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.
I ran product design and documentation at DigitalOcean through the hardest stretch the company had faced: more than 600,000 customers, over $1B in ARR, enterprise buyers arriving, and AI rewriting what a cloud product could be. The team was fifteen-plus designers and writers, and I stayed hands-on in Figma and critique because a team trusts a leader who can still do the work.
Enterprise adoption rose 60% after we shipped IAM, RBAC, organizations, and billing. Handoff friction between design and engineering fell 40% after I rebuilt the Walrus Design System. The copilots we built reached more than 800,000 users.
Two clocks ran at once: a slow one to mature the practice at the platform level so every release got better, and a fast one to ship every week on a real roadmap. Holding both is most of this story.
This page is the overview. The deep dives are linked below.
The remit
Two clocks: mature the practice, and ship every week.
Platform work pays off everywhere, later. Rebuilding Walrus meant designers and engineers stopped duplicating components. Career ladders for UX and documentation meant people could see what growing looked like. None of that shows up in one release. It changes every release after it.
The fast clock kept the practice honest. While the system matured, we shipped IAM and RBAC, organizations, and billing, the infrastructure enterprise customers need before they commit. Embedded AI came next, and it has its own case study.
Lean too far into the slow work and you get a beautiful system nobody ships on. Lean too far into shipping and you get debt and burned-out designers. Leadership is keeping both going.
The org
A place where designers own their outcomes.
I'm proudest of building 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 start to finish. My job was to define the outcome clearly (what we're solving, why, and how we'll know it worked), then get out of the way on how to do it. The squad owns the solution. That ownership is where good work comes from.
When a designer gets a ticket, they execute. When a squad gets an outcome, they invent. I spent my leadership energy on outcome definitions clear enough that a squad could move without me hovering, and a culture safe enough that they'd take real risks.
For the new inference cloud, I set the vision, built the squads around it, and ran an acceleration program across every discipline so teams could move fast.
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 ten-year vision down to a single create flow. Each has its own case study.
do.next is the ten-year vision for DigitalOcean, told as four short stories about the people who use it. The seven-minute video got the company on one page, and the plan underneath it became the roadmap teams ship from.
Read the do.next case
The Copilot journey took a docs widget and grew it into a copilot embedded across the product, then into a platform other companies build on. Four words held the team to it: embedded, explainable, editable, trustworthy.
Read the Copilot case
Database Create Copilot is the platform idea in one flow. Describe the database you need and the copilot sets it up with you, every choice editable and every choice explained. It was the first feature built on the platform.
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 at all-hands. Design's job in those moments is to make people feel where we're going, which is a performance skill I learned in theatre: read the room, build a moment that lands. A vision felt by hundreds at once becomes direction the whole company moves on, instead of a deck someone showed once.
By the end the design org thought at the platform level, shipped every week, owned its outcomes, and understood design as something the company feels every day.
The work I'm proudest of doesn't show up on a screen. It's a team that got better at design faster than the roadmap got harder, designers who own outcomes instead of executing tickets, a company that feels where its product is going. I got to build the practice, ship every week, give people room to own results, and keep my hands in the work. It's why I came to DigitalOcean.
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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