Sales is tough. And it is toughest for the first sales rep at any startup. Which in most cases, or at least those B2B startups which manage to get somewhere, happens to be the founder.
The B2B founder as the first sales rep may sound intuitive. After all, there are many good reasons for this to be a naturally compelling proposition.
1. Belief: Nobody can believe in the product if the founder doesn’t have sufficient conviction in it. When it comes to convincing customers about the value which the product offers, the founder should be the one doing it. Their passion and conviction create the emotional foundation that transforms skeptical prospects into loyal customers.
2. Problem understanding: Most founders have lived experience of the problem which they have developed a product for. This gives them an insight into the user’s pain that can be effectively articulated such that it resonates deeply with prospects. Nothing can help build trust faster than the knowledge of this shared struggle.
3. Technical understanding: Developing the product gives the founder an edge about explaining the technical aspects as well as handling any technical objections. They can dive deep into architecture discussions, explain why certain design decisions were made, and pivot the conversation when technical concerns arise.
4. Product development: Customer conversations provide feedback regarding the product viability as well as performance and features, which are useful for product refinement. Every sales conversation becomes a product research session. It’s not just selling what exists — it’s about discovering what should exist. This direct feedback loop between customer needs and product evolution is invaluable during the early stages when product-market fit is still being refined.
5. Skin in the game: Sales reps are exceptional at a later stage of the business when the product has matured to find PMF, the sales playbook is ready and the cycle has become predictable. Early on, they can be an overkill, especially since they may not be as invested in the business. On the contrary, the founder has everything to lose. And if they don’t stake it out for themselves, nobody else is.
The Reality Check
In practice, this isn’t the easiest thing to do. Sales doesn’t come naturally to most people. I know this, because it didn’t come naturally to me. There were parts of it which came naturally, but there were parts which I had to learn, work on and develop. It hasn’t been very different for some of the best performing salespersons I know. The natural salesperson is a rare creature.
Most founders are builders, problem-solvers, or domain experts—not sales professionals. The transition from creating something in isolation to convincing strangers to pay for it can feel jarring. You might find yourself uncomfortable with rejection, uncertain about pricing conversations, or struggling to balance confidence with humility. This discomfort is normal, but it’s not an excuse to delegate sales too early.
The key insight is that founder-led sales isn’t about becoming a slick salesperson overnight. It’s about leveraging your unique advantages while systematically developing the skills you lack. Your authenticity and deep product knowledge will carry you further than polished sales techniques in the early days.
The Marathon Approach
Sales at an early stage startup is like preparing yourself to run a marathon in short bursts of sprints before settling into a regular cadence. Here’s how to build that endurance:
1. Routine: Develop one. Set aside a block of time for sales. Treat sales activities with the same seriousness as product development or fundraising. Block out specific hours for prospecting, follow-ups, and customer calls. Make it non-negotiable. The biggest trap founders fall into is treating sales as something they’ll do “when they have time.”
2. Analyse: Keep a record of as much as you can of customer conversations. Don’t worry if you don’t see any patterns immediately. Over time, they will start emerging. Use them to settle on a handful of key metrics which can be used consistently, eventually laying the foundation of your sales playbook.
3. Improve: Try to do more, have more conversations, each week. When you can’t have more conversations, try to have better conversations. Continuously refine your messaging, improve your demo flow, and get better at handling objections.
4. Grind: The number one rule of sales. Go after more, every day. Keep going after people. Take rejection on the chin. There will always be someone who will want to talk to you. As long as you keep casting a wide net, day after day. It is brutal, but it builds the much needed resilience that a founder needs to excel in their role.
5. Belief: Know that it is only a question of finding the right person who has that problem you are solving, and then the next person, and then the next. As long as you are really solving a problem that exists and is important enough for someone to pay to solve. This belief isn’t blind optimism—it’s based on the fundamental assumption that your startup exists because you’ve identified a real problem worth solving. Trust that assumption, but validate it ruthlessly through every customer conversation.
Your Path Forward
The transition from founder to founder-salesperson isn’t just about learning sales techniques—it’s about evolving your relationship with your own creation. You’re not just building a product anymore; you’re building a business. And businesses are built one customer conversation at a time.
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