Sell It Yourself, Dammit: The Case For Founder-Led Sales

Why Hiring Salespeople Too Early Almost Never Ends Well

Welcome back to Scaling With Soul!

Today we’re talking about why founders make the best first salespeople for their startups—and how hiring salespeople too early can kill your company’s chance to thrive.

I had a "holy shit" moment this week at the Startup Grind Global Conference. It happened when a speaker articulated something my co-founder and I did intuitively but never had the words to describe.

Joe DiMento from Bain Capital was presenting on "Moving from founder-led to AE-led sales," and I found myself nodding so vigorously I probably looked like a dashboard bobblehead on a dirt road.

"Try to get to $1M ARR before hiring your first Account Executive," he advised.

I nearly jumped out of my seat. "YES! That's exactly what we did!"

When building Boardroom Insiders, my co-founder, Lee—supported by me—handled all sales for four years. Not because of some brilliant strategic insight, but because we were bootstrapped and couldn't afford to hire anyone. Every dollar we paid someone else came directly out of our own pockets.

DiMento laid out a framework that made so much sense to me as I reflected on how Lee and I handled sales over 12 years as we bootstrapped our way to a $25 million exit. As I sat listening to his presentation, I realized that financial constraints had accidentally forced Lee and me into the optimal strategy. Sometimes the best decisions are the ones you make because you have no other choice. Mind blown, I knew I had to share DiMento’s recommended approach with as many founders as possible.

The Power of Founder-Led Sales

Here's why founder-led sales isn't just a bootstrapper's necessity—it's a strategic advantage every startup should embrace, even if you have millions in venture capital in the bank:

1. You Can't Outsource Product-Market Fit

When founders sell, they're not just closing deals—they're conducting valuable customer research. Every objection, every question becomes immediate product feedback.

At Boardroom Insiders, I'd take copious notes during sales meetings. Sometimes I'd immediately say to Lee: "We need to add this capability ASAP—we had three prospects ask for it this month."

This feedback loop gets destroyed when you insert an Account Executive between founders and customers. The insights get filtered, delayed, or lost entirely.

2. You're Building Your Sales Playbook in Real-Time

DiMento emphasized that "the early sales process is iterative." Yeah, it is.

We experimented with dozens of approaches to selling Boardroom Insiders. Different offers and pricing models, sales channels, messaging, objection handling techniques. Some worked brilliantly; others crashed and burned.

One memorable failure: we tried selling an industry specific “packet” of our executive profiles à la carte instead of as part of a database subscription. Seemed logical—let customers pay only for what they need. We quickly found out that our ICP (ideal customer profile) just didn’t buy products like ours that way. We pivoted back to subscriptions within weeks.

Had we hired AEs to execute this flawed strategy, we would have burned through time, capital and leads before realizing our mistake. Instead, we could adjust course immediately with minimal damage.

3. You're Learning What Type of Sales Leader You'll Eventually Need

The most valuable insight from DiMento was about sales leadership evolution. Your first sales leader should be a "player-coach"—someone who can both close deals themselves and train and mentor new salespeople, all the while learning, digesting and refining your sales model.

This was another accidental win for us. When we finally hired our first salesperson, Lee directly managed him, continuing to close deals himself while teaching our new hire the ropes.

We never did hire a dedicated sales leader; two high-performing AEs carried most of our business, supported by two customer success reps. This lean approach got us to $5M ARR and a $25M acquisition.

The Costly Mistake of Premature AE Hiring

The flip side of founder-led sales is the danger of hiring AEs too early—a mistake I've seen countless founders make, especially those flush with venture capital.

DiMento put it bluntly: "If you have underperforming AEs, you not only waste time and money—you burn leads."

This is a devastating double-whammy:

1. You're burning cash on salaries and commissions for people who aren't producing

2. You're burning through your limited pool of potential customers who may never give you a second chance

I've seen startups hire experienced AEs from much larger competitors, pay them $300K+, and then watch them fail spectacularly because the startup's reality was nothing like their enterprise gig.

These enterprise AEs are execution machines, not discovery pioneers or scrappy go-getters. When dropped into the chaos of an early-stage startup with an evolving product and unclear ICP (Ideal Customer Profile), they typically flounder.

The "MVP/ICP Handshake" Moment

So when is the right time to hire your first AE? DiMento introduced a concept I love: the "MVP/ICP handshake."

This is the moment when:

• Your Minimum Viable Product is getting traction, proving product-market fit

• You've clearly identified your Ideal Customer Profile

• You have a (somewhat) repeatable process for finding and converting these customers

If I'm honest, we never fully nailed number 3 at Boardroom Insiders. In the early days of our success when we had about 30 closed deals under our belt, we tried to analyze patterns but couldn't see any. Every deal was different, and we didn't have enough data to conclude anything meaningful.

Still, we had enough evidence to know:

• Our product resonated with enterprise tech companies

• Our primary buyers were in marketing

• Our value proposition around C-suite engagement was compelling

• Our pricing model was sustainable

Only then did we feel confident bringing on our first dedicated salesperson.

