Leading a content design team: A conversation with Roxanna Font

Roxanna Font is a writer and design leader based in San Francisco. She currently leads the Services UX Writing team at Apple, and previously led teams at Cruise and Dropbox. Before transitioning into tech at Ancestry, she was a book and magazine editor for many years.

Queenie: Can you tell me about your journey to content design? How did you discover this field? 

Roxanna: Like a lot of content designers, my path to content design wasn’t at all straightforward. 

When I was in college, content design wasn’t even a blip on the radar. User experience, in general, was just starting to get its sea legs. Of course, it always kind of existed, but as a profession—and as something that you could pursue or even study—it wasn't really big. 

I actually started in publishing. I was an editor for a long time, working in magazines and books. I loved my career as an editor. I was probably in publishing for around 14-15 years and then, at some point, I realized that I wanted to transition into the digital space. I didn't know exactly what type of digital space I wanted to move into, but I knew that that was on the horizon for me. 

I’d had some design experience during my time as an editor. One of my first jobs, in a small publishing house, included graphic design and designing book jackets. So I definitely had some design fundamentals under my belt, but language was still my primary mode of design and communication. I also got a Masters in poetry, so writing was really core to the way that I operated. 

When I started looking at different options in the digital space, I thought about everything from content marketing to more design-centric disciplines. As it turns out, I happened to interview at Ancestry for this role that was really interesting. Ancestry is all about genealogy and tracing your roots; they have a whole DNA product. I'd done a lot of work on my own family history, so the product itself was intriguing to me. And then the interview was based on UX!

I interviewed with two people and they were like, “OK, Roxy, what would you change on this homepage to make it more enticing?” I just used my intuition and started talking about all the different things that I thought would make it more interesting and clear, and would get website visitors to take the next action. So, in a way, I was organically talking about the fundamentals of UX that help guide and get people to the right place at the right time. I worked at Ancestry for 3.5 years and I really earned my stripes in UX fundamentals at that point. 

Queenie: Thanks for walking me through your foray into UX. Can you name some of the skills you brought with you as you made this transition from publishing to UX? And which ones you had to intentionally develop as you advanced in your career?

Roxanna: I’m very passionate about helping people who are “outside” of tech come into tech because there's so much opportunity here and there are so many skills that do translate. I would say 80%, at least, of what I do as a content designer draws on skills that I utilized as an editor.

I often describe a novel as a quintessential end-to-end experience. As an editor, you’re looking at the big picture and then pulling back and saying: 'What's the arc of this whole narrative here? What’s the story that we're trying to tell?' And then, as an editor, you also have to zoom in at the chapter level, right? You’re thinking: 'Should we reorder the chapters here? Because that would make the progression clearer.' And you also go all the way down to the words and ask: 'Wait, what’s the tone that we’re trying to get at here?' That to me is the work of UX writing. So I can say that I already had all of those skills coming into my work as a UX writer. 

What I had to do was reframe that work in a tech context. When I was working on books and magazines, I had a hard product. I had something I could hold in my hands. Going into the digital space, it's all very ephemeral. So I had to change my definition of a product.

I also had to expand my understanding of interaction design and UX and wrap my head around what success looked like in a digital space.

I think those were some of the key things I had to learn as I made that transition. I learned a lot of it on the job. I did some research and read up on things too. To me, so much of UX and UX writing—especially if you’re somebody who’s deeply embedded in the world of language—is about leaning into your intuition and really listening to the things that are going to speak to you. At the end of the day, we’re all users of digital products, and as users we innately have skills to understand what does and doesn't work.

Queenie: That’s beautiful. I love the way you described a novel as an end-to-end experience. As both a creative writer and a content designer, that really resonates.

Sticking with this same topic about your career, I’m curious: you started as an IC and then progressed to Head of Content Design at Cruise and now you’re a Head of UX Writing at Apple. How intentional were you in charting your career trajectory? What advice would you have for someone who wants a career graph like yours?

Roxanna: As an editor, I had some leadership experience. And in different parts of my life, in different phases of my life, I have been a leader. So I knew that that was something that I gravitated towards. 

