Episode 19: Karen Cross, Atlassian - Building a Content Design Team

May 7, 2019

Karen Cross is head of content design at Atlassian, an Australian-based company known for their suite of software development and collaboration tools like Trello and Jira. Karen’s work to build a centralized content design team at Atlassian has unified their various product teams and finally brought writers and designers working together. The ultimate goal? More efficiency and better experiences for their customers. In this episode, Karen describes some of the tactics she’s used to build this new team, and some of the challenges she’s overcome along the way.

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About this week’s guest

Karen Cross

Karen Cross is the head of content design at Atlassian—makers of Jira, Trello, Bitbucket, and Confluence—and is passionate about creating compelling content-driven experiences that solve real user problems. She holds a Master’s degree in human-computer interaction from Carnegie Mellon University. Her background spans user experience design, information architecture, conversational UIs, workflow analysis, and user research.

While working at companies such as lynda.com, Microsoft, and Adobe, she pushed the future of online education, enabled multimodal interaction between voice and touch input, drove formative research for Ford SYNC, and contributed to the research and design of Adobe Photoshop Elements. Currently at Atlassian, she manages a team that crafts content, UX writing, and long-form documentation to connect the dots for a customer from choosing what products they need, to learning and mastering those products in ways to best unleash the potential of their team.


Episode transcript

Kristina: Hello again. Welcome to The Content Strategy Podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at BrainTraffic.com.


Hey, friends. Welcome back. I am here today with Miss Karen Cross. Karen is the Head of Content Design at Atlassian. They are the folks behind Jira and Trello and Bitbucket and Confluence. Karen is passionate about creating compelling content-driven experiences that solve real user problems, one of my favorite things.

Karen holds a master’s degree in human-computer interaction from Carnegie Mellon University. Her background spans user experience design, information architecture, conversational UIs, workflow analysis, and user research, making her the perfect person to lead a content design practice. Karen, welcome to The Content Strategy Podcast.

Karen: It’s nice to meet you, Kristina. Looking forward to this conversation.

Kristina: I know. I’m really excited. We spoke briefly several weeks ago. Atlassian is a very wonderful sponsor of Confab this year and we appreciate your participation and support. So, while we were chatting about that, we also started talking about how you have been building out the content team and associated disciplines at Atlassian, and I said, “Oh, I know people who would be interested in that and they’re the people who listen to this podcast.” So thanks for agreeing to come on and chat.

Karen, tell me a little bit about your position at Atlassian. What is it that you do?

Karen: Absolutely. I am part of our product design org. And about four years ago, we brought in all of our formerly technical writers into our product design org. But about eight months ago, I unified all of our technical writers into our new team called content design. What I do is, basically, together we own all the words and all the information that our customers use inside our products and across our products to use them more effectively.

Kristina: That’s pretty amazing because I think that a lot of product development companies, the tech writers or the UI writers or the UX writers or whatever it is that they’re called, the folks who are responsible for the words, sort of sit with the different products and report up through different product managers. Whose idea was it to bring these folks together? Whose sponsorship did you need? And tell me a little bit about the process of how that unfolded.

Karen: Absolutely. In terms of the process, I was part of the original conversation to bring our writers into our design org about four year ago. And the main reason is that we saw, no pun intended, the writing on the wall. And we saw that increased importance of the copy inside our products to help and support across our products as we move forward.

And we’re like technical writers were originally part of our quality assurance group. They still have a critical part in that side of our journeys. But we really see this need to do proactive content design and not just reactive, not just cleaning up after poor decisions or sometimes the best compromise we could make in shipping something, but actually being in the process from the get-go.

We brought everyone in but we did have them, just as you said, independently reporting to different product design structures. It was a step forward, but it was just a step. And then, over the past couple years, we’ve seen both the benefits of that start to play out, so we’ve started to see designers and writers become more and more integrated in process, collaborating together. But we also saw challenges.

