Early Sales Management and Scaling Concepts

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Early Sales Management and Scaling Concepts

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

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

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

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

Scaling Anti-Patterns

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

Premature Scaling

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

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

exampleImagine a scenario where a founder thinks that he’s figured it all out, even though he hasn’t sold the requisite few dozen deals on his own to prove that the product solves the problem that it seeks to solve, that the customer does indeed get value out of it, and that the customer is willing to pay for that value, and do so on an ongoing basis. Instead, in this scenario the founder hires a VP of Sales at ~$250K total compensation, with a six-month draw (the leader gets his whole target salary, ~$125K, for at least six months while the team ramps up), and that sales leader in turns hires three SDRs at ~$80K each, and three AEs, each of who target a ~$150K total compensation, each of whom are on a three-month draw. In this scenario the founder just added around ~$70K of month burn. Now, this can be totally fine, at scale, if each of those AE and SDR combos that costs ~$20K a month can deliver something like ~$80K+ of bookings (ideally paid up front) per month.

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But that’s the sort of sales efficiency you would typically see only after the sales and success motion has been honed by a founder who engaged in founder-led selling for dozens and dozens of opportunities, resulting in a couple dozen deals, and then proved that this could be repeated with some reps that the founder herself hired. Rather, in this case, what you would typically end up seeing is a bunch of AEs who don’t cover their own costs—because they can’t close enough business to cover their own salaries plus that of their SDR partners and their share of the sales leader’s salary they need to cover. And then things get even worse from there.

Because the AEs are being relied on to define the Ideal Customer Profile, and simultaneously are expected to close business, they’ll start selling to anything with a pulse, regardless of whether or not that prospect will actually get value out of the solution. And sometimes those reps will have success—which of course is good in the short term, because that AE will at least defray some of his own cost, but in the long term is terrible, as that “bad” customer becomes a drain on customer success resources. Moreover, when that customer comes up for renewal, and churns out, it will hurt your metrics, and your ability to raise further capital, because it’s clear that customers aren’t getting value out of your solution. It’s no good.

cautionSome good recent examples of premature scaling can be seen in the cautionary tale of Zenefits, who sold epic amounts of deals without fully considering the costs associated with servicing the customers they brought onboard—creating a situation where as reps sold more and more deals, they had more and more negative unit-economic customers on the books bleeding the company dry of resources. Eventually this led to massive layoffs of these inefficient reps who loaded the company with upside down customers.

The payments company Square had a similar situation when trying to take their Square Stand product to market into higher-end retail outlets beyond basic coffee shops in 2014. Instead of de-risking their go-to-market and first validating at a smaller scale that this new product fit the new market they were going after, Square hired 20 fairly senior AEs—all with substantial salaries—raising the burn of that business unit dramatically, under the assumption that they would be selling into higher end segments. They eventually realized that the product did not have the functionality required for those customers, which showed up in unsatisfactory win rates as compared to lower-end, coffee-shop deals that had previously been their bread and butter. They started to react to that, but unfortunately their hiring profile for AEs was far more senior than necessitated by the high velocity, transactional sale that Square Stand coffee-shop opportunities required. Ultimately most of the team left or was let go after having wasted large amounts of time and salary expense.

The good news was Square has senior leadership whose reputation made it easy for them to raise lots of capital, and they had an existing Square Reader and Register business at the low end to help sustain them. But it put a huge cash divot into that business unit while they were figuring it out—the kind of cash divot that would destroy a smaller company with less capital firepower behind it.

Lagged Scaling

The other anti-pattern you commonly see in scaling is simply not doing it. This is different from organizations that think that they don’t need to do sales—we already addressed that in the first section of this book. Rather, this is the situation where a founder or early salesperson has gotten good at selling the solution and can reliably and repeatedly turn new meetings into closed deals at a consistent win rate. But rather than recognizing that they need to move on from just turning the crank on more deals, they get stuck doing just that, either motivated by running up the customer count, or because they’re unaware of the need to move on, or afraid of the next set of challenges that need to be addressed.

cautionWhatever the cause, this failure mode, while less common than premature scaling, and also less existentially threatening, is problematic in its own way. Unlike premature scaling which threatens to burn cash reserves and shorten your runway, lagged scaling is more about eating opportunity cost. Once you have proven that a founder can reliably sell the solution, the next step in scaling the organization is packaging that ability so it can be scaled out across multiple sales reps—which is the key to scaling a B2B sales organization’s revenue acquisition. The more time that is wasted before moving from doing to packaging and then proving that this de-risked sales motion can be replicated by others, the more time is lost as your runway shortens. (You likely have far more engineering salary expense than revenue at this point—so the quicker you can ramp up your revenue acquisition, the faster you can get to cash flow.) And that time is lost to competitors attacking the market.

Moreover, consider that your goal in building your org is to build enterprise value as quickly as possible. The means by which organizations are valued for either acquisition or public flotation is multiples of revenue, so time lost acting as a sales rep when you could be acting like a sales manager, and adding multiple units of revenue production (sales reps!), keeps you from building enterprise value in your org.

When Is the Right Time to Scale Sales?

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

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

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

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

exampleImagine that a rep can do five new prospect demos a week, and 10 other follow-up meetings in a week. That’s 20 new potential deals a month (5/week times 4 weeks in a month), and if he can win four of those deals (20%), and each deal is worth ~$10K, that’s ~$480K in a year—not a bad clip. But now imagine that the win rate is 10%—even still doing 5 new demos a week, with 10 follow-up meetings, and the same average contract value of ~$10K, that rep will only be able to do ~$240K in revenue per year. If he costs you ~$100K all in with base salary and commission, that’s a 40% cost of sales—only ~$140K is left over for marketing expenses, customer success costs, paying for engineering salaries, and so forth. No good.

This is why having a good win rate, coupled with a good average contract value and a reliable and consistent deal cycle is a good leading indicator of being ready to scale up to that first step. Otherwise, you’ll be hitting the accelerator on a car that leaks most of the gas out of the engine.

Abstraction and Specialization of Sales Roles

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

Full-Blown Role Specialization

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

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

Ultimately, assuming you have the revenue model that can support it, specialized roles, with SDRs setting appointments, AEs pitching and running deals, and CSM/AMs farming accounts, is the gold standard of a B2B revenue acquisition apparatus in the twenty-first century. That said, there can be situations where specialization is not merited. If the majority of your deals are one-call-closes—transactional, with low average sales prices—then it might just make sense for you to have junior reps who act like closing SDRs.

Generally speaking, specialization makes sense when efficiency gains offset enlarged coordination and complication overhead—which for higher-sales-price, longer-sales-cycle situations is typically always the case, with some exceptions.

Specialization and Sales Maturity Stages

importantOf course, I don’t recommend jumping straight to the end state of a fully specialized sales organization just as you start to scale up. Rather, you need to approach the scale out of your sales and success organization by validating hypotheses like you did when proving your sales motion—by getting more complex, step by step, and figuring out what’s broken along the way, and then fixing it before you take the next step. This is your number one job at this stage of the organization.

What are the steps? And what do you need to be focusing on at each stage, and what are the exit criteria for moving on to the next? We detail them below.

Founder Doing It All

This is what we’ve largely been addressing up to this point in the book. A business founder engaging in lead gen, outbound appointment setting, pitching, demo, and closing, and then customer success for an early set of customers. The goal of this stage is to prove that you can reliably convince customers that your solution is valuable, get them to use it in a way that demonstrates that your product moves the relevant business metrics for the customer in a way that they desire, and prove these customers will pay for the right to have those business metrics positively impacted like this.

The exit criteria for this stage is a handful of early customers paying money in exchange for the value your product provides. And, after being implemented and using the solution, that group of customers continues to both use the solution (acceptable levels of engagement) and believes the solution provides the value being paid for—such that if another prospect asked them about the solution, they would say it’s worth the money. And when it comes time for renewal, they will do so.

The main anti-pattern for this stage (as is largely the topic of this whole book!), is hiring a “salesperson” to figure it out—throwing the product over the wall to someone who was not involved in customer development to execute. “Sprinkle some sales on it.”

Other anti-patterns are not charging for the solution, thus not proving the actual value exchange and, a common one, selling the solution but not investing sufficiently to prove that the customer attains the promised value (you got money, but they did not get value, and they’ll eventually churn).

Founder Plus SDR or Founder Plus CSM

This is the first step of abstraction we referred to quickly in Down Funnel Selling. Because the process of prospecting qualified accounts and contacts, and then engaging them with outbound email and calling behavior with the goal of setting up appointments is more basic and packageable than pitching and giving demos, assisting a founder-seller with an SDR can be one of the first ways of putting specialization into your sales org. It’s a tried and true way of getting leverage for a founder-seller, and leaves you with more time to focus on nailing repeatable selling and success activities by filling your calendar with new pitch meetings, relieves you of prospecting work, and leaves you more time for doing customer success.

Figure: Adding an SDR to Increase Specialization

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Source: TalentBin

That said, another way of providing specialization can be by adding a Customer Success management resource to assist the founder-seller in supporting these early customers that you’re onboarding. This approach can make sense when lead generation and appointment setting isn’t a time suck for the founder-seller. If, for instance, the founder-seller is very well networked, and getting access to new prospects to engage is relatively easy, then the more important place to get leverage can be in packaging up the to-date validated customer success model and handing that to a CS rep or CS lead to run with and evolve, so the founder-seller can focus her time on scaling up customer acquisition faster. In both cases, the notion is to abstract off part of the founding seller’s workload into another specialized resource.

