Are you using personalization to connect or just to fill a placeholder? A friend recently suggested I write about the most memorable email I’ve ever received. Interesting idea, but the truth is, what makes an email memorable to me might not be what makes it memorable to you. I’m captivated by development, design, and strategy — you might be taken by message or timing. As my friend described his favorite, I realized what he found memorable was the human connection; what I found memorable was the execution. And that got me thinking about how much we’re wasting personalization today.
When personalization meant something
Back in 1995, when I founded The World-Wide Power Company — the world’s first international distributor of all (graphics) extension-based technology — we didn’t have AI, APIs, or dynamic content engines. We had FileMaker Pro. But even though we were simply a software distributor, we also had detailed, structured data: customer purchase histories, product versions, quantities, even their hardware specs. That data made our direct-mail campaigns personal — not Hi, [FirstName] personal, but we-know-exactly-what-you-own-and-why-you-care personal.
Our most successful campaigns were our weekly postcards and letters — the PUN (Product-Upgrade Notice) and CUN (Competitive-Upgrade Notice) series. Each message was generated directly from our invoice database. We mailed to a quarter-million contacts every week, and the copy was something along the lines of:
Customer Number: 001097
Leslie Strongman, XYZ PrintingDear Leslie,
According to our records, you currently own 8 copies of QuarkXPress 4 and Imposer XTension. To maintain compatibility when upgrading to QuarkXPress 5, you’ll also need to upgrade your XTensions.
Imposer Pro adds [benefit] and supports [new software version]. For a limited time, upgrade each copy for $199 (regularly $399). Offer expires March 31.
These campaigns achieved response rates north of 50% — with a record-breaking 80% at their peak. That’s the power of true personalization: relevance, not just recognition.
The modern problem with personalization
Fast-forward to today. Most marketing platforms insert a first name, maybe a company name, and call it personalization. But let’s be honest — that’s table stakes. If your most advanced use of data is a variable greeting, you’re not connecting; you’re auto-filling.
While technology has advanced, there are many times I’ve seen creativity isn’t keeping pace. We know triggered messages (such as abandoned cart reminders) perform incredibly well, yet we don’t apply that same contextual thinking to everyday marketing. Why not? Too hard? Too technical? Too busy? Probably all of the above.
You don’t need big data to personalize meaningfully. You just need to look inward — at the data you already own. Your accounting system, CRM, and analytics tools are treasure chests of context waiting to be used.
Small data, big impact
Consider these ideas for more thoughtful, non-invasive personalization:
- Use milestone data. Celebrate customer anniversaries, renewal dates, or even one-year-since-you-joined moments.
- Revisit historical data. Reference their first purchase, first event, or most-used feature — even if it’s imperfect, it shows awareness.
- Integrate behavioral cues. A click on a specific product page or blog topic can trigger content that feels like a natural continuation of the conversation.
- Pull from the human side. Ask your sales or support teams what customers mention most often — that’s qualitative data worth gold.
Another friend told me about an email from Hyatt that thanked him for staying at their hotels 75 times and even mentioned his first stay. He admitted most of the details were wrong — but he still smiled. Why? Because they remembered him. Personalization doesn’t have to be perfect to be powerful.
Make it meaningful
Personalization is wasted when it stops at the greeting line. The next time you send a campaign, ask yourself: am I just inserting data, or am I creating connection? Can I include something that makes the recipient pause — laugh, remember, or feel seen?
Rule of thumb: If your personalization could be done with a mail merge in 1997, you’re not doing enough in 2025.
Editor’s note: I wrote this article some time ago — but the principle hasn’t changed. This lightly updated version reflects current tools and practices while keeping the same lessons intact.
AI disclosure: This content was originally written by me and later updated with assistance from OpenAI’s GPT-5 for light editing, fact-checking, and modernization. Every word has been reviewed and approved by a human — specifically, me — before publication.