Episode 14

Funding the Future of Health Innovation

with Dawn Owens

June 17, 2021

Dawn Owens
Chief Executive Officer at TripleTree Holdings

Dawn Owens is the Chief Executive Officer of TripleTree Holdings, responsible for leading the firm as it advances and supports the healthcare industry in its role as both strategic advisor and investor. In her role, Dawn engages industry stakeholders, from innovative and earlier-stage companies to Fortune 200 leaders, to understand the market forces driving disruption and the potential for continued innovation in healthcare.

Dawn brings extensive healthcare experience to the firm, including 5 years as the firm’s President and a national reputation as a dynamic leader who has lead companies through various stages of growth, from turnaround to high growth.  Prior to joining the firm, Dawn served as CEO of OptumHealth, a multi-line UnitedHealth Group company.  Under her leadership, OptumHealth became one of the nation’s largest and most respected health and well-being companies.  Dawn’s prior roles include Chief Marketing Officer of Ingenix (now OptumInsight) and President of Uniprise (now a part of UnitedHealthcare). She started her healthcare career at Aetna Health Plans.

Dawn earned a B.A. from Grove City College.

There's a lot of wisdom—if you allow there to be—that you capture in your career as you journey through your life and your career.



Gary Bisbee  0:06

Healthcare leadership is hard work, but what if you could learn from the most brilliant and influential minds in healthcare and beyond? What would you ask them? Would you ask about politics, policy, or maybe leadership? On The Gary Bisbee Show, I’ll do just that. You’ll hear from healthcare’s most successful leaders and those experts who they listen to, as together we’ll explore how the healthcare economy is transforming.


Gary Bisbee  0:36

Why would the CEO of one of the largest companies in health care leave to become president of a much smaller, albeit high-performing partnership? Dawn Owens did just that and she became CEO of TripleTree Holdings, a highly successful merchant bank. She has a unique philosophy about taking risks to pursue attractive leadership opportunities. In doing so, she followed a founder and long-standing CEO, which I know from personal experience is not an easy task. Why did she make this transition? How does she justify the risk? We’ll get to the key criteria that Dawn used for this career-defining decision. Dawn has a very wise perspective on leadership, whether hiring the right people, motivating and managing teams, maintaining a flexible mindset, or building a diverse organization. Dawn is a highly successful leader who knows how people tick and how to motivate them, all of which we’ll explore in this conversation.


Gary Bisbee  1:41

Good morning, Dawn. And welcome.


Dawn Owens  1:43

Good morning, Gary. Great to see you.


Gary Bisbee  1:45

We’re pleased to have you with this microphone. You’ve done a fantastic job at TripleTree and before that at OptumHealth. Looking back on your career, what are the major leadership lessons you’ve learned?


Dawn Owens  2:11

First and foremost, I found that—when I am doing what I love, what I enjoy, what I’m passionate about—I can be very good at it and infectious as it relates to my role as a leader, but it’s a lot more than that. The second thing is the importance of a team. As you ascend into leadership positions, it can’t be all about you. It has to be about the people who are around you and a part of the organization you’re leading. As a leader, getting a great team and having alignment with that team professionally and personally is super important. The third thing has been the importance of putting myself in a position where I’m constantly learning and growing, where I’m not just doing the same thing over and over again. I like the freshness of learning new things and applying those learnings. Then finally, as I reflect back, being willing to take calculated risks in my career. It isn’t always about having a clear path to some big, high goal of being the CEO of this or that. Rather, how do I apply who I am what I’m passionate about with the opportunity to learn? Where do I take risks to pursue new things that I can continue to satisfy my career objectives with? Those are the things that have been important to me over the years.


Gary Bisbee  3:42

We’re going to cover the risk question in several specific topics we’ll get to in a minute but, in terms of the team and hiring people that fit the team and the culture and your preferences and so on. any tