In a startup’s earliest days, founders are the only salespeople by default. And founders who don’t have any previous sales experience are often surprised to find that they’re very effective at it. But this makes sense; after all, they’re the one who first saw the need for the product and drove its creation.
A few years ago, I received a call from the CEO of a nascent but fast-growing and well-respected enterprise software startup. He had a problem. His company had expanded to a 20-person sales force with a VP of sales at the helm, yet the sales team still needed his help to close most large deals and had missed their revenue targets for two consecutive quarters. He simply couldn’t continue to be the backstop for all the company’s salespeople.
I began working with the CEO to figure out why his sales team couldn’t reproduce his success. I started by asking his VP of sales a simple question: “Do you use a sales playbook?” The VP’s response was alarming. Not only did his team not use a playbook, he wasn’t even aware the team needed one.
Beyond a certain point, you can’t rely on intuition to drive sales. You need formal, repeatable processes that transform sales into a disciplined function rather than an improvised and inconsistent art form.
Replicate yourself
The playbook is a step-by-step description of the practices and behaviors you’ve found will lead to a successful sale. It’s how you teach your sales team what has worked for you, the founder and first salesperson, so it becomes second nature to them.
Over the course of a few weeks, this CEO and I prepared for and debriefed after customer meetings to figure out his recipe for closing deals. Once we’d done this, we analyzed the key phrases the CEO used to describe the product and its value, then translated them into a set of narratives for the sales team to use on customer calls. In a matter of weeks, they started closing more deals without the CEO’s help.
The key message for startup founders at this stage is: Replicate yourself. The best way to do this is to analyze and document the winning strategies and tactics that have enabled you to sell successfully in the early days.
Avoid at all costs reaching a point where you have a team of 10 or 20 salespeople all doing their own thing, forcing every new sales hire to reinvent how to sell.
If new salespeople are successful and making quota, you know your repeatable sales motion and playbook are working. If they aren’t, then you need to return to refining your playbook before hiring more salespeople. I can’t stress this enough: If your salespeople aren’t consistently making quota using your expanded playbook, you have more work to do, and you’re not ready to go for growth and add additional—and expensive—salespeople to your payroll.
Step on the gas
Only once you’ve proven you can bring new salespeople on board, teach them the playbook, and have them reliably hit quota should you begin scaling and hire more than eight to 10 salespeople. The scaling phase is the time to step on the gas and accelerate growth. If revenue grows as expected, the sales organization could be 50 or 100 people strong within a couple of years.
Upgrade your executive team
As the demands on you and the business increase, not everyone will successfully scale in their role. An $80 million company must be run differently from a $20 million company. The team you need now might be very different from the one you had in the early days.
This is often a moment when you have no choice but to significantly upgrade your go-to-market leadership, which can be a brutal process. Not only do you have to recruit senior talent that complements the leaders and team you already have—including your initial trailblazer hires, who are often more junior than what you’ll need at this stage—you might even have to make tough decisions to let go of people who have been with you since the earliest days.
If your VP of sales is barely holding it together with a team of 10, imagine them with a team of 50 or 100. If that thought makes you nervous, you’ll know you have to bring in a chief revenue officer (CRO) above them sooner rather than later, or maybe even replace them.
Layer in a sales management team
You’ll also layer in a sales management team reporting to the VP of sales or CRO, who will run and scale increasingly specialized sales teams. You’ll need two types of leaders as you grow: Those who report directly to you, and those who report to your executive team, sometimes called the middle management layer.
As you accelerate, you’ll hire one manager for roughly every eight salespeople. The sales team managers you hire will now take over the day-to-day operations, performance, and culture of their teams.
Form specialized sales teams
Once you grow past 10 or 15 salespeople, you’ll likely find it necessary to specialize your sales team. Until now, you might have loosely segmented salespeople by use case, customer size, or geography. If so, now is the time to formalize this specialization to make the team more efficient. For example, you might have a small and medium business (SMB) team, a midmarket team, and an inside enterprise team.
Hire or promote high-performing sales leaders for each of these teams with experience in that specialization. With these hires also comes an important change to your pipeline cadence. Each team will conduct their own pipeline meeting, run by the specialized team leader. The VP of sales will then conduct pipeline meetings with only these team leads, who will be their direct reports.
Give sales more space, but stay on top of your metrics
One of the challenges you’ll face as the company grows is to give direct reports like the VP of sales more room to maneuver without your becoming disengaged from the function. When scaling up, you’ll want to give your now-proven VP of sales the space to lead their organization and keep their teams motivated. But at the same time, you want to keep an eye on team performance. You should never be surprised if your sales leader suddenly doesn’t make their number, or learn about the sales team’s struggles only close to quarter end when it’s too late to take action.
I have talked about how you need to replicate yourself and teach new salespeople to use the key phrases and tactics that have worked for you. That replication will be harder to achieve with such a big team, and new salespeople probably won’t mimic you as easily and as much as the early team did. That is just part of growing a business.
Even if your company is tiny, you need to be preparing for a time when it won’t be. The best way to do that is to move at the right time beyond the intuition and improvisation of the early days toward analysis, intentionality, and a structured and systematic approach to building out your go-to-market. Now go off and build. Your company, and your team, need you.
Adapted from Built to Grow: A Handbook for High-Performance Sales Teams by Stephanie Friedman, published on October 13, 2026 by Stripe Press.
