What’s up, everyone! 👋🏻

Today, I want to talk about VP of Sales hiring—one of the most pivotal roles in any company looking to scale. It’s also one of the roles most often hired poorly. If you’re thinking about bringing on a VP of Sales, read this first.

Step 1: Get Advice from Someone Who’s Done It

Too many founders rely on recruiters who’ve never actually sat in a VP of Sales seat. Sure, they’ve hired them before, but recruiters don’t understand what it’s like being responsible for revenue, or being in the trenches. My advice? Tap into your network. Find the people you trust who’ve been successful VPs of Sales themselves and ask for referrals.

You can ask:

• Who do they trust?
• What questions should you ask?
• What red flags should you look for?

It beats handing over tens of thousands of dollars to a recruiter who’s financially incentivized to close a deal—not necessarily to find the right fit for you. Plus, referrals come with built-in credibility.

Step 2: Don’t Hire Too Soon

Timing matters. A LOT. A VP of Sales is rarely the first go-to-market hire you need. That’s because early-stage companies often require someone who can build the foundational blocks—not just lead a team. Hiring a VP of Sales too early can lead to misalignment and turnover within 2-3 years.

Step 3: Find Stage-Appropriate Talent

This is where founders start to stumble. They’re told to hire someone from Big Company X, so they bring in a VP from Oracle or Salesforce for their small, Series A startup with less than twenty employees, only to watch it fail. WHY?! The skills required to run a massive, established team are worlds apart from those needed to build from scratch.

At an early-stage startup, you’re not hiring a “VP of Spreadsheets and Strategy”—you’re hiring a ditch digger. Someone ready to:

• Operate with urgency and grit.
• Get in the mud and build.
• Do some IC work.

Big corporate hires usually lack the speed and hunger that startups call for. Their motor doesn’t rev high enough anymore. You need someone who’s ready to get their hands dirty—not someone who’s just managing by dashboards.

Step 4: Stop Over-Indexing on Industry Experience

This is the bane of my existence. Founders say, “We need someone with logistics experience,” or whatever their niche is, because they tried hiring outside the industry once it didn’t work out. But when I dig deeper, it’s clear the failure wasn’t because of the hire’s background. It was because:

• There was no (or very little) onboarding process.
• The hire wasn’t set up for success.
• No playbook existed.

Industry experience is the easiest thing to teach. Sales acumen? Leadership skills? Those are much harder to develop.

I love using my time working at Qualia, a title insurance company, as an example of this. When I joined, guess how much I knew about title insurance? Absolutely nothing. To be honest, I barely know now! But I knew how to build and scale a sales team, and I had the sales skills to do it. That’s what mattered. And today? Qualia’s worth billions. Imagine if they’d passed on me because I didn’t have industry experience.

So, what should you look for when hiring your VP of Sales?

Prioritize:

1. Stage Experience: Have they built at your current stage before?
2. Hunger: Do they have the fire to roll up their sleeves and build?
3. Sales Acumen: Can they sell and lead a team to sell?
4. Urgency: Will they operate with the speed you need?

Industry experience? That’s just extra credit in my opinion.

Focus on what matters: stage-appropriate experience, a builder mentality, and raw sales leadership. Forget the industry box-checking—find someone who’s ready to scale and grow with you.

Comments, thoughts, feedback, suggestions? Just hit reply.

– SL