Figure: Adding a CS Rep

chapter10-founder-lead-selling2.png

Source: TalentBin

The exit criteria for this stage would be a few dozen customers acquired, onboarded, and getting to success, along with a clear, repeatable, documented sales motion, ready to be tested on one or more new, non–founder-sellers, all while maintaining healthy sales KPIs, like win rate, attainment (in a monthly or quarterly period), and so on.

cautionThe anti-pattern here would be trying to get someone else to do this for you—hiring a “salesperson,” or even worse, a VP of Sales to prove out that this is repeatable a handful of times. Another is acquiring a bunch of customers, only a fraction of which get to success—also known as “spraying and praying.”

Founder Plus SDR and Two AEs

This is the stage where we start seeing the beginnings of true leverage setting the stage for scale. The goal of this stage is to prove that someone other than the founding seller can sell the solution. The key activities here are the hiring, training, and management to success of one or more sellers (typically two, to start), aside from the founding seller. There can be continued selling activity by the founder, but increasing time should be focused on proving that these additional sellers can sell the product, in a repeatable fashion. Training, management, coaching, inspection, correction, and tooling are more and more the focus.

The exit criteria for this stage would be those sales reps engaging prospects, presenting, and closing ideal customer profile customers, who are then getting to success and value, at least as efficiently as you were previously.

cautionThe anti-patterns in this case are twofold. This is a Goldilocks scenario. You want to do it just right. The first anti-pattern is gaining too much leverage by hiring too many, too fast. Hiring too many raises burn rates without proof of success, and too many reps makes it difficult for the manager-founder to get each to critical mass. Instead, you try to boil the ocean and none of them end up succeeding.

The second anti-pattern is non-leverage. Instead of focusing on proving AE1 and AE2 can get to success, the founder spends too much time still playing instead of coaching. Doing so robs the future of the company by slowing the process of packaging and distribution of the sales motion into something that can be dropped into 5, 10, n reps in the future.

Figure: Adding Account Executives

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Source: TalentBin

Initial Sales Pod

This is the next step in specialization and scale out, where the founding seller now steps entirely out of the day-to-day work of selling. The goal of this stage is to prove the successful performance of a complete unit of revenue production, including lead gen, selling and closing, and onboarding. The founding seller is now focusing her time fully on sales orchestration refinement and management, sales process definition and implementation, along with tooling creation and adoption. If previously there were no specialized customer success or sales development staff, now is the time to introduce that specialized role and work to cement the interaction and rules of engagement between the various functions to ensure they are tight and without gaps.

The exit criteria for this stage is the unit producing revenue at a predictable rate, all members hitting their goal KPIs (meetings product by the SDRs, deals closed for AEs, onboarding customers with high NPS scores for CS), with smooth handoffs and proper back-checks to prevent dropped balls. The unit of revenue production and retention performs with solid unit economics—where the unit more than pays for its own salary costs and throws off cash to the business. You are confident you can now clone this.

Figure: Adding Your First Sales Pod

chapter10-founder-lead-selling4.png

Source: TalentBin

Sales Pod Abstraction and Initial Scale

This is the point at which you can really start to see the power of scale out via replicability, where, by cloning that initial sales pod, you are able to double or triple through throughput of your team.

While the activities to focus on here are largely the same as before, there will be more managerial complexity, as you will be adding more staff, and thus there will be more of a focus on metrics and analytics. This might be the stage at which you add a professional sales manager—though there can be value in proving the successful hiring and onboarding of another cohort or two of additional reps in order to fully develop those management motions before handing them off to someone else.

The exit criteria for this stage is for the complete unit to be producing revenue at a predictable rate, with all members hitting their goal KPIs and successfully returning lots and lots of contribution margin back to the business. You are now confident that you could hand a unit like this to a professional sales manager, and she would be able to manage it, and start cloning these units out, herself.

cautionThe anti-pattern here, though not entirely clear, potentially could be handing the beginnings of this unit off to a manager before fully baking it yourself; or racing through this stage to the next one before proving that this stage was successfully achieved. Another could be not tending to the additional complexity or ensuring that there is sufficient lead generation to power the incremental AEs.

Figure: Cloning and Scaling Sales Pods

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Source: TalentBin

Figure: Fully Scaled Sales Team of Teams

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Source: TalentBin

Sales Operations

As a note on sales operations as part of scale out, as described above, sales operations (and also sales enablement, sales effectiveness, and sales strategy) are efforts that are focused on making the entire machine that is the sales organization more fluid and effective, using metrics analysis, process refinement, and technology adoption to facilitate that goal. You might think that this is something that is the responsibility of sales leadership and management, in general, and of course you’d be right. But sales operations is a pure refinement of this—where their job is purely focused on those efforts, whereas those efforts are just one thing of many that sales management and leadership are responsible for.

Typically, introducing sales operations will make sense when you have enough reps that a single sales ops headcount salary, blended across all the reps, will be worth the time savings and revenue lift that stems from the addition of that headcount. It can vary, but this could be as early as ten reps.

exampleIf an ~$80K sales operations person can help each of your five sales pods composed of one AE and one SDR each deliver ~$50K more in bookings per year through better process, automation, and technology adoption, then ~$80K of salary for ~$250K in incremental bookings seems like a sweet deal to me! Now imagine that leverage with ten sellers. Sales ops is a powerful tool.

Even before you decide that your sales org is ready for that investment, that doesn’t mean that this isn’t anyone’s responsibility. Rather, it falls on the shoulders of you as the leader, other leaders and managers, and even to the reps themselves. I like to think of this as product management of the sales org, where we are constantly looking to enhance the go-to-market through the removal of existing friction and problems (product bugs), and by adding functionality to the sales org (product features).

Early Sales Management

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

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

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

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

The Role of the Sales Manager

Much the same way we discussed Mindset Changes for First-Time Sales Professionals at the beginning of this book when characterizing how the mindset and behaviors of acting like a salesperson are substantially different from that of other professionals, it’s important to proactively point out here that moving from the role of founder-seller (or even just seller) to sales manager also requires a substantial mindset change.

importantMost of the changes in actions and mindset flow from one high-order change: you are no longer supposed to be doing sales but instead are now focusing on helping others do the selling. As noted above in the discussion of scaling, the way that B2B sales organizations get leverage is through more reps—your job is now to achieve that scale through the successful hiring, onboarding, training, monitoring, and coaching of reps. So any time you find yourself doing actual individual sales work—doing a demo, sending a prospect-facing email, and so on, you want to ask yourself if you need to be and consider instead a manager activity you could be doing instead.

As an example of why this matters, let’s say you’re a really good founder-seller. Because I mean, you read the first parts of this book and totally took it to heart and implemented it, right? So now you’re a total killer. You close 30% of the first demos you take, and do so at a ~$50K average deal size. And your poor reps, they’re good, but not as good as you. They only close deals at a 20% rate, and their deal sizes are only ~$30K. So you should be running deals right? You’re so much better, right? Nope. Wrong conclusion.

That incremental ~$80K you book per month, ~$30K over your other reps’ ~$50K per month is nothing compared to adding four more reps, each of whom becomes a machine pumping out ~$50K a month. Moreover, it’s unlikely that you’re inherently magical (sorry), and that only you can close ~$80K of business per month. If you can, they probably can, and thus you need to be figuring out how to make it such that they have the same win rate and average deal size as you. Again, the goal is to hire, onboard, and get your incremental reps to ongoing success. That is the way you will win as a sales manager.

cautionI see this anti-pattern all the time in more mature organizations—especially when seasoned sales management is brought in from larger sales organizations like an Oracle or IBM or SAP or what have you, where there are specialized recruiting, onboarding, and sales operations functions in the organization that take care of many of the true tasks of management. When these managers transition to startup sales management, rather than realizing that the key lever they have to hitting their numbers is in adding more successful reps and instrumenting their success, they instead spend their time doing actual selling activity alongside reps rather than tending to the pipeline above the pipeline—the hiring pipeline. Don’t make the same mistake—and when your org gets to that larger scale, don’t let your sales managers make that mistake.

Manager Activities

What do you need to be doing with your time instead of selling activities? If there’s a compressed rule of thumb, it’s that you want to be doing sales management activities with leverage. Building systems, playbooks, processes, and materials. Engaging in hiring and onboarding activities, and then later systems and tooling for hiring and onboarding. Monitoring, inspecting, and coaching reps, and later building processes for doing just that. I generally yell at managers who are not doing high-leverage things. When considering what to spend time on, always think “does this action have recurring impact? Does it make more than one person more successful?”

And once you are clear on that set of activities you ought to be engaged in, you need to make space on your calendar to do them. As a manager you can frequently be tempted to jump on calls for the sake of being the big authority in the room—but doing that three times a day means you’ll be robbing yourself of all the time you could better be spending on, say, phone screens with new sales candidates, or mock pitches with new reps, or reviewing team metrics to identify potential soft spots in your team. Make room for the activities of management or they won’t get done—and then you’re not getting leverage, and you risk having a bunch of inefficient, expensive reps bleeding your org instead of contributing recurring revenue.

With all that said, these are the set of management activities that you’ll want to be filling your days with.

Hiring and Onboarding

If the way to get to scale in a B2B organization is the hiring, onboarding, and ramping to success of a large number of reps, then the first step in that process, clearly, is hiring and onboarding. Ensuring success in the pipeline above the pipeline,—your hiring pipeline—is the first step on the way to scaling up. More on this in High-Impact Sales Hiring to follow, but approaching hiring with the same sort of rigor, process orientation, and execution as your selling activities is key.

And while hiring is the first step to success, hiring without rigorous and excellent onboarding and ramp to success is self-defeating. Discussed in greater depth in High-Impact Sales Onboarding and Training, intense, detailed, and rigorous sales rep onboarding is paramount. The old school approach of hiring a class of five or ten AEs, with the expectation that 50% will wash out is a vestige of a time before high-quality, instrumented hiring and onboarding and is massively wasteful.