But I didn't set out to do it, to be honest. It wasn't like as soon as I was at Ancestry, I was thinking to myself: 'I want to head a UX team.' When I went to Dropbox, I was the fourth UX writer there at the time, so the team was still very small. I came to Dropbox and the only thing I was thinking is that I was so excited to learn from my peers. I was working with these amazing individuals in the content and UX writing space, John Saito and Chris Baty among them—just great teachers and people. Eventually, as the team grew, Chris knew we needed to have another manager and that that was something that I was interested in, so we talked about it. I started by leading, at first, a small team for Dropbox Paper. Then, eventually, I became the head of the team.

I will say that it’s a bit scary whenever you take that step into a whole new space—it was, for me too, with each of these phases. But I also learned so many things! I feel like what was motivating to me in that moment too was that now I had the opportunity to not just grow an individual, but the opportunity to grow an entire team! I had the opportunity to create visibility for a discipline and to influence the culture of a design organization, which was super exciting to me.

This is what I always advise somebody who's trying to decide between IC work and management: You have to love people, you have to love to grow people, and you have to find motivation and energy from their success. I think that when we think of leadership, sometimes we think: 'Oh, I'm going to lead the team into this new space.' And of course, that happens too—there are different types of leaders out there. There are people who approach leadership very differently than I do. That's part of the joy of diversity, right? People have different styles, people are going to be resonating with different folks. For me, though, leadership still, at its core, is about people. 

So yeah, that gives you a little bit of my trajectory into leadership.

Was it intentional? I talk a lot about curiosity. It's one of my core leadership principles—to really listen to your curiosity at a given time. It's literally guided each of my career moves and lots of choices in my life.

Like I said earlier, UX writing or content design wasn't a thing when I was in college. And so, if I hadn't listened to the curiosity of that first moment at Ancestry and said: 'Wow, this is really lighting me up,' then I might never have continued to pursue it and be where I am today. Similarly, I think my pathway to management and ultimately to leading teams was very much about listening to that voice of curiosity again and saying: 'Yeah, this is what’s speaking to me right now. This is really something that’s energizing me.' That to me was more important than any sort of goalpost I could have set out for myself. 

I know many wonderful, successful people who have very specific, intentional ways in which they pursue success, but my method is a very organic, curiosity-led one.

Queenie: I love that—the idea of asking: 'What’s lighting me up right now?'

I want to dig a little bit into what you said about creating more visibility for content design as a leader. This is a very broad question, so answer it as you will, but I'm curious: what were some of the tangible steps you took to accomplish that goal of increased visibility?

Roxanna: Great question. I think a good way to touch on this is to talk about how I ended up at Cruise. 

So, I was at Dropbox for almost 5 years. I love staying at places for a long time because I think that that's when you get to see the fruits of your labor, especially when it comes to things like impacting culture or making meaningful change in an organization. That stuff takes time, it’s never an overnight thing. And depending on how deep the culture is, you're not going to be able to make an adjustment alone, right? 

When I was looking for my next opportunity after Dropbox, one thing that was really important to me was: I wanted to make sure that content design had a seat at the design leadership table. That's not always the case in every organization, depending on the structure and the hierarchy, or rather, how important hierarchy is within an organization. But it was really important to me. I wanted to be seen as a partner to product designers, to researchers, to design ops, to PMs, to all the other functions that we collaborate with on a day-to-day basis. 

So I had conversations with different companies, different people. And eventually, I had a wonderful conversation with Anisha Jain, who eventually became the VP of Design at Cruise. She was really committed to that vision too, to making sure that content design is an equal partner. That really drew me to Cruise.

I will say that you absolutely need the advocacy from the top-down to have that visibility. It's very difficult to get that visibility if all you're doing is pushing bottom-up over and over. It's going to ultimately be quite frustrating. Part of what I’ve worked on is to create this partnership with senior leaders whenever I can—to build that advocacy at the top levels—because it's not a given that everybody understands the impact of content design. 

That's one of the hard things that I also hear a lot about—people not always understanding the impact of content design. The thing is, this is going to persist.

We're going to continue to have to advocate and speak the language of senior leaders in order to accomplish that piece. It's really important to be okay with continuing to have that elevator pitch for why content design is impactful, in order to help people understand it and see that vision. It's just not something that we can assume. 

