This week, we’re tackling one of the trickiest hires to get right for early-stage startups, with advice from Dropbox, Figma & Stripe.
0-$5M: When, Who, and How to Make Your First Sales Hire
After grinding away with founder-led sales, an early-stage startup finally hires its first dedicated seller. The founding team is stoked — the new hire’s sales pedigree is stacked, and they’re a proven quota-crusher. It’s only a matter of time before the leads start rolling in and ARR skyrockets.
But cut to months later, and the vibes are not nearly so optimistic. Deals languish in the sales funnel. The seller can’t close at the same rate as the founders could. It seems like no contract gets signed without some sort of deep discount. What gives?
When early-stage sales is flailing, is it a process or a people problem?
The answer, according to Mike Molinet (who scaled Branch to $100M and is now building his second startup, Thena), is probably a bit of both. “Any scientist will tell you that you don’t want to test multiple variables at once. But when you make a sales hire too early, you’re now evaluating, 1) whether that person is successful. 2) Whether you have a repeatable sales process. And 3) whether the product is even aligned to solve the right problem,” he says.
These are the types of chaotic conditions that can make sales an easy scapegoat — and it’s a trap Molinet himself has fallen into when he was building Branch as a first-time founder.
“When we first started to monetize, I went out and hired a VP of Sales and gave them 100 things to figure out. But there’s no way a sales hire can be successful while figuring out the CRM, the ICP, the persona, building the team and figuring out sales development,” he says.
So in our second installment in our new 0-$5M series, First Round Partner Meka Asonye sat down with Molinet along with an epic group of early sales hires from Dropbox, Stripe, Figma and more to answer some of the biggest questions on this critical first hire. Here’s a preview of the advice they have in store:
- When is the right time to hire? Anything before 10 customers is too early, probably closer to 25 is a safer bet. Becca Lindquist (VP at dbt Labs) adds an important caveat: “Having 10 customers who are all your best friends doesn’t count.”
- Who should you hire? Aside from the usual criteria (some early-stage experience, familiarity with your sales motion), Eric Lasker (who was one of Stripe’s first sales hires) adds an underrated trait. “I'd rather hire the salesperson from the second-best company rather than the first — that person probably had a 10x harder time than the person who was selling the category winner.”
- How do you evaluate talent? Lean take-home exercises, not resume run-downs, says Michael Loiacono (who’s been a first sales hire six times in his career). “I don’t over-index on your sales stats from your last two jobs, which are likely the result of a whole bunch of things outside of your sales chops. I don’t care that you were in President’s Club.”
- How do you set them up for success? When Kyle Parrish joined Figma as sales hire #1, he was itching to start closing customers. But founder Dylan Field had other plans. “He asked me to not do anything on the sales side but just to spend time in the support queue, working on bugs, understanding the ins and outs of the product.”
We hope you’re enjoying this new series — let us know if there are other topics you’d like us to cover. You can send Meka Asonye ideas to @BigMekaStyle on X.
Thanks, as always, for reading and sharing.
-The Review Editors
Recommended resources:
-Why Notion’s Ivan Zhao says you should “sugarcoat the broccoli”
-Molly Graham on the “career stairs”
-A small, useful tip for your product demo