Successful sales managers focus on filtering the wrong people out in the hiring process and getting the right people onboard and trained up, through tons of hands-on repetition, and off to success—so the manager can then turn to repeating that process with a new cohort of reps.

Process Construction, Adherence Monitoring, and Tooling Adoption

Once reps are hired and onboarded, they need an operational framework within which to perform. It’s your job to construct that, as prototyped in your own founder-selling work, and now formalize that into a stepwise process. The inputs of selling are made available to SDRs, AEs, and so forth, and they are able to act on them, and the outputs are then passed to other parts of the organization for next action, like customer success, all the way to eventual renewal. This typically means investment in documentation of that process—written out in a bulleted process flow, or perhaps graphical flow chart—generally known as rules of engagement. This is where you start to really understand the difference between being an individual seller and a manager of sellers. No longer can you keep in your head what the qualification criteria are for an ideal-customer-profile prospect. You have to write it down, make it available in a Google Doc, and make sure all of the SDRs and AEs have seen it, know they are responsible for acting based on those criteria, and have a means by which to come back to it and refresh themselves if they forget.

This is particularly important when you have a multi-step, specialized sales motion that involves SDRs, AEs, and maybe even CSMs or AMs, where there are points of customer handoff, and where responsibilities are split amongst different actors.

With this process formalized and well documented, then the work turns to monitoring the execution of the process parallelized across the reps that you have, verifying adherence and looking for soft spots where either reps need to do a better job of adherence or the sales process itself needs refinement. Also involved in this is tooling selection and administration, in that tooling (like better CRM administration, reporting and analytics, and various sales automation solutions) is typically a force multiplier. This function is what’s typically thought of as the bread and butter of sales management—but in an early-stage environment, it’s only one part of the job, and is contingent on the above described prerequisites being in place.

Metrics Harness Construction and Monitoring

importantWe discuss this in far more detail below, but the construction and monitoring of a sales performance metrics harness is the sibling of sales process excellence. Understanding the quantity and quality of sales activities that need to be done by your reps, who is meeting that bar and who isn’t, and why, is a requirement of the modern sales manager. A good metrics harness will help you with all of the above and below sales management activities by providing an early-warning system for if things are not going according to plan, either for an individual in his ramp period, a rep who’s been selling for a year, or, more importantly, across a whole team or team of teams, which can be indicative of a shift in the market. A strong metrics harness will allow you to see all of this and act accordingly to correct. (Making this way easier and way better than the status quo is why we started our performance analytics company Atrium.)

Inspection, Coaching, and Correction

Beyond getting out of the business of doing pure sales work, the second biggest shift in mindset required in sales management is getting used to telling reps what to do and correcting them when they are off. As a first-time manager, this can be truly mind warping, but it’s of paramount importance. If you’ve hired and onboarded a set of reps but aren’t ready to proactively instruct, coach, and correct them when they go astray, you’re setting yourself and your org up for eating substantial opportunity cost. You can have the most rigorous, efficient sales process specification in the world, but if reps diverge from it, and you don’t correct them, it doesn’t matter. You can have the most precise, nuanced metrics harness, but if you aren’t willing to take a concerning metric (say weakness in the ratio between first meetings and follow up meetings for an AE, or even just the raw number of customer meetings an AE is having) and dig into its root cause with a rep, and correct the causal behavior, what’s the point? Inspection of sales activity and identification of improvement areas, coupled with the correction of underlying issues, is vital.

I understand that it may feel weird to tell someone, “No, you said that wrong,” or, “The way to present this slide is by saying, X, Y, Z,” but it’s something you’re going to have to get good at. Otherwise you’ll be at the mercy of the reps you’ve hired and their ability to magically self-coach and correct—which, don’t get me wrong, if you’ve hired and onboarded well, may be a pretty solid ability. By why would you stop there?

importantYour ability to inspect activity and then communicate correction like this is key to your success as an information router in your sales org. You are the one responsible for routing the correct behavior in the pertinent context to a struggling rep, or discovering an emergent best practice innovated by a rep, centralizing it into your sales org’s collective knowledge, and then, importantly, pushing it back out to the rest of the reps—and ensuring that they adopt. If you aren’t comfortable with digging into a rep’s activity as necessitated by something you saw in the metrics or heard on the sales floor, you’ll end up with reps not adhering to process, not presenting messaging in the best way possible, and ultimately injuring their win rates and bookings.

cautionAnd if you aren’t comfortable with identifying the root cause, communicating the shortfall, working with the rep to resolve it, and validating that the fix has stuck, not only will your sales efforts suffer but you’ll also end up fostering an environment of moral hazard in your sales org—if reps know that they can get away with not adhering to process, unsurprisingly, you’ll see less process adherence. Moreover, if they know that you know process non-adherence is happening, and you still aren’t doing anything about it, well, now you have a situation where you can end up with a full-blown rudderless sales org.

What other things will you not correct? Seller activity levels? What about quota requirements? What else? This is why this behavior change is so key as a manager. There are plenty of resources on how to best navigate those conversations, but you must, with directness. This article on being a good boss (based on the related book Radical Candor by my friend, Kim Malone Scott), is one of my favorites. And this document on making performance conversations easy from Atrium is a good one too.

importantAs a note, the above is why it is so important that you, as a founder-seller, initially sell a statistically significant number of deals yourself. By doing so, not only are you discovering and building the selling motion that other reps will adopt but you are building your confidence in that sales motion. You are fully empowered to correct divergences from this process because you know it works. You did it. And that puts you in a strong place from which to inspect, coach, and correct. Imagine the alternative.

If you have not sold a number of these deals yourself, you may have a hunch about why something isn’t working—but do you really have much proof as to why one approach over another is the right one? And even if you’re right, are you in a strong spot to make that argument? “Come on, you’ve never sold a day in your life, it’s clearly the product isn’t any good.” And so forth. A terrible spot to be.

Same with an excellent metrics harness (more on this below). If you are without a solid instrumentation harness monitoring your team, and the individuals within it, you’ll be hampered in not only your ability to catch issues early. But even if you are able to catch issues early, your ability to coach them will be impinged.

exampleImagine a scenario where a rep is having bookings attainment issues. You have a theory it’s because he’s not winning as many of the opportunities he is assigned as his peers. But unfortunately, because you don’t have win rates instrumented, you may have a hard time making that argument. Moreover, he might just say, “it’s actually because I’m not getting enough new opportunities” (get ready for the age-old “We need more leads” rep complaint—you’ll hear it a lot). Without having a good metrics harness in place that instruments all parts of the sales motion, you’ll be hampered in your ability to diagnose and then act to correct, because without data, there can be room for disputes. And guess what—sales reps are good at objection handling and persuasion!

Materials and Documentation

Another key sales management activity you need to prioritize spending time on is documentation and material creation and maintenance. Exciting, right? Nope, not at all. But extremely important. As you grow, building materials for asynchronous consumption by onboarding reps, and reps who are already ramped, is a key way to get leverage in your org. No, it’s not sufficient to write an email to your reps once with the proper way to handle an objection. Or dumping it into a Slack channel, never to be found again. (Lol.)

Rather, these are opportunities for building documentation and tooling that houses this information in a way that is consumable by reps, on their own, or even if they struggle to find it themselves, you can quickly route them to the information rather than having to re-create and re-articulate the information. Yes, we are quite literally taking advantage of that age-old technology, the written word—well, and video recordings, and online shared documents, and so forth. But the core tenet is the same: you should be looking for opportunities to document processes, messaging, materials, and so forth.

You might be thinking “Ugh, that really sounds like a lot of administrative, secretarial work,” and you’d be totally right! But this is your job now! Unfortunately, the reality is that your reps won’t proactively decide to create a centralized document with common objections and their answers. And they won’t proactively decide to centralize a repository of call recordings from the best demos your team has done. And they won’t create new slides to reflect newly shipped features. So you have to. Because if you don’t, they won’t have access to that right answer, and instead will make something up. Or they’ll do their best, and present a partially right answer, which is better than nothing. But it’s nowhere near as good as it could have been if they had that information collated for them. And they certainly won’t take the time to update those materials on an ongoing basis.

importantEvery time you do this, and every time they leverage those centralized email templates, objection responses, new slides for new features, updated and fresh sales deck, they will be selling better because of your efforts. And this is a key point of managerial leverage. You making sure that all your reps are equipped with the latest sales deck, with all the most refined messaging and product screenshots, published into Docsend, Showpad, HighSpot, or whatever tool you use for sales materials management will be multiplied across all 5, 10, 20, and so on of your reps. But if you don’t do that, instead all 5, 10, 20, and so on of them will be dying a death of a thousand cuts, day in and out, as they don’t have access to those materials. So do it!

Performance Management, Professional Development, and Offboarding

The last major bucket of activities to spend your time on as a budding sales manager is people and performance management—the professional development of staff, and, in the event that the development doesn’t meet requirements, the managing out of reps who aren’t performing at required levels.

With respect to professional development, this will be focused on identifying growth opportunities for individual staff and soft spots that need correction, and then working to resolve them. Typically this is implemented via staff one-on-ones (more on this in operational cadences below) and quarterly/bi-annual/annual performance reviews. But the key to successful performance reviews is to ensure that frequent, regularly cadenced, documented performance management conversations are happening. In the short term, these sort of performance conversations would revolve around tactics to improve desired sales outputs—for AEs, more and bigger deals and for SDRs, more and better opportunity creation, and so forth. This would be the venue where issues that were discovered in metrics review can be discussed, potential solutions can be prescribed, and progress against these prescriptions can be checked in on until the issue is resolved.

exampleIf you had noticed that an SDR was having problems with his appointment hold rate, this would be the place to investigate what the root cause of that problem might be and prescribe a potential solution. Your course of action might be sending meeting reminders to prospect attendees the morning before they are supposed to have a meeting—and then setting a reminder to yourself and the rep to see if this prescription is being implemented, and that it’s having the desired impact (raised meeting attendance rates) two weeks in the future from that.

