From start-ups to large-scale organizations: Uber Health’s Caitlin Donovan on the leadership capabilities that have helped her thrive

In this next episode of The Heidrick & Struggles Leadership Podcast, Heidrick & Struggles’ Josh Clarke speaks to Caitlin Donovan, global head of Uber Health. Donovan shares what attracted her to an operational role and the healthcare ecosystem, what kept her engaged in the sector, and how she believes a strong operational focus has benefited her as a business leader. Speaking from her experience having worked with both early-stage start-ups and large-scale organizations, she also shares what leadership capabilities have helped her thrive in all these different environments as well as what new things she had to learn when starting out in each; her perspective on building thriving teams and striking a balance between functional expertise and general best athletes; and her approach to recruiting, engaging, and retaining talent in different market environments. 

Below is a full transcript of the episode, which has been lightly edited for clarity. 

Welcome to The Heidrick & Struggles Leadership Podcast. Heidrick is the premier global provider of senior-level executive search and leadership consulting services. Diversity and inclusion, leading through tumultuous times, and building thriving teams and organizations are among the core issues we talk with leaders about every day, including in our podcasts. Thank you for joining the conversation. 

Josh Clarke: Welcome to The Heidrick & Struggles Leadership Podcast. Hi, I’m Josh Clarke, a partner in Heidrick & Struggles’ Boston office and global leader of our Health Tech Practice. Today, I’m thrilled to be joined by Caitlin Donovan, global head of Uber Health. Prior to Uber Health, Caitlin was the chief operating officer at MyOrthos, EVP of operations at LogistiCare, Circulation, and chief operating officer at Circulation, Inc.

Caitlin, thank you for joining us today. 

Caitlin Donovan: Thank you so much for having me, Josh. 

Josh Clarke: Well, let’s jump in. You started your career as an investor at Bain Capital and as a member of the internal consulting group at Summit Partners before shifting into operating roles. What was it that initially attracted you to an operational role, and the healthcare ecosystem specifically, and what has kept you engaged in the sector over the past eight or nine years?

Caitlin Donovan: That is a great question, and I think, to me, it was a winding path to find my way there, mostly because I had no idea what I wanted to do when I graduated college. Unlike a lot of our peers that have known that they want to be in the healthcare industry, or a doctor, or adjacent to it, I just had no idea.

So when I graduated college, went to a company where I wanted to learn as much about the way the world worked as I could, which is how I found myself as an investor at Bain Capital. And it was really on the advice of a mentor who told me I came to every single investment committee with an operating plan for the companies we were investing in and asked me, “Do you think you want to be an operator?” that I thought maybe I should look into this. 

So ended up at Summit in their internal consulting arm really to put my toe in the water, to figure out, “Do I like that? Do I like advising companies on their business plan? Would I like that—to help operate one?” And consistently found that, one, yes I did, and two, the companies I really felt myself gravitating toward were health tech and services companies, partially because it feels really good at the end of the day when you help the company help someone else.

And two, the problems that you need to solve, given the complexity and the regulatory environment of the ecosystem, are fun and challenging, and that combination is . . . why I like coming to work every day. 

Josh Clarke: That’s great. And just kind of building on that, you’ve worked with early-stage start-ups, you’ve worked with larger scale organizations, and even within large public companies. What leadership capabilities have helped you thrive in all of these different environments, and what have you had to learn fresh in each? 

Caitlin Donovan: I feel very lucky that I’ve been able to work across a lot of different stage of companies. I have found that most people that I know tend to specialize in a particular stage.

And to your point on what is the leadership criteria you need at each of those, I think as the company matures, you need slightly different things. But having a view of what it’s like to operate in each of those environments, I think can, one, set up early-stage companies for success, and two, help later-stage companies maintain that innovative environment that you tend to get at start-ups.

So I think the criteria for what it means to be a good leader at each stage is, one, having a bit of vision. Two, being willing to delegate decisions, not just tasks. And what I mean by that is make sure that you’re holding your team accountable for the full results so you can move in parallel, not just in sequence.

And three, introducing process only at the right time when there’s a purpose to it, not just for the sake of it. I think as you graduate into larger and larger companies, you end up with a little bit more of a number three, a little bit more process, so that you can continually repeat what you naturally get from a small team around innovation and teamwork.

