I’ve spent my career a step ahead of the next shift.
I’m Michael Rosenfeld, a fractional Chief Digital Officer and the founder of WebConnection, which I started in 1995. I’ve led digital strategy for B2B companies through every shift that rewrote how buyers find them, the dot-com crash, mobile, social, and now AI. The throughline has never changed. I see the next shift coming and move my clients before it leaves them behind.
How did I get here?
I didn’t start in tech. I started in candy. I owned a small chain of candy stores, and I went back to school at night for my MBA. In a class called Internet and Business, I watched the web arrive and decided, right there in the classroom, to start WebConnection. That was the first time I saw a shift coming and moved on it. It would not be the last.
For years, WebConnection was a full-service web design firm. I led the digital strategy, with designers and developers building the sites I directed. A year-long engagement with the U.S. Army let me lead pure strategy without ever touching the build, and I knew that was the work I wanted. So when the design business began to commoditize around 2012, with WordPress, Joomla, and Drupal everywhere and GoDaddy, Network Solutions, and Squarespace putting website builders in everyone’s hands, I pivoted for good, to the role I lead today, a fractional Chief Digital Officer. Now I’m doing it a third time, out in front of AI.
How do I approach the work?
A few things have held true for me no matter what the platform of the moment was.
Get the message right before you chase tactics.
The sharpest campaign fails if the site and the story underneath it are unclear. I fix the message first.
Lead, don’t just advise.
A strategy nobody executes changes nothing. I set the direction and stay in the work until it is implemented.
Sit on the client’s side of the table.
I answer to what is best for you, not to a scope of work. That is the difference between a leader and a vendor.
Keep what works, drop what doesn’t.
Most of my work is analyzing every initiative and acting swiftly on what to keep and what to eliminate.
Why do I do this?
The honest answer is the people and their journey. I love hearing my clients’ entrepreneurial stories. Every business is different, and getting to learn how someone built theirs, what makes it work, and where they want to take it is the part of this I have never gotten tired of. It is also why I taught it. I was an adjunct professor of Introduction to Entrepreneurship at the University of Maryland, Baltimore County, a class the Baltimore Sun named a must-take. Entrepreneurs are who I do this for.
“Mike was an outstanding partner throughout the development of our firm's new website. He took the time to understand our vision, was incredibly patient through the many iterations, and was always responsive and supportive. I especially appreciated that he wasn't afraid to challenge my thinking when it helped improve the final product. The result exceeded our expectations, and I highly recommend Mike to anyone looking for a strategic digital marketing leader.”
Michael Strauss,
Strauss & Associates, CEO
The next shift is already here.
This one is AI, and I didn’t wait around to be ready for it. I completed an AI certification at MIT, regarded as one of the best programs of its kind, so the person leading your strategy actually understands what is changing. If you want someone who has navigated every shift before this one, start with the free AI visibility check. It shows where you stand today, and it is the simplest way to see whether I am the right person to have in your corner. I am based in the Baltimore and Washington area and work with B2B companies across the country.