turns out, they’re pretty used to it, since they know that this information is readily available on the web. And moreover, they view it as a positive, because it demonstrates that you’ve gone the distance in actually qualifying them for this potential role, as compared to many recruiters who just spray and pray job opportunities willy-nilly. So yeah, they prefer this approach! In fact, you can see how preferable it is by the 3x email response rates recruiters get with TalentBin, versus sending generic LinkedIn InMails, based on a study our customer success team ran.”

Competition Objections

Competitive objections can be a really helpful way of proactively framing the conversation around other players in your market. While bringing up competition proactively can be problematic, if the prospect brings it up, you should jump all over it. First, if you already know, based on your discovery questions, that the prospect has a competitor in place, or is considering one, you can take the initiative to address it. Or, if that didn’t arise in discovery, but a question asked later in the pitch indicates that he is thinking about competition, you can run with it.

importantWith competitive objections, be sure to not just address the one-off objection—which might show up in the form of a single feature-comparison question—but rather to frame the competitive conversation in the context of your existing messaging. That way, if the prospect ends up interacting with the competition again before you close the deal, you’ve planted seeds of how to think about the holistic comparisons between the two solutions.

exampleTake TalentBin again. Occasionally we would get asked about code scoring for the recruiting profiles our talent search engine built, because one of our competitors, Gild, had long ago acquired a small code-analysis project. They ostensibly used the technology to make judgments about the quality of a given engineering candidate based on the code she had published on GitHub. When given an opening, rather than just addressing that one point, we would use it as an opportunity to frame the whole conversation about competition, specifically around how our solution was vastly superior when properly evaluated along all relevant vectors (not just this one particular one).

For example, we might say something like “Well, that’s a great question! We actually use a number of data signals in helping to understand what a given candidate is into, professionally, and we can talk more about that in a second. But importantly, when we think about talent search engines, it’s important to think about all parts of the talent search process: search and discovery, qualification information, contact information availability, and then outreach and pipeline management functionality and automation. Your question touches on data that can be used for both search and recall, and also qualification of particular candidates. On that front, TalentBin consumes candidate data from the broadest set of sources available—not just places where code is published, like GitHub, but dozens of other sites like Meetup, where folks demonstrate their interest in various software engineering technologies. We look at candidates’ online activity with the widest possible lens to make sure you can see all the engineers who have a skill you’re looking for. Isn’t that great?”

So we would take the one-off question, “Do you score code?” and address the question that’s under that question: “Can you help me understand how you use data to help me hire software engineers, and how does your approach compare to this other approach over here?” This strategy works for most objections. As they talk about in press training, “Answer the question you wanted them to ask.”

From a materials standpoint, like with other solution-specific objections, it’s good to have a slide, or potential slides, to support this conversation. To start, you could have a slide that presents the competitive framework that’s pertinent to your solution and the ways your solution wins out in those buckets. And assuming you have multiple competitors, you could have one of these competitive roll-up slides for each. (You wouldn’t want to feature multiple competitors on one slide. There’s no need to present to a prospect the other solutions she might want to research.) Later, a more advanced version of this is to have competitive mini decks for each competitor of merit, including a handful of slides that describe how your solution and the competitor stack up in each bucket of your messaging framework. But that’s pretty advanced. To start, a single slide per competitor of merit is good.

Generic Objection Flow Loop

Regardless of the type of objection, whether it’s one of the more generic ones or one that is solution-specific, the pattern of handling them remains the same. You want to catch the objection; turn it to the question under the question; respond to the objection with quantitative and qualitative arguments that prove the case, supported by visual and textual sales materials; validate understanding of these arguments (“Does that answer your question? Does that make sense?”); and then pick up where you were before that objection. As you drive to a close, keep uncovering any further objections with questions like, “Do you have other questions, or are you satisfied that this would be a fit for you?” As you can see, this is a loop, where you handle an objection and then return to your close to handle the next objection, repeating until there are no more objections left (or the prospect has made it to the other side of the persuasion threshold, and they’re willing to take the leap even with other objections outstanding).

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.”

By setting these meetings, you are minimizing the risk that open-ended tasks will derail your opportunity. Meetings are a great way of doing this, but you can also use methods like setting a CRM task for yourself as a reminder to note whether the prospect executed on their commitment (“Did Jeff get back to me about pricing?”). If the micro-contract was articulated in an email (which I recommend, even if it was already made over the phone or in person—better to memorialize it in text), then there are helpful tools like Boomerang, Yesware, and Tout that let you bring an email thread back into your inbox at an appointed time, depending on whether or not the recipient responded. In the case of these micro-contracts, I like to set the backstop to bring the thread back into my inbox regardless of whether the prospect responded to it, because I would hate to forget about it just because he responded with a quick, “Yep!”

Then, once a micro-contract for the next action is concretely agreed, execute on it as quickly as possible. This is one of the reasons why in Prospect Outreach and Demo Appointment Setting we discussed the importance of having time blocked directly after a demo to allow for immediate execution of follow-up actions. If you have to jump right into another demo, you will be less likely to immediately execute on your part of the micro-contract, which puts you at risk of forgetting about it. I have found that prospect commitments have a time decay rate. The faster you deliver on the part that you owe them, the faster and more likely they are to execute on their commitment. So in addition to being clear about who owes whom what, be quick in the delivery of what you promised.

importantWhile there are different permutations of follow-up based on what was discussed in the call, there is a set of actions that I feel should always be included. You need to always follow up a demo with a summary email, ideally in the thread that set the appointment (or perhaps in your demo reminder email) to provide continuity. By systematizing this, you’ll always have a virtual venue where you can deliver on the commitments you made in your call, and provide a digital trail for your prospect to refer back to. In addition to whatever items you committed to deliver in that follow-up email, I am a big fan of including the version of the sales presentation you used in the call, as we discussed in the Early-Stage Sales Materials Basics chapter. You may have had an amazing demo, and blown their socks off, but human memory is a fickle thing. If you send a deck, with any appendix slides that were particularly important, you’re guarding yourself against lapses in recollection.

And like the generic objection loop that we discussed above, this post-meeting follow-up loop continues after every meeting, unless the opportunity is either closed-won, or closed-lost.

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

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.

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