A photo taken out of a plane window looking at the ground

Never mind “Autopilot.” What about the people who are afraid to fly? Thoughts on creating website building software for small businesses.

If there’s one thing I’ve learned over the years it’s that no matter how easy something may be, some folks have a tendency to stay clear away from it. And not because they don’t want […]

The simple mistake we all have made, and how to avoid it

We all make assumptions all the time. In fact you likely made an assumption about this article before you clicked on it. It’s human nature for our brains to fill in blanks and make connections […]

Your goals are our goals

Recently, Automattic design and research teams paired up to conduct a foundational research study to learn more about small business owners. One of the insights that immediately stood out as I made my way through […]

Help me succeed

I know I need to be writing articles. […] Do that for me. I hate writing articles. I despise it. “I despise it”  – these words from one of our customer interviews caught my eye, as they are […]

I need a website, and I need it yesterday

Recently I’ve been thinking a lot about my dentist. Like most dentists I’ve been to, it’s a small operation — basically just one dentist and a couple of assistants. They’re not necessarily interested in marketing […]

Concepting through the Hypotheses – Part Two

When I speak about my work as a Design Operations lead I often focus on the  three pillars of design operations to help ground the conversation in the framework of Process, People, and Projects and […]


In recent months, we’ve done a fair amount of research on small business owners, and how a website can help them find their presence on the web. As I paged through some of the results […]

The Business Listing

When I was younger and needed a plumber, I’d open up a thick phone book and sort through listings alphabetically. There were names like “Al’s Plumbing,” or “AA Plumbing,” and even an “AAA Plumbing.” All […]

Things I Thought I Knew and Then Some

Musings on Six Months as Head of Design Operations @Automattic – Part One Coming into my role as Head of Design Ops from a prior career in design consulting building out similar types of practice areas […]