Success Story: From Sabbatical to CMO in 18 Days

Total Search Time

• May → September (officially started search mid-August)

Lead Source

• Reconnection with a recruiter at The Cole Group—initiated through proactive outreach to past contacts.

Job Landed Time (First Interview to Offer)

• 18 days from initial recruiter conversation to verbal offer.

Search Approach

• Took intentional time off after leaving last company to recharge.

• Focused on network-driven outreach, not applications on LinkedIn or job boards. 

• “I didn’t apply for any role—I relied 100% on my network.”

• Re-engaged old recruiter threads via Gmail and LinkedIn, reigniting dormant relationships.

• Used GenAI tools—ChatGPT and Perplexity—for research, SWOT analyses, and dry-runs before interviews.

Interview Process

• Rapid 3-week sequence: CEO → CTO → CRO, SVP of AI → CEO & CRO → Chief People Officer → CEO again (in person).

• Final step: Presentation on category creation and AI-driven marketing, inspired partly by learnings from CMO Huddles on AEO and AI strategy.

• Hired as CMO, despite being a first-time CMO, thanks to credibility from leading product marketing at big B2B tech brands.

Negotiation Process

• Negotiated a signing bonus to offset a modest salary reduction.

• Secured favorable equity vesting terms (6-month half-cliff on double trigger).

• “It doesn’t hurt to ask—the only thing they can do is say no.”

Lessons Learned

• At-bats matter: Each interview sharpens your story and comfort level.

• Attack your weaknesses: Shift focus where you underperformed in prior processes (e.g., brand & demand).

• Network relentlessly: Recruiters, former peers, PE firms—any warm contact may open the next door.

• Use AI as a co-coach: “I practiced my story with ChatGPT—it helped me hear how I actually sounded.”

• Be curious and professional: Long-term relationships pay unexpected dividends.