In the ever-evolving world of tech, few journeys are as compelling—or as human—as that of Diana, Head of Design at GitHub. Her story isn’t just about climbing the corporate ladder; it’s a startup story in the truest sense: one of self-reinvention, curiosity, and the relentless pursuit of building things that matter. From a humble apprenticeship in a UK print shop to leading design for one of the world’s most influential developer platforms, Diana’s path offers powerful lessons for designers, founders, and creators navigating the AI revolution.
This is not just a career retrospective—it’s a masterclass in adaptability, empathy, and the quiet courage to bet on yourself when the world says “print is dead.”
The Accidental Designer: Where It All Began
Diana never set out to become a designer. Growing up in the UK, she didn’t even know that web or graphic design could be a legitimate career. Like many creative minds before her, she stumbled into her calling almost by accident—through an apprenticeship at a local design and print shop.
There, she discovered something magical: the perfect fusion of technical precision and artistic expression. “It was both a bit technical as well as creative,” she recalls. “The perfect marrying of the things I was interested in.”
This duality would become the throughline of her entire career. In an industry often divided between “creatives” and “coders,” Diana refused to choose. She leaned into both—and that decision would change everything.
Crossing Continents: A Leap of Faith to Australia
By her early 20s, Diana felt the walls closing in. The UK was entering a recession, and the print industry—once stable—was crumbling under the digital tide. “A lot of people were saying, ‘Print is dead. The web’s going to take over,’” she remembers.
Rather than wait for opportunities to vanish, she bought a one-way ticket to Australia. No job lined up. No safety net. Just a backpack, a portfolio, and the belief that she could rebuild her life somewhere new.
It was a bold move—but it paid off. She landed a design role and spent the next 7–8 years honing her craft in Sydney’s vibrant creative scene. Yet even as she thrived, a quiet restlessness grew. She wanted more than just client work. She wanted to build products, not just mockups.
Her turning point came during a hackathon.
The GitHub Epiphany: When Designers Speak Code
At the hackathon, engineers were collaborating on GitHub—a platform Diana had never used. When they invited her to join, saying, “You know a bit of front-end development, so you should be in the same place we’re working,” something clicked.
For the first time, she saw design not as a siloed discipline, but as a collaborative act—one that happened alongside engineers, in real time, in shared repositories. She started uploading her personal projects to GitHub, experimenting with Jekyll (GitHub’s static site generator), and reveling in the thrill of shipping real code, not just static images.
“There’s something exciting about being able to make the thing you have in your head… and put it out there on the internet where other people can use it,” she says. “That feels so much more powerful than just making a picture of something.”
This mindset shift—from visualizer to builder—was her secret weapon.
The Call from GitHub: A Dream Realized
Years later, an email arrived from Mark Otto, the creator of Bootstrap and a legend in the design systems world. He asked: Would you be interested in GitHub?
To Diana, it felt surreal. “Mark Otto was a bit of a celebrity to me,” she admits. But beyond the star power, she recognized a deeper alignment: GitHub wasn’t just a tool—it was a philosophy. A place where collaboration, open source, and craftsmanship converged.
And let’s not forget the Octocat—GitHub’s beloved mascot. Diana had spent late nights illustrating her own versions of the Octocat just for fun, captivated by its quirky charm. “I had an obsession with GitHub’s brand,” she laughs.
When she joined GitHub nearly nine years ago, it wasn’t just a job—it was a homecoming.
Building Primer: The Design System That Bridges Teams
One of Diana’s first major contributions was transforming Primer, GitHub’s internal CSS framework, into a full-fledged design system.
But this wasn’t just about aesthetics. Primer became a shared language between designers and developers—a common vocabulary that reduced friction, accelerated development, and ensured consistency across GitHub’s sprawling product ecosystem.
“We wanted to make it easier for people to use the design system than not to,” Diana explains. “If you’re spending less time recreating the same button or modal, you can focus on solving bigger problems.”
She led a grassroots team of passionate contributors, prioritizing high-impact improvements and winning over skeptics by demonstrating value—not enforcing rules. Her philosophy? Constraints fuel creativity, not stifle it.
