How to Build a Successful Founder-Led Sales Strategy

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  Walter RothFounder
  Simple Lens

How to Build a Successful Founder-Led Sales Strategy

Hi, I’m Walter, and I coach startup founders to break through their preconceived notions about whether sales is a good a fit for them (spoiler alert: if you’re a founder, it is), as well as how to approach sales from first principles, and how to be as methodical about sales as you would any engineering project. In just a moment, I’m going to go very, very in-depth in my advice, but I’ll start with a quick summary of key steps that I recommend for any new startup founder:

1. Embrace Founder-Led Sales

As a founder, no one has more passion for solving the particular problems in your domain. And so, no one can answer questions about your product better than you can. It’s widely considered a best practice for early-stage startups for founders to act as first sellers, not just because of their deep product knowledge, but also because it builds important strategic muscle that will help you scale your company in the future.

2. Maybe Rethink Those Preconceived Notions About Sales?

Contrary to what you might have heard, sales has very little to do with being charming and persuasive, and much more to do with the same kind of methodical engineering processes in which you’re already an expert: Careful searching, pattern-matching, scoping the scale and size of problems, and even unit testing. (Yes, really!)

3. Start From First Principles

I’ve met with and advised brilliant technical founders who are big fans of first principles when building products. You can take the same approach to sales by focusing on three key questions that should be the focus of all of your sales calls. Don’t worry, we’ll go over those questions, and how to ask them, in depth.

4. Sell From a Place of Empathy (Yes, Really)

Even though getting on the phone and asking a lot of questions might seem intimidating, you can base all of your sales efforts in deep empathy for your prospective customers. It turns out that success in sales maps directly to earnestly wanting to solve your customers’ problems–or determining as quickly as possible that you’re not a good fit.

5. Build on Your Experience as a First Seller

Once you understand the core principles of founder-led sales, you’ll unlock many important benefits for yourself and your startup, including a much clearer vision for how to hire and manage your first sales teams.

6. Debug Last Principles

As I cover below, some founders find places where unconscious beliefs and reactive behaviors act like bugs in the machine to sabotage your sales process. Once you identify them, you can remove or mitigate them with results that are massive and more or less instant. I’ve worked with many founders who, after increasing their conscious awareness of reactive patterns, went from hating sales to loving the process. No, really.

Ready? Let’s get started.

Early-Stage Sales Is Intimidating for Founders (But Shouldn’t Be)

Important Takeaways on How to Make Sales Less Intimidating:

• At an Early Stage, Founders Being First Sellers Makes Sense: It’s an efficient use of headcount budget and no salesperson will ever have your passion for solving the problems you’ve identified. When you don’t have to “sound like” the stereotypical salesperson–and you don’t–you will likely become very good at the discovery process.
• Sales Isn’t Just About Bothering People With Cold Calls: Sales is an essential skillset for founders that will future-proof your business, even if you’re initially going bottom-up and selling directly to developers. In time, when your startup scales to need top-down sales, you’ll be glad you built up the muscle memory.

There’s no clear, uniform path to founding a technical startup. Engineers of all stripes, former CTOs, and completely non-technical founders have all created successful developer-first organizations. However, one of the most common barriers to early-stage startup growth is sales. Not necessarily because sales is difficult (it is), or because it’s time-consuming (it is), but often because startup founders simply don’t feel comfortable stepping into the role of first seller. In my opinion, being the first seller is a crucial step in the maturation process of founders to leaders who can scale an entire organization, beyond product and engineering into important go-to-market (GTM) functions such as marketing and customer success. But founders I speak to are also concerned because, to them, B2B sales is about calling people. Messaging people on LinkedIn. Emailing people. Bothering people. People, who, like a lot of engineers and technical professionals, don’t particularly care to talk to sales themselves.

As it happens, there are ways to significantly speed up the transition from first-time founder to successful first-time seller. One of the most profound transformations in the process occurs when technical founders understand how much working in sales is like working in engineering. It’s something I cover in detail when founders consult with my organization Simple Lens. Let me explain.

Being the first seller is a crucial step in the maturation process of founders to leaders who can scale an entire organization.”

