Hiring your First VP of Sales

Avoiding Hiring Mistakes: Questions and Key Characteristics for Your First VP of Sales

In one of my previous posts, I talked about how tech founders often stumble when hiring their first VP of Sales. It’s an easy trap—you're looking for a unicorn who can close deals, build a team, and scale your business. The wrong hire can cost you valuable time and momentum. But the right hire? Game-changing.

So how do you find them? Here’s a practical guide to help you get it right.

The Right Characteristics

Your first VP of Sales isn’t just another hire—they’ll define your sales culture, processes, and growth trajectory. Here’s what to look for:

1. Builder Mentality: They’ve built sales teams and processes from scratch in early-stage companies. This isn’t about inheriting a playbook—it’s about creating one.
2. Hands-On Leader: Early on, they’ll still be in the trenches, closing deals alongside the team while setting up for scale.
3. Data-Driven and Strategic: They know the numbers that matter: CAC, LTV, conversion rates, and sales velocity. They use data to inform decisions and refine processes.
4. Collaborative Mindset: They’ll work closely with you and the heads of product and marketing to align on Go-to-Market (GTM) strategy and customer feedback loops.
5. Cultural Fit: This person will shape your sales culture. Are they aligned with your values, mission, and leadership style?

The Key Questions

Here are the questions you should ask—and why they matter:

1. What’s your experience building sales teams in early-stage startups?
2. How do you approach defining and refining the Go-to-Market (GTM) strategy?
3. How have you transitioned from founder-led sales to a scalable team-led approach?
4. What metrics do you focus on at this stage, and how do you use them?
5. Can you share a success story of scaling revenue in a startup environment?
6. How do you collaborate with marketing and product teams to improve pipeline and close rates?
7. What’s your approach to recruiting, onboarding, and developing sales talent?
8. How do you balance short-term revenue goals with building for long-term success?

Red Flags to Avoid

1. “Big Company” Syndrome: If their experience is primarily from large, established organizations, they may struggle in a resource-constrained startup environment.
2. Too Much Reliance on Existing Playbooks: Startups often require creativity and adaptability, not just cookie-cutter solutions.
3. Lack of Metrics-Driven Approach: Beware of candidates who talk in vague terms about success but can’t back it up with data or specifics.
4. Poor Cultural Fit: Even the most talented sales leader won’t succeed if they clash with your company’s values or team dynamic.

The Payoff

Hiring your first VP of Sales is one of the most important decisions you’ll make. With the right person in place, you’ll not only see revenue growth but also build a sales engine that scales with your company.

Remember, this isn’t about finding someone who’s “good at sales.” It’s about finding a leader who can grow alongside your business, roll up their sleeves, and build something extraordinary.

What’s been your biggest challenge in hiring sales leaders? Let’s discuss below! 👇

- Vince Beese

I’m a Fractional CRO for $1M–$10M ARR Tech Startups Scaling Enterprise Sales | 5 Successful Exits & $1B+ in Revenue Growth for Companies Like Meta, CheetahMail, and LivePerson. Let me know if I can help.