Design at DigitalOcean
Driving a product design practice to maturity: building at the platform level, shipping every week, and making space for designers to own their outcomes.
DigitalOcean built its reputation on a single promise: make the cloud feel simple. I came in as Head of Product Design and Documentation to carry that promise through the hardest stretch it had faced. The platform was serving more than 600,000 customers and supporting over $1B in ARR, the customer was getting more sophisticated, enterprise expectations were arriving, and AI was about to rewrite what a cloud product even was.
I looked after the whole experience: core platform, AI, design systems, and documentation, with a team of 15-plus designers and writers. I ran it as a player-coach, setting direction and building the org while staying in Figma and in critique, hands on the work, because a design team only really trusts a leader who can still do the work.
The job had two clocks running at once. One was slow: mature the practice at the platform level so the whole product gets better, everywhere at once. The other was fast: ship, every week, against a real roadmap. Most of what follows is the story of holding both without dropping either.
This page is the overview. The deep dives are linked throughout.
The remit
Two clocks: mature the practice, and ship every week.
Platform work is the kind that pays off everywhere, later. I rebuilt the Walrus Design System so designers and engineers stopped remaking the same components, which cut handoff friction by about 40% and made every team faster. I built career ladders for the UX and documentation folks so people could see what growing looked like and aim for it. None of that shows up in a single release, but it changes every release after it.
The fast clock kept the practice honest. While we matured the system, we shipped. We supported the launch of IAM and RBAC, organizations, and billing, the connective tissue enterprise customers need before they'll commit, and that work contributed to a 60% increase in adoption across enterprise accounts.
We also took DigitalOcean into embedded AI, building copilot experiences that reached more than 800,000 users. That work has its own story, and its own case study, below.
The trick was refusing to treat the two clocks as a trade-off. The mature system is what makes shipping every week sustainable, and shipping every week is what keeps the system honest. Lean too far into the slow clock and you get a beautiful design system nobody ships on. Lean too far into the fast one and you get a pile of debt and burned-out designers. The leadership job is keeping both wound.
The org
A place where designers own their outcomes.
What I'm proudest of building at DigitalOcean was a way of working where designers do their best because they own what they deliver. I moved the org toward squads: design, product, and engineering together, owning a problem from start to finish. My job as the leader was to bring a really clear definition of the outcome, the what and the why and how we'd know it worked, and then get out of the way on the how. The squad owns the solution, and that ownership is where the good work comes from.
That collaboration with product and engineering was the unlock. When a designer is handed a ticket, they execute. When a squad is handed an outcome, they invent. I spent a lot of leadership energy making the outcome definitions good enough that a squad could run hard without a leader hovering, and making the culture safe enough that they'd take the risk.
For the new inference cloud, I set the vision, built a squad model around it, and ran an acceleration program across every discipline so the teams could move fast enough to matter. The point was the same as always: designers who own their outcomes do their best work, and their best work is what the company needs.
The work
Vision down to shipped surface.
A practice is only as credible as what it puts in front of customers. Three bodies of work show the range, from a decade-out vision all the way down to a single create flow. Each has its own case study.
do.next is the long-term vision I led for the next decade of DigitalOcean, told as four short stories about the people who use it. A seven-minute vision video got the whole company on the same page about where we were headed, and the work underneath it became the roadmap teams ship from.
Read the do.next case
The Copilot journey took a small docs widget and grew it into a copilot embedded across the product, and eventually a platform other companies build on. We held the team to four words, embedded, explainable, editable, trustworthy, and used them to make AI users would actually rely on.
Read the Copilot case
Database Create Copilot is the whole platform idea made real in one flow: describe the database you need, and the copilot sets it up with you instead of making you click through every decision. It was the first feature built on the copilot platform we'd invested in, which is the whole reason you build a platform in the first place.
Read the Database Copilot case
Culture
A room is a stage. I know how to work one.
Some of my biggest impact at DigitalOcean happened in front of the whole company. In broad all-hands settings, design's job is to make people feel where we're going. Doing that well is a performance skill, and I came to it honestly through a background in theatre. I know how to read a room, build a moment, and land an idea so it stays landed. When a vision is felt by hundreds of people at once, it stops being a deck and becomes a direction the company moves in together.
Culture work and craft work are the same work. The all-hands moments set the direction, the squad model and the design system gave teams the means to chase it, and shipping every week proved it was real. Being a player-coach kept me close enough to lead from inside the work instead of above it.
By the end, the design org thought at the platform level, shipped every week, owned its outcomes, and believed design is something a company can feel.
The work I'm proudest of at DigitalOcean doesn't show up in any single screen. It's a team that got better at design faster than the roadmap got harder, designers who own their outcomes instead of executing tickets, and a company that learned to feel where its product was going. I got to build the practice, ship every week, give people room to own the result, and keep my own hands in the work the whole time. I love this job.
Why
- DigitalOcean
- Cloud and Developer Tools
- AI
- Head of Product Design and Documentation
- Design Leadership
- Org Building
- Product Strategy
- Player-Coach
- Design Leadership
- Design Systems
- Product Strategy
- Research
- Visual Storytelling
- AJ Zichella (Design)
- Soyun Park (Design)
- Isabel Shic (Design)
- Kevin Carrillo (Engineering)
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