I'm a sales coach for high-growth founders and founding teams. I've raised venture capital, been an entrepreneur-in-residence at a VC fund, helped set up sales for several early-stage companies (as I’ve spent time at larger orgs such as Oracle)–and I have an engineering degree, which heavily influenced my approach to sales. I consider myself a sales founder. My specialty is helping any kind of founder, whether from a developer, product, or other background, become a sales founder too.

To be successful first sellers, founders need to learn the fundamentals of go-to-market strategy (which involves more than just writing out a value proposition, or having your marketing team launch a podcast). They need to learn how to do customer development, and how to articulate where their organizations are in terms of proving out sales. Founders must also learn what kind of founding sales leaders they will eventually want on their team, how to hire them, how to delegate to them, and how to manage them. When founders invest in themselves to become successful first sellers, that means from the start, there's sales DNA in the company. Even for startups that are launching with a product-led growth model, at some point, when they need to move towards having a formal sales motion, building out a founder-led sales strategy early helps you perform the initial thinking and planning in advance, so you don’t design yourself into a corner.

More Resources on Early-Stage Sales:

• Video - Early Inside Sales to Enterprise Success with Alex Malinovich
• Video - From Dev to Enterprise Sales with Andrew Levy

Good News, Founders: Sales Isn’t What You Think It Is

Important Takeaways on Founder-Led Sales Strategy:

• Sales Is Fundamentally About Cultivating Search-Based Skills: A winning smile helps, but sales is about pattern-matching for prospects that fit your startup’s ideal customer profile.
• Top-Down Sales May Be Hard to Avoid: While going developer-first is a fantastic way to sell meaningful products to passionate users, most successful startups have eventually had to scale to hiring a sales team. Which isn’t a bad thing, since you can learn how to properly hire and manage those, too.

I say this to a lot of founders: There are actual first principles to sales. And for the most part, sales isn't what they think it is. A lot of people think that sales is about persuasion and influence, but when you're selling something new to a potentially new market, persuasion isn't enough. Your task is actually searching for relevant people. So, the skills that you’ll be using don’t necessarily involve wining and dining customers until you’ve won them over. The skillset you need to cultivate is a search-based skillset.

Secondly, a lot of startups try customer development–trying to figure out the value of their product to end users. But as an early-stage founder–maybe you just quit your day job, and you have a finite amount of runway from bootstrapped personal savings or funding from an investor like Heavybit–there's only so much time that you have.

The good news is: You don’t need to develop a bunch of new skills. You actually can use the existing skills that made you a successful engineer or product manager.”

So what you need to do is put just enough of a sales lens on to look into the future and see if what you’re building is not only something that is of value to end users, but is something valuable enough to an organization that it will actually buy it. So in addition to building a product that people need, you're also building an organization that can sustain that valuable product. In those early stages of product growth, the good news could be that you get growth–but the bad news will be that your targets get higher.

And at some point, you really have to have a sales motion. So even if you’re the kind of early-stage founder who just quit your day job, you really owe it to yourself to not just build an interesting technical product that has value to end users. You need to make sure you’ve got something that you can build an organization around with a sustained vision.

The good news is: You don’t need to develop a bunch of new skills. You actually can use the existing skills that made you a successful engineer or product manager. You just have to be aware that there are some first principles of sales that you have to integrate into your customer development process and your overall thinking.

More Resources on How to Think About Sales:

• Video - Things I Have Learned About Sales So Far with Fred Stevens-Smith
• Video - Heavybit Sales Master Class with Bridget Gleason

Founder-Led Sales From First Principles: The 3Ws

Important Takeaways on How to Make Sales Less Intimidating:

• Winning at Sales Means Focusing Attention on Deals that Will Close: By focusing only on deals that will close, and disqualifying deals that won’t, sellers set themselves up for success.
• Your Sales Conversations Should Focus on Three Fundamental Questions: A winning smile helps, but sales is fundamentally about pattern-matching for prospects that actually fit your startup’s ideal customer profile.

