Total Search Time: 5 months 

Lead Source: Previous CEO

Pipeline-First Job Search

• “I doubled down on pipeline. It was all consuming.”
• Daily Routine: Packed with prep, calls, scheduling, outreach, following up; kept afternoons lighter to avoid burnout.
• Friend-Assisted Prospecting: Ask close exec friends to co-review your target list weekly and make surgical intros (bring them the shortlist).
• Hidden Network: Youth sports / school parents because unexpected corporate nodes → multiple warm doors opened.

ICP & Targeting (Getting At-Bats)

• Focus Rule: Only applied to Chicago-based listings
• Narrowing the ICP: The candidate stuck to the categories/stages they were strongest
• “You can try to go into other industries, but if you're never getting the at-bats, it makes it very difficult for you to practice your story.”

3 Opps, 1 Table

• Source — LinkedIn Apply
• • Result: 1 callback
  • Lesson: Hundreds of apps (15/week), low ROI
• Source — CMO Community
• • Result: Offer (declined)
  • Lesson: Gut said wrong fit in terms of stability
• Source — Previous CEO
• • Result: Offer (accepted)
  • Lesson: Had a great gut feeling, and really trusted previous CEO’s rec

Interview Mastery: Control the Meeting

• Followed recommendations set forth in “Never Search Alone”
• Open with structure: “We have 40 minutes. What makes this successful for you? For me, I’d love to tell you a little about myself.”
• 30-minute discipline: Always cap at time; it shows respect and control
• Caution “Captain Casual:” One PE convo began breezy; guard dropped; feedback became: “You didn’t tell me enough about you.”

Handling the “Why Did you Leave” Question

• Own it early in your intro; don’t wait for the landmine:
• “PE diligence didn’t prove out; so, the US shut down, which is common in PE. I owned outcomes, learned, and I’m ready to build again.”

AI-Assisted Prep and Feeback Loops

• Project thread in ChatGPT: log every call; it learns your story and blind spots
• Voice role-play: Use GPT audio to practice aloud; ask for harsh critique (“don’t be nice; flag filler words; push on weak logic”)
• Persona drills: Feed profiles of CEP/CFO/CRO; have AI interview you AS them; then grade you AS them.
• Company Alerts: Set AI/news alerts where you’re in the running so you’re never scrambling pre-call.

Comp Negotiation: Levers & Timing

• “The CMO salary band is all over the place.”
• One opportunity was more lucrative base-wise, but the bad gut feeling told the candidate it wasn’t worth it. Here’s how the candidate made up for it:
• Get creative: Propose milestone-based unlocks (e.g., on pipeline, ARR, CAC/LTV, retention, time-based cliffs).
• “I think I earned more respect because I understood the size of the company and the margin”
• Caution: The candidate’s friend made it to the end of the interview process and “asked for what she was worth.” The company immediately pulled out.

Interview Process Insights

• All interview processes were lengthy — multiple rounds and weeks between convos
• One CEO initially suggested a part-time contract hire. Response: “Respectfully, that’s not what you need. I was recommended by a previous CEO, so I want to do right by them and help you. Here’s what I would do…”
• Over the course of several casual touchpoints (~every 3 weeks), the CEO shifted to offering a full-time CMO role.
• Decisive factor: Her clear GTM plan and brand revitalization strategy — not just pedigree.

Lesson Learned: Always Be Networking!

• “I will not be caught off guard again in terms of network.”
• “You can’t control the market. What you CAN control is how much time you spend once you get a job nurturing your network.”
• Commit to Nurture while Employed: Lunches, events, authentic touchpoints.
• Routine: Weekly scan texts; reach out if it’s been >2 weeks. Always tie to something authentic.
• “They were there for me, and now I need to give back and continue to cultivate that.”
• Invest now: Reach out to people, go to CMO events, send things of value to your contacts