Hiring Your First VP of Sales: When It's Time and What to Look For

The VP of Sales hire is the one that keeps founders up at night. Get it right, and your revenue engine scales itself. Get it wrong, and you've just burned $200K+ in salary, lost two quarters of momentum, and probably demoralised the AEs you already have.

Here's the hard truth: most startups hire their VP of Sales too early, too senior, or for the wrong reasons. Let's fix that.

When to Hire a VP of Sales (And When It's Too Soon)

There's a specific moment when a VP of Sales makes sense. Before that moment, it's a waste of money. After it, you're leaving revenue on the table.

You're ready for a VP of Sales when:

• You have at least 2-3 AEs already producing revenue
• Founder-led sales has proven the playbook works (repeatable process, not heroic one-off deals)
• Your ARR is past €1M-€2M and you need to get to €5M-€10M
• You're spending more time managing sales than running the company
• You have enough pipeline that the bottleneck is execution, not demand

It's too early if:

• You don't have product-market fit yet (a VP of Sales can't fix a product problem)
• You have zero or one AE
• Founder-led sales hasn't closed at least 20-30 deals
• You're hiring a VP of Sales to "figure out sales" — that's founder work
• Your ARR is under €500K

The expensive mistake: Hiring a VP of Sales at €150K+ before you have a working sales motion is like hiring a general before you have an army or a battle plan. They'll spend six months "building strategy" while your runway burns.

Player-Coach vs Pure Leader: Which Do You Need?

This is the single most important distinction in VP of Sales hiring, and most founders get it wrong.

Player-Coach (what most Series A startups need):

• Still carries a personal quota (usually 30-50% of their time selling)
• Manages 2-5 AEs directly
• Builds the playbook, CRM processes, and forecasting from scratch
• Comfortable doing the work AND teaching others to do it
• Typically comes from a Senior AE or Sales Manager background at a startup

Pure Leader (what Series B+ companies need):

• Doesn't carry a personal quota
• Manages sales managers who manage AEs
• Focuses on strategy, hiring, and board-level reporting
• Experience managing teams of 10-30+ salespeople
• Typically comes from a VP or Director role at a scale-up

The mismatch problem: If you hire a Pure Leader for a Series A company, they'll immediately want to hire managers, implement complex processes, and stop selling. But you have 3 AEs and €1.5M ARR — you need someone in the trenches, not in the boardroom.

If you hire a Player-Coach for a Series B company with 20 AEs, they'll get overwhelmed by the management complexity and revert to what's comfortable: closing deals themselves while the team flounders.

Rule of thumb: If your sales team is under 8 people, hire a Player-Coach. Over 8, hire a Pure Leader.

What Great Startup VP of Sales Look Like

Forget the VP of Sales from Oracle who managed a $50M book of business. Here's what actually predicts success at a startup:

They've built before, not just managed. The best startup VPs of Sales have taken a team from 2-3 AEs to 10-15. They've built the playbook, hired the team, and created the reporting — not inherited it.

They sell with data, not just charisma. They can tell you their team's conversion rates at every funnel stage, average deal cycle length, and CAC. If they can't quantify their impact, they're a storyteller, not a leader.

They've operated with constraints. Startup sales means no brand recognition, limited marketing support, and a product that's still being built. They need to have thrived in that environment, not just survived it.

They hire well. Ask them: "Walk me through how you'd hire your first two AEs here." Their answer tells you everything about their judgement, speed, and standards.

They know when to discount and when to walk away. A VP of Sales who drops price at the first objection will destroy your margins. One who never flexes will lose winnable deals. You need the one who knows the difference.

Compensation: What to Expect

VP of Sales comp is base + variable + equity. The variable component is significant and usually tied to team quota attainment, not personal deals.

Base salary (2026):

United States:

• Series A (Player-Coach): $150,000-$200,000
• Series B (Pure Leader): $200,000-$280,000

Europe (Netherlands, Germany, UK):

• Series A (Player-Coach): €110,000-€150,000
• Series B (Pure Leader): €140,000-€200,000

Variable / OTE:

OTE is typically 50-60% base, 40-50% variable:

• Series A Player-Coach: $250K-$350K OTE (US) / €180K-€250K OTE (EU)
• Series B Pure Leader: $350K-$500K OTE (US) / €250K-€380K OTE (EU)

Variable is usually paid quarterly, tied to team quota attainment. Accelerators above 100% of quota are standard and expected — a great VP of Sales should be able to earn 150-200% of their variable in a good quarter.

Equity:

• Series A: 0.5-1.5%
• Series B: 0.25-0.75%

Standard 4-year vesting, 1-year cliff. VP of Sales candidates will often negotiate for quota relief during their first quarter (ramp period) and accelerated vesting on change of control.

The Interview Process

VP of Sales interviews should test three things: can they sell, can they build, and can they lead?

Stage 1: Culture and vision (45 min with CEO) Do they get excited about your market? Do they ask smart questions about your customers, competition, and go-to-market? A VP of Sales who doesn't sell you on themselves in this meeting won't sell your product to customers.

Stage 2: Go-to-market plan (60 min) Give them your current metrics: ARR, team size, average deal size, win rate, sales cycle length. Ask them to present a 90-day plan. You're evaluating:

• Do they ask clarifying questions or just present generic frameworks?
• Is the plan realistic given your resources?
• Do they prioritise quick wins or only long-term strategy?

Stage 3: Pipeline review (45 min) Ask them to walk through their current or most recent pipeline in detail. How do they forecast? What's their methodology for qualifying deals? How do they decide where to spend their time? This reveals operational rigour.

Stage 4: AE ride-along or mock scenario (45 min) If you have AEs, have the candidate sit in on a deal review or do a mock coaching session. How do they give feedback? Do your AEs respond well to their style?

Stage 5: Reference checks (3-4 calls) Talk to:

• AEs who reported to them (would they work for this person again?)
• Their previous CEO/founder (did they deliver on their plan?)
• A peer from another department (how did they collaborate cross-functionally?)

Move fast. The best VP of Sales candidates are off the market in 2-3 weeks. Your entire process should take 10-14 days.

Red Flags in VP of Sales Candidates

"I need to hire X people before I can start selling." A startup VP of Sales should be closing deals in week 2, not building an org chart.

They can't explain why they left their last role. Sales leaders change jobs. That's fine. But if they can't give you a clear, honest reason, dig deeper.

Their references are all CEOs, none are AEs. Managing up is easy. Managing down is where it matters.

They want to change everything immediately. Your sales process got you to where you are. A good VP of Sales improves it incrementally, not torches it.

They've never missed a target. Everyone misses. If they say they haven't, they're either lying or they've only had sandbagged quotas.

How Funded.club Helps

We've placed VPs of Sales, Heads of Sales, and sales leaders at startups across Europe, the US, and beyond. We know the difference between a player-coach and a pure leader because we see who succeeds at each stage.

Our fixed-fee model: $15,900-$21,900 for a VP of Sales search. Traditional executive recruiters charge $40K-$70K for the same role.

What you get:

• Dedicated recruiter who specialises in go-to-market hiring
• Candidates screened for stage-appropriate experience
• First candidates in 7 days, shortlist in 14
• We'll tell you honestly if you need a VP of Sales or a strong AE team lead