To clarify, the first principle of sales that I help founding teams learn isn’t something I invented. It was actually invented by tech sales veteran Steve Browne. Steve started at Oracle in 1987, and within a year or two, he was able to reverse-engineer the process we’re about to describe below. It was a period of astounding growth at Oracle, with the company going from a $50M valuation at the time to about a $1B valuation in the early 1990s–seemingly doubling in value every year. However, Oracle’s growth came at a cost–while the company was making headway in sales, it also fired half its sales team annually, and realized it needed to stop the attrition. Starting in 1998, Oracle asked him to teach incoming sales representatives what made him so successful at winning big deals that no one believed could be closed. He agreed on one condition: That he could write his own course, a condition to which Ray Lane (then President and COO) agreed. His course focused on the three important questions we dig into below, also known as the “3Ws.” Today, many sales leaders at some of the biggest tech companies reference the 3Ws, as do many popular sales books, including those that focus on the MEDDIC sales framework. Frankly, Steve is too humble to take credit for the wide use of this strategy in sales today, but I consider him to be the godfather of the 3Ws.

Here’s how Steve’s story started: He was an engineer until he learned that salespeople made five times more money than he did. And that offended him. He figured, “I'm just as smart. And I want a share in the value I can provide.” So he decided to become a salesperson. But being a smart engineer, he wanted to figure out the process first. So he became a solution engineer at Oracle, which gave him a front-row seat to watch all the greatest salespeople and all their sales efforts in action. The deals, conversations, and stories all became case studies for him.

What he found was the best salespeople only spent time on deals that were going to close. He says, “Great, I just have to spend time on closing deals that are actually going to close.” But the question is, how do you do that? And so, he realized that he’d have to figure out which deals were not going to close quickly–after which, he would spend no time on them. And at that point, he was thinking, “OK, great. Now how do I do that?” So after looking at all the deals that didn't close, he would interview all the sales reps. They all had about a million sad stories about how one guy did this, or how they got shafted by some other guy. And what he found was that you could take all those sad stories and categorize them into three buckets, which we now call the “3 Why’s,” or “3Ws” for short:

1. Why Buy Anything: One type of deal wouldn’t close because there wasn’t a good answer to the question: “Why buy anything?” In other words, there weren’t clear enough (or severe enough) pain points to generate activation energy for the prospect. Which meant doing nothing was an acceptable course of action.

2. Why Buy Us: Another common sticking point was why their solution would have to be the one that potential customers would buy. Even for prospective customers that did need to make a change–that felt they ‘had to do something’–sales teams would lose the deals because they couldn’t state a strong enough case for their own product versus that of a competitor, or the option of building an in-house solution.

3. Why Buy Now: The third bucket of common objections was about timing. For prospects wondering about the cost of waiting until next year's budget, sales teams couldn’t state a strong enough case for urgency to buy now. Or, if prospects were considering buying a solution a quarter or two from now, and acquiring that solution ended up delayed for a few months, what would the cost of that few months’ slippage be? Would that cost be acceptable?

I met Steve when we worked at a startup together. And because I had an engineering degree, he broke down sales for me in such a way that I was able to realize: Sales is just another process–like many I had been tasked with managing as an engineer. And he had a way of driving conversations that made people think that he was going to be upfront with them if they were aligned. And during the conversation, Steve would actively try to determine whether what he was offering, and what prospects were looking for, were aligned. Were the people on the phone the right buyer personas to speak to? And if they weren’t, Steve would be more than happy to call attention to that fact. As he explained to me, sales is a process of searching.

What I’ve found with startup founders is that they're incredibly smart. They know processes. They know how to solve problems. And a lot of them love first principles. And so this process that Steve created is essentially what I consider to be the first principles of sales. What I’ve noticed is that when founders understand these questions, and start to get better at getting the answers to these questions, our “3Ws,” they become just as good at sales as the first reps and managers that they hire. Even if they ‘hate’ sales, or think they do, they usually end up becoming fans of it, as unlikely as that sounds.

More Resources on Alternative Founder Perspectives on Sales:

• Video - Things I Have Learned About Sales So Far with Fred Stevens-Smith
• Video - Heavybit Sales Master Class with Bridget Gleason

Why Do Early-Stage Founders Hate Sales? (Or Think They Do?)

