Dear SaaStr: What Are A Few Top Tips to Hiring The Right First VP of Sales?
Hiring a great VP of Sales is one of the most critical decisions you’ll make as a founder. Get it right, and they’ll scale your revenue and team. Get it wrong, and you’ll lose a year—or more.
Here’s how to approach it:
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Timing is Everything
Don’t hire a VP of Sales too early. If you don’t have a repeatable sales process or at least two reps hitting quota, you’re not ready. You need to figure out the basics yourself first—close the first deals, build a small team, and hit some traction (ideally $1M ARR or close to it). A VP of Sales can’t create a process from scratch, they scale what’s already working . -
Focus on Recruiting Ability
The number one job of a VP of Sales is to recruit a great team. If they can’t hire 8-10 high-performing reps within their first year, they’ll fail. Ask them directly: “Who did you recruit at your last company?” If they didn’t hire at least three to four strong reps themselves, they’re not a true VP of Sales. Inheriting a team doesn’t count. -
Avoid the Big Logo Trap
Don’t get seduced by candidates from big-name companies like Salesforce or Oracle. These folks often come from environments with massive resources and established processes, which don’t translate well to startups. You need someone scrappy who’s scaled from $1M to $10M ARR, not $30M to $150M. -
Pre-Recruit and Take Your Time
A great VP of Sales hire can take 6-12 months. Start building relationships early. Meet potential candidates even before you’re ready to hire. The best ones are often not actively looking, so you need to sell them on your vision and opportunity. -
Test for Realism and Honesty
During interviews, ask them, “What will our revenue look like in 120 days if you join?” This question reveals a lot. Avoid candidates who give insane, overly optimistic answers—they’re likely “yes” people who won’t tell you the hard truths. You want someone confident but grounded in reality. -
Look for Player-Coach Skills (Early On)
For your first VP of Sales, they often need to be a player-coach—someone who can close deals themselves while building the team. If they’re not willing to roll up their sleeves and sell, they’re not the right fit for an early-stage startup. -
Watch for Red Flags Early
If your new VP of Sales isn’t working out, you’ll know within 30 days. Look for signs like poor recruiting, inability to close deals themselves, or a lack of urgency. Don’t wait too long to make a change if it’s not working.
Hiring a great VP of Sales is hard, but it’s worth the effort. Take your time, focus on their ability to recruit and scale, and don’t settle for someone who looks good on paper but can’t execute.
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