Know when to hire

It’s the evergreen founder question: “When should I make my first sales hire?”

Wait as long as you possibly can

It’s better to hire too late than too early, because you risk missing the value that comes from the founder as seller.

Salespeople aren't Band-Aids. Hiring for sales and asking them to figure out sales is a high-risk move.

Mark Tanner, who co-founded Qwilr in 2014 and advises other startups on sales, describes it as “the worst case of magical thinking” to assume that a sales professional can come in and succeed without at least the outline of a playbook.

At a minimum, you should know who your ICP is, how you handle pricing, and where you source the best leads. These are things you figure out through doing sales yourself.

Use this simple checklist to help you decide if it’s time to scale

You’re maxed out on customer calls.

Be honest here. In the early days, anything up to 10 customer conversations a day is not unusual. Yes, you’re going to be exhausted at the end of your day. That’s the reason that salespeople earn so much money—it’s hard work.

If you’re doing so many calls with prospects that you can’t scale sales independently anymore, that’s your sign.

Deals aren’t closing because of you.

Tofu’s Elaine Zelby says she didn’t hire until she started dropping a lot of balls mid-sales cycle.

“Given all the other things I was doing—I was essentially the only marketer, the only CS person—there was just a bandwidth constraint where I was dropping a lot of balls,” says Elaine. “That was a signal to me, that even if I was doing initial demos, I needed somebody to go and take the deals and run with them.”

Similarly, Pylon’s Marty Kausas realized that not only was he at risk of declaring calendar bankruptcy, but the company was losing revenue because of his “resistance to hiring our first salesperson.”

You’ve dialed in your ICP and use cases.

Equals built a “super horizontal” product, says co-founder Bobby Pinero, but they only began to see real market success when they defined the product's use cases and the people who buy solutions for them.

“For us, I can tell you with a high degree of specificity, there are three people who buy Equals,” Bobby says. “It's a first finance hire, an early RevOps hire, or a founder. They're coming to us because they can't consistently report on their SaaS metrics revenue, and they're either fundraising or have just started a job, and things are kind of messy.”

Hire your first salesperson before you have that level of insight into your buyer and what they are buying your product for, and you risk setting them up for failure.

You can turn what you’re doing into a system.

Without that degree of specificity—who buys your product, what do they use it for, and what are the events that drive them to purchase—it’s too early to start thinking about scaling sales.

“Before I could name any of that specificity, I couldn't train a salesperson to join the company, to go outbound to somebody, to get on a call with them, to be able to know who was a good prospect, who was a bad prospect, to know how to onboard them properly, to know how to price that solution properly,” continues Bobby. “Once you have that, you can build a system around it.”

You’re seeing increasing signs of PMF.

As mentioned previously, your North Star at this early stage of your company is achieving product-market fit (PMF). If you don’t have PMF and no signs it’s getting stronger, it’s too soon to think about scaling; it’s time to get back on customer calls.

In broad brushstrokes, you should be seeing clear patterns in the problems that customers are coming to you with, your message should be resonating, and product feedback should mostly be iterative. As a result, you should see far less churn, and your main priority should be acquiring more customers.

For more on PMF and the levels of it, check out First Round’s definitive resource on the topic.