And so, about eight months ago, I talked to my manager, our head of global design, a wonderful man named Jürgen Spangl. We talked about some of the things that we’d been hearing independently from all the writers across our design org. They had shared frustrations around career growth and development, about feeling like their needs and their voices, while being amplified by their particular product design managers, were just part of many different competing pressures that those heads of design had to deal with. And also, they felt like they were doing a lot of inefficient and frustrating experiences in terms of constantly trying to strive to catch up to what’s happening, to what our customers need. And so there’s a lot of inefficiencies as well.

So Jurgen came to me but then I jumped on it and said, “Hey, look, now is the time to actually mature and leap forward with our content experiences.” We both agreed it was and so we made it happen in a fairly short turnaround, about a month or two of conversation. I had unified all the team. I’d renamed the team into “content design.” I had shared internally my basic approach towards the organization and how I was going to approach the next six to 12 months for the team. And now I’m starting to approach my first full year moving into our fiscal year planning in July.

Kristina: And tell me what that looks like, when you say, “Here’s how I’m going to approach the unification of the team.” What does that mean?

Karen: Absolutely. So, this was an interesting case where I wanted to think about, okay, do I take really bold moves in unifying the team? And so, we did the same thing with our research team about 12 months prior. What our wonderful leader there did was, she was very bold. She had a very small team, so it was only about a dozen researchers scattered across each of our product spaces. And they were struggling in terms of having impact and being too reactive, and not being strategic. And so, she made a really bold choice. She’s like, “I’m going to pull them all out and do strategic research for the next 12 months.”

And so, when I was looking at content design, I’m like, “Well, I can be as bold as she was, but is that where we are in terms of our maturity, in terms of where our state of the union is for content design?” One of the big principles organizationally that I believe are around the role of content design and product. And I came up with three organizational principles.

The first was that I believe our current and future users need great content across journeys, not just moments. I believe, as part of that, we need to move away from simply just doing a doc or a piece of copy in one element, but instead think about the end-to-end journey for our customers. And I wanted to make sure that our team was organized to look across that journey.

The second thing, however, I realized that was different from our research team, was that in particular for content design, the product and domain expertise has been and will be, and will continue to be critical to crafting great experiences with content. This means that you can’t pull out a writer who’s been working on Jira and put them on Confluence and expect them to be successful. It’s a different set of audience. It’s different set of users and needs and problems.

Same thing. You can’t take someone who’s been deeply enmeshed in Bitbucket and then move them over to a very different product as well. We need to build and leverage on that product and domain expertise that they’ve been growing and establishing to actually be able to amplify their work and make it more effective for customers. And so, those were the first two organizational principles.

The third, the one I think I’ve made the least strides on so far but I’m hoping for fiscal year ’20, is that we need to value and invest in growing the specialized skills of UX writing, help content, and developer content.

Those three principles, the journeys, the product and domain expertise, and investing in growing the specialized skills of UX writing, help content, and developer content were my three organizational principles that led me towards a fairly matrix-structure of continuing to have the embedded content designers in each of our product fields, but still rolling up to me and starting to have that strategic and horizontal connection across the journey as well.

So I have those deep set of content designers in our tech products like Jira and Jira Family, and a different set that already focused on our more all-teams kinds of products, more generally used, like Confluence.

And then I have a different group that goes horizontally across the journeys with our platform and standards, as well as our buyer experience of getting people into our products effectively, delivering on the promises set by marketing, and then going deeper across into support and growth through mastery in our products.

Kristina: Oh my gosh, I have so many questions. That was amazing. Thank you. Okay. I’m interested to hear ... because what you’re describing is what a lot of folks I think have their eye on as maybe we need centralized content oversights, centralized content development, where all the content folks are operating from the same playbook and yet they go out and they sit with these different teams.

Are you able then to bring all of the content folks together as a team or feeling like they come home to one another from these different product teams? Are they still pretty split? I guess, tell me about what benefits you have seen about centralizing the content folks the way that you have.

Karen: Absolutely. Yeah. I do invest very heavily in community, so we do a couple things along that line. We do have quarterly town halls to share the outcomes and the major successes we’ve had, not just in helping our customers, but how we’ve approached those problems, what kind of relationship-building tactics we’ve found working with product managers or engineers or designers, or what kind of process improvements that we had. We had that quarterly town hall. That’s one of the elements.

