In early-stage startups, founders are often the first sellers. No one knows the business, product, audience, and purpose better. For the same reason, no one is as invested or busy as the founder. These qualities are exactly why this person is not only the first sales lead—but also the best. As revenue targets grow and responsibilities multiply, however, founder-led sales can become a growth ceiling. Knowing when and how to transition to a professional sales team is critical.
This article offers a playbook for knowing when it's the right time to hire, how to define the role, what to look for in a candidate, how to support long-term success—and what mistakes to avoid. The counsel is pulled from numerous sales talent authorities, including John O'Brien of Sales Talent Group and Bart Fanelli of Skillibrium, both guests of the Extraordinary Pursuits podcast.
The decision to hire often crystallizes in the boardroom. That's where data, investor expectations, and operational realities collide. Founders realize they are stretched too thin. The team (if there is one) is failing to close deals. Pipelines begin to dry up. Everyone is at risk of burnout.
"There's usually a moment during a board or leadership meeting where the numbers tell the story...it's clear that something has to change," said John O'Brien, founder and CEO of Sales Talent Group.
The signs that the time has come to move past founder-led sales include:
This strategic inflection point demands alignment and a strategic plan. Too often, a founder will begin the hiring process with a job description. But job design should come first. While a job description outlines duties, a job design defines outcomes. The latter aligns teams and accelerates success.
The best way to weigh the importance of a job design against a job description is this: it's unlikely that someone would get fired for missing a task on the job description. It's much more likely they would be replaced for failing to deliver on the job design – the reason for their role and the critical target outcomes. Job design questions to ensure alignment between the founder, team, and board include:
This person is not just another hire. It's the most vital and challenging sales hire you'll ever make. This person is not stepping into a mature system. They're building it as they go. This comfort with 'wet sand' is one reason why founders should avoid over-indexing on 'big logo' experience. Enterprise backgrounds don't typically translate to early-stage effectiveness. Traits to prioritize in the interview process include:
Hiring one person to sell and lead seems efficient. Unfortunately, It rarely works. O'Brien speaks from experience, saying: "Hire a player. Let them sell. Then, add a coach." Start with a seller. Monitor sales performance, and when they have stabilized into predictable, repeatable cadences, recruit a coach.
First and foremost, this title should reflect reality. Call someone a VP only if they're truly managing the function. Compensation comes into play once the title, job design, and job description are set. Benchmarking tools (e.g., OpenComp, Carta) are helpful in assessing market rates. Studying recent sales hires within similar-stage companies will help clarify roles, titles, and packages. If you have access to recruiters, talk with them about roles and the best structure for compensation packages.
The compensation structure for a sales lead can be particularly challenging. You'll need to budget for more than salary. Sales leaders need quality CRM and sales tools, travel or field budgets, and marketing and sales enablement support (which could include more hires). Equity can be an attractive part of a total package, but it should not serve as a substitute for market pay.
One way to align incentives is by building Milestone-Based Objectives (MBOs) into the offer. These triggers can look like:
Founders don't need to build a complete RevOps system before hiring, but the infrastructure is crucial. Even if they have the right traits, the first sales hire can only succeed if sales fundamentals are evident.
"Without foundational elements, even the best can't perform," said Bart Fanelli, co-founder and CEO of Skillibrium.
Here's where the job design comes back into play. If the company is at this inflection point, it should have a well-defined ICP, product-market fit, and clear messaging about the company and product. A general checklist should include the following:
Even for the most accomplished sales leaders, closed-won deals can take months. Set, monitor, and use leading indicators to measure sales success from the start. A few early indicators will offer a measure of the efficacy of sales efforts:
"You either had meetings with unique personas this week, or you didn't," said Fanelli. "That's not subjective. That's the kind of clarity you need." Monitor objective metrics that reflect customer experience and internal execution, including:
The first sales hire sets the tone for your revenue function. It's a million-dollar decision—literally and figuratively. O'Brien advises, "Treat it like [a million-dollar deal]. Be methodical. Do the diligence. Don't fall in love too fast." Most founders get this hire wrong. Not because the person lacked talent—but because they lacked structure. Define success. Build the foundation. Hire the seller. Then, scale.
________________________________________________
Learn more about John O'Brien and Bart Fanelli.
.jpg)
