Dear SaaStr: I’m a solo-founder, bootstrapper, 3M ARR. SO far I have run the sales team myself. I have 2 fulltime sales managers, and 2 part-time SDRs. I want to transition out of the interim VP sales roles I ‘m having, and look for my first “real” VP of sales. What advice can you give me?
First off, congrats on hitting $3M ARR as a solo founder and bootstrapper—that’s no small feat. You’ve clearly built something that works, and now it’s time to scale. Transitioning out of the interim VP of Sales role is a big step, and hiring your first “real” VP of Sales is one of the most critical decisions you’ll make.
Here’s how to approach it:
1. Make Sure You’re Ready for a VP of Sales. You Probably Are at $3m ARR, But Make Sure
At $3M ARR, you’re at the right stage to bring in a VP of Sales, but only if you’ve already established a repeatable sales process. If you’re still figuring out product-market fit or your sales motion, it’s too early. A VP of Sales isn’t there to figure it out for you—they’re there to scale what’s already working. Since you’ve been running the sales team yourself and have two full-time sales managers and SDRs, it sounds like you’re ready to make this move.
2. Look for Someone Who Can Recruit and Build a Team. And That Has 1-2 Folks Ready To Come With Them.
The #1 job of your VP of Sales is recruiting. They need to be able to hire 2-3 great AEs immediately and make them successful. If they can’t do that, they’re not the right hire. Ask every candidate: “Who will you bring with you?” A strong VP of Sales will have at least 1-2 top reps from their previous roles who are eager to follow them. If they don’t, that’s a red flag.
3. Avoid the “Big Company” / Great LinkedIn Trap
Don’t hire someone who’s only worked at big B2B companies like Salesforce or Datadog. Or even late stage leaders like Stripe. They won’t know how to operate at your stage. You need someone who’s been in the trenches at a startup around $3M-$10M ARR and knows how to scale to $10M-$20M ARR. If they’ve only worked at $40M+ ARR companies, they won’t have the playbook for your phase.
4. Test for Hands-On Execution
At this stage, you need a VP of Sales who’s willing to roll up their sleeves and do the work themselves. They should be comfortable jumping into deals, coaching reps, and even closing deals if needed. If they’re looking to delegate everything to a team of directors and managers, they’re not the right fit for a $3M ARR startup. Make sure they’re ready to hustle and execute. Will they learn the product cold? Will they sell it themselves?
5. Ask the Right Questions in Interviews
Here are a few key questions to ask during the interview process:
- “How many reps have you hired, and who were they?”
- What’s your plan to get us from $3M to $10M ARR?”
- “What’s your approach to coaching and developing a sales team?”
- Who will you bring with you, and why?”
The best candidates will have clear, specific answers and a proven track record.
More here:
6. Aim for a Stretch Hire, But Not a Stretch Too Far
A stretch VP of Sales—someone who’s never been a VP before but has potential—is probably your best choice. But if you go this route, make sure they’ve at least hired and managed a small team of AEs before. A double-stretch hire (e.g., a top-performing AE who’s never managed anyone) almost never works.
7. Trust Your Gut, But Verify
You need to 100% believe in the person you hire. If you have doubts during the interview process, don’t move forward. At the same time, verify everything they say. Talk to the reps they’ve managed, check their references, and dig into their track record. This is too important a hire to get wrong.
8. Be Ready to Invest in Them
A great VP of Sales isn’t cheap. They’ll want a competitive base salary, a strong variable comp plan, and meaningful equity. But if you hire the right person, they’ll more than pay for themselves by scaling your revenue and building a high-performing team.
This hire will set the tone for your sales organization and determine how quickly you can scale. Take your time, be thorough, and don’t compromise. If you get this right, you’ll be in a great position to hit $10M ARR and beyond.
