Dear SaaStr: I’m a solo-founder, bootstrapper, $3M ARR. I have been managing the sales team myself, with 2 full-time sales managers and 2 part-time SDRs. I want to step out of the interim VP sales role and hire my first “real” VP of Sales. Any advice?
Congratulations on reaching $3M ARR as a solo founder and bootstrapper—that’s impressive. You’ve created something successful, and it’s time to scale. Shifting from the interim VP of Sales role is a significant step, and hiring your first “real” VP of Sales is crucial.
Here’s how to handle it:
1. Ensure Readiness for a VP of Sales
At $3M ARR, you’re likely ready for a VP of Sales, but only if you’ve established a repeatable sales process. If you’re still identifying product-market fit or your sales motion, it’s too soon. A VP of Sales is there to scale, not to figure things out. Given you have a sales team with full-time managers and SDRs, it seems like you’re ready for this step.
2. Recruit a Team Builder
Your VP of Sales must excel in recruiting. They need to quickly hire 2-3 strong AEs and help them succeed. Ask candidates, “Who will you bring with you?” A strong VP should have 1-2 top reps ready to join them. If not, it’s a warning sign.
3. Steer Clear of “Big Company” Experience
Avoid hiring someone with experience only at large B2B firms like Salesforce. They may not be suited for your stage. Look for someone with startup experience around $3M-$10M ARR who knows how to scale to $10M-$20M ARR.
4. Test for Hands-On Execution
Your VP of Sales must be ready to work hands-on, engage in deals, coach reps, and even close deals when necessary. If they prefer delegating everything, they’re not right for a $3M ARR startup. Ensure they’re ready to learn the product and sell it themselves.
5. Conduct Insightful Interviews
Ask candidates these questions:
- “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 provide clear, specific answers with a proven track record.
6. Consider a Stretch Hire, But Not Too Much of a Stretch
A stretch VP of Sales—new to the VP role with great potential—might be your best option. However, ensure they’ve led a small AE team before. Avoid a double-stretch hire like an AE with no management experience.
7. Trust Your Gut, But Verify
Fully believe in your hire. If you have doubts, don’t proceed. Verify claims by speaking with their past reps, checking references, and reviewing their track record. This decision is too important to be wrong.
8. Be Prepared to Invest
A great VP of Sales requires a competitive salary, strong variable compensation, and meaningful equity. The right hire will scale your revenue and build a strong team, making them worth the investment.
This hire will greatly influence your sales organization and scaling speed. Be meticulous, thorough, and firm. Success here aligns you towards $10M ARR and beyond.