A bad executive hire costs 12-18 months and often the function they were hired to run.
Executive hires are the highest-leverage decisions founders make between $5M and $50M ARR. A great VP Sales unlocks the next stage; a bad one burns 12-18 months, the pipeline, and often the reps who were performing before they arrived. The failure rate for first-time executive hires at growth-stage startups sits between 40% and 50%. Almost all of that failure is preventable with a rigorous process — but the process is completely different from hiring individual contributors or first-line managers.
Written before sourcing begins: the specific business outcomes this executive owns in years 1 and 2, the team they inherit and the team they need to build, the top three decisions they'll make in the first 6 months, the stage of company they're joining (Series A ≠ Series C), and how success will be measured. Skipping this step produces the most common failure mode: hiring someone who was excellent at a different stage or a different problem, and discovering the mismatch 6 months in.
Executives at the caliber you want are not on job boards. Sources that work: portfolio-company introductions from your investors, warm intros from your board and advisors, executive search firms (retained, typically $80-150K per search), and direct outreach to people you've been tracking. Expect a 90-day search minimum. The strongest candidates are usually not looking; the pitch is to a specific problem worth solving, not a generic company description.
Executive interviews that consist only of conversations select for candidates who interview well, not candidates who perform well. Add: written case study specific to your business (48 hours, 3-5 pages), 90-minute working session with the team they'd lead, backchannel references from people who worked FOR them (not with them) at previous roles, and a paid trial project when the situation allows. Every executive hire we've seen fail had at least one of these steps skipped.
Off-list backchannels matter more than on-list references. Structured questions: 'What would this person's team say about them if you asked? What did they struggle with? Where did they blindside you? Would you hire them again for a $10M ARR company, a $50M ARR company, a $500M ARR company?' Vague positive references are usually a signal — great executives have specific stories told about them.
Structured 30-60-90 with the CEO before start date: who they'll meet, what context they'll get, what they should NOT change in the first 60 days, what decisions to bring back before making. Weekly CEO 1:1s for the first 90 days, non-negotiable. Explicit permission to disagree with the CEO privately, expectation to align publicly. Executives who arrive without this structure spend 6 months figuring out the org rather than running it.
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