Josh Clarke: And moving beyond stage of company, you know, one of the other things that stands out about your background is you have a very strong core competency in operations. That’s where you started your career outside of consulting and investments. But today your mandate expands in a much more broad way than that, beyond operations.

How have you navigated and led through this career evolution and how do you think a strong operational focus has benefited you as a business leader today? 

Caitlin Donovan: For me, I love now that my mandate is extended beyond operations partially because I love talking to people and you need a little bit of both once you start leading go-to-market teams as well.

But what I found, especially in healthcare and health tech and in a really complicated ecosystem, is any new product or any new health tech, any new service really requires an operational mind to make sure that it goes well and goes right. And so when we think about. So, how we work with our customers, approach our customers, operate as a sales partnership, business development, go to market team, we all have an operational lens where a lot of the questions that we ask are “What do you do today? How is it working? Where’s the break in the process?” so that we aren’t selling a product, we’re selling a solution that fixes a real problem that our customers have quite tactically.

And I think that’s really important because the whole purpose of what we’re all doing is . . . not to sell things for the sake of it, but to truly fix, and that requires really strong operations. 

Josh Clarke: And, you know, extending this thought here to the team itself, can you tell me more about your approach to building teams?

And how do you strike the balance between industry expertise or functional expertise or just general best athletes? 

Caitlin Donovan: I think if you hire a team that is one note, or you look to hire just folks that look like yourself, whether you’re a general athlete or an industry expert, you will fall flat. Some advice that I got very, very early on that has really stuck with me and has panned out is to make sure you know your blind spots and hire for your blind spots first, and then try to fill in that well-rounded team that, yes, gels and works with each other, but has appreciation for certain areas of expertise.

In practice, what that means is, I’ve typically ended up with a team with about half experts and about half general athletes because that’s where you really see the magic happen. A general athlete with no context may produce the wrong product, and an expert with no ability to zoom out may produce the wrong product. So how do you find a team that’s willing to learn from each other, lean into what they know, but have the humility to listen to other points of view is, I think, where you find that right balance. 

Josh Clarke: You know, I’m curious to get your thoughts on your approach to recruiting, engaging, retaining talent in different market environments, and in particular, Caitlin, over the last few years, of course, we’ve all lived through what is probably the highest of highs in terms of investment, in terms of access to capital in the healthcare and health tech space. And now over the last 18 months or so, we’ve seen kind of quite the opposite of that. So how is your approach consistent in those different environments? How does it change? And what do you find to be the right approach to really retain and engage people on the team?

Caitlin Donovan: Oh, I think especially now, that’s a very appropriate question. I tend to start by thinking about team culture that we want to build and then backing into recruiting strategy. So, for me, the right team culture is a team that can move in parallel and trust each other to catch balls. And what that means is every person on the team has sort of full authority to own their area.

I think a lot of my observation is a lot of companies talk about doing that, but what happens in practice is sometimes there’s a decision-maker that’s a bottleneck or questions their peer. And really thinking about that first team’s mentality of “How do we move as one, trust each other, focus on the areas where there’s issues with handoffs?” When you think about a recruiting strategy, you have to think about the type of team culture that you want to create. And to me, that’s really about giving everyone enough rope to run so that they feel full accountability and authority over what they do, because no one likes to be micromanaged.

Really thinking about how you do that in practice matters to keep folks happy, because even though a lot of teams say they do that, in my experience in practice, sometimes there’s that one peer that’s always the naysayer, that one decision-maker who’s always the bottleneck, and so how do you consistently operate with that first teams principle where everyone trusts each other and where there’s handoffs, that’s where you spend time perfecting how you work together as a team.

The reason I say that is I think in creating that culture and making sure that you do so at a company with a strong mission, my recruiting strategy tends to be about career growth, ownership, people that you work with, so that we are all tackling a mission together and then all of the other benefits that rise and fall with funding environments are icing on the cake.

That’s a long way of saying I think there’s a lot of ways to treat people well, and my approaches. How do you think about the nonmonetary things first? So that those things become, not secondary because they’re certainly important, but a piece of the conversation, not the whole conversation. 

Josh Clarke: Great. And in our previous discussions, you and I have talked about the role mentors have played in your career trajectory.

How do you dedicate time to mentorship today? And what advice do you have for mentors and mentees to ensure that they get the most out of that relationship? 

