Before the director titles and the enterprise clients, there was a lot of hands-on work that built the foundation for all of it.
In the late 1990s and early 2000s, I was designing and developing websites when most businesses didn't have one yet — building multimedia CD-ROMs and early web experiences at HealthStream and SilverPlatter Education, then moving into visual design and UI work at Show and Tell Inc. Those years taught me to think about usability before there was much of a vocabulary for it.
From roughly 2001 through 2010, alongside my other work, I freelanced for small businesses and several school districts — building and maintaining websites, helping organizations figure out what their digital presence should even be. Many of these clients had never worked with a web professional before, which meant translating technical decisions into plain language was part of the job from the start. That experience is a big reason I'm just as comfortable working with a solo financial advisor as I am with a Series B software company.
At Needham High School, I wore several different hats over the years — district webmaster, technology support, and briefly, teacher. I taught Photography and Graphic Design, secured a grant to bring digital photography into the curriculum, and ran adult education courses in web design. Teaching turned out to be useful training for consulting: you get good at explaining things clearly, meeting people where they are, and making complicated subjects feel manageable.
My very first professional web role was at Curry College, where I developed and maintained the college's first-ever website while managing their Educational Technology Services Office. It's a long way from there to leading a platform migration to Contentful and React — but the thread connecting all of it is the same: figure out what someone needs from a digital experience, then build it as well as you possibly can.