What's Different About the First VP Search
A first-time hiring CEO brings several things to a VP search that an experienced CEO typically doesn't: a genuine uncertainty about what they need, a tendency to over-index on their own functional expertise when evaluating candidates, and a deep personal investment in getting the decision right because they feel the weight of it.
None of these are weaknesses. They are the conditions of a first search. The process needs to be designed around them.
The Most Common First-VP Mistake
First-time CEOs almost universally write VP briefs that describe the person they wish they could clone — someone who combines the strategic thinking of a seasoned VP with the execution speed of an IC, costs like a senior manager, and will stay for five years without equity. That person doesn't exist. The brief needs to be rebuilt around what the business actually needs in the next 18 months.
The Brief Conversation
With first-time VP hiring CEOs, we spend significantly more time on the brief than in repeat engagements. The goal of the brief conversation is not to extract requirements — it's to help the founder distinguish between what they think they want and what the business needs.
Start with the business problem, not the role
We ask: what is not happening today that needs to happen in 12 months? What is the company unable to do that this person will unlock? Starting with the role itself — its title, its scope, its requirements — produces a wish list. Starting with the business problem produces a brief.
Clarify the founder-VP authority structure
One of the most common causes of VP failure in a first-time hire is an unspoken disagreement about how much authority the VP actually has. Does the founder expect to be consulted on every hire? Every strategy decision? Every customer interaction? If the VP expects genuine autonomy and the founder expects a senior IC, the role will fail within 9 months regardless of the individual's quality.
Set stage-appropriate expectations
We help founders understand what a VP at their stage typically looks like versus what they might assume from talking to later-stage companies. A VP Sales at $2M ARR is not the same role as a VP Sales at $20M ARR — and the candidates who thrive in each environment are often different people. See: Founder-VP Fit Model.
The Assessment Process for First-Time Hires
For founders making their first VP hire, we build more structured assessment into the process than we would for a repeat engagement. This includes a formal evaluation framework — see Startup Leadership Scorecard — and structured reference conversations designed to surface the specific failure modes that first-time CEOs are most likely to miss.
The most important assessment dimension for a first VP hire is not functional capability. It is the candidate's track record of building a productive working relationship with a first-time CEO — because that is the relationship they are entering, and it is fundamentally different from working for an experienced operator.
Related: Series A Leadership Benchmarks 2026 | Why Startup Executive Searches Fail | Search Readiness Assessment
"41 days. A $275K search. Two firms failed in 60+ days. That's not luck -- that's a different system."
-- Majhi Group placement record. Read the full process anatomy