The Role of the CEO in Startup Sales
This issue keeps surfacing in multiple early-stage companies I’m supporting as they push toward product-market fit (PMF) and begin scaling.
In the early days of a startup, the CEO plays many roles — strategist, communicator, product lead, marketer, fundraiser, recruiter, and more. But arguably the most critical role is acting as the company’s first Chief Sales Officer. Early-stage sales can’t simply be delegated or outsourced. The sales motion, what to sell, how to sell it, and to whom, must be developed through hands-on experimentation. It’s a process of testing, refining, and learning in real time. The CEO must lead it: early sales are how the company gathers essential feedback, proves its value in the market, and ultimately, survives.
Before PMF, startup sales are about discovery, not revenue. The goal is to engage directly with prospects to uncover pain points, understand workflows, and learn what real solutions they need and would pay for. These insights come from honest conversations, not surveys. The founder-CEO is best positioned to lead this, bringing conviction, adaptability, and deep context. Their involvement shapes company culture, instills urgency and accountability, and embeds sales as a core, mission-driven function—not just a future hire’s responsibility.
The CEO’s role in sales evolves as the company grows. In the “zero to one” phase, the CEO personally leads most sales activities—crafting the pitch, negotiating deals, and refining pricing. The goal at this stage, depending on the technology and market, is to land the first set of customers — typically around 20 for B2B software — while learning what resonates. As repeatable patterns emerge, the CEO begins documenting what works and may start testing one or two early sales hires. This marks the “playbook formation” phase, where founder-led sales transitions into a scalable system. Eventually, once the playbook proves effective, the CEO hires a Head of Sales, builds out the sales organization, and shifts from direct selling to managing, while still staying engaged in strategic accounts and reinforcing the company’s vision.
Many CEOs make one of two delegation mistakes: they either delegate sales too early or wait too long.
Delegating too soon risks building in a vacuum or pushing sales without clear messaging or buyer personas. Early deals require founder involvement—only they fully understand both the product and the customer’s pain.
Delaying delegation for too long can confuse customers and demoralize the sales team. This often occurs when the PMF is elusive or the CEO has a strong sales background and struggles to step back.
To succeed in the role, a CEO should always be talking to customers, even after a sales team is in place. First, it provides very valuable knowledge going into company board meetings, financing presentations, and ultimately exit discussions. The CEO should listen to customer objections, help arrange references, review sales pitches, and promulgate the company’s long-term vision based on customer use cases that they know something about. Being connected to sales deals informs hiring, marketing, channel, partnerships, and fundraising, as well as other internal discussions.
When should you delegate — and when should you stay in the fray?
The short answer: start asking this question once you’ve achieved a solid signal of PMF. Other key moments include hitting new sales milestones, expanding into new segments, or preparing to hire your first sales executive.
After reflecting on your instincts, seek perspective from those around you. Talk to experienced founders and operators in your space, especially those with sales and marketing backgrounds. Lean on your board, lead investors, and advisors; that’s what they’re there for. Consult industry experts, even your early customers. And don’t overlook the wisdom of your partner or spouse; they often see things you might miss.
Whatever the timing, treat it as an active process. Build a transition plan, test it, and refine it often. Delegation isn’t a single decision; it’s a series of adjustments based on the company stage, team strength, and what the moment demands from you as CEO.
Conclusion
Sales is the proving ground for every early-stage startup, and the CEO is the one who must lead the charge. From the first pitch to the first playbook, the founder’s direct involvement in sales is what grounds the company in reality, shapes the product, and sets the pace for growth. Over time, the role shifts, but never disappears. The best CEOs know when to lead from the front and when to empower others, staying close enough to customers and deals to guide the company with clarity and conviction. In startup sales, delegation is not about stepping away, it’s about stepping back just enough to scale what you’ve learned.