Over longer time spans, staff professional development should focus on helping reps grow and achieve the next step in their career. While addressing performance shortfalls and improvement areas in the short term is important, you also want to keep an eye on helping them get to the next natural step in their career, because if you don’t, someone else will, and you’ll be left with reps churning out of your organization.

If your goal is to hire, onboard, and then successfully maintain productive reps, leaking them out the backdoor is not an effective way of achieving this goal. The first step to doing this is identifying what that desired path is for a given rep. Does she want to progress from SDR to AE? Or is she more interested in moving from SDR to SDR management? Same with your AEs. Are they interested in moving into more complex deal cycles? Or moving into sales management? Identifying that desire is the first step, which is followed by putting in place actions to help them achieve that goal over a set timeline. Does a rep want to try her hand at some managerial activities? Assigning her responsibility for a particular managerial task from your plate—like perhaps being the owner of all objection-handling information can be a good way to give her the beginnings of that experience.

Many orgs implement these as “10% projects,” where, assuming a rep is hitting his numbers from an output standpoint (bookings, meetings created, and so forth) he can have a project that he can spend up to four hours a week (blocked, on the rep’s public calendar, and identifiable) that helps the organization and specifically helps him advance toward those professional development goals. Another example here might be a rep who desires to move into more substantial enterprise selling cycles to ride along with a more senior rep on one of her enterprise deals, to watch how that is done, in the flesh.

It’s not separate from professional development, but within this bucket is the notion of monitoring employee engagement and morale. One of the things you as a manager will need to be aware of with your staff is their engagement and general morale. While positive or negative morale can frequently be seen in performance metrics—generally people who are happy are higher performing and engaged, and people who are performing will often be happier—it’s not 100% guaranteed.

cautionYou can have reps who are performing well from a pure output standpoint, while having impacted morale. While a good metrics harness can sometimes catch this in degraded performance over time, sometimes this can result in a rep that unexpectedly gives notice, even before negative performance indicators start showing up. This is, of course, no fun because we want to retain great reps, and we certainly don’t want to flush an entire pipeline worth of deals. So being on top of staff morale, again through the mechanism of one-on-ones and other performance conversation checkpoints, is key.

If you look back across the preceding few pages and look at the types of activities you need to engage in as a manager, you can quickly see that it is a whole different ball game compared to when you were doing individual selling activity yourself! Importantly, though, this is the way that your organization will start on its way to scale—by you getting out of the business of selling, yourself, and instead getting into the business of taking what you’ve learned and validated is a repeatable, predictable selling motion and spreading it across a growing number of reps.

importantYou’re no longer a player, but a coach, and no longer a doer, but a teacher. Moreover, when you eventually move from being an early-sales manager yourself to either managing other managers, or getting out of the business of directly managing the sales org altogether, knowing the above activities cold will help you monitor whether they are happening sufficiently within your managerial base—because sometimes even seasoned managers will skip out on any number of these activities, which of course is bad for your organization.

The Modern Metrical Sales Manager

We touched on the importance of a rigorous metrics harness above, but it’s so important in modern sales management, I believe it merits its own section.

In old-school sales management, the process of hiring, onboarding, and getting reps to success typically relied on spending lots of time riding along with reps either on their sales calls, whether in the office via phone or web presentation, or out in the field. And by doing this, managers were able to identify potential issues with a rep’s sales motion before it turned into attainment issues by visually or audibly inspecting selling activity. In modern sales organizations, however, thanks to better instrumentation with the rise of modern CRMs, the model has flipped to where sales managers use metrics to continuously monitor the quantity and quality of reps’ selling activities. Based on this information, they can identify potential soft spots in their reps’ performance, before then zooming in on that specific part. This is in contrast to simply being along for the ride and hoping to catch a potential problem with a rep in that particular call that the manager sat in on or the follow-up email that she was cc’d on.

This isn’t to say that managers in modern sales organizations don’t ride along for calls or don’t get cc’d on occasional correspondence. Instead, a metrics-driven approach allows managers to focus in their time on places where it can be most effectively deployed to address rep improvement areas, rather than being inundated and overwhelmed with tons of rep activity—even if it doesn’t need inspection.

How can you as an early-sales manager achieve the above? It’s a process that builds on top of prior steps.

Goal Setting

First, you have to be explicit about what your goal is. In sales, conveniently, this can be pretty straightforward, in that you’re trying to drive revenue. That said, depending on an organization’s stage or priorities, pure revenue acquisition might take a backseat to acquiring more customer logos. And for different roles, that goal might be a bit different. For SDR teams, that goal likely is the creation of qualified appointments for the AE team to execute on. But importantly, first, you have to define that goal clearly, so all are on the same page, and have a metric around that goal. For example, ~$80K of new business bookings closed per month, per rep. Or ten new qualified meetings per SDR per week.

Sales Methods Definition and Benchmark Setting

The next step is to clearly document and define the methods by which you achieve this goal. Conveniently, this was the aim of all the founding selling that you did yourself before you decided that you were ready to add more salespeople. You will likely already have a very clear idea of the kind of selling activities, and stages, required to get a deal done, based on having done a good number of them yourself. And not only do you need to have an idea of what those actions are but also the quantity and quality that is required to get a deal done, and, thus, in turn, five deals done, ten deals done, twenty deals done.

You’ll need to identify the number of meetings, the type of meetings required (initial discovery meeting, demo, proposal, security review, and so on); the amount of customer-facing calling and, the amount of customer-facing email; the total number of unique accounts engaged within a time period; the number of opportunities being worked. You need to not only have these component parts listed out, but also have their relative quantities noted.

  • How many meetings need to be done, per AE, per week?
  • How many of them should be first meetings with a prospect?
  • How many should be follow-up meetings?
  • How many opportunities should a rep be interacting with per week?
  • How many new opps should an SDR be creating per month?
  • How many emails per week?
  • How many accounts do they need to be engaging with per month?

These baselines are important, because it will allow us to validate that our reps are engaging, again, in the necessary quantity and quality of selling activity, once we actually start measuring it. This is a good example of a framework for explicitly documenting the levels of activity and mix for your sales motion.

Recording and Capturing Selling Activity

Once you have the above clearly set, the next step is to ensure that these activities are properly instrumented so we can definitely say that we are indeed engaging in the right quantity and quality of selling activity as prescribed in our selling motion, such that we will get to our goal, or if we’re not, we know it before it turns into a problem. Of course, this starts with the recording of deals closed, and revenue booked, but that’s only the very basics of things.

If we know that customer-facing meetings are an important part of selling motion for account executives (and generally, they are), we need a means by which to record those. So too with different types of meetings and other parts of the sales motion (email, calling, presentations, proposals, and so forth). The most common means by which this is done is with a CRM for ease of reporting on, but to start, this can be as basic as a whiteboard with people’s names on it, and daily, weekly, monthly tallies for various tracked items.

But the important thing is to start recording these actions, because we’re going to need to report on them. Even better is if you can record this in an automated fashion—like having email activity automatically logged in the CRM, or using software like Zoom and Chorus to record digital presentations that are delivered.

Metrics Consumption

Once you have this metrics harness in place, the next most important step is to ensure that you’re actually monitoring it. Having this information instrumented and ready to compare to intended baselines, but then not actually doing that, is a big problem, in that as a sales organization, you’ll be flying blind with very little conception of if you are actually advancing against your stated goals. Moreover, it can be one of those things that can slip by the wayside in the crush of reps asking you questions, one-on-ones, team meetings, and more. This is why regularly reviewing these metrics is vital.

The best way to ensure that this gets done is to bake metrical review into the day-to-day, week-to-week, and month-to-month operational cadences of your sales org. Set a recurring calendar event for yourself to do just that at different intervals. And not only do you, as the manager, need to be cadencing the consumption of these metrics, but you need to be ensuring that your team and reports are doing so as well. Create a metrics section in your team meeting wherein you review team metrics and call out divergences from intended baselines. Review individual slices of these metrics in one-on-ones with reps. In your monthly post-mortem, reviewing the prior month’s performance, have a section that focuses on these metrics on both an aggregate and per-rep level.

Anomaly Detection

All of the above culminates in your ability to sniff out potential issues in your sales org before it turns into underperformance of the team and individuals in the form of insufficient bookings. How do you do this?

As you’re consuming these metrics in your operational cadence as noted above, you should be looking for potentially concerning divergences. Those can be divergences from a stated goal: “Our sales reps should be having at least fifteen customer-facing meetings per week, and Joey has had eight customer-facing meetings per week for the last two weeks.” Or it could be a divergence from what the rest of the team is doing. If all of your sales reps win 25% of the new opportunities that they engage with, and one of your reps starts winning 20%, and then the next month 15%, while the others maintain at 25%, that would be concerning.

Anomalies can be positive divergences as well. If a rep suddenly is engaging 100% more accounts than he has historically, or that his colleagues are in the same time period, that could potentially be a good thing—where he has innovated some sort of process to make himself more efficient—or it could be an indicator that he is doing that activity instead of other activities that might be more important, which could be a bad thing. Either way, it’s something that you as a manager will want to investigate and discuss with the rep to make sure that everything is cool.

