I have spent the better part of my career at the intersection of two disciplines that don’t always get mentioned in the same sentence: digital commerce and customer education. For years I worked on the operator side – helping major retailers connect customers with the right products at the right moment through digital merchandising, onsite search, and eCommerce strategy. Then I crossed to the other side, building the education programs that help customers and professionals in that same space develop the knowledge and confidence to succeed. One discipline is about removing friction between a customer and a product. The other is about removing friction between a professional and the knowledge they need. Done well, they are more similar than they appear.

That intersection has always fascinated me. Over the past month during a period of intentional reflection between roles I had the rare gift of uninterrupted time to explore a question I had been carrying for years:

How are leading companies actually approaching customer education? And what role is AI playing in how they build, deliver, and scale their programs?

Rather than reading about it, I decided to experience it firsthand. I enrolled in certification programs across a range of platforms from global technology companies to specialized SaaS tools to AI platform providers completing ten courses in roughly thirty days. My goal was not to collect credentials. It was to dive into areas of interest and observe, as a practitioner, how each organization thinks about education. What philosophy drives their content decisions? How do they balance scalability with human connection? Where does AI show up and does it impact the learner experience?

What I found was more varied and more instructive than I expected.

Each platform made a different bet on what matters most in customer education. Each had real strengths but also some weaknesses that need to be examined. Taken together, they painted a comprehensive picture of where customer education is today, where it may be heading, and provided some interesting ideas as to what future programs will need to get right.

Across the five programs I completed, five themes emerged consistently. Each revealing a different dimension of what separates good customer education from great customer education. No single platform got all five right but each one had something worth learning from.

If you would rather not spend the next 30 days taking courses to have similar learnings don’t worry. Over the next five weeks I will share a series of articles where I will dive into these findings and share practical takeaways for anyone building, leading, or evolving a customer education program.

Here’s what’s coming:

Part 1: The Research and Why It Matters
Part 2: The Philosophy Question – Are You Teaching Features or Outcomes?
Part 3: Human Warmth vs. Scalability – A False Choice
Part 4: Currency is a Feature, Not a Footnote
Part 5: The Learner Experience Layer – Content Alone Is Not Enough
Part 6: Summary and Key Takeaways

Where my observations are positive I’ve named the programs. Where I offer constructive criticism I’ve kept platforms anonymous out of professional courtesy. These are intended to be observations about patterns and choices, not indictments of individual companies or programs.

I hope you’ll follow along. Whether you’re building a customer education program from scratch, evolving an existing one, or simply curious about where the discipline is heading. I hope you will find something useful in what I discovered.