Working at Atlassian

A few weeks ago, Atlassian held our annual user conference in Amsterdam: Team ‘26 EU. After a quick stint in Paris and a rejuvenating design retreat, I’m en route to Sydney for work. I’ve been at the Sydney-based teamwork company for 2.5 years, and the top question asked amongst my peers is, “Why did you join Atlassian?”

It’s a tale of two stories: the perception and the aspiration. The perception is a mix of unfamiliarity, and I hear mixed sentiments. Why would I go work on Jira? The UX is terrible. Atlassian is where aquisitions go to die. Don’t you want to work at OpenAI or Anthropic? Are you simply resting and vesting at this point in your career?

The answer is none of the above.

I’ll tell you exactly why I work at a company more than twenty years old, in the midst of an alleged SaaSpocalypse. I’ll share what mattered to me when choosing a company, with the hope that it’ll help you think through your own next move.

A new experience layer for AI

During the summer of 2024, my original plan after leaving Replit was to take a break; something I always say after leaving a company and never doing it. I pondered moving away from design and finally moving into venture capital full-time. However, Atlassian was looking for a Head of Design for AI at the time. The landscape was different from now. Much of the conversation and attention was around chatbots and RAG. Agents was an early discussed concept.

I deliberately didn’t want to join a model company. First, their teams are stacked with talent and I’m not sure what value I’d add at that point. What was more interesting to me is finding a space where AI could fundamentally change things for the positive.

Atlassian’s focus on teamwork, collaboration, and workflows was exactly that. What do you do with all that capability? How does it change the way someone plans a project, makes a decision, or works with a team? Those felt like design questions worth spending my time on.

Creating an AI layer on top of the data, context, and applications was a very interesting problem space to me; leapfrogging instead of catching up.

Re-imagining the future of teamwork

I didn’t join Atlassian because enterprise software was a safe place to hide. I joined because it felt like an area that would be deeply disrupted, creating an opportunity to build something different. The SaaSpocalypse is shorthand for the fear that AI will undermine the software businesses we’ve spent decades building. If an agent can do the work, what happens to the application people used to do it in? That’s a real question. But generating software doesn’t automatically solve the problem of coordinating a team. People still need to understand what’s happening, who’s responsible, and which decisions need their attention. I’m interested in designing for that.

The people

Aside from my time at HTC, Atlassian is the most global company I’ve worked for. I’ve had the pleasure of visiting our teams in Sydney, Melbourne, Bangalore, Gdansk, New York, and San Francisco. We also have teammates working remotely across the world. It’s a diverse group of people I feel lucky to work with. When you’re building tools for teams around the world, it helps to have different perspectives within your own.

Beyond being nice and thoughtful, the people here keep giving me reasons to be optimistic about what we can make. The talent density is growing. We still have a lot of work to do, but the opportunity to learn from the people around me is a big part of why I stay. At this point in my career, I want to work with people who challenge my thinking and care about the quality of what we ship.

Finally, I wanted to be somewhere founder-led. For most of my career, I’ve worked with founders who are also the CEO. That’s a personal preference, not a rule for everyone. Founder Mode is a vibe, for sure. People might complain about how founders push and get involved in every detail. To me, that involvement shows they still care. What I say when people complain about working for founder CEOs is, if you don’t like working for a CEO who cares, just wait until you work for one who doesn’t.

Atlassian Design

It may be obvious to say I work at Atlassian for design. But as I mentioned, there was a point when I considered moving away from it. The opportunity to make an impact through design here was too great to turn down. Mike, our CEO, cares deeply about design and the details. There was also the opportunity to work with Charlie Sutton, Atlassian’s Chief Design Officer, someone I’ve known for years and hoped to team up with someday. Now it’s real.

With its range of products, locations, and skill sets, Atlassian Design feels like a built-in design community. We have designers writing Swift code for mobile, exploring agentic project management in Jira, designing multimodal documents in Confluence, and working through complex enterprise security problems. There are so many different kinds of craft to learn from. A designer thinking about how an agent asks for permission has something to learn from a designer working on security. That breadth is part of the appeal of working at a company this size.

Finally, I believe we’re stacking the talent here. There were already some amazing designers here, but it since I joined we’ve added people I’ve dreamed of working with in my career.

Team Anywhere

While many companies are returning to the office, Atlassian continues to operate distributed-first through Team Anywhere. Though I’ve worked remotely for more than ten years of my career, my personal preference is working in an office. I’m glad the company has offices around the world, including the San Francisco office I go to most often, with a new Sydney headquarters on the way—Atlassian Central. Having that choice matters to me. I can enjoy being in an office without expecting everyone else to work the same way.

For me, the more interesting question is how we work together across those settings. Atlassian has multiple modes of asynchronous and synchronous communication: Looms and Zooms. A recorded walkthrough gives someone in another time zone a way to catch up without another meeting. A live conversation can help when a decision needs discussion. The design problem is choosing the right mode for the work, then making sure people can contribute wherever they are.

Meaningful problems at scale

Re-imagining Jira for the agentic era is one of the most consequential design opportunities I’ve had. The frustrations people bring up about Jira are part of the work to take seriously. A tool can be essential to a team and still ask too much of the people using it. When I led Jira Design in the interim, I viewed it as an honor. There is a lot to improve on the experience, but what’s most important is customers rely on it every day. The opportunity ahead is to work together with them to find a new way of working and design the high quality experiences they need.

The company started by helping people track software work. Now there’s an immensely exciting opportunity to figure out how people and agents work together. When an agent takes on a task, how do you know it understood the goal? How do you review what it did, or step in when it’s heading in the wrong direction? These questions affect the whole team’s work. At Atlassian’s scale, even a small improvement in clarity can matter across a lot of projects. The hard part is introducing new ways of working while respecting the teams who depend on the product today.

Reflections

I feel like the journey is only beginning at Atlassian. That doesn’t mean the company is guaranteed to get this transition right. There are existing products to improve, customers depending on them, and new expectations forming quickly. That’s a lot to take on. It’s also why the work feels worth doing.

If you’re thinking about your next role, reflect on these questions:

What are you optimizing for?
What kinds of people do you want to work with every day?
How does the size of a company influence the experience you want?
What type of impact are you looking to make at this point in your career?

When it comes to my career, I try not to overthink it. My guiding question is whether I’m moving toward work I genuinely want to do. The answer can change over time. Earlier in my career, I wanted the experience of building at an early-stage company. Today, I’m drawn to the opportunity to rethink tools that teams already depend on, alongside people I want to learn from. That’s what I’m optimizing for now.

If you want a solved problem, this probably isn’t it. If you want to help define how people and agents work together, that’s the work in front of us.

P.S. We’re hiring for a few roles if you’re interested in working at Atlassian:

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