Dear SaaStr: How Do I Hire a Great VP of Sales?
It’s a classic SaaStr topic and a great deep dive is here:
Hiring a great VP of Sales is one of the most critical decisions you’ll make as a founder. Get it right, and they’ll scale your revenue and team. Get it wrong, and you’ll lose a year—or more.
Here’s how to approach it:
-
Don’t hire too early. If you don’t have a repeatable sales process or at least two performing reps, you’re not ready for a VP of Sales. They need something to scale. If you’re under $1M ARR, you’re likely still figuring out founder-led sales. Wait until you’ve hit initial traction—ideally $1M-$1.5M ARR—and have a couple of reps closing deals consistently.
-
Focus on recruiting ability. The #1 job of a VP of Sales is to build a great team. Ask them directly: “Who did you recruit at your last company?” If they haven’t successfully hired at least 3-4 strong reps, they’re not ready to be a VP. A great VP of Sales will bring in 8-10 high-performing reps within their first year, not just warm bodies.
-
Pre-recruit and take your time. This hire can take 6-12 months. Start meeting potential candidates early, even if you’re not ready to hire yet. Great VPs of Sales are often making $400K-$500K+ at their current job and won’t jump unless they see a huge opportunity. Build relationships with them over time.
-
Test for truth-telling and realism. You don’t want a “yes person.” Ask them tough questions like, “What will our revenue look like in 120 days after you join?” Listen carefully to their answer. If they’re overly conservative, they won’t push hard enough. If they’re wildly optimistic, they’re not grounded in reality. You need someone who can confidently but realistically assess the situation.
-
Look for someone who’s done it at least partially before. Ideally, they’ve scaled a team at a company similar to yours. But at least, they’re hired themselves 2-3 reps that have hit quota. Find out — for real. Be wary of candidates who inherited a successful team but didn’t build it themselves. Logos on LinkedIn are nice, but they don’t always tell the full story. Dig into their actual contributions.
-
Make sure they’re still a great salesperson. Your VP of Sales needs to be able to close deals themselves, especially early on. If they can’t sell, they can’t lead a sales team effectively. They should be able to jump in and close a deal when needed. Many don’t really want to sell themselves anymore, just manage a team. You don’t need those candidates.
-
Don’t over-title someone. If you’re hiring someone who’s never been a VP before, be cautious. They might be a great stretch hire, but they’ll need more support. If you’re betting on potential, make sure they’ve at least built and managed a small team successfully.
-
Set clear expectations. You’ll know within 30-90 days if they’re going to work out. If they’re not recruiting, closing deals, or improving your sales process by then, it’s a red flag. Don’t wait too long to make a change if it’s not working.
This hire is too important to rush or get wrong. Take your time, dig deep into their track record, and make sure they’re the right fit for your stage and goals.