“If you’re an artist, you don’t mix every color from scratch. You have your paints ready. The same goes for design systems.”
The Dark Mode Dilemma: Designing in the Dark (Without Feedback)
Perhaps Diana’s most memorable project was launching GitHub’s Dark Mode in 2020—a feature users had begged for years.
But there was a catch: GitHub wanted to unveil it as a surprise at their annual conference. That meant no user testing. No beta feedback. Just pure intuition, research, and guts.
The team scoured GitHub itself—analyzing user-created themes, browser extensions, and custom CSS overrides—to understand what “dark” really meant to developers. They discovered a spectrum: some preferred near-black contrast; others favored softer, “dimmed” palettes.
The solution? Ship a balanced default—dark enough to feel immersive, but not so stark it caused eye strain—while building a system flexible enough to support future variants.
The risk paid off. Years later, the default dark theme remains the most popular, with the “dimmed” option used by 20% of users. “That told us we got it right,” Diana says. “We solved a real problem—and did it with care.”
Design in the Age of AI: Empathy Is the New Superpower
Today, as generative AI reshapes every corner of tech, Diana sees both opportunity and responsibility.
“New technologies come out all the time,” she notes. “Right now, it’s AI. But the core skills of a designer remain essential.”
She emphasizes three timeless pillars:
- Empathy – Understanding real user needs beneath the noise.
- Storytelling – Communicating ideas clearly and compellingly.
- Problem-solving – Navigating ambiguity to create elegant solutions.
And crucially, she urges designers to get comfortable with code. “You more or less have to use the same tools engineers do,” she insists. “Being fluent in the language of development gives you a leg up—especially when designing AI experiences, where the boundary between interface and intelligence is blurring.”
AI won’t replace designers—but designers who embrace AI will replace those who don’t.
What Makes a Great Experience? It’s Not About Output—It’s About Impact
For Diana, success isn’t measured in shipped features, but in human outcomes.
“Did it solve a problem? Did it make someone’s workflow better? Do I feel proud of what we shipped—and does it represent GitHub well?”
This outcome-focused mindset is vital for startups and scale-ups alike. Too many teams obsess over output (features shipped, hours worked) while ignoring impact (problems solved, joy created).
Her advice to founders? Start with the ‘why.’ Clarify the outcome you seek before writing a single line of code or sketching a wireframe.
And if you’re a non-technical founder? Tools like Lovable—an AI-powered platform that builds full-stack apps from plain English—can help you prototype and launch without waiting for engineers. (Diana’s own team at EO is using it to build their new EO School platform.)
But even with AI, the human touch remains irreplaceable. “The fun of tech is that there’s always something new to learn,” she says. “That’s not going away.”
Lessons from a Designer Who Built Her Own Path
Diana’s startup story isn’t about venture capital or overnight success. It’s about:
- Curiosity over credentials – She learned by doing, not by pedigree.
- Adaptability over perfection – She embraced change when print died and the web rose.
- Collaboration over ego – She sat with engineers, spoke their language, and built bridges.
- Brand love as fuel – Her passion for GitHub’s Octocat wasn’t quirky—it was strategic alignment.
For aspiring designers and founders, her journey proves that your background doesn’t define your future. Whether you’re in a print shop in Manchester or a co-working space in Tromsø, Norway (yes, cold-weather lovers, the north is calling!), what matters is your willingness to build, ship, and learn.
Final Thoughts: Meet the Moment
“Good design is about meeting the moment,” Diana says. And right now, the moment is defined by AI, remote collaboration, and the democratization of software creation.
But at its core, design remains a human discipline. It’s about listening. Understanding. Solving real problems for real people.
As GitHub’s Head of Design, Diana doesn’t just shape interfaces—she shapes culture. And her story reminds us that the best products aren’t built in isolation. They’re built by hybrid thinkers who code, care, and dare to ship.
So whether you’re sketching your first wireframe or pitching your startup idea to investors, remember Diana’s mantra:
Embrace change. Build with empathy. And never stop shipping.
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