Hiring Your First AEs: Counterintuitive Advice

When you do reach that MVP/ICP handshake moment, DiMento shared some specific advice:

1. Hire Two AEs at Once This gives them someone to learn with and gives you a better read on whether problems stem from the product or the rep. We didn't do this initially, but when we expanded our sales team, we brought on two reps simultaneously and saw exactly what DiMento described.

2. Favor Smart Generalists Over Industry Veterans DiMento mentioned that Stripe famously hired former consultants as early AEs—not because they had sales experience, but because they could learn fast. Our most successful early sales hire had agency experience but no formal sales background. What made him effective was his curiosity, intelligence, and ability to deeply understand our product and customers. He became a high performer and a leader in our company and now is a seasoned SaaS sales vet.

3. OVERPAY Your Early AEs This one makes perfect sense and tracks to what we saw. Your early AEs are taking a massive career risk joining your unproven startup. They're also doing much harder work than AEs at established companies—they're helping create the playbook, not just executing it. We didn't consciously overpay our first sales hire, but we did give him a compensation structure that rewarded him generously for success. When he started closing deals consistently, he made excellent money—and we were thrilled to pay it.

The Player-Coach: Your First Sales Leader

Perhaps the most valuable insight from DiMento's talk was about the first sales leadership hire. You need a "player-coach" for the first 12-18 months of sales traction—someone who can both sell and manage.

This is radically different from the traditional VP of Sales role. You don't want someone who immediately builds a team and then disappears into forecasting spreadsheets. You need someone in the trenches, closing deals while simultaneously developing your junior salespeople.

At Boardroom Insiders, Lee effectively played this role until we reached about $3M ARR and then our reps had enough experience and confidence to close big enterprise deals. However, they nearly always checked in with Lee, because almost every deal brought some new wrinkle that we had not seen before. We never did hire a dedicated sales leader. Lee served this role until we sold the company.

The Founder-Led Sales Playbook

If you're in the early stages of building your company, here's my advice:

1. Embrace founder-led sales for longer than feels comfortable. Push to $1M ARR before hiring your first AE if possible.

2. Document everything. Every call, every objection, every closed deal—create a living repository of what's working and what isn't.

3. Experiment aggressively with your sales approach. Try different offers and pricing models, pitches, and contract structures. You can pivot quickly as a founder; this gets harder with a team.

4. Look for the MVP/ICP handshake moment. When you can clearly articulate who your customer is, what problem you're solving, and have some insight into how to find and convert these customers, you're ready for AEs.

5. Hire smart generalists who can learn, not industry veterans who are set in their ways. Your first AEs need to be pioneers, not execution machines.

6. Invest in a player-coach as your first sales leader. Find someone who can both close deals and develop junior talent. Ideally this role is played by one of your founders, because no one else is going to be more motivated and or have more skin in the game. 

7. Don't rush to scale your sales team beyond your first early performers. Adding a lot of AEs before you have a repeatable process is like adding more people to push a car with no engine—it just burns more energy without getting you anywhere faster. And it sets your new AEs up to fail, which isn’t good for anyone.

The beauty of founder-led sales isn't just that it's economical—it's that it forces you to truly understand your customer and your value proposition in a way that no market research or customer survey ever could.

As founders, we often rush to delegate sales so we can focus on "more important" things like product or strategy. But in the early days, nothing is more important than being face-to-face with customers, learning directly from their reactions to your offering.

Sometimes the best strategic decisions come not from brilliant foresight, but from the constraints that force us to do things the hard way. In the case of founder-led sales, the hard way is the right way.

Note: If you like the stories I shared here about me and Lee, you will love my book, Scaling With Soul: How I Built and Sold a $25 Million Tech Company Without Being an A**hole. You can get a free digital copy by subscribing to this newsletter for FREE. Or, become a paid Founding Member and get a signed hardcopy mailed to you (US only)!

What challenges are you facing in your business? Email me at sharon@sharonkgillenwater.com with your questions, and I might address them in a future issue or an office hours session (for paid subscribers only).

Founder Finds is a weekly roundup of what captivated us this week. Like our main feature above, this week’s finds were inspired by my favorite sessions at Startup Grind. Note: I don’t get paid for these. If I decide to take a commission for a recommendation, you’ll be the first to know.

1. A VC’s Optimistic Vision: In an industry that feels increasingly dark and dystopian, this conversation with Navin Chaddha of Mayfield Fund was refreshing and perfectly aligned with my own mission to democratize entrepreneurship. Chaddha calls AI “the great equalizer…Everybody should lean forward and say, 'This is my time.'" He envisions a world where anyone with an idea can become an entrepreneur, regardless of technical background. I was the person who actually started the round of applause when he suggested that maybe VCs need to feel some heat and pressure from the barriers being broken down by AI. "Why should entrepreneurs only feel challenges? Everybody should be in the hot seat." His concept of "vibe coding" suggests AI won't replace humans but elevate our skills to "superhuman" levels. If you're questioning whether there's still room for newcomers in tech, this conversation is the antidote you need. It's a powerful reminder that the best innovations happen when technology empowers more people to solve problems—not fewer.