Important Takeaways on Why Some Founders Shy Away from Sales:

• Hesitating at the Wrong Moment in Sales Conversations Costs You Deals: While some founders aren’t comfortable working with the kind of exploratory questions you need to ask in a sales conversation, stopping short of asking the right question can be the difference between winning and losing.
• Feeling Awkward? It Could Be Learned Behavior (That Can Be Unlearned): Sometimes an aversion to sales conversations can come from our individual beliefs–beliefs that founders can change.

Here are some of the objections I hear a lot from founders who, for whatever reason, feel an aversion to working in sales:

• “I don't want to bother these people.”
• “I can't ask these questions directly.”
• “Maybe I need to give them a lot more information before they can answer questions.”

And the aversion to asking questions, to ‘bothering’ people, can make them stop short in those crucial sales calls. They ask a question and they stop at features–which logically seem like the only answer to ‘why buy our product.’ That nagging self-doubt that causes founders to stop short becomes less of an objection and more of a pitfall that sabotages a startup’s sales process.

But if you start with those important preliminary questions, shouldn’t every sales conversation just be an easy thing that everyone flies through? Not exactly. I believe there are also last principles to sales that can help founders win more deals. They may think they have a handle on the “3Ws,” but when founders get into a conversation with a prospect, especially an intimidating executive, or maybe a celebrity developer, they start to feel this pressure. And all of a sudden, the first principles, the game plan...it all goes out the window.

I recently covered this in a conversation I had with the co-founders of a startup, but I believe that what happens is that founders have some ‘hidden principles’ that replace what they planned to talk about. They’re afraid they can't ask questions directly because someone's going to say ‘no’ and then hang up. If we want to get touchy-feely for a moment, these seem like they could be maladaptive patterns we developed as children to protect ourselves from rejection and the fear of being abandoned. Even though founders try to use our first principles, they may come to think that they’re conditional and only ‘work’ in certain situations.

What I tend to do with founders as I coach them is to review situations in which they tried to use those 3Ws and try to locate where they may have stopped short when receiving a challenging or disapproving response from the prospect. Obviously, not every question you ask on a sales call will elicit an enthusiastic response, but sometimes, when prospects pause or do something unexpected, founders may interpret the response as disapproval, or an urgent prompt to show more product. As I’ve found, such breaks in the conversation are usually more of an opportunity to find alignment between you and your prospect over what they really need–which can then guide what product to show, if any.

And what you find is that all of a sudden, they had sensations in their body or suddenly found themselves discovering limiting or unconscious beliefs they held that prevented them from asking the questions. In the process of going from hating sales to loving sales, you start to identify what beliefs are blocking you from the first principles. Maybe you have conscious beliefs. Maybe you’re fixated on how you think you have to demo everything just to drive interest rather than working to understand your prospect’s context to then engineer that magical “Aha!” moment that moves them to the next step. Or, maybe you have unconscious beliefs along the lines of, "I can't be direct with my needs," or "my needs are bad or unimportant," or "I have to trick them to get my needs are met"–when you might be better served focused on the 3Ws to ensure “we both get our needs met" and that once you get through the 3Ws, you can ascertain whether prospects can get what they want...once they know what they want..

Breaking Into Sales Can Mean Breaking Down Unhelpful Beliefs

Important Takeaways on How to Flip the Script on Being Sales-Averse:

• Asking Discovery Questions Doesn’t Necessarily Hurt Relationships: It’s possible to ask sales discovery questions for the express purpose of trying to help your prospects solve the pain they’re experiencing.
• One of the Keys to Discovery Questions is Disqualification (Also a Good Thing): One of your most important goals in early sales conversations is understanding whether the prospect is a good fit for what your startup offers. If it’s not, you can be the first to let them know–and get back to focusing on deals you’re more likely to win.

Here are some examples of those awkward thoughts and feelings that founders have related to me in those moments:

• “I don't want to ruin the relationship.”
• “Asking too many questions, or questions that are too direct, must be annoying for them.”
• “I don’t want to be seen as too sales-y or too pushy.”

