A complete hiring checklist for fractional CMO engagements - 20 questions every CEO should ask before signing a retainer agreement.
Hiring a fractional CMO is one of the highest-leverage decisions a growth-stage company can make. It's also one of the most misunderstood. The wrong hire costs you 6-12 months of momentum. The right hire changes the trajectory of your business. This checklist gives you the 20 questions every CEO should ask before signing any fractional CMO agreement.
1. What industries have you served, and do any match ours? 2. What company stages have you worked with - pre-revenue, Series A/B, bootstrapped, PE-backed? 3. Give me an example of a go-to-market you built from scratch. What was the result? 4. Have you ever inherited a broken marketing team? What did you do first? 5. What's the biggest marketing mistake you've made and what did you learn from it?
6. What does your first 30 days look like - specifically, what will you do and what will you deliver? 7. How do you run a marketing audit? What do you actually look at? 8. How do you prioritize when everything seems urgent? 9. How do you handle a CEO who disagrees with your strategic recommendation? 10. How many clients do you work with simultaneously, and how do you manage conflicts of interest?
11. What KPIs will you own, and how will you report on them? 12. What does success look like at 90 days? At 12 months? 13. Have you ever been in an engagement that wasn't working? What did you do? 14. Can you show me examples of dashboards or reports you've built for previous clients? 15. Will you be the person doing the work, or will you be managing others to do it?
16. What's your notice period / termination clause? 17. Who owns all work product and IP created during the engagement? 18. What are your specific deliverables for the monthly retainer? 19. What access do you need to do your job effectively - tools, data, team members? 20. Are you willing to provide 3 references from clients at similar company stages, and can I speak directly with the CEO?
Candidates who can't answer questions 1-5 with specific examples. Anyone who talks about strategy without mentioning accountability for outcomes. CMOs working with 10+ clients simultaneously. Vague answers about deliverables - 'I'll add value' without specifics. Reluctance to provide direct CEO references. Contract terms requiring 90+ days notice or heavy cancellation fees.
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