Meet DesignEx: Design Operations at Automattic

That’s a lot of creativity. And a lot of complexity.

Enter the Designer Experience (DesignEx) team: Automattic’s version of Design Operations. Our job is to support designers working within a distributed, ever-evolving ecosystem. We exist to help design thrive—not only for our designers, but for the entire company and the millions of people who use our products every day.

And we’re reimagining what DesignOps can be:

Less overhead, more flow.
Less process theater, more clarity, connection, and momentum.

Who we are

🌀 Cliona O’Sullivan
Connector of people and ideas. Builder of Human Operating Systems. A big fan of post-its, well-curated playlists, and saying “yes, and…”

🔍 Toto Castiglione
A Mediterranean soul with a systems mind. Brings equal parts empathy and precision. Always down for a Figma file audit or a gelato.

🥕 Leila Byron
Rethinks frameworks, reroutes inertia, and rallies people with purpose. Believes in growth you can feel and vegetables you can grow.

✨ Melody Michaud
Our accessibility champion. Thoughtful and quietly tenacious, Melo turns messy systems into meaningful ones with joy, rigor, and an eye for the human side of design.

**What we do (and love doing)**

Our mission is simple: amplify the impact of design at Automattic. We do that through shipping focused, hands-on work in three core areas:

🧪 Quality + Impact

We raise the bar by building systems, rituals, and reviews that connect design to product strategy and real user needs. We reduce friction, clarify priorities, and keep quality at the heart of the work.

🌱 Talent + Culture

We’re hands-on partners in hiring, onboarding, and shaping a design culture that feels connected, inclusive, and alive. Our goal: a community where designers thrive and want to stay.

📚 Learning + Growth

We help designers shape their own paths. We define what great design looks like, and offer tools, training, and templates to get there without needing to fit into rigid levels or tracks.

What we’re working on

To put our mission into practice, here’s a look at what we’re shipping right now:

🧪 Quality + Impact

Design Reviews that go deep
We’re hosting async and live reviews across product and brand work. More than a checkbox, they’re becoming critical points of connection and clarity.
Unifying our work in Linear
Designers now plan and track work right alongside engineers in our favourite tool, Linear. Same projects, same visibility. Less friction, more flow.
Customer insights at designers’ fingertips
We’re making it easier for designers to access real user voices, building better bridges between feedback and design decisions, by partnering with Lyssna as our user research platform.
Design systems, open-source and open-hearted
We help run (and grow) our design system as both an internal resource and public good through shared tokens, open contributions, and thoughtful governance.

🌱 Talent + Culture

Hiring and onboarding, done together
We support teams in hiring amazing talent and welcoming them with structure, clarity, and care.
Design presence in the world
We’re growing Automattic’s design voice externally through events at our beautiful NoHo space, blog posts (like this one!), and community-building.
Town Halls, Snaps, and Slack magic
From all-hands moments to async Slack prompts, we’re shaping rituals that connect and celebrate our distributed design team.

📚 Learning + Growth

Clarity around what “great” looks like
We’re rolling out expectations that define success in our context: clear, supportive, and actionable.
A Growth Template with soul
Think of it like a personal compass: not just goals and metrics, but a place to reflect, name what matters, and grow intentionally.
Real growth paths, not just levels
From changing teams to work in new domains, to switching roles from IC to Lead, we support nonlinear, personalized growth journeys.

What we believe

Culture isn’t what you say. It’s what you practice. Here are the DesignEx principles we try to live by every day:

💛 Empathy in action
We create spaces where everyone’s voice is heard, valued, and respected. Kindness isn’t soft, it’s foundational.

🔎 Curious & grounded
We ask good questions, gathering data and stories before jumping to solutions. Insight first, then action.

🎯 Strategic by design
Everything we build—tools, rituals, templates—connects craft to business goals. We’re here to move the needle, by intention.

🤝 Together, on purpose
Collaboration is our superpower. We bring people together around shared goals, shared knowledge, and shared momentum.

Where we’re headed

2025 is a big year for design at Automattic. We’re centralizing and shifting toward more shared practices that boost our scale and ambitions to design an open web. Some of our current focus areas:

Elevating design’s role in product development.
Increasing feedback loops with our users.
Exploring how AI can positively influence both the products we build and how we build them.
Growing and governing our open-source design system.
Building a shared language and definition around design quality.

We’ll be blogging more as we go, so…