What I find myself doing is holding these founders close to reality, and expanding what range of reality is acceptable to them to remain fully resourced–to have access to all the options that are available to them. Sometimes I have to ask follow-up questions, or even challenge assumptions, which we do in a non-hostile way that usually involves having a sense of humor. But the conversations I have with these founders often boil down to the question: “OK, that's your current belief–so how do you replace it with another belief that reflects your values and the value they'll get from becoming your customers?”

What if asking these questions would actually build your relationship with your prospect? What if you could drive the conversation in a way that was more collaborative? Would that build the relationship? What if this was a form of curiosity that's aimed at trying to end the suffering of the developers you’re talking to (and trying to sell to)? And you’re trying to find reasons for why your product is not a fit? And if your product is not a fit, you’re actually causing more suffering by trying to sell them something they don’t need. So by asking all these ‘annoying’ questions... you're actually preventing that.

And so, the thinking comes around to figuring out how to ask these questions to ensure that you're compassionate. You’re conducting a search, as I mentioned earlier, for people who are suffering in the exact way that your product was built to cure. You’re basically trying to find potential customers who fit your ideal customer profile (ICP). And if your product fits their needs, you'll share more. If there’s no fit, and you weren’t talking to someone who fits your ICP, you'll be the first to tell them. You're committing to curiosity. You ask questions, and based on their answers, you're asking more-refined, deeper questions to get to that root cause analysis. Because what is that pain, really? How can you quantify it? How can you find other people who are impacted by it? How do you find out, if this developer you’re speaking to has this pain, who within the developer’s organization has the power to help them get what they want?

And lastly, collaboration. As a founder, you're committing to making this process collaborative. Not dominating the conversation by just showing them everything without letting your prospects contribute. You're actually going back and forth, gathering information in the process. And I’ve found, especially for developers who become founders, all of a sudden they realize that they had these false beliefs of why they ‘couldn't do’ certain things. And very quickly, they come to know how to get to those three values–the words come to them because it's more aligned with what their core beliefs and values are. You start to identify and become aware of those self-limiting beliefs and personal triggers–then move away from them. Does that mean that every startup founder needs to go to therapy? I sometimes jokingly refer to these conversations as a ‘welcome mat for therapy’ since some founders do take that next step and it can be very fruitful for them.

Regardless, founders need to perform, using the technical term, functional analysis. It’s not a bad idea to ask questions such as: “What functions are being served by these beliefs?” When you get to the root cause of not just why a prospect is a ‘good prospect,’ but also why you're not asking the questions, it tends to be the fastest way to transform how you're selling.

Getting Signal: How to Know You’re on the Right Track

Important Takeaways on How to Track Your Progress:

• Make Sure You’re Asking Questions with Enough Specificity: It’s important to ascertain whether prospects have enough pain to take action, who would be affected by the decision to move forward, and who in your prospect’s organization has the budget authority to make a decision.
• You Don’t Need Answers to All “3Ws” In One Conversation: Even if you can’t get direct answers to every question in one call, or find yourself blocked, that’s fine. Because you just determined where you need to do more searching and information gathering to make the next conversation valuable.

For my playbook, I use a series of templates and slides, including a worksheet for the 3Ws M.A.P. (along with specific deal review we’ll go over in the next section) that help founders take notes during meetings. I try to coach founders to make sure they not only ask our 3Ws but that they ask the questions correctly. I call it asking “deep enough, wide enough, and high enough.”

• Deep Enough: Are you getting details on issues that are quantifiable? Are you identifying that there’s enough pain to warrant making a change?
• Wide Enough: Who are all the people impacted by your prospects’ problem? What are the second-order impacts? Who are the champions?
• High Enough: Have you mapped out the power structure and the escalation plan? If something's blocking the prospect from getting what they want, who are the right people to talk to, and how?

This can be an iterative process as you talk to different people in an organization. For example, you may find yourself making traction in conversations with developers, but let’s say the conversation moves up the totem pole to include a high-ranking executive or someone in procurement, and it blows up. That’s actually good! You’ve pinpointed the extent to which you’re fully resourced–that you know and have everything you need to continue. Which means you focus your next session on identifying the blockers, understanding the key players, and as you digest this new information, you expand the range at which you can be fully resourced.

