How to Hire Your First VP
Before You’re Ready
Every founder waits too long or moves too soon on their first VP hire. The ones who get it right aren’t lucky — they know what “ready” actually means, what profile to hire for the stage they’re at, and how to avoid the traps that turn a great VP hire into a six-month setback.
- The signal that tells you it’s time
- What a VP at your stage actually looks like (it’s not what you think)
- The “big company VP” trap
- How to evaluate VP candidates without being one yourself
- The 30/60/90 day plan that separates real VPs from interview performers
- Equity and compensation for a first VP hire
- What to do in the first 90 days
The Signal That Tells You It’s Time
You’re ready to hire a VP when: you have a repeatable process in that function (however rough), you understand the work well enough to evaluate whether someone is doing it well, and the constraint on growth is capacity — not clarity. Hiring a VP to figure out what the function should be doing is hiring a consultant on a salary. It rarely works.
For VP of Sales specifically: you’ve closed at least 10–15 customers yourself, you can describe the sales motion in repeatable steps, and the bottleneck is volume of activity rather than figuring out what works. For VP of Marketing: you have a clear ICP, a product narrative that resonates, and at least one channel producing consistent inbound. For VP of People: you have 20+ employees, you’re spending more than 30% of your week on people operations, and it’s costing you in quality of hiring and culture.
The most expensive VP hire is the one made to solve a problem that isn’t actually a people problem. If sales aren’t closing, it might be the product, the pricing, or the ICP — not the absence of a VP Sales. Hire the VP when the function needs to scale, not when you need someone to figure out what the function should be.
What a VP at Your Stage Actually Looks Like
A seed-stage VP is not the same profile as a Series B VP. The seed-stage VP needs to be hands-on — writing copy, running calls, building the system and doing the work simultaneously. The Series B VP manages managers, sets strategy, and rarely touches the actual work directly. Hiring the Series B profile at seed stage produces an expensive person who feels underutilised and eventually leaves.
The profile that works at seed/Series A: someone who has taken a function from zero to repeatable at a company one stage ahead of you, is comfortable being an individual contributor as well as a manager, and is motivated by building rather than scaling. They may not have VP in their title yet — which is fine. The title matters less than whether they’ve done the work at the right stage.
The Big Company VP Trap
The temptation is enormous: a candidate with a VP title at a well-known company, an impressive LinkedIn, and a confident pitch. The reality: big company VPs have been operating with resources, brand, process, and teams you don’t have. The skills that made them successful there — managing a large team, navigating internal politics, operating within established systems — are largely irrelevant and sometimes actively counterproductive at early stage.
The tell: ask them to walk you through a specific thing they built from zero. Not managed, not scaled — built. If the answer involves a team of 10 and a pre-existing system, keep looking. The person you want can describe in detail the specific process they personally designed, tested, and iterated — and what didn’t work along the way. See our Head of Sales hiring guide for the specific interview approach for sales leadership.
How to Evaluate VP Candidates Without Being One Yourself
The problem with hiring above your level: you don’t have enough domain expertise to evaluate the quality of what they’re telling you. The solution: structured reference calls and a work sample.
Reference calls: speak to people they managed, not just people who managed them. Ask: “What was something they built from scratch? What did they struggle with? Would you work for them again?” The answers to the third question are almost always more honest than you’d expect. See our reference check playbook for the full question set.
Work sample: a paid, time-limited project that reflects a real challenge the VP will face in the role. For a VP of Sales: audit your current sales process and identify the 3 highest-leverage changes. For a VP of Marketing: propose the GTM strategy for the next 6 months with rationale. The quality of their thinking on a real problem tells you more than any interview.
“I’m interviewing VP [Sales/Marketing/Product/People] candidates for my [stage] startup. My company: [describe product, stage, team size]. What I most need this VP to do in the first 6 months: [list 3 specific outcomes]. Help me build a structured interview scorecard: (1) The 3 most important competencies for this role at my stage specifically — not generic VP competencies, (2) For each competency: 2 behavioural interview questions and what a strong vs weak answer looks like, (3) The 3 red flags in a VP candidate that are particularly dangerous for an early-stage company, (4) The one question that best distinguishes a startup VP from a big-company VP. Format it as a usable interview guide.”
The 30/60/90 Day Plan That Separates Real VPs
Ask every finalist: “If you joined next Monday, what would your first 30, 60, and 90 days look like?” The answer reveals everything. A strong VP candidate describes: 30 days of deep listening (customers, team, data) before making any changes, 60 days of identifying the 2–3 highest-leverage changes and beginning to implement them, 90 days with early results visible and a written plan for the next 6 months.
A weak candidate describes what they’d implement from day one based on what worked at their last company. This is the pattern that produces expensive mismatches — they’re solving for the last company’s problem, not yours.
Equity and Compensation
Seed-stage VP equity range: 0.5%–1.5% depending on stage, role criticality, and whether they’re taking a below-market salary. Series A: 0.25%–0.75%. Use our free Compensation Band Builder to set the salary range, and see our equity guide for the full framework on what to give and when.
Standard vesting: 4 years, 1-year cliff. Double-trigger acceleration on acquisition (meaning the vesting accelerates if the company is acquired AND the VP is let go or their role materially changes) — push for this, especially for early and senior hires.
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