Anyway, that's been my hope and intention. The way that I'll continue to lead teams is to do my work as a leader to build those connections at the top levels. And the work of the team is to continue to execute in a way that really fulfills the promises that I’m making and those intentions that I'm sharing with senior leadership. 

Queenie: That makes a lot of sense. In a way, you’ve already started to answer the next question I’m going to ask. Obviously a big part of your job is building those connections, doing that advocacy work, getting that sponsorship from senior leaders. Beyond that, or maybe including that, what does your day-to-day look like? 

Roxanna: I think partly why I'm so drawn to the discipline of content design—and especially my role as a leader in that space—is the range of skills you employ and things you have to do on a day-to-day basis. 

I would say that on a day-to-day basis, as a content design leader, so much of what’s required is balance—balancing organizational needs with individual needs, balancing short-term goals with long-term aspirations, balancing what your team wants to accomplish with business goals for the company at large. I believe that it's really important for content design leaders to hold space in both of these zones and be dynamic in their leadership. 

Some might call that dynamism “flexibility,” but I think it's also about being able to flex with whatever is thrown at you in a given moment. I might go into a one-on-one where I'm coaching somebody on my team and helping them think through how they might approach something on their project, and then immediately after, I might have to go into a meeting with design leads to talk about our goals for next year as a design organization. How do you hold both of those things and be really present in both of those rooms? I think that that’s the work of a content design leader—to stay present and be really thoughtful as you're bouncing back and forth between different things.

Queenie: Do you, as a content design leader, get the opportunity to get into the weeds of projects anymore?

Roxanna:

I love getting into the details. I also deeply trust the people on my team to execute. I believe so much in diversity when it comes to the way that I build teams. I don't expect somebody to be thinking or having the same ideas that I have. Some of the most exciting moments for me are when somebody blows me away with their novel approach to a particular problem, and I’m like: “Wow, I’d never have thought about it that way!”

That being said, when I came to Cruise, I was the first content designer there. I was building the team from scratch. I worked with Margot Merrill and her amazing agency Wordland, but we didn't have any IC content designers. So I was the IC and I was the head of the team. I’d do the IC work—getting in the room with product designers and researchers and all the fun stuff that we get to do as content designers—and then as I hired people, I would slowly hand off and say: “OK, here you go. I've established these foundations. This is now your baby. Go, have fun with it, run with it, and lead the way forward.” 

But long answer short: Yes! I think for a leader who's establishing the function, there's absolutely an expectation that you're going to be doing a fair amount of IC work. 

Whether or not content design leaders do IC work really varies because it’s so specific to the product, the company, and the size of the team that you have. One leader might have to lead an initiative for something that spans the entire scope of the content design voice and tone, for example, while another may have people on their team that are leading that work. It really depends. 

Queenie: I want to stop here and linger with the fact that you built the team at Cruise from the ground up. Wow! What was that experience like? What do you look for when you're building your team? What advice do you have for somebody who's in a similar place, starting out as a single content designer and slowly growing their team? 

Roxanna:

One thing I’ll say is that it's really important to spend some time listening and thinking through what an organization needs. When you're building a team, it's not a one-size-fits-all situation at all. It largely depends on what a particular product will need to be successful and what the company is ready for.

I think that one of the most important things in building a team is being super thoughtful about hiring. That seems obvious, but what I mean is: Every person that you hire on a team is going to impact the vibe, the culture, the skill level of the team. Every person you hire will inevitably change the dynamics on that team. 

As I was building the team at Cruise, it was such an exciting thing to know that those early hires that came on were going to be my partners. Especially at the beginning, I was looking for people who were not just specialists in one particular type of thing, but could flex and do a whole range of things. 

Kendal Sparks was the first person I hired. He was amazing and able to flex all the way from the top-of-funnel marketing tone stuff into deep support experience-type UI and UX. The second person I hired was Angela Gorden, who I'd worked with at Dropbox as well. She was highly gifted in the new user experience—education—space. When I was thinking about the product space at Cruise, I was constantly asking: “What do we really need?” We needed to help people understand and trust the service. It's a self-driving car company, after all! 

