Jenna Bilotta’s career spans design leadership at Google, Dropbox, and Spotify, as well as her current role as Head of Product – Frame.io at Adobe. Across these experiences, she’s developed a philosophy of building a career with intention — making conscious choices about opportunities, advocating for underrepresented groups, and finding balance between work and life.
In this interview, Jenna shares how she navigated the transition from design to product leadership, why she mentors others to “own their careers,” how she coaches leaders to build healthier organizations, and her take on the myths and realities of work-life balance — especially for new parents in tech.
Bringing a designer’s mindset to product
You spent the first 20 years of your career as a designer before moving into product leadership. Can you talk a little bit about what prompted that shift and how you approached it with intention rather than just following momentum?
That’s a great question and that’s something I talk to my teams about all the time. If you talk to anybody that's been on my teams for the last 10 years, you’ll hear them say I’m a broken record about being intentful about decision-making. I probably learned that lesson about 15 years too late in my career.
I’ve always been interested in design. As a kid, I thought I might want to be an architect because I loved designing spaces and thinking about how people moved through them. Then I realized the precision of architecture wasn’t for me and that people were messy. I became interested in software because it’s disposable — you can build and unbuild it quickly, and respond to changing human needs faster.
I studied design, earned a master’s in information design and HCI, and became fascinated with the psychology of how people interact with technology. I leaned into that super hard for like 15–20 years, moving into design leadership. The material beginning of my career was at Google, where I learned about designing for massive scale — creating common experiences accessible to people from all types of backgrounds.
How did that lead you toward product leadership?
Mid-career, I realized my inclinations in design projects had drifted more toward the problem statement rather than the solution. One day I woke up and thought, “Am I a product manager?” My time was more on the solution side than really getting crisp on the problem, and that felt dissatisfying. I wanted to solve big problems in big contexts.
Also, other people’s perception of design in software often had a much narrower aperture than mine. It became frustrating to work in environments where executives undervalued the breadth of design. In product, the aperture is naturally wider — you’re thinking about the problem, the context, the industry, the competitive set — so I moved in that direction.
Did the transition feel natural?
It was the most natural thing in the world. Sufficiently senior designers who do the full stack of design — from problem to solution and execution — think very much like excellent product managers. Early in your career, you might design a calendar widget. Then maybe a whole page, then an end-to-end feature, then a product, then a suite of products. Eventually, you’re thinking about the vertical the product sits in, adjacent industries, and customer needs. At that altitude, product and design are, for me, indistinguishable.
Very senior leaders in product, design, and engineering should be largely interchangeable outside of hard skills. They need to think about context and customers at the same level. I trust my counterparts in those disciplines to guide teams in my absence because we’re aligned in altitude and perspective.
Your career belongs to you
When you mentor people, you talk to them about building a career with intention. What does that mean to you? And how do you mentor people to do that?
This is one of the things that I’m a broken record about. I coach on intent a lot and I’ve been coached on intent a lot. I have an excellent coach named Ken Norton — he’s a lovely, wonderful human, and I recommend him to everybody.
A lot of software development and career events can feel like they’re out of your control — your boss quits and they make you a manager, the business moves you to a new role, there’s a RIF and you have to find a new job. There’s also day-to-day stuff that feels out of control, like executives making decisions without knowing what’s happening on the ground.
I coach people to figure out what is in their control and make an intentful decision about what they will own and what they will let go of. My coach Ken always says: take responsibility for what you’re responsible for and let go of the rest.
When I join a new company, I do a listening tour — 60–90 minute interviews with everyone who will report to me (directly or indirectly) plus adjacent disciplines. I typically meet with 40–50 people in the first three months. What I hear over and over again is people telling me, “I ended up where I am because other people made choices for me.”
And when you hear that, what do you say?
I remind people — especially women — that their career is their most important financial instrument. People treat their careers like something that happens to them instead of cultivating it like a garden. Figure out what you’re going to plant in this company, and what this company can offer to get you closer to your bigger journey.
Your career belongs to you, but the job belongs to the company. Jobs come and go, but your career is yours, and you have to take control of it.
So when you’re coaching people, how do you get them to put that into action?
It starts with, “What do you want to be when you grow up?” That might be starting a company, becoming a founder, doing zero-to-one projects. Once we know the destination, we mine the company for opportunities — get you on zero-to-one projects, into entrepreneurship classes, onto work that builds the skills you’ll need later. Jobs are short, careers are long. The goal isn’t just to draw a paycheck; it’s to build skills.
At bigger companies, that could mean staying a long time but doing many different things. Or it could mean going out into the world as a speaker, founder, or leader. Either way, you practice those skills now so you’re ready when it’s your turn.