We also have a regular fortnightly sparring since it’s Australian, so every two weeks is a fortnight. We spar every two weeks in terms of sharing some of the work that we’re doing, helping each other be more successful, helping each other see what kinds of questions are we forgetting to ask, what kinds of ideas might we have from a process or relationship perspective, to actually make it even better for our customers.

Third, we have a fortnightly asynchronous team meeting. And so, we use our internal Confluence instance to share what each of us as content design leaders are thinking about, what’s keeping us up at night. We also have embedded Trello board and our asynch team meetings where people share photos of their families, or their location, or their gardens when it’s winter in one part of the world and summer in another. Atlassian is a very Australian company and so we try to reflect that and incorporate that in a very inclusive community.

So we’ve had these kinds of knowledge shares that continue to happen, and I think that’s where we started to see a lot of the benefits from working as a unified team. And we’re also excited to have our very first Content Design Day when we go together in Sydney, Australia, in a couple weeks. We’re actually going to be talking about some of the shared problems and wins that we’ve had across the team, and how do we leverage each other and learn from each other.

Kristina: Are you the person who’s driving these, “Okay, now we’re going to do these fortnightly sparring, and now we’re going to do the town hall, and now we’re going to do this?” Is that you who’s driving those? Are you sponsoring those?

Karen: Yes. It’s me for a lot of it, but it’s actually my leadership team as well as from the ground up too. It’s a mix of all, and I do believe that you need both top-down and bottom-up changes in awareness of potential problems and solution spaces. So, for example, the fortnightly sparring was the brain child of some of my leadership team, including a wonderful man named Tony Starr, but a bunch of others as well, to kind of figure out how do we share across the globe? How do we actually help each other regardless of where we’re located?

The notion of having time in Sydney together and taking advantage of that ... I started by saying, “Hey, look, what do you think about taking advantage of the fact that we’re all going to be there for our annual overall design org event and do something for content?” So I had originally, say, a question that I sent to my team. And immediately a bunch of different folk raised their hand and said, “Awesome. That sounds cool. Can I run with it?” And of course my answer’s yes. From then, they’ve taken it into directions and ideas that I would never had come up with myself.

So it is, it’s a group effort. It needs to go from top-down, bottom-up. It needs all of us keeping our eyes open to what’s working and what’s not working and how might we make it better.

Kristina: Karen, how many people do you have on the content design team overall?

Karen: There are 61 of us right now.

Kristina: Oh, that is like a dream come true.

Karen: [laughs]

Kristina: How large is Atlassian overall?

Karen: Right now, I believe the official numbers are around 3,000.

Kristina: Okay. And where is everybody located? I mean, is it just kind of all over the world? Are people remote?

Karen: Absolutely. So, as I mentioned, we are an Australian company. While I’m based here in Bay Area, California, I’d say about two-thirds of the company is in Sydney, Australia. The remaining third is scattered across a couple of offices as well as remote. So I’d say we have a large contingent here in the Bay Area. We have two offices in San Francisco and Mountain View. We also have an office in Austin, Texas. We have offices with content designers in Gdańsk, Poland, and we’re slowly growing up a new office in Bengaluru, India.

In addition to that, we have a couple of folk that we’re bringing in now as remote, and we’re starting to mature as a company in embracing, What does it mean to be a remote company. How do you have teams that are fully remote? How do you set them up for success? So, yes, we’re basically all around the world, which has its own challenges as well.

Kristina: I think that what you need is a content strategy podcast host to go on site with all your locations and do individual interviews with people. What do you think?

Karen: I need that plan. It’s a lovely idea.

Kristina: Great. Yeah, I have a host in mind. When we started talking, you said you’ve realized some really amazing benefits from centralizing your content folks. Tell me about any challenges that you’ve faced. As much as organizations I know would like to say, “And now, we’re magically centralized, and now all our content problems have disappeared and all communications are way better,” of course that never happens. Tell me about some of the challenges that you’ve faced.