Root Cause Inspection

Frequently when an issue shows up in rep and team metrics, that metric itself won’t be the ultimate root cause.

exampleIf a sales rep’s revenue attainment in a quarter doesn’t get to the goal that you’ve set, that itself is not the root cause. There’s something underneath that metric that likely points to the issue in question—which in the future you probably would want to monitor ahead of time to see leading indicators of the issue, rather than the unfortunate outcome that shows up months later. This is where diagnosing the root cause of a sales issue that you discovered through metrics is important. How do you do this?

It’s helpful to think of metrics as being composed of the metrics that flow into them, and those metrics being composed of those that flow into them, forming a sort of tree. While bookings is an important metric, if a rep is having a bookings issue, there are a number of things that go into bookings. Did he close fewer deals than usual? Or did he close the same number of deals as usual, and they just happened to have smaller deal sizes, each? If this was the case, was this because he was engaging a different class of prospect who were smaller, and thus had less potential demand for the solution he was selling than the prospects he had previously been engaging? Or had he still been engaging with the same segment of customers and for some reason selling less of your product into them? Or is he instead selling the same amount of product (as measured maybe by number of seats of software), but putting more discounting into the deals than usual?

Or, running it back, if instead he did indeed have the same average deal size as usual but just ended up closing fewer deals than in a usual month or quarter, was that because he won fewer of the opportunities that he engaged in that time period than usual, impacting his win rate? Or did his win rate maintain as usual, and he just had fewer opportunities to engage? Or did he have the same number of opportunities to engage as usual, but somehow did a poorer job than previously at running these opportunities, perhaps as indicated by his frequency of interacting with his opportunities or his total level of customer-facing meeting, email, and calling activity?

By starting with the loose thread and starting to pull to see where it leads you, as a sales manager you’ll get closer and closer to the root cause of the issue and then fixing that issue at the root. And by doing so, you can solve that issue before it turns into a bad outcome by being repeated, eventually compounding into poor output performance for that rep, or even worse, across the entire team and company.

This process can be repeated any time you see a potential anomaly in a key performance indicator, even if that indicator is further up the funnel from attainment.

exampleIs a rep down on the number of customer-facing meetings he’s supposed to be having per week? That could be concerning, but perhaps he has ramped up his prospecting activity to fix that customer-meetings weakness, which prospecting activity would then show up in a commensurate rise in his customer-facing email and calling activity. Has he done so? If not, why not? Or was the decline in customer-facing meetings because he was overwhelmed with a bunch of internal training meetings, so this was a momentary blip. Either way, you want to know.

Sales Motion Inspection

Of course, while a good metrics harness can help you flag potential leading indicators of issues and in many cases be enough to diagnose exactly what the issue is, it won’t always be enough to allow you to come to an out-and-out conclusion. In those scenarios it will require specific inspection and getting your hands dirty with the rep. While seeing a dearth of rep activity metrics, like customer-facing meetings or email, is typically solved—“Hey, I need you to focus and get these numbers higher”—issues of selling quality typically will require you to dig into the actual content of those activities by inspecting the actual calls, meetings, and emails.

To go back to our example above about a degradation of win rate, once we were confident that it wasn’t an issue of prospect selection, it would likely make sense for the manager to dig into how the rep is running his deals, either by listening to recorded calls (again, this is where software like Chorus, Gong, and others can be helpful) or by making sure to ride along on a number of this rep’s new deals.

As noted at the beginning of this section, this is how a manager can use metrics to spotlight an issue that needs deeper engagement to diagnose—versus spending all of his time riding along on calls and meetings with all his reps, even the ones that don’t have problematic win rates, which is a more old-school sales management approach. That approach, while nice and hands on, requires far higher ratios of managers to reps than otherwise, since managers spend a lot of wasted cycles paying attention to things that don’t need their attention—this is how being metrically excellent can make your org more efficient. If you’re only paying a ~$200K sales manager per every eight reps instead of every five, you’re paying 40% less management overhead which makes your cost of sales, and your organization’s Saas valuations, that much better.

exampleYou might have an SDR whose meeting creation metrics are lagging as compared to his prior performance and compared to that of his peers. By looking at his metrics, we might see that his calling, emailing, and unique accounts engaged metrics are steady as compared to his own previous performance and that of his peers, but that for some reason the response rates on his outbound emails seem to have degraded while others’ have stayed steady. This would be the point at which the manager would dig into what those emails looked like—digging into the CRM to see what the subject lines, email content, and so forth, looked like to see if there was a specifically identifiable issue that popped up to be coached.

Coaching and Spreading Success

Once your inspection reveals what you think is the issue, you need to fix it—this means specific coaching of what you have identified as the problematic behavior. If your inspection of degraded win rates leads you to riding along on some calls, which then leads to identifying that a rep was having specific issues handling certain objections, well, that’s now your job to fix with him. This can be done a couple of ways, but normally it involves the specific identification of the shortfall of the selling activity—in this case, handling an objection—demonstrating the correct way to execute that selling activity, and then engaging in mock repetitions of that activity until the rep gets it right. If this sounds hands on, you’re right. But it’s a far better approach than letting the problematic behavior persist. If you or the rep have trepidation about this sort of hands-on management, perhaps thinking it sounds like micromanagement, get over it.

Think of the kind of diagnosis, coaching, and practice repetitions that occur in professional sports. At-bats, snaps, shots, and so forth, are recorded and diagnosed when the stats point to particular issues, at which point the right way of executing that shot, snap, play, and so forth, are practiced until it is nailed. Can you imagine a scenario where a professional baseball player or football player has an identified performance issue and the coach was afraid to help him resolve it because it felt like micromanagement? The concept sounds absurd. Sales management is no different. Dig in and be hands on.

If some of this sounds reminiscent of the sort of work that should be done with reps during new rep onboarding, you’re exactly right. In fact, many potential problems in selling behavior can be prevented by rigorous and thorough onboarding, which we discuss in High-Impact Sales Onboarding and Training. But even the best onboarding can’t prevent all issues, and even solid reps have improvement areas that can make them better—raising their win rates, contract values, and attainment—and humans being how they are, issues will crop up from time to time even for behaviors that previously were just fine.

And in cases where your inspection of something like a particularly high win rate, aberrantly high contract values, or ramped customer meeting counts leads you to identifying what appears to be a new best practice and additional feature to be added to your sales motion, it is similarly the responsibility of sales management to capture that new best practice, and seek to spread it around to the rest of the sales staff. Is this micromanagement? No, it’s management. And it’s going to make the rest of your reps more successful, you a better manager, and everyone’s stock worth more money more quickly.

Stage-Specific Sales Management Rigor

cautionWhile above I map out the framework by which to have rigorous, metrics-driven, performance-centric management, as usual, there’s a maturity ramp to how far down the rabbit hole you need to go based on how developed your organization is, and especially how large it is. There are rarely demerits for being too rigorous too soon, and you can often get away with being looser in a smaller organization—but there are huge downsides to being a more scaled sales organization with the management capacity of an infant. That’s how you kill a company.

Early On

Early on in your sales organization, like when you have your first couple reps, this process of training and expectation setting, monitoring, inspection, and coaching can be more organically done. That is to say, early on, as it’s paramount to get your first couple sales reps to success and prove that this solution can indeed be sold by people other than the founder, it’s fine to over-invest time in monitoring and inspection. So you might be sitting in on calls, being cc’d on prospect communication, and so forth, so you can have a far more granular understanding of how deals are progressing and how reps are, or are not, taking the right actions to progress them.

While the instrumentation overhead here will be substantial, to start (if you’re sitting in on two reps’ worth of calls a day, you won’t have much time to yourself for metrics review and hiring and onboarding work, not to mention all the other things you probably need to be doing), it’s worth it to make sure those reps get to success, and so you can see quickly if they’re going sideways. What you’re doing now, in addition to making sure that these reps get to success, is learning the common places where reps have issues with your sales motion, so you can iterate your onboarding and training to proactively address those issues ahead of them showing up in later cohorts of reps.

At Scale

At larger scale, like a half dozen reps or more, it will be much harder for you to do this sort of instrumentation via osmosis, and rather it will be incumbent on you to have a solid metrics harness in place so you can see early warning indicators of potential problems, and then be able to zoom in on potential hot spots. Getting good at this early on will be a benefit for your organization, but also when you get to the point where you are hiring sales management. You will be able to give them this metrics harness and methodology for monitoring that will help them be better at ensuring good yields on hiring classes (few hires that flame out), quick ramps to success, quicker identification and managing out of bad hires, which, in general, will lead to a more effective sales org. That is to say, the same way that earlier on, you were focused on creating the model for selling your solution, so that you could eventually get out of that business and teach it to others, now you are engaged in creating the model of managing those reps, as required for your specific business.

Sales Performance Instrumentation

So if instrumentation is so vital for modern sales management, what are the right metrics? As with so many things in early-stage organizations, you can start basic, and gradually get more advanced. But the important thing is to start.

Quantity, Quality, and Mix

importantOne thing to internalize is that successful sales behavior comes from a high quantity of high-quality customer-facing selling activity. As such, that is what we need to instrument. It’s not enough to simply measure outputs.

cautionFrequently you will get old-school sales managers saying things like “I don’t care about inputs, I just care about the outputs.” That’s the hallmark of a sales manager who is too afraid of management and metrics to do either. Look for him to probably be unemployed soon. Don’t fall into this trap.

