I'm Jon. I lead Content Design at Microsoft AI Monetization where I work at both the systems level and the screen level. I design the frameworks that scale content quality across teams, author the content design that powers our AI tooling, and still write the strings, principles, and patterns that ship in the product every day.

The work has changed a lot over the last few years. The shift to AI-first content production has made the question of how content gets made as important as the content itself. I spend most of my time thinking about that shift: what content designers do when AI handles the first pass, which decisions still belong to humans, and how to encode content design judgment in systems that scale beyond any one designer's bandwidth.

I lead a team of content designers and publishers, and partner across product, design, engineering, research, and support. The work is most rewarding when it's both: shaping strategy and writing copy in the same week.

I didn't start in tech. I started in classrooms.

I taught elementary school for eight years, first in Florida and later in the Pacific Northwest. Teaching was, and still is, the thing that shaped how I think about content design. Both jobs are about taking something complex and making it clear enough for someone to act on. Both require attention to who you're talking to, what they already know, and what's getting in the way of them moving forward. Both reward patience with ambiguity. Both punish jargon.

Once a teacher, always a teacher. I left the classroom but I never really left the work. Today I teach designers how to write microcopy. I teach PMs how to think about content as part of the product. I teach AI agents how to apply content design judgment at scale. The audience changed; the underlying job didn't.

After teaching, I made my way into content design through technical writing: first as a contractor at Microsoft, then as a full-time technical writer, then publishing manager, then content design leader. Each step expanded the scope, but the question never changed: how do you make this clear to someone who needs to act on it?

I think the best content design work happens when content designers are part of the design conversation, not at the end of it. The framing of "content review" treats content as a final pass on someone else's design. I'd rather treat content as one of the materials we're designing with from the start.

I'm comfortable being the most opinionated person in the room about copy, and I'm also comfortable being wrong. Good content design requires both. I push hard on craft decisions when they matter and let go quickly when they don't. I try to be diplomatic without being soft, and direct without being sharp.

My team knows I care about them as people first, and that the content design craft is something we build together, not something I impose from above. When something isn't working, I'd rather we name it honestly than perform agreement.

I'm a husband and a dad. I used to think my job was the hardest thing I'd ever done, and then I started raising a toddler. It's also the best and most rewarding thing I've been a part of.

Two rescue pit mixes and a cat round out the household. Mostly the cat is in charge.

The Pacific Northwest has been home for years now. We hike around it whenever the weather lets us, which is more often than people from Florida (my home state) would believe.

I play guitar and write music. Both started long before content design and will outlast it. There's something about songwriting that has the same shape as good content design: you have a thing you want someone to feel or understand, and you have to find the words and structure that get them there without losing them along the way. I don't think that's a coincidence.

Most of what I'm reading and writing about is how content design will change as AI gets better at the first-pass work, and what content designers should focus on as that shift accelerates. My short answer: less time writing strings, more time defining the standards that strings get measured against. More time on systems, more time on judgment, more time on the calls that AI still can't make.

But I'm still figuring it out. Most of the work I do these days is itself an experiment in what the next version of content design looks like.