How I stopped overthinking AI and made it part of my job

Welcome to Evidently—the bi-weekly newsletter where I share my biggest hits (and get honest about my misses) as a first-time VP of Marketing. If this was forwarded to you and you like what you saw, you can subscribe here.

I used to freeze at the blinking cursor.

Staring at ChatGPT. Not knowing where to start.

Didn’t want to sound like I was faking it with some over-engineered prompt. Didn’t want to be bad at something that looked easy for everyone else.

So I avoided it.

Not because I didn’t think AI was useful. I just didn’t want to feel small while learning something new.

And because I had other things that felt more urgent.

But the cost of staying stuck was real.

It slowed me down in all the places I needed to move faster:

• Strategy and planning

• Team clarity

• Internal communications

• Internal marketing

Eventually, I got tired of feeling behind. I stopped overthinking it and committed to using ChatGPT every day.

Not to automate my job, but to keep pace with where things are headed.

That shift changed how I work, how I lead, and how I learn.

What actually got me unstuck

Talk instead of type

The ChatGPT desktop app changed everything for me last September. Not kidding.

I talk into my computer like a total weirdo and it gives me something to work with.

Way easier than worrying about how to write the perfect prompt.

Save what repeats

Founder updates, one-on-ones, kickoff decks. Each one has its own Project with pinned prompts and past examples.

I even use ChatGPT to help me write better instructions for ChatGPT, so I’m not re-explaining the same stuff every week.

Feed it real context

Screenshots. Slides. PDFs. Call transcripts. Whatever gives it more to work with.

I also tell it what I don’t like about what I’ve given it. It learns faster that way.

6 ways I use AI every week as a marketing leader—plus 2 prompts to steal

This isn’t about using AI to write faster. It’s about removing friction across how I work and lead.

1. Coach myself on how I show up

After big meetings (or conflict), I don’t trust gut feel alone. I drop the transcript into ChatGPT and ask it to break down how I actually came across.

Was I clear? Did I talk too much? Did I create space or did I steamroll?

What it does: Helps me analyze how I communicate, not just what I said.

Why it matters: I get real-time feedback and adjust how I show up in the next meeting.

2. Poke holes in strategy before the founders do

Before I send anything to Evan or Ray (GTM plans, quarterly OKRs, etc.), I run it through ChatGPT.

It helps me reframe things at a more strategic level. It analyzes my V1 draft, flags what’s missing, and spots the gaps in my recommendations.

Where are the objections? What’s under-explained? What’s wouldn’t hold up?

What it does: Analyzes the plan like a founder would—before it hits their inbox.

Why it matters: I spend less time defending the basics and more time focusing the conversation on what matters.

3. Punch up copy before hitting publish

Whenever copy I’m working on feels soft, I’ll drop it into ChatGPT and ask:

What would Eddie Schleyner think of this copy? How would Devin Reed tear it down?

Where’s it vague? Where’s it trying too hard? What wouldn’t land with a buyer?

I’m not trying to write like them (no one can). I’m using their lens to see what’s missing.

What it does: Rewrites with clarity, tone, and intent.

Why it matters: I hit the bar faster and don’t waste time polishing the wrong things.

4. Rewrite messaging from the POV of each persona

I use ChatGPT to analyze how it lands for different buyer personas based on their jobs-to-be-done.

How would a VP of Product Marketing read this? What would a Head of Customer Marketing care about?

What’s missing for someone trying to defend this decision to their CFO?

What it does: Reframes the message through the lens of real buyers with real stakes.

Why it matters: We stop pitching what we think sounds good and start speaking to what actually drives action.

5. Write internal updates that people want to read

Weekly recaps, launch docs, async updates—I word vomit into ChatGPT and get back something structured I can actually use.

It’s not a replacement for my voice. It just saves me from spending 30 minutes formatting a Slack post.

What it does: Turns raw notes into clear, focused updates that don’t waste anyone’s time.

Why it matters: I spend less time explaining and more time executing.

Here’s a more structured prompt I’ve used in ChatGPT for prepping internal team updates.

6. Mine Gong calls for competitive messaging

We exported call transcripts from Gong with specific competitor mentions and created a custom GPT to improve our competitive messaging.

It flags key objections, repeated themes, and the specific points that landed—or didn’t.

What it does: Surfaces competitive intel and objection themes.

Why it matters: We learn how to preempt objections and position more clearly vs. a direct competitor.

Here’s a more structured prompt I’ve used in ChatGPT for this idea.

This is how I work now

AI’s not replacing the work. It’s removing the drag.

It gives me feedback before I tap someone else. Clears the grunt work between first draft and final version. It’s a force multiplier, not a shortcut.

Same goes for the marketing team as a whole.

I encourage them to use AI to get their work 80% there. Poke holes in it. Make some edits. Then they can bring it to me if they still want feedback.

That mind shift alone makes us more effective—individually and together.

Stuff I’m digging this week

• Highline is getting real—A few people dropped (summer travel, back-to-school, totally fair). It’s just making us more intentional with the final spots. We’re focused on filling the “room” with the right mix of in-house marketing leaders.

• AI, Sales + GTM in 2025/26 with Lemkin + Kyle Norton—One of the best convos I’ve seen on what AI’s actually doing to sales orgs. Real talk on GTM efficiency, team structure, CRO expectations, and why “being curious” about AI isn’t optional anymore. Worth the full watch.

• Captivate Collective’s CAP Certification series—Most “certifications” are just recycled slides. This isn’t that. It’s 6 hours of live, discussion-based sessions for customer marketers who want to go deeper—real examples, real debate. Starts June 3–5.

Hold up—what does UserEvidence do again?

Product marketers, marketing leaders, and customer marketers need more than generic testimonials to prove value.

UserEvidence helps create real customer evidence that Sales, Marketing, and Customer Success teams can use to increase buyer confidence.

We make it easy to collect and share case studies, testimonials, competitive intelligence, product stats, and ROI data—proof that helps move deals forward.

Need a stat to prove ROI? A competitive insight to handle objections? A case study that closes the gap between interest and decision?

UserEvidence helps you capture and share the proof buyers need.