Quantity metrics are frequently counts of things: number of customer-facing meetings, number of first meetings, number of new opportunities created, number of emails sent, number of calls made, number of presentations made, number of proposals sent, number of opportunity forward progressions, number of contacts engaged for the first time, number of accounts engaged, number of opportunities currently in the pipeline, amount of pipeline value, number of deals won, number of deals lost, amount of revenue booked, and so on. But quantity metrics without quality metrics are severely impeded in their efficacy. That said, you can get pretty far based purely on quantity metrics, so if you can only choose one, start with quantity metrics, but aim to add quality metrics as soon as possible.

What are good quality metrics? Of note, quality metrics are typically ratios and averages and are helpful in understanding how an AE or team of AEs are doing with the activity they’re engaging in. For AEs, some examples of quality metrics would be win rate—the number of opportunities that are won as compared to the number of opportunities that are opened or first meetings that are taken. Other examples would be average deal size, average deal age, average age of opportunities in the pipeline, pipeline conversion rate, number of contacts engaged per account, number of meetings per opportunity, average time between interactions with an opportunity, average age of an opportunity in a stage, ratio of first meetings to follow up meetings, and so forth.

These metrics, or their relative level of focus, will change when it comes to different roles. With sales development reps, who are primarily focused on setting appointments and creating pipeline for AEs (assuming your sales motion can support a two-stage sales process), the metrics will tend to be more activity focused. The quantity and quality model applies here as well, but will be applied to behavior that engages a broader set of accounts less deeply, versus AEs who will be working a smaller number of opportunities, but more deeply over a longer time interval.

Some good quantity metrics for tracking SDRs are meetings created, of course, but then amount of pipeline created (the summation of the projected revenue of all the opportunities that this SDR created), emails sent, calls made, connected calls, talk time, number of accounts engaged, number of contacts engaged, and so forth. For SDR organizations where reps take care of the discovery part of the opportunity, this would also include the number of meetings held.

With respect to quality metrics from SDRs, these could be response rate on emails, connect rate on phone calls, contacts engaged per account, number of activities per contact, activities per account, conversion rate of accounts engaged to meetings created, all the way to quality metrics on the outputted pipeline created, like win rate on opportunities created, average deal size on those created opportunities, and so on.

An especially nice thing about quality metrics is that in addition to being able to compare between reps, and track historical changes, you can also use them for reporting on deals that have indicators of less-than-stellar quality of execution. That is to say, while tracking untouched opportunities over time is valuable for assessing how on top of their pipeline a given AE is compared to his colleagues, the list of opportunities that right now, this instant, have gone 30 days without an activity can be a very helpful to-do list of what a rep needs to be spending his time on—namely, close those out, work them, or explain why it’s OK for them to not have that activity! Or with respect to SDRs, an example might be the list of accounts they are engaging that have fewer contacts engaged than a specified goal, say, three contacts per account—assuming you’re doing a serious enterprise sale that touches many stakeholders.

As you can see, these metrics can go from pretty basic, like number of customer meetings, to pretty advanced, like the average time between interactions on an opportunity. At TalentBin we got pretty far along. By the time the company was acquired, for AEs we were tracking, with respect to quantity metrics, bookings (of course), demo meetings, proposals sent, and email activity. With respect to quality metrics on a per-rep basis, we tracked win rate, average deal size, average deal cycle, and untouched opportunities. With SDRs, for quantity we did demo creation, email and calling quantity, and unique accounts engaged; and for quality, we did calling connect rates and win rate on opportunities created.

Clearly we could have done more, but I would give that metrics harness a solid B/B+ especially for an organization without a formal sales ops function and with ~10 sales reps. Nowadays the metrics harness I use on myself and my reps is far, far more advanced, especially with the help of Atrium, but again, it’s OK to start basic with an eye toward getting more advanced later. But at minimum, you have to start or you’re flying blind.

Reading Metrics

What does a great metrics harness like this get you? Importantly, it gives you a fingerprint of the behavioral information for each of your sales reps. And once you have this behavioral fingerprint, you can use it for all manner of effective management needs. First, you can use it to understand, demonstrably, the behaviors your best reps engage in. You know who your best reps are based on their bookings outputs. But when you are able to see what all of these other metrics look like for those top performers, you can see that it’s not really that they’re magical sorcerers. Rather, you find the specific behaviors and ratios that are different for them as compared to your other reps, which allows you to dig into what allows those top performers to achieve those metrics.

Spoiler alert—very frequently it will just be that your best reps do more work. But it may also be that their selling behavior is better in certain regards. Their higher win rate may be due to them involving more stakeholders in the deal earlier on—which would show up in their higher metrics of contacts engaged per account, for example.

Further, with this behavioral signature of success, you are better able to see changes of rep performance over time. A key example of this is in new hiring. If you are onboarding a new class of five sales reps, having a metrics harness like this in place allows you to see the degree to which the new hires are starting to engage in the quantity and quality of behaviors that are demonstrated by the existing top-performing reps. If those new hires are ramping into band with your existing ramped and top-performing reps, this is a good thing!

Alternatively, if one or more are not, now you know, and you can move to address that issue quickly—and specifically with respect to whatever the metric points to as an issue (for example, do they not have enough customer-facing meetings? Or is it their opportunity creation quantity that’s problematic? Or are they not getting to second and third meetings?). And if whatever the issue is isn’t solvable—even with coaching directed at improving the selling behavior that is showing up in the problematic metric, the behavior doesn’t improve—then you’ve realized this far ahead of time. You now can proceed to remove the rep from his seat, rather than allowing him to burn salary expense and opportunity cost (in the form of the prospects he’s working, poorly, that another rep could be working successfully), and replace him with someone who will be successful.

Not only can these sort of changes in metrics be helpful during onboarding, they can be helpful in sniffing out potential issues with rep motivation that can pop up from time to time, which unchecked can turn into unwanted attrition. If a rep’s metrics start negatively diverging from his existing behavioral signature, that can be an indicator of potential issues. Having a great metrics harness in place can help you see that before it turns into major problems.

Managerial Operational Cadence

importantYour first step to success is knowing what you, as a manager, need to be doing and knowing what your reps need to be doing. Making sure that those activities actually take place is how to take that to scale. If you know that you should be taking time to consume the metrics of your team and look for potential issues, but then your entire workday and week is eaten up by sitting in on calls with your reps—you’re never going to get around to those important tasks.

This is why operational cadences or rhythms are so helpful for managing teams, and yourself. Rather than treating your workdays, weeks, and months as never ending, monolithic expanses, it’s far more effective to chop them up into manageable time blocks with checkpoints marked down at specific intervals, and recurring times where specific activities happen.

The most common means by which to do this is with meetings, including standups, team meetings, pipeline reviews, individual one-on-ones, monthly retrospectives, and quarterly business reviews. Meetings of course get a bad rap most of the time because they are typically terribly undefined and executed and end up just wasting time. However, done correctly, they will ensure that the things that need to get done, as a manager, and for your reps, will have a designated time and place for them to be done—and as such will actually be executed, allowing you to capture the value from doing them.

Meetings

You might say, “Wait a minute?! Meetings are those things that waste time and are for big companies!”

On the contrary, meetings are for richly communicating information, and receiving it. They are for ensuring that the things the organization is supposed to be doing are being done, that people within the organization understand what the larger goal is, their place in it, what they need to be doing to proceed toward that, and to raise issues if they see divergence there.

cautionIf you don’t do them, the core needs will still be there, and they’ll just get served other ways. If you don’t have private venues for surfacing issues, like one-on-ones, they will happen in backchannel conversations in ways that erode morale. If you don’t have a means to communicate, and reiterate, top priorities, then people will work on whatever is in front of them, or things they like, versus things that the organization needs. If people don’t know when information will be shared with them, they will assume you’re hiding it from them. Fix all of this with a thoughtful meeting cadence, wherein certain meetings have a certain purpose (and stated anti-purposes), and proactively handle these information distribution and feedback solicitation needs.

And no, a company-wide Slack channel does not count.

Implementing Operational Cadence Meetings

Meetings should have a stated purpose, a stated set of attendees, a format (which supports the purpose), a specified length, and a cadence to them.

The best way to do this is to use calendar invites, setting the recurring time frame to what the recurring period is specified to be, inviting the relevant attendees, and putting the specific format and recurring agenda in the meeting description. (Avoid making people optional as much as possible. If you think they’re optional, they’re likely not needed, and should be doing other things.)

Figure: Example Sales Team Meeting Invite

chapter10-sales-team-meeting.png

Source: TalentBin

Figure: Example Pipeline Review Meeting Invite

chapter10-recurring-pipeline-meeting.png

Source: TalentBin

There’s a few consistent factors you should consider for your meetings:

  • Breadth of attendance. You can be most efficient with meetings by evaluating whether most of the attendees sitting around are not receiving information or contributing information in the meeting. They’re probably not required, so think about splitting that meeting into a bunch of individual ones.

  • Cadencing. This serves the purpose of letting staff know that if something doesn’t get covered this time, it can be put on the agenda for next time. It also ensures that staff knows that what was discussed and agreed in this meeting will indeed be checked on next meeting—so promises can’t be empty. Cadence also needs to be appropriate to the attendee base, depth of the meeting, and purpose. There is no need for weekly all-hands. You’re likely handling things in that meeting that need to be handled in others. One-on-ones done monthly is probably too infrequent—you run the risk of staff irritation boiling over if they don’t have a release valve.

  • Time frame. The duration should be constrained to what is needed, as well. No sprawl. If you have more content than can be handled in the meeting, prioritize the content, and then save the unhandled stuff for the next one. Either have a tracking document to record what was covered, and action items, or actively put the next content in the next meeting’s Description field. If there is special content that is required, can it be handled in an email? If none of that will work (it better be an emergency), put another meeting on the calendar to address that specific topic.

