How I Used ChatGPT to Land a CMO Gig… Almost
Image by Alex Schuler from Pixabay
Let me just say it:
I did not get the job.
But for two months, I was this close to landing a Chief Marketing Officer role at a private equity-backed company. I met the CEO, the exec team, the boardroom—hell, I probably met the person who waters the office ficus. And while I didn’t walk away with the title, I walked away with something arguably weirder (and possibly more valuable): a brand-new way of thinking about what AI can do in a job search.
Here’s how I used ChatGPT like a full-blown entourage—think research analyst, strategist, speechwriter, therapist, and hype team rolled into one.
🧭 1. The Research Partner I Didn’t Know I Needed
I asked for a little company background. I got an entire competitive landscape.
I asked about industry trends. ChatGPT gave me five-year projections and SWOT analyses.
I asked for talking points for my interview. It handed me a mini MBA.
It was like having a research assistant who worked 24/7, didn’t require coffee, and somehow already knew exactly what I needed next—even before I did.
🎯 2. A Career Coach That Doesn’t Flinch
You know those job application questions that make you doubt every decision you’ve ever made?
“Tell us about a time you drove $X in revenue.”
“How do you scale a team under pressure?”
“What’s your favorite episode of Ted Lasso and why?”
ChatGPT helped me draft answers that actually sounded like me—just a slightly better, more polished, future-CMO version of me. It pushed me to be specific. To connect dots. To tell better stories. Basically, to stop sounding like a human LinkedIn post and start sounding like a leader.
🛋️ 3. A Therapist Who Types Fast
There were moments in the process when I needed to vent. To reflect. To reframe. ChatGPT was… surprisingly good at this.
It reminded me of past wins. Helped me name (and quiet) impostor syndrome. And when I needed to re-center before a big call, it didn’t just say “you got this”—it told me why I got this.
🪜 4. A Ladder-Climbing Buddy Who Always Said “What Else?”
This was maybe the wildest part. Every time I thought a task was done, ChatGPT would say something like:
“Want me to draft a follow-up?”
“Need help turning that into a one-pager?”
“Want to prep for the next meeting with some mock Q&A?”
It didn’t just respond—it built momentum. It made me better by showing what “more” could look like.
🧰 5. And Then There Were the Extras…
There were the SWOT analyses.
The executive profiling.
The role-playing of tricky Q&A sessions.
The brand positioning writeups.
The customized thank-you emails.
The three-page summaries of meetings I barely remembered having.
Honestly, it felt like I had a team of specialists backing me up. Not a tool. A team.
💡 Final Thought: Not Just AI. A-Team.
In the end, I didn’t get the job.
But I got damn close.
And I did it without a coach, resume writer, or agency.
I did it with a keyboard and a ChatGPT window open.
If you’re job hunting, here’s my advice:
Don’t treat ChatGPT like a smarter Google. Treat it like a squad. A crew. An actual team that’s got your back.
Because it can be. It was for me.