In some cases, the process is a one-and-done because there's one major blocker, and you can find a good enough solution for it. But in others, you might not be able to walk away with the “3Ws.” So in your session, you need to find out what's blocking you from doing that. Whether it’s conversations about pricing or other roadblocks, such as selling to a bigger company, what founders start to realize is that over time, they have to be disciplined about their approach. In every sales conversation, you're trying to either get the 3Ws, test the 3Ws, or use the 3Ws to move your deal along.

If you’re getting to those key questions, congratulations, you’re probably making that transformation into your startup’s first seller. If you’re not, you go back to the drawing board, but you can also look over your call logs and notes to figure out how to debug the process.

Like Debugging Code? You’re Gonna Love Debugging Sales Deals

Important Takeaways on How to “Debug” Sales Deals:

• Debug Deals in Play by Determining How Clear Your Answers are at Various Stages: You can “unit test” sales deals by stage, which are determined by variables like having the 3Ws for the organization, champion, and sponsor along with other variables.
• Early-Stage Sales Pipeline Probably Won’t Be a Flywheel: And that’s OK. One of your main goals as an early-stage founder should be to figure out why winning deals win, and why losing deals lose–so you can do more of the winning stuff and less of the losing stuff.

You can “debug” your deals, either as you’re pursuing them, or after a deal is won or lost, which gives you the opportunity for a deeper postmortem. I’ll often review sales pipeline with the founders I coach from a first principles perspective, reviewing deal details like amount, close date, and stage. Then, we look at what's changed since the last review, what's the next step, and what the biggest concerns or challenges are. These items need to be fields in your CRM and displayed sequentially to help you build the “muscle” of getting through ~1-minute updates for each deal in this order.

What I find is that founders don’t always give good answers to these questions. So we’ll often start with the biggest concern. When we answer that question, we’ll effectively identify what unit we should start to test first. And we’ll grade deals by percentage to completion–maybe at 20%, the sales representative or founder believes that they have good answers to the 3Ws for the org. But if you want to advance your deals to a 30% completion, you have to have identified a champion, not just the contact, but someone who has power. 40% completion means you have the 3Ws in the words of the sponsor–the person who has the budget. And then at 50%, you've now developed a plan based on the 3Ws–if needed, you’ve already got a competitor map. As we mentioned earlier, one of the most important things to determine early on is qualification of each deal–is the person you’re talking to a good fit for what you’re selling? If not, you end the conversation ASAP and move on to someone who is–and this process can also turn into a feedback loop that helps you learn more about, and refine, the persona you want to target for sales.

You can unit test ‘Why Buy Anything,’ almost like an algorithm, a standard operating principle to actually get deeper, wider, higher answers, and then come up with the next step.”

Sometimes, deals will get stuck at 20-30% completion, and for others, startups will win them but not know why. In other words, early startup pipeline often does not resemble that mythical, repeatable flywheel. The goal here is: For every deal you win or lose, you should know why. Because that’s how you identify the stuff that works to make you win more and do less of the stuff that leads to losing deals.

It’s pretty common to see people claim all their deals are at 70% completion in my first conversation with them. As part of the debugging process, I ask about what has changed, and the biggest concerns–which often helps me determine which step they might have missed. Who's a champion? What's their unique answer? Who's the sponsor? What’s their unique answer? What's your plan? Each of these are units to test.

So for example, if you have a deal you say is at 70%, which means you should be in the negotiating stages, but then you have a big concern about the prospect having gone dark or not hitting the agreed-upon timeline. As part of the debugging process, I’ll observe that not hitting the timeline suggests the prospect doesn’t have a good answer to “Why Buy Now?” That's an alignment with a closed date. They might not have a sponsor who has a “Why Buy Now?” They might only have a champion. And maybe for the champions, “Why Buy Anything” might be weak, because they haven't given you access to a sponsor who could then escalate and make sure that the timeline is moving along.