Advocating for women and underrepresented groups
Advocating for women and minorities in tech is paramount to you, and you’ve been open about navigating both privilege and disadvantage as a white woman in tech. How has that lens shaped the way you mentor others and design for more inclusive career paths?
I’ve done a lot of reading about this, though I wouldn’t call myself an expert. My journey started one day at Google, when I was in a meeting with 14 people and realized I was the only woman. It was the first time I can remember feeling “other.” I had a hard time getting a word in — even for me, not a wallflower — and it made me start paying attention.
From there, I got interested in how interviewing pipelines work and how systemic bias works, particularly against women but also against other underrepresented minorities. What might take someone in a position of privilege 10 years could take the rest of us 15 or 20 because of systemic bias.
When I was a design manager, I brought in a program called Racism Untaught. It gets you to examine your identity classes, privileges, and biases, and see how they affect your design work. I’ve used it at multiple companies, and it’s the best material I’ve found for opening eyes to the subtle ways bias shows up.
And how do you bring that into your coaching?
I coach gender minorities on tactical skills like negotiation, advocating for visible projects, and removing passive language from performance reviews. I encourage them not to apologize for how they show up, and to intentionally create a leadership profile that’s authentic to them — no need to copy a prototypical male leadership persona.
You can be successful and heard without mimicking a man. You can find your own communication style and cultivate that into a leadership persona that you can switch into when needed.
I also encourage self-promotion that feels authentic, because men are often promoted on potential while women are promoted on performance. Collectively, we don’t tend to self-promote as well, so I push people to share their expertise publicly in ways that feel right for them.
I use a visualization in my diversity talks: people in positions of privilege are running on a clear track; everyone else is running a track with hurdles. My job is to give people tools to remove those hurdles so they can run faster.
Parenting and work-life balance
In startup environments, new parents often face identity and career questions. What patterns have you noticed? And what advice do you give people when they feel like they have to choose between ambition and parenthood?
I wish someone had told me the answer before I had my first kid. The identity crisis can happen to anyone, but it’s more acute in startups because they attract achiever types, often younger. They pour everything into the company, work long hours, and then later start families.
There’s nothing that prepares you for parenthood. People can tell you it’s hard, you’ll lose sleep — but you don’t really understand until you’re in it. Even if you were a disengaged parent — which most aren’t — you still wouldn’t have the same hours, sleep, or energy you had before.
What’s the biggest misconception you see?
That you can “have it all.” Especially for women, that message creates huge feelings of inadequacy. We see high-profile women writing about how they “do it all,” but what you don’t see is the massive paid support — nannies, cleaners, cooks — that most people don’t have. You can’t maintain a relationship, be the parent you want to be, do a full-time job, and keep a perfect home. It’s impossible.
Hearing that matters, because especially for women, there’s this expectation that not only can you do it all, you should. And if you don’t, you’re failing. That mindset is toxic.
So how do you help parents reframe that?
First, I tell them they literally can’t do everything they were doing before. The sooner you accept that, the better. Men and women face different biases — women are expected to put family first, men to put work first — but both are broken. Your worth isn’t defined by how much of a company’s bottom line you can optimize.
We’ve over-indexed on productivity as the measure of human worth. People feel guilty if they’re not “producing value” at all times. That’s the first thing we try to undo: disconnect your self-worth from capitalism and productivity.
Do people actually follow that advice?
Some do, especially when they hear it from a leader. Permission matters. Modeling matters. Leaders should coach people to show up as whole humans — you’ll get better outcomes that way, and the company will be fine.
It takes repetition to undo the internal talk tracks. I try to model it, my boss models it, and I want my leaders to model it so it spreads. New parents trying to optimize for work while adjusting to huge identity changes are going to struggle. Recognizing and supporting that transition is critical.
I made mistakes with my first child — went back to work too early, didn’t take full leave. I can’t get that time back. With my second, I took the full leave and was fully present. And the company survived just fine without me.
Values-driven leadership
What should organizations be doing to help employees flourish?
When I’m building my organizations, I look for values-driven leaders and ICs. If they don’t have written values when they join, we create them together. Values guide big and small decisions, so you should be intentional about them and about how they show up in your decision-making.
There’s a difference between values-driven and outcome-driven leaders. Outcome-driven people will use any means to get a result. Values-driven leaders still achieve great outcomes, but the “how” has high integrity and humanity. You can get great results without compromising those things — anyone who says you can’t, I disagree with completely.
If you could sit down with your 20-year-old self and give her one piece of career advice, what would it be?
It was the most natural thing in the world for me to end up where I am now, but I didn’t learn the intentful lesson until my mid-career. If I’d had someone coaching me on that early on, it would have changed how I made career decisions.
And I would tell myself that the work you produce does not define your value. If I’d learned that much sooner, I think my career would have looked different and I would have felt better about it along the way.
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