Having these two individuals who could flex in lots of different directions as my first hires was important. It was also important for these first hires to be people who were already deeply skilled and senior. Again, when you're hiring a team, those early hires are your partners. You're going to have a lot to do as a leader, and you want to have some senior folks around who can also flex and move with you in those initiating moments, those initiating conversations with people. 

So I think my main advice here is: Take your time, be really thoughtful about the hires that you make, spend a lot of time listening to other leaders at the company and understanding the product space and product needs in terms of content design. And then move forward with a lot of intention. Also be open to changing based on what you learn.

Cruise was an incredibly dynamic, exciting place to be at; it was really a frontier space for design and as such, we were learning every single day. 

Queenie: Great advice. Do you also have any advice for people stepping into a people management role for the first time? What have your biggest lessons been as a content design leader?

Roxanna: I hope I don’t embarrass John Saito too much by this... When I became a manager at Dropbox, Chris Baty told me I was going to be managing John. John did a lot of those initial blog posts about UX writing that put the particulars of the craft on the map. I was like: “What? I'm going to be managing John Saito? That makes no sense.” He was more senior than me! 

At that point, my idea of leadership was that as a leader, you have to know more than your reports. Guess what? You don't.

That was one of the biggest learnings I had as a leader, and now I’m really passionate about leading people who are more senior than me. I actually think that's probably one of the most underutilized approaches in organizations. It can be such a beneficial, powerful thing for both people in that dynamic. 

I think of myself as a service leader—I'm in service to the people that I lead. They aren’t in service to me, as their manager. I might be leading the team, but my job, as a leader—as I was saying at the beginning of our conversation—is to help the people on my team grow, to help them succeed in their career journeys. And guess what? If they're succeeding, that means that the team is succeeding. That means that the product is succeeding. That means that the company is succeeding. And so, I really do believe that happy people make amazing products! By “happy,” I mean people who are fulfilled and engaged with the work that they’re doing.

I think that was one of the biggest lessons for me as I was coming up the ranks of management in the world of design. 

I think the advice that I would give to others freshly stepping into a management role is, again, to spend a lot of time listening to people. Understand the individual needs and motivations of the people that you're managing. 

It can be hard to draw boundaries at a certain point because you get so deeply invested in the careers of the people that you're managing. But then, as your team grows, or as you start managing more people, part of the work in growing as a manager is figuring out how to strike a balance. Again, that word “balance” that I used earlier on—so much of leadership is about balance. 

Really, though—spend a lot of time listening, be thoughtful in the way that you’re shepherding and helping the people on your team grow, and just know that it's also okay for you to have missteps as a leader. It's okay for you to be vulnerable as a leader too, to not always make the right choices. It's okay to show up as a whole person as a leader. I think that's the other thing: sometimes, as leaders, we feel like we can't really show that we’re struggling in a certain moment. 

During COVID, when I was leading the Dropbox team, those were really hard times for everybody. As leaders, many of us were struggling ourselves, but we really wanted to be there for our teams. Honestly, I think that those were some of the strongest bonding times with my team because we were all showing up as our authentic selves and really trying to navigate the unknown together. 

Authenticity is another one of my leadership values. All that really means is that you show up as yourself, just as you're asking the people on your team to do. Sometimes that means being vulnerable in moments that are difficult. That, to me, shows strength as a leader. 

Queenie: I love that. All of that. I was particularly taken by your account of leading people who are more senior than you. That's something that I’ve rarely heard people talk about. Love to hear how it became such a beautiful give and take, where you learned so much and could also help them grow in the ways that they wanted to. 

Roxanna: Absolutely!

So much of leadership is just conversation. It's just about being a reflector and helping people make the discoveries that are already inside of them.

John is now working as a product designer. He ended up making that transition when we were at Dropbox, and this next step became clearer through our career conversations, from talking through the things that he was really excited to do. But he already knew all those things himself. I was there just to be a reflector to him and to do what I could to help shepherd some of the next steps. 

Queenie: Let’s talk about career trajectories. What kinds of career paths have you seen content designers take as they grow in their career? What are the possible ways that people can grow after they've become a content design leader?

Roxanna: I like this question a lot. 