I’ll find myself asking founders in this situation why they’ve provided the reasons they did. For example, I’ll ask why the prospect doesn’t just keep everything the same. They might answer, “The problem is that if they don’t make a change, they won't make money.” OK, what happens if they don't make money? “Well, they’ll lose their job.” OK, did they tell you that? “No.” OK, if they might, in fact, lose money, how much? How much money would they have to lose before they're actually going to do something? The 3Ws are all “Why” questions–and one of the best ways to unit test each one is to examine the opposite “Why not” question.

And so, you test for assumption, and then your next step might be to email this person and ask for clarification. “Hey, you mentioned this, but I didn't understand how big of a problem it is. What happens if you don't have that?” It’s a way to unit test “Why Buy Anything,” almost like an algorithm, a standard operating principle to actually get deeper, wider, higher answers, and then come up with the next step.

Being the First Seller Helps You Scale Sales Successfully

Important Takeaways on How to Scale Sales:

• Learning to Be the First Seller Helps You Hire and Delegate: Having that deeper, firsthand understanding of how to sell your product and what your customers look like will be enormously beneficial in hiring your founding sales team when it’s time to scale.
• Learning to Be the First Seller Helps You Hold Sales Accountable: Once you understand how to sell your own product, you can also generally identify issues with your sales team’s selling motion in short order.

For several reasons, it’s considered a best practice to go with a founder-led sales strategy in the early days of your startup. When you, the founder, becomes the first salesperson, you save budget on headcount, for starters! No need to hire that first seller if you’ve already got the position covered. And as a founder, you have unparalleled expertise in the problem space you built your company around, and the pain your prospects feel. So if anyone can answer questions about it, it’s you. Sometimes it’s as simple as building up that comfort level to ask the 3Ws.

And once you feel comfortable asking the questions, and know which questions to ask and why, you’ll find you’re going to be better than an outside sales rep, which is something to watch for when it’s time to scale and start onboarding a formal sales team. Founders sometimes find that reps they interview don't have answers to questions about their past deals because for a lot of companies in Silicon Valley, the best resumes come from companies that already had strong product-market fit and were generating a healthy amount of annual recurring revenue (ARR). In some cases, reps that sell for established organizations don’t really have to sell with this amount of precision, but as a founding team, selling something unknown into an unknown market, you have to.

When you have that firsthand experience, you can implement metrics you understand, and unit test them from the first day, in the first month, and so on, and apply them to sales activities as they’re happening.”

I should mention that one trend I’ve seen with PLG startups that launch by selling directly to end users eventually have to scale to a point where they hire a sales team. And those newly-hired sales executives will say, “If you want me to sign off on these big targets, you've got to give me authority to do whatever I want, and hire whichever team members I want.” Sometimes sales teams forbid founders from attending pipeline meetings, and sales becomes this inscrutable black box. At that point, you’re waiting nine to 18 months to figure out whether you hired the right person.

When you become the first seller at your startup, you gain important abilities, such as calling the tune for sales enablement that helps your sellers sell, and understanding how to hold your reps accountable. However, you’ll also be able to build your own sales roadmap, which will include the kind of sales leaders you’ll want to hire. It's like an API. You figure out how to talk with them so that you can delegate sales. Now you can manage them and see the typical hiding places that sales leaders hide behind. When you have that firsthand experience, you can implement metrics you understand, and unit test them from the first day, in the first month, and so on, and apply them to sales activities as they’re happening. So what’s arguably at stake here is not just your early sales, but also how much power and control you give to sales teams you hire.

Sometimes people think of sales as the “tail” of the company, that follows after the product and engineering teams create and ship new products. But sales can start wagging the dog if you don't have a certain amount of sales competence and awareness. The thing is, figuring out whether your sales team is working doesn’t necessarily take that long. Sometimes you can figure it out in one session. Sometimes you’ll find yourself maybe spending a quarter or so of weekly pipeline reviews and digging deep, but it’s usually a pretty quick process. In any case, what a lot of startup founders realize is that the things that made them successful in coding, project management, and innovation are the same things that make them successful at sales. They just have to make the connection. And they don’t have to adopt a separate “sales persona” that drives a fast car and wears a power tie. They can show up, as themselves, doing what they do well. And love doing it!