🤖 AI read the data. I made the call. 📊

AI Creativity Chronicles
Use AI Well. Stay Human.
Build What Matters.

Every week, I resend one of my clients' emails to the people who didn't open it the first time. My favorite email marketing platform, Kit has a built-in feature that makes it easy. And for months, I let it slap "Resending:" on the same subject line and called it done.

Then I got curious.

Illustration of a man at a desk reviewing an email performance dashboard on his laptop, writing "New Subject Line: Worth Opening?" in a notebook. Overlay text reads "The numbers were talking. Someone had to listen." — The data was sitting there the whole time.
The only thing missing was the question.

🔍 What a year of send history had to say

I asked the AI, Claude Cowork, to pull a year of send history from my client's Kit account. This was possible because this Kit account is connected to Claude via MCP. (Most people don't know you can do this yet.)

The AI came back with the numbers and a suggestion. The resends were stuck at a less than 10% open rate, and the reasoning was hard to argue with: those readers had already passed on the first subject line. Why would it land the second time?

So now, thanks to AI, every resend gets a fresh subject line. A small change, but a valuable one, and one I might never have made on my own.

🤝 Who made the call?

Here's the part that kept it HUMAN. The AI read the data. I made the call.

That division of labor is the whole game right now. AI as an analytical partner that notices what you've stopped seeing, and I am a human creative director who recognizes when the suggestion is right and acts on it. Neither one gets there alone.

Most of the public AI conversation is still about slop, or more generally, about generating things. Fewer people are talking about the ways you can point AI at the information you already have so that it can ask better questions. This leverage is hiding in plain sight.

💭 This week's reflection

What's a corner of your marketing that deserves that kind of curiosity? A report you stopped reading, a default setting you never questioned, a "good enough" that's been sitting there for a year?

Experiment. I would love to hear what you find. Just hit reply.

And if having someone bring this kind of attention to your email sounds good to you, that's exactly the work I'm doing now. I'd love to talk: cal.com/jon-leland

Until next time, stay curious.