Dear SaaStr: What if I’m not sure that my VP Sales is the right person?
🤷♀️If you’re not sure your VP of Sales is the right person, you’re already in a tricky spot. The reality is, at the VP level, you can’t “fix” them if they’re not a fit. And that’s likely your fault for hiring them. Not theirs.. A VP of Sales / CRO may struggle or fail in one environment and thrive in another. I’ve seen it all the time.
A VP of Sales is the owner of their department, and if they’re not delivering, the damage compounds quickly—bad hires, wasted capital, slower deals, unhappy customers. The faster you address it, the better.
But also … a “pretty good” VP of Sales is almost always better than no VP of Sales at all. Be careful cutting anyone doing a reasonably good job. Even if you want more. More on that below.
Here’s what I’d do to assess the situation:
1. Look at the Metrics: Has revenue per lead or net new bookings gone up? At least a bit?
If not, that’s a red flag. A great VP of Sales should be able to move the needle, even a little, fairly quickly. At least a little. If deals are slowing down after they started, discounting is increasing, and/or close rates are dropping, those are signs they’re struggling to sell your product effectively. More on that here:
2. Check Their Team: Have they hired anyone great in the first 60 days?
The best VPs of Sales bring in top talent quickly—people they’ve worked with before or know can crush it. If they’re hiring weak or junior folks, that’s another warning sign. A related post here:
3. Gauge the Team’s Confidence: Does the team believe in them? And does the VP of Sales believe?
If your team isn’t gaining confidence in the VP within the first 30 days, that’s a problem. The team knows when someone is improving things—or not. And if the VP of Sales themselves doesn’t believe, there’s really no chance. Once confidence is lost, it’s just almost impossible to get it back.
4. Assess Stage Fit: Are they the right profile for your stage? You may have gotten this wrong.
A VP who’s great at scaling might not know how to build from scratch, and vice versa. If they’re not aligned with where your company is right now, they’ll struggle to deliver. More here:
5. Trust Your Gut: If you don’t believe in them, it’s almost impossible for them to succeed.
It’s hard enough to be a VP in a startup without the CEO’s full confidence. If your gut says they’re not the one, it’s probably time to move on. More here:
▶️ If you’re seeing these signs, don’t wait too long to act. The damage from a mis-hire at this level only gets worse over time.
But if you’re still unsure, dig into the metrics and have an honest conversation with them about expectations and performance. Sometimes, clarity comes from just putting everything on the table.
And expect some quick progress — but don’t expect miracles. A Head of Sales that keeps momentum going but doesn’t totally change the game is often one you still want to stick with. More on that here:
And more on the general topic here:
And here:
