Hiring Your First VP of Sales: A Founder's Survival Guide
This is one of the most consequential hires a founder makes — and one of the most commonly botched. The checklist we give every client.
Why This Hire Goes Wrong
The most common mistake: hiring a VP of Sales who was a great individual contributor or a great manager at a much larger company. Neither profile works. You need someone who has built a sales function from scratch at a similar stage — not someone who managed 50 reps at a Fortune 500, and not someone who was your best AE. Those are different jobs.
The Profile That Actually Works
The right first VP of Sales has three things: they've carried a bag (they know what it's like to sell), they've built a team from 0 to 10 reps (not managed an existing team), and they've done it in a company at a similar revenue stage to yours. That last point is critical. The skills required to go from ₹0 to ₹10 crore are completely different from ₹50 crore to ₹200 crore.
The Interview Process
Ask them to walk you through a sales process they built from scratch. Ask what their first 90-day plan would be. Ask them to critique your current pipeline. The best candidates will ask you hard questions back — about your ICP, your churn rate, your product roadmap. If they don't ask hard questions, they're not the right hire.
Before You Hire
Before you bring in a VP of Sales, make sure you have: a documented sales process (even a rough one), a CRM that's actually being used, and at least two reps who are hitting quota. If you don't have these, you're not ready for a VP — you need a Fractional CSO to build the foundation first.
Not sure if you're ready to hire a VP of Sales? Let's find out together.
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