  • Timing. Scheduling team meetings during lunch (one of the benefits of bringing lunch into the office) makes it such that you don’t stomp on productive time during the rest of the day. Otherwise, schedule meetings at the edges of the day—either at the very beginning, to compel a sprinter’s start, or at the end of the day, when people are burned from their day of work and can use a break.

  • Content and Format. Set the agenda explicitly. If there is lack of clarity as to what this meeting is for and what content is to be covered, you will dilute the purpose of the meeting and keep you from achieving the goal of the mee from its purpose.

Examples of Sales-Centric Operational Cadence Meetings

Sales has a faster, more frequent tempo than the rest of your organization, typically, along with a set of actions that requires more instrumentation and accountability than, say, engineering, so the meetings cadence will reflect that.

Sales Stand Ups
  • Purpose. To provide a checkpoint to the day, promote shared learning, and promote transparent accountability. Quick and up-tempo to help maintain in-day tempo.

  • Anti-purpose. Not for exhaustive rehashing all work done, questioning strategy, and so forth.

  • Attendees. Sales team pods. If you have three AEs and three SDRs, this can be done together. If you have eight AEs and eight SDRs, each pod has their own standup.

  • Format. ~30 seconds per person on key metrics that were achieved in the prior interval—demos set or done, calls made, emails sent. Show up to the meeting with the numbers, and put them on a shared whiteboard dashboard as a means of shared transparency. Share any key items of note (could be exciting wins, could be big flubs to share, for others to avoid). If someone is out of the office (working), they need to dial in for it. If they are occupied at the time (try not to be) with a demo, traveling, working from home or such, numbers and comments should be emailed to the team ahead of time. Field sales team members can report out via a set-format email to a dedicated list-serve or slack channel.

  • Cadence and Timing. It depends. For a small team including SDRs, could be twice a day. Noon just before lunch and 5:00 p.m. For a larger team, could be once a day at noon.

  • Length. ~10 minutes. If you get to a size of organization where ~30 seconds per person will add up to greater than 10 minutes, split the group as noted above.

  • Owner. Sales lead.

Sales Team Meeting
  • Purpose. To review prior week’s metrics; outperformance or shortfalls; promote team shared accountability and transparency; and provide information and solicit feedback as regards product to date and product future, and customer success.

  • Anti-purpose. Not a roundtable, ideation session. Not a group bitch session.

  • Attendees. Entire sales team (and potentially CS team if it is embedded in your sales team). Product leadership representative, customer success representative.

  • Format. Have key team metrics that the team is focusing on achieving, and start meeting by reporting on them. Demos held prior week, month-to-date, revenue month-to-date, and so on.

    • Have a segment of the meeting (5–10 minutes) focused on product leadership sharing what shipped last week, what is shipping this week, and soliciting product feedback.

    • Have a segment of meeting (5 minutes) for Customer Success to share information, make requests, and solicit feedback. Product and CS participation can be front-loaded so those representatives can peel off after their role is concluded.

    • Then the team should go around and share a personal win and something they learned from the prior week.

    • Review any particular information that needs to be underscored in a group environment (which may have been emailed, previously). Are there particular new programs that are shipping? New materials for reps to be aware of? Changes to CS protocol? (Again, many of these could have been previously emailed, but may need reiteration to ensure they stick.)

    • Solicit questions and feedback on the go-to-market, and issues that might impact the whole group (not personal issues). Solicit feature requests on sales operations, marketing materials, and so forth (as long as it touches the whole team).

    • If this is the first meeting after the end of month, or end of quarter, use it as a retrospective. The meeting owner should have 15 minutes calendared ahead of this meeting to ensure that the content is in order for the meeting and to review the metrics that will be discussed as a team, ahead of time.

  • Cadence and Timing. Weekly on Mondays at lunch. Bring lunch in.

  • Length. 60 minutes.

  • Owner. Sales leader.

Pipeline Meeting
  • Purpose. To provide a venue for shared accountability and focused work on pipeline maintenance.

  • Anti-purpose. Not an ideation or bitchfest meeting.

  • Attendees. Full sales team of AEs (not SDRs). As the AE team gets larger, split into pods at ~five AEs per pod.

  • Format. Each seller reviews last week’s closed deals, and which deals will likely come in this week. Time is spent on concerted down-funnel work around pipeline maintenance (ensuring that relevant opps are in correct stage, closed-losting dead opps, and general pipeline). Because this is unpleasant work that reps avoid, compel it in a group environment. And bring in pizza to make it suck less. Close meeting with reporting of activity in the meeting (opps closed, opps updated, contacts touched). People mustn’t miss this meeting. Or schedule demos over it. It’s here to be a place to make sure work that may not otherwise get done actually gets done.

  • Cadence and Timing. Weekly on Wednesday at the end of the day. Get pizza.

  • Length. 60–120 minutes.

  • Owner. Sales leader.

One-on-Ones
  • Purpose. The purpose of this is solely for the direct manager to proactively extract issues as viewed by the rep, and share information in a private setting.

  • Anti-purpose. This is not a status meeting. This is not a pipeline review. Those are handled in other places. The focus is purely on rep issues and their needs and career development discussions.

  • Attendees. Direct manager and sales rep.

  • Format. Have a recurring set of items to go through, every time. I like the format “What do you need from me?” (As in, what needs to be better?) “What do I need from you?” (As in, how are you performing, and what changes do I need?), and “What do you need to know?” In the “What do I need from you” case, it’s appropriate for sales staff to review past-week, month-to-date, or quarter-to-date metrics to ensure that things are tracking appropriately. If there are performance issues, this is where that needs to be addressed and remediation plans made. As regards information sharing, this is “What information do I need to share with you with commentary that may not be suitable for a public setting?” By always following a format, it will be a forcing function to surface this information and ensure you don’t have blowups and surprises. Focus deeply on extracting issues. If you have observed things in the wild that you feel are underlying issues, bring them up. In sales orgs, issues typically show up in metrics, and should be discussed here.

  • Cadence and Timing. Every two weeks. Ideally the team has all their one-on-one meetings on the same day (if the team is larger, have them on consecutive days). If there is a topic that needs to be addressed privately with team members in parallel, one-on-one, having them all on the same day, or quickly together, will allow you the megaphone to do this. Do NOT skip these. If you have to skip, do NOT skip. Move the meeting to later that day. Or the next day. DO NOT SKIP THESE.

  • Length. 30–60 minutes, depending.

  • Owner. Sales lead (whoever is the sales rep’s manager).

Monthly Retrospective
  • Purpose. Akin to the weekly sales team meeting, but with a specific aim to look back over the prior month and ahead for this month. This meeting specifically allows the manager and staff to take stock of the prior month’s performance, evaluate if the team hit desired levels or, if not, to figure out why, quickly, before the underperformance becomes chronic.

  • Anti-purpose. As with a sales team meeting, this is not a roundtable or ideation session.

  • Attendees. Entire sales (and potentially CS) team, and potentially product leadership and customer success representative.

  • Format. Start with a restating of standard metrics that the team had previously agreed to as goals, and then review the team’s metrics harness to see if goal metrics were actually attained. This is not just lagging indicators like booking but rather all quantity and quality leading indicators, as well. Do so on a team level, but also on an individual level, specifically citing metrical outperformance, and eliciting sharing from out-performers on what drove that performance. It’s like a big weekly team meeting. Share what’s coming up. Diagnose issues. Share successes that need to be shared around. Reinforce accountability.

  • Cadence and Timing. Once a month, at the beginning of the month—but with enough time standoff from the end of the month for the sales leader to do sufficient analysis on what outcomes were and what he or she wants to focus on in the meeting. I like to take over the existing sales team meeting with this meeting. Ideally over lunch.

  • Length. 60 minutes.

  • Owner. Sales lead (whoever is the sales rep’s manager).

End of Time Period Celebration
  • Purpose. After a successful month, I like to do something like a team lunch or dinner as a means by which to drive team camaraderie, and so on. It doesn’t have to be huge, and if you want, you can make it contingent on the team hitting certain goals, but generally I like to have some sort of team-wide recognition of the completion of the just-ended sprint.

  • Attendees. Full sales team when you’re small. Split into pods once the full team gets bigger than a dozen folks.

  • Format. Dinner or lunch.

  • Cadence and Timing. Monthly, after the close of the prior month, during the first week when folks are taking a small breath, and before you get too far into the next time period.

  • Owner. Sales leader

Example of an Operational Cadence Calendar

Below is an example of a calendar month-based operational cadence for a ~10 person sales team composed of SDRs, AEs, and CS.

Figure: Monthly Operational Cadence for Small Sales Team

chapter10-cadence-calendar.png

Source: TalentBin

On a quarterly cadence, you would add a quarterly business review that is a more robust version of the monthly retrospective team meeting, but with similar content focused on clear-eyed evaluation of what has been executed to date, what you expect to be the case going forward, and where adjustments need to be made.

Executive Meeting: Non-Owner Executive to Owner Executive
  • Purpose. Track progress against stated sales goals, as measured via agreed key metrics.

  • Anti-purpose. Not a one-on-one as relates to performance or extracting issues.

  • Attendees. CEO and Sales Lead (if they are separate people).

  • Format. Review key agreed metrics that track success of sales organization, their improvement, and degradation. Discuss and identify constraints that are blocking forward progress. Agree and prioritize proposed solutions to constraints, and document next steps for execution and timeline in Google Doc, for review at next meeting. At the next meeting, review agreed outcomes from prior meetings, and success or divergence.

  • Cadence and Timing. Every two weeks. End of day. (To avoid mid-day work disruption and occupying manager time while the team is executing.)

  • Length. 30–60 minutes.

  • Owner. CEO (who is not a sales lead).