Caitlin Donovan: I think it’s the single most important thing that has shaped the way I think and certainly try to pay it forward. You know, I was very lucky to leave an investing and consulting environment and jump into operations, and I think so often you don’t know what you don’t know, and the way to find that out faster is to ask people. 

And so not being afraid to ask, to say, “What would you do differently?” To have a strong opinion loosely held is critically important to getting it right closer to the first time—I won’t say always the first time—I think is one thing. And then paying that forward to other people and being a brainstorming partner really, really matters. 

The second piece that one of my mentors did, and so I repeat, is I make sure to have skip levels with every single person on the team. So it’s not just about “How’s it going? Have you done this task?” But much more around “What do you want out of your career? Are we giving you that experience?”—really open-ended conversation so that we can contextualize what’s happening in our business and what’s good for that person too. Which I think, coming back to recruiting strategy and team environment, I think it creates a better business, I think it creates a better team environment, and I think allows for some of that mentorship that hopefully pays it forward.

You can ask the team whether it actually has with me, but that’s at least the intent. 

Josh Clarke: That’s great. And just one final question as we begin to bring this conversation to a close. I’d love to hear your perspective on the future of health tech. What do you think are the most exciting possibilities on the horizon, and how do you envision these advancements shaping the healthcare landscape?

Caitlin Donovan: When I think about health tech, this might be a unique perspective. I think about it less from the tech innovation alone and more how it more broadly fits into the ecosystem. I think this comes back to an earlier question you asked, Josh, around why a strong operations background matters. The healthcare ecosystem is so complicated. Care teams are so large. How many people patients touch—it’s very expansive. That one solution alone I don’t think is going to fix the system. And so I spend a lot of time thinking, “How do you fit into existing processes? How do you work with services? How do you connect with other point solutions in a way that matters?”

So the couple things that I’m particularly excited about, one is—I think everyone’s excited about AI, but I’m excited about the AI in the context of process more than as a stand-alone solution. And two, I think we’re starting to see interesting platform models—maybe I’m biased because Uber Health is one—that doesn’t deteriorate the need for point solutions and the specificity required for excellent clinical care, but think about how you package them together to solve a complex problem.

And so really excited to see more of that pop up over time. 

Josh Clarke: And just an extension on that question, Caitlin, before we wrap up, I’m curious to hear your thoughts on where you see opportunities for further collaboration in the healthcare ecosystem between technology, services, traditional healthcare providers, and payers.

Where do you see the opportunity in the future for further and enhanced collaboration? 

Caitlin Donovan: I think there’s a lot of opportunity. I’d say that there are three areas I’m particularly excited about. One is . . . just in general, starting to see more and more point solutions come together, or with a wrapper of services around them, that I think is critical in actually delivering the right care.

So I’m very bullish on what that looks like and how you use technology as the way to convene the types of things that individual patients, and especially patients with complex chronic conditions need. The second thing that I’m also quite bullish on is . . . innovation in payment models, because I think too often, even when there’s the right desire to align incentives, in practice, it’s really, really hard, just given some of the regulations around how those payments work.

So for example, with value-based care arrangements and the way that you have to code patients appropriately, sometimes there can be missed incentives that don’t meet the reason behind that initial regulation payment scheme, etc. And so some of the payment models that we’ve started to see, I’m excited about.

And a lot of those are tech-enabled. And the third that I’d love to see more of, and where it’s one of the places we’re really focused at Uber Health, is how do you break down the walls between the payer and the provider? I think so often in health tech, we focus on direct-to-consumer, direct-to-patient activity, because that’s easy to have a one-to-one relationship between a health plan and their members or a provider group and their patients. But that leaves out a big piece of the population that is really dependent on their provider for recommendations for care, etc. And seeing some of the innovations on how to have that omnichannel approach to patient access, direct to patient through provider, through community-based organization, and so on, I think is really needed to transform care delivery. 

Josh Clarke: Well, Caitlin, thank you for taking the time to speak with us today. I appreciate it. 

Caitlin Donovan: Thank you so much for having me, Josh. Loved the discussion. 

Thanks for listening to The Heidrick & Struggles Leadership Podcast. To make sure you don’t miss more future-shaping ideas and conversations, please subscribe to our channel on the podcast app. And if you’re listening via LinkedIn, Twitter, or YouTube, why not share this with your connections? Until next time. 

About the interviewer

Josh Clarke (jclarke@heidrick.com) is a partner in Heidrick & Struggles’ Boston office and a member of the global Technology Practice.