Sometimes movement in life is not an upward trajectory. Often, we think about success as moving up: becoming the head of a design team or the head of a product. Of course, it's a very personal thing and it can mean that, but for me, growth isn’t always upward. I really try to stay open to where my curiosity is leading me. I ask myself: 'What's pulling at my attention? What’s lighting me up?'

As an example, I’m going to take this back to before I was a content designer, to when I was an editor. I wore all the hats in editing: I designed book jackets; I was writing press releases and doing publicist-type things for the publisher; I did acquisitions; I did developmental editing, copy editing, proofreading. I was a managing editor for a long time, doing production management—managing vendors’ and freelancers’ schedules. And then, at a certain point, I transitioned to become an editor-at-large. And I remember I had a friend who said: “Roxy just demoted herself. She went from being a Managing Editor to an Editor-at-Large.” I said: “Why do you see that as a demotion?” For me, I feel like it was the next thing that I wanted to be doing. It made a lot of sense for me, at that time, to move in that way!

I would say the same thing about being a content design leader who leads a team. I get a lot of joy now from leading teams. Systems light me up. I love building coherence and culture. And those are things that are so fundamental to the work that you do as a content design leader. I love that part of my job! 

I think at every stage, when I've gone from one job to another, I ask myself that question: “Do I want to keep leading?” I asked myself that question when I left Dropbox. I wondered whether I should move into a principal-type IC role or whether I should keep leading. And to decide on that, I came back to: What do I love doing? I love growing people. I love building systems and infrastructure for teams. I love helping teams optimize their impact within an organization. Those are things that you do as a leader! So it made sense for me to keep being a content design leader.

That being said, I've seen many people go from leadership to IC work. Because they ask themselves that critical question and respond in a different way than I did. That’s a possible path too. 

People can lead multidisciplinary design teams too. A lot of senior content design leaders end up leading teams that span product design, content design, and even research. That's a fair trajectory as well. 

And then there's all sorts of pivots that content designers and content design leaders can make because our discipline is so multifaceted! Content designers have such a range of skills that we can flex in so many directions. We can go deeper into the world of research, the world of interaction design and product design, or even product management if that's the thing that one’s really excited about. 

I think it's hard to say that there's only one pathway forward for somebody in a content design leadership role. There are so many pathways out there! 

Queenie: I love that amoebic way of thinking—that we can grow our tentacles in all these different directions if we so choose.

Roxanna: Yes absolutely! I think in those very first moments, when you're getting into UX writing or content design, you already start to see the things that you love about the discipline. Some people go really deep in one particular area or another. Others remain in that generalist space where they can flex across skill sets. Those are two different types of content designers too. So when you talk about leaders, again, there are so many different kinds of leaders who are going to spike in one area or another!

Queenie: My last question to you grows out of recent tech developments like GenAI and then also the current macroeconomic climate. Taking all this into account, what do you think is the future of content design?

Roxanna: That’s a hard one. To be honest, I don't know what the future of content design is. What I do know is that it's really imperative that, as content designers, we continue to highlight the things that make us unique and impactful within an organization and that we be open and flexible to applying our skills in different ways.

I think no matter what industry you're talking about, there are always going to be changes. The world of publishing is a great example of how many revolutions can come along—all the way back from the way that books were originally printed to printing on demand. A lot of these things were scary for people in the industry, and a lot of times people thought: “Oh no, it's going to eliminate all these jobs.” Not to say that some of that concern wasn’t valid… 

However, with every revolution, there’s an opportunity to find a new place for yourself. There's a new sort of job and skill set to explore. And I think it's important for us to stay open.

I know that a lot of people, especially with GenAI, are deepening their skills in prompt engineering. I think that's smart. It's important to understand that space. 

I think as content designers, it's also important for us to understand how others might be looking at our discipline. So, it's not so much about us predicting what's going to happen to content design, but rather thinking about how a business leader might be looking at this technology as it applies to our work. Given that, how do we continue to embrace the things that make us incredibly valuable as UX writers? How do we highlight the very human aspects of our work that can't be replicated by automation? 

All this to say: I really don't know what the future is. I hesitate to make any predictions, but I can't wait to see what the future brings, and I'm hoping to stay open, flexible, and adaptive to meet it when it comes.