Adding Managerial Layers

The goal of sales management is to make individual sales staff, SDRs, AEs, and so on, more successful by having someone (or a group of someones) that is purely dedicated to that success. But as we also detailed above, the activities that managers need to be engaging in to make their staff more successful are many! It turns out that management is a lot of work! And given that there are only eight hours in a workday, at a certain point, your ability to manage your staff will cap out, and you’ll start dropping balls and being unable to fully execute all the management tasks you need to. And this will be the point at which you should probably add some managerial help under you.

When to add management help? The time to add management help is the point at which your ability to do the work you need to do, outside of managing sales, becomes impossible. Partially this is related to when you decide that you want to professionalize your sales leadership function (for example, bringing in a VP of Sales). But if you consider all of the tasks listed above—one-on-ones, stand ups, team meetings, cross-functional org meetings, pipeline reviews, and so forth—the time really starts to add up, even before you get to things like metrics consumption, coaching and training, riding along on calls, and so forth.

In part, your ability to manage successfully before adding more managerial help is related to your ability to manage by metrics. The better your metrics harness, the less time you’ll spend uselessly inspecting work that doesn’t need inspection, and instead, you’ll be able to spot precisely the issues that need your attention and work, and spend time on only those, saving your time and forestalling your need to add more managerial help. But that still only goes so far. The same applies to the rigor with which you keep one-on-one notes and improvement areas that you’re working on with a rep. The more rigorous you are, and the less you rely on remembering these topics, the more folks you’ll be able to manage concurrently before you need additional help.

Another thing to keep in mind is the diversity of roles that you’re managing. Managing fewer types of roles means more shared managerial tools and materials, so the more diverse the group of staff you’re managing—for instance, AEs, SDRs, and CSMs—the more challenging as compared to a similarly sized group of, say, just SDRs.

Conventional wisdom typically notes that a manager starts having issues keeping full understanding of her reports’ performance in her head anywhere between six and nine reports, so you should probably use that as a rule of thumb yourself. At what maturity stage does this show up? Somewhere between having an initial sales pod and having a group of sales pods is probably the right time to add some help.

What does that look like? Early on, your management structure could be you as the early-sales manager managing a couple SDRs, AEs, and CSMs, together. As you add more pods—as in this example—you could add an SDR team lead to manage the day-to-day metrics-based performance of the SDR team, leaving you to directly manage the AEs and CSMs.

Team leads can be a helpful short-term force multiplier, where you take an outperforming individual who has a professional development interest in management and give them partial responsibility for managing a pod of a certain function. This frequently shows up in SDR and CS, and the slice of management that the team lead takes on is typically metrics monitoring and reporting. They would be a first line of defense when there is a question about product, rule of engagement, and so on, intercepting those questions, and handling them, along with any number of other managerial activities discussed above. This saves your time for other managerial activities for other teams and higher leverage managerial activities like hiring, onboarding, and performance management topics. Relatedly, the management activities that are typically not given to a team lead are people-management topics—like one-on-ones, performance management, professional development, hiring, and onboarding.

That said, team leads can only get you so far, and at a certain point, all of the one-on-ones, team meetings, professional development work, and so on, will add up to beyond the point of your ability to do it all in a 40–60-hour work week. At that point, you’ll know the time will be right for adding a managerial layer that can shoulder those responsibilities for you.

cautionBe wary of waiting too long to do this, in that, like the failure mode of lagged scaling discussed above, while it might feel like you’re being efficient, because you’ve gotten so good at sales management, the likely reality is that your AEs, SDRs, and CS team are probably underperforming by 10–30% as compared to if they had dedicated high-quality management versus you, spread across ten of them.

Moreover, if your organization is having this level of success, probably the highest point of leverage for your time would be more hiring and onboarding versus all of the other managerial activities detailed above. So get some managers to handle all that, and you focus on hiring and onboarding or, even better, building the machine that does that function without your involvement!

Professional Development and Promotion Paths

Depending on how long you plan on managing sales staff before you bring in the pros to take over management, you’ll likely have to consider the professional development needs of your staff (and once you have professionalized sales management you’ll want to make sure they are paying attention to that as well). While SDRs and AEs hitting quota and making their targeted compensation, or beyond, is our primary goal, your staff will want to understand how their role will help them develop toward bigger and better things. Being mindful of this will be key in one-on-ones (“What do you need from me?”), and in keeping your staff growing, happy, and retained in your org.

Further, professional development in a sales org is something that can be an extremely powerful driver of value creation for your organization. If SaaS startups are valued on multiples of their revenue (say, 5–10x revenue), and each additional AE, once ramped, adds, say, ~$40K in annual recurring revenue per month, each additional AE you add who successfully adds ~$40K in ARR per month is adding ~$400K in value to the organization per month. This reiterates why successful sales hiring and onboarding is so important. But now imagine that you have a team of SDRs who are primed to become AEs—each SDR that you are able to successfully promote from SDR to AE, who then gets to success in ramping into that ~$40K in bookings-per-month range, has now added another piston adding ~$400K in enterprise value per month.

Similarly, while professional development for AEs typically revolves around moving into larger and more complex deal situations, this too can be extremely beneficial to your sales org. A mid-market AE, depending on market, can do between ~$30K and ~$60K in bookings a month at ~$10K–~$20K deals at a time, netting to ~$400K–~$700K in bookings a year; whereas an enterprise rep working with much larger deal sizes, north of ~$50K can do ~$1M–~$2M in bookings a year. Again, if an organization is judged on its recurring revenue, developing a mid-market rep to an enterprise AE can add millions of dollars in value to your organization. So don’t skimp on the professional development plans!

What do those professional development plans typically look like? Well, it depends on the role. For SDRs, AEs, and CSMs, you can have the traditional individual contributor progression path—which for SDRs is moving from SDR to senior SDR, then junior account executive, and beyond. The activities that you would want to layer into their professional development work would be specifically those needed to progress—like practicing discovery calls, open-ended questions, presentation and demonstration, and objection handling—to all the things that you would expect to cover in an AE onboarding. And these can be done on a recurring basis—a couple hours scheduled weekly specifically for these tasks—with managers, or riding along with AEs on discovery calls and demos (or, even better, listening to recording of these outside of calling hours.) For AEs and CSMs in the individual contributor development path, this would typically involve working with larger and more complicated deals and clients. In this case, this can involve helping more senior AEs with their accounts, or being specifically assigned individual larger opportunities that a senior AE or management helps out with.

There’s also the managerial development path to consider. Which path a given rep is more interested in is something you need to specifically discuss with them and then help them progress toward. In this latter case, the best kind of professional development exercises usually revolve around implementing programs that make others on the team more successful, or helping with specific management tasks that you might otherwise have to deal with yourself. This could be tooling or process projects, or even being responsible for analyzing and improving a specific part of your organization’s sales motion—whether prospecting, outbound engagement, inbound response, pipeline management, and so on.

Building a Strong Organizational Culture

Early on in a sales organization, and in early stage organizations more generally, culture can often be a bit of an afterthought. This is unfortunate, because a strong culture can be a source of competitive advantage through supporting and cementing an organization’s ability to execute, by how attractive it is as an employer, and via retaining talent once hired.

Because it’s often an amorphous thing, we’ll define culture here as the set of implicit behaviors and mores an organization considers appropriate, rewarding and celebrating them, and conversely, the behaviors that your organization considers not OK and censures. These rewards, celebrations, and censures can be both explicit and implicit. As Netflix once put it in their famous culture deck, company values (and thus culture), are shown by who gets rewarded, promoted, or let go.

importantI like to think of organizational culture as the operational spackle that fills in the gaps between management processes. While your values and culture inform how you manage, there will always be gaps in even the best run management harness, and this is where culture acts as an operating directive in absence of explicit instructions and helps people do the right thing. Given that there can be lots of ambiguity in an early-stage startup sales org, even if you’ve taken to heart the various recommendations of this chapter, a robust culture ends up being more important than you expect.

cautionConversely, without a strong culture that aligns with the needs of your organization, you can end up with all kinds of bad things happening. Many people are familiar with the issues that organizations like Zenefits ran into when a culture of skirting regulations, taking shortcuts, relying on hacks, and partying collided with a market steeped in rigor and regulations, dealing with extremely sensitive topics: healthcare coverage for customers employees. The results can range from company-killing fraud, to rampant attrition, to hideous Glassdoor reviews that make it impossible to hire.

Specification

The first step to fostering an intentional sales org culture is having a sense of what your culture should entail. Well, what kind of organization do you want to run? What kind of organization do you want to grow into? What markets do you sell into? Are you selling into conservative markets like healthcare, HR, or government? Or more informal markets like developer tools? Who do you want to be able to recruit? A more junior or more senior staff base? What is the existing culture that has accreted into place over time from founders and early employees?

Documentation

Once you know what you want your culture to be, you need to document it for distribution and reference. It doesn’t need to be as involved as that Netflix deck, and it won’t be set in stone, either. It can evolve, of course, but at minimum, bulleting out the things that your organization values and those it doesn’t in a shared Google Doc is needed for broadcasting and repeating these values, again and again. That way whenever you want to give a shout-out to someone who has done something great in line with your culture, you can point directly to the document, and the specific line item when doing so, thereby reinforcing its importance.

Articulation

Once you have your culture specified and documented, the next step is to proactively share and articulate it. This needs to start all the way back in the beginning of an employee’s experience with an organization—at the hiring and interviewing stage. Being up-front about your org’s culture early in the hiring process can help you screen out folks for whom it’s not a fit and will be an attraction for those who are fired up about it. And then take steps to ensure that it’s woven into all parts of employee experience, from onboarding, to team meetings, all hands, and beyond.

Further Reading on Sales Management

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