Karen: Absolutely. I’d say there are two main challenges. One is the individual challenge. As you sort of alluded to, as a content designer, if you’re embedded and sitting with, for example, the Jira team, you have almost tribal affiliation with the Jira team. But you are also a content designer by craft, and so you often have a tribal affiliation with your Jira content designers. And then you have a looser affiliation with just about 60 folk. And so, this can be hard for people. It’s like you can feel almost all of all ... a member of all teams, but also a member of none. Do you feel like you’re always an orphan in one group or another and you never quite know who are your people? And so, that feeling of “teammanship,” of how do you be part of a global community, be part of many teams in a way that makes you truly feel part of many teams and not an orphan step child of all those teams. So that personal and team challenge is one of the ones that we struggle with.

Second, as wonderful and grateful that I am that we have such a large team, we’re still not, in many ways, large enough. We struggle with over a dozen products that we support. We support end-to-end experience from getting people into our products effectively with onboarding and change boarding, with copy inside of our products, with support experiences outside of our products, with helping a growing community and setting up the right structure to help our communities start to have user-generated content. So I feel like we’re still spread really thin across all of those dozen products, across the many different systems that we have. And so, I think prioritization and how do we focus on the most impactful work, and forgive ourselves for not doing all the things all the time. That area of prioritization is something that we are still struggling with.

Kristina: Do you find that since people are reporting to you and are not necessarily being specifically managed by their product teams, do you find that they are better empowered to say, “This is best practice,” or “This is what I recommend,” or “This is my expert opinion?” and that they are better heard versus you or somebody that needs to fill words into the product and you’re going to do what I say? Do you know what I’m saying? That was very, very ill-put, but you get my point.

Karen: I totally get your point. I would argue that I haven’t seen or heard of enough success stories of, because we are now centralized, we are having bigger impact. Instead, what I’ve seen is that it continues to be very much a case of the particular investments we’ve had in relationships between the content designers and their designer counterparts and the product managers. There are many teams at Atlassian that I think are actually quite mature in terms of bringing content designers from project kickoffs and moving forward, and getting into a room together of a designer, a content designer, a product manager, and starting to riff and co-create experiences and craft them sometimes from content-first perspective, sometimes with simply thinking through where is the user coming from? Where do they need to go? How do we take all of our specializations and make it effective?

So we’ve had a lot of successes, but I wouldn’t argue that it’s necessarily argue that it’s due to the centralization. I think, thus far, has been due to that investment in relationships, the types of individuals, the way that those teams have worked. What I want to see as we start to move forward is how do we start to push that expertise in a way that’s not dictatorial of, “Listen to us because we’re the experts,” but instead is helping bringing people into our problem space, helping them be aware of what we’ve learned from the industry, from best practices, from how we might tackle some of the problems that we have through great content design.

And so that is something that I think we need to do more of as we move forward because I feel like the wins we’ve had on that side have not been due to the centralization, and I want to have more. I want to have some of those teams that have struggled start to have some successes as we move forward.

Kristina: So when you mentioned that you are able to come to the table to say, “Look, here are some of the skills and the insights that we’ve learned as best practices,” where are you turning for those skills in the industry?

Karen: Good question. In terms of what we’ve learned from the industry, I think the challenge there is we haven’t seen a lot of great examples. To me, this is just like when people ask me, what’s the best product design you’ve seen? And I always struggle because I see problems everywhere, and I see opportunities everywhere. I don’t see one company as a game changer. I don’t see one company as perfect. I see a lot of things I want to pick and choose and cherry-pick from to come up with a wonderful set of fantastic experiences. So, to me, on those cases, I’ve seen some good work obviously from Stripe, from Shopify. I’ve seen good work from Microsoft. I’ve seen good work from a lot of different companies in terms of how they’re approaching both product content strategy as well as how they unify that with marketing content strategy.