2. The Critical Distinction Between Early and Scalable Product-Market Fit:

   This conversation between Shernaz Daver (Khosla Ventures) and Stacy Brown-Philpot (Cherryrock Capital) illuminates a subtle but important distinction that is not often discussed: the difference between early product-market fit and scalable product-market fit. Brown-Philpot, the former TaskRabbit CEO who sold the company to IKEA and recently raised $172M for her first fund, articulates it perfectly. As she explains, many founders mistake initial customer enthusiasm for true product-market fit, only to hit a growth ceiling later. "Early product market fit is when you're selling to a customer who doesn't mind trying something out to see what works," she notes, contrasting it with scalable product-market fit, where you've created a repeatable process that someone else can execute. What makes this insight so valuable is how it reframes the fundraising conversation. Daver, drawing on her extensive experience at Khosla Ventures, emphasizes that investors are looking for evidence of scalable product-market fit—not just happy early adopters. This explains why some founders with seemingly successful products still struggle to raise capital. For founders navigating the gap between initial traction and true scale, this conversation offers a practical framework for distinguishing between the two stages of product-market fit—and why understanding the difference is essential for both fundraising and sustainable growth.

Share YOUR Finds: Have you stumbled across a game-changing resource for entrepreneurs? Send it my way at sharon@sharonkgillenwater.com. Whether an insightful article, a powerful tool, an under-the-radar newsletter, or a mind-shifting podcast—if it helped you, it will help our community. Contributors of featured resources get full credit and my eternal gratitude!

Q: I'm a founder with young children, and I constantly feel like I'm failing at both roles. Do I have to choose between being a successful entrepreneur and being a good parent?

A: This question hits close to home. When I was building Boardroom Insiders, my kids were young, and I constantly worried about the time I spent working instead of being with them.

Here's the unvarnished truth: entrepreneurship and parenting are both all-consuming roles. Anyone who tells you that you can give 100% to both simultaneously is selling you a fantasy.

But that doesn't mean you have to choose one over the other. It means you need to be willing to let go of perfection in both domains.

When my kids were little, I was juggling two gigs and building Boardroom Insiders. I wasted so much time beating myself up about shortchanging or even damaging my children. I missed school events, stole hours from family vacations, and constantly had my head in a laptop.

What I couldn't see then—but can clearly see now that my boys are adults—is that they were absorbing powerful lessons by watching me. They're proud of what I accomplished. I overhear them talking to their friends about my work. They—and their Gen Z peers—connect with me on LinkedIn and seek my career advice. The very thing I thought was taking me away from them has become a source of connection and mutual respect.

Here are some hard-earned insights from my journey:

1. Spouse/partner selection is everything. I couldn't have built a $25M company without my husband taking on the primary parenting role. He loved nothing more than shuttling our sons to and from school, playdates, and parks. Our complementary strengths made everything possible. If you don't have a supportive partner, you'll need to build other support systems.

2. Quality matters more than quantity. When I was with my kids, I tried to be fully present. No checking email, no half-listening while thinking about work. This wasn't always possible, but it was the goal.

3. Let go of what others think. Even in ultra-progressive San Francisco, I faced judgment for my choices. One Saturday, my husband took the kids to a neighborhood garage sale while I had a spa day with a friend. When a mom asked where I was and my husband told her, her sarcasm said it all: "Wow! That must be nice!" We got comments like that all the time. You have to develop a thick skin.

4. Involve your kids when appropriate. As my boys got older, I occasionally hired them to do data entry for Boardroom Insiders and one of them joined our summer internship program with one of his high school buddies. They learned about the business, work ethic, attention to detail, and the satisfaction of earning money. These experiences shaped them in positive ways.

5. Remember that seasons change. The intense startup phase doesn't last forever. There were years when I had to prioritize the business more heavily, but there were also periods after I had built a team when I could shift more attention to family.

There's no single right way to balance entrepreneurship and parenthood. You'll make trade-offs and compromises. But you're modeling persistence, passion, and purpose for your children—qualities that will serve them well throughout their lives.

Most importantly ditch the guilt—it serves no one, least of all your kids.

Ask Me Anything: Got a burning question about building or scaling your business? Drop me a line at sharon@sharonkgillenwater.com. I personally read every email and respond to as many as possible. The most interesting questions might be featured in future issues (with your permission, of course). No question is too basic or too complex—I'm here to help you succeed!

Come to My Office Hours: Paid subscribers to this newsletter now have access to office hours with me and other founders. Our next session is May 7th from 10-11am PT. Is $10/month worth chatting with me and a bunch of other founders a few times a month? You bet it is, so maybe you should upgrade here. Would love to see you and hear about what you are working on!

Follow Me on Social Media: I love engaging with entrepreneurs and have a lot more to say on all of these topics, so connect with me on TikTok, YouTube and LinkedIn.