Dear SaaStr: I've Gotten to $1m ARR Selling Myself. What Should I Look For in My First Ever Head of Sales?
You’re in a good spot—above $1M ARR and still founder-led sales. That’s a strong foundation. Now, as you’re automating and refining your sales process, you’re getting close to the right time to bring in a VP of Sales.
Here’s how I’d approach it:
1. Get two reps hitting quota first
Before hiring a VP of Sales, make sure you’ve got at least two sales reps consistently hitting quota. This shows you’ve got a repeatable sales process that a VP can scale. If you don’t have this yet, focus on hiring and training those reps first. A VP of Sales can’t build something from nothing—they need a foundation to work with.
2. Hire a “stretch” VP of Sales. Don't chase the veteran with the great LinkedIn.
At this stage, you don’t need someone who’s already scaled a $50M ARR company. You need someone who’s been a Director or Senior Director of Sales at a similar company and is hungry for their first VP role. They’ll be more hands-on and willing to roll up their sleeves, which is critical at your stage. But they have to have experience recruiting. They have to have recruited at least 2 successful reps before. Ask. And go talk to them.
You need a stretch head of sales. But not someone that hasn't proven they can recruit. That's a stretch too far.
3. Look for someone who can recruit and build. And that has someone good to come with them.
Per the prior point -- your VP of Sales’ #1 job will be hiring and scaling the team. Ask them directly: “Who would you bring with you?” If they can’t name 2-3 great reps they’ve worked with before, they’re not the right fit. The best VPs of Sales are magnets for talent.
4. Test their ability to sell your product Don't skip this step.
During the interview process, have them pitch your product back to you. If they can’t sell it to you, they won’t be able to lead your team effectively. This also shows whether they’ve done their homework and understand your business.
5. Onboard them closely. And stay close to at least all bigger deals.
Don’t just hand them the keys and walk away. Spend the first 30-60 days working closely with them to ensure they understand your sales process, your customers, and your goals. This will set them up for success and help you spot any red flags early. And tell them you'll join as many calls and Zoom as they want -- and want to join all the big deals. Make sure they know you're still a key part of the sales team. Just no longer the head of sales.
6. But also --be ready to let go once they've leveled things up.
This sometimes is the hardest part for founders. You’ve been running sales yourself, and it’s tough to hand over the reins. But if you’ve hired the right person, trust them to take over and focus on scaling. Your job will shift to supporting them and ensuring they have the resources they need to succeed.
And once they've proven themselves, they'll hire people and run things differently than you would. Once they've proven themselves -- that's OK.