I still struggle with having a lot of it. One of the things that we’re trying to hire for right now is our very first principal content designer, and we really want to have a thought leader there. And we want to have someone who has rolled up their sleeves and dove into a similar problem space and starting to figure this out together and collaboratively, and having that impact. And we struggled with finding that person, honestly, because there just haven’t been people that are approaching it from a product perspective, from helping people use our products effectively, and the same kind of multi-product challenges that we have at Atlassian.

Kristina: Yeah. Interestingly, I’m hearing that same challenge from a lot of other product organizations. And I think that part of it is simply that the practice of content design, where, again, I think that folks call it product content strategy, the UX writers or UI writers is a term I’ve seen too, that these practices are really only recently being recognized as specific areas of specialty that are strategic contributors to the success of a product. And to your point, that content is something that needs to be treated strategically across the entire user journey and not just on this button here and in this user manual here, and in this sales copy over here.

I think that we will see, in the years to come, that level of expertise popping up more and more regularly. But right now it’s just a practice that is being built. And that’s why I was so excited to hear about the work that you’re doing, the paths that you are forging because I think that that in and of itself is the best practice that organizations can look to.

Karen: I agree. Honestly, it’s one of those cases where I’m just basically keeping my eyes and ears open, what can I learn from different teams and different companies? One of the things that we realized at Atlassian, and I think a lot of companies have realized, is that our customers, everyone’s users, experience a product as a journey. They don’t just come in and arrive out of nowhere and then try to do something. And so, how do we look across the end-to-end? And I think the realization that we’ve had from our content design org is we are that thread that weaves that connected human experience across the journey. We are the ones. We use our techniques and our practices and our information to help hold our customers’ hands and help them from where they start, wherever that is, to actually ideally getting value and feeling proud and confident of the work that they’re able to do.

Kristina: Karen, I really appreciate your taking the time to come and speak with me on The Content Strategy Podcast. Before we wrap up, tell me, as you look into the next years to come, tell me what is most exciting to you. One of the things I think that you mentioned before that I know is exciting, motivating to you, is the idea that folks were feeling sort of stalled in career growth and opportunities and now you have this opportunity to grow these folks beyond the work that they’re doing now and take on more leadership roles. I know that you’ve mentioned seeing best practices and how inspiring those are.

For you, in your career and in your position, what are you really looking towards in the next couple of years that’s exciting for you?

Karen: Oh, so many things. The nice thing for me is that I do think this might take time, but I actually think that time is a really important aspect to doing a great outcome. And that it will shift and change our users and their maturity will change. But right now I think I’m excited by many things. One is, can we take the original foundation that we formed? We have a public facing set of components and standards at our design.atlassian.com site. Can we take that and build on that with stronger content or with stronger design principles? How do we better start to crack the hard challenge of scaling? And so, the scale problem is going to be fascinating. How do we improve the process as part of the scaling problem?

And, to me, the other part is we are moving into a world where people have a range of deployment options. People have self-hosted products. They have a lot of work in the cloud. Things are changing every day. How do we help our customers navigate that change? How do we help them not feel scared or worried or in the dark about what they’ll have and what they’ll experience as they come in to work the next day as they try to work better in teams and deliver better impact for their own customers? So that change boarding and navigating to that change and fear and emotion that our customers go through is fascinating to me from an experience design and from a content design perspective.

Kristina: I am excited too. You are incredibly inspiring and I know that my listeners are going to feel the same way. It’s just you’re forging cool, new paths for writers and content strategists and content designers within Atlassian. And I hope that we can stay in touch so I can hear what great things are yet to come.

Karen: Sounds wonderful. Thank you so much, Kristina.

Kristina: Thank you, Karen.


You’ve been listening to The Content Strategy Podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at, of course, BrainTraffic.com. Thanks and we’ll see you next time.

About the podcast

The Content Strategy Podcast is a show for people who care about content. Join host Kristina Halvorson and guests for a show dedicated to the practice (and occasional art form) of content strategy. Listen in as they discuss hot topics in digital content and share their expert insight on making content work. Brought to you by Brain Traffic, the world’s leading content strategy agency.

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