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.
My remit was the whole arc of the experience: core platform, AI, design systems, and documentation, with a team of 15-plus designers and writers. I ran it as a player-coach. I set direction and built the org, and I was still in Figma and in critique, hands on the work, because a design practice only earns trust when the person leading it can still do the thing.
The job had two clocks running at once. One was slow: mature the practice at the platform level so the whole product gets better, not just the next screen. 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-level work is the kind that pays off everywhere later. I revitalized the Walrus Design System so designers and engineers stopped rebuilding the same things, which cut handoff friction by roughly 40% and made every team faster by default. I built career ladders for the UX and documentation functions so people knew what growth looked like and could aim at it. These are the investments that don't show up in a single release but change the slope of every release after.
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 body of work has its own through-line, and its own case, below.
The discipline was refusing to treat the two clocks as a trade-off. Platform maturity is what makes weekly delivery sustainable. Weekly delivery is what keeps platform work grounded in something real. Run only the slow clock and you get a beautiful system nobody ships on. Run only the fast clock and you get a backlog of debt and burned-out designers. The leadership job is keeping both wound.
The org
A place where designers own their outcomes.
The most durable thing I built at DigitalOcean wasn't a screen. It was a way of working where designers thrive because they own what they deliver. I moved the org toward squad-based work: cross-functional squads of design, product, and engineering that own a problem end to end. Leadership's job in that model is to bring sharp outcome definitions, the what and the why and how we'll know it worked, and then get out of the way on the how. The squad owns the solution. That's where the energy 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.
To stand up the new inference cloud experience, I created the vision, developed a new squad model around it, and ran an acceleration program across every discipline so the teams could move at the speed the moment demanded. The point of all of it was the same: designers who own their outcomes do their best work, and their best work is what the company actually 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 North Star all the way down to a single create flow. Each has its own case study.
do.next is the North Star vision I led for the next decade of DigitalOcean, told as four vignettes about the people who use it. A seven-minute vision video got the whole company on the same page about what we were becoming, 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 platform thesis made concrete in one flow: describe the database you need, and the copilot configures it with you instead of making you click through every decision. It was the first feature built on the copilot platform, which is exactly how platform work is supposed to pay off.
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, not just hear about it. That's 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 altitude. The squad model and the design system gave teams the means. The weekly delivery proved it was real. And being a player-coach kept me close enough to all of it to lead from inside the work rather than above it.
That's the practice I drove to maturity at DigitalOcean: a design org that thinks at the platform level, ships every week, owns its outcomes, and believes design is something a company can feel.
The work I am proudest of at DigitalOcean is invisible in any single screen. It is a team that got better at design faster than the roadmap got harder, designers who own outcomes instead of executing tickets, and a company that learned to feel where its product was going. Mature the practice, ship every week, give people room to own the result, and do it all with your own hands still in the work. That is the whole job, and I love it.
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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