Your first few sales reps have to be … different. A bit of a product savant. A passion for the product and space that almost doesn’t make sense. And someone you can trust with your few, precious leads.
Here’s a checklist to get it right:
1. Would You Buy From Them?
This is the ultimate test. If you wouldn’t buy your own product from them, don’t hire them. Leads are too precious in the early days to waste on someone you don’t trust to clos.
2. Have They Sold at Your Price Point?
Selling a $100/month product is very different from selling a $100,000/year solution. Make sure they’ve sold at a similar price point before. Early on, there’s no time for them to learn this on the job.
3. Do They Know How to Sell Without a Big Brand?
Be honest here. Avoid reps who’ve only sold with the backing of a strong brand like Datadog or HubSpot or Adobe. Selling for a startup is a completely different game—it’s scrappier, harder, and requires more creativity. And selling at the #4 player in a space is so much different from selling at #1.
4. Have They Thrived in Chaos?
Look for someone who’s worked in an unstructured, early-stage environment before. They need to be scrappy, self-sufficient, and able to figure things out without a playbook. Be very wary of hiring anyone at an early-stage startup who has never worked at one before. They almost always need far more support, training, and onboarding than you have.
5. Do They Understand Your Product? And Can They Demo It Before They Start?
They don’t need to be engineers, but they need to learn your product inside and out. If they can’t explain how it solves customer pain points better than anyone else, they won’t close deals.
Don’t hire any reps in the early days at least that can’t demo your product well, and understand it well — before they start. Don’t cut corners here. You’ll almost instantly regret it.
6. Have They Sold Somewhere Where It Was >Harder< To Sell Than Selling Your Product?
Yes,look for someone with a track record of hustle—maybe they’ve done door-to-door sales or worked in a tough outbound role at least once. These experiences build the grit needed to succeed in a startup. Too many just quit when selling is hard.
But go beyond that and look for folks that have sold a product that was at least a little harder to sell than yours. Then they just fly.
Folks that have only sold products easier to sell than yours will fail 95 times out of 100. Sales is never easy. But there’s a relative element here.
7. Would You Trust Them With Your Top Customers?
Make sure they are someone you’d want on your team, talking to your early customers. Those early customers have to be successful. There just aren’t enough of them.
Later, when you have a VP Sales you trust, they can hire folks you might not true with precious leads. Because they’ll backfill them. But you can’t make these hires in the founder-led stage.
8. Have They Been an Early Rep Before?
Ideally, they’ve been the first or one of the first reps at another startup. This experience is invaluable because they’ve already navigated the challenges of selling in an early-stage environment.
9. Are They Comfortable Being Both Micromanaged … and Ignored? 🙂
That’s reporting to you … the CEO. Can they really report to you? In the early days, you’ll need to work closely with them. They should be okay with this dynamic and see it as an opportunity to learn and grow. Not everyone can report to the CEO. Even of a tiny start-up. Most can’t, really.
10. Interview Enough
Interview at least 30 candidates. There’s probably only one or two you will talk to that are even the right fit for your stage. Hire quirky, but don’t settle—keep looking until you find someone who checks the boxes.
If nothing else, only hire reps you’d honestly, truly buy your own product from. Never cut a corner here at least.
Use this checklist to avoid the common pitfalls of hiring your first sales rep. If you get this hire wrong, it can set you back months. But if you get it right, they’ll help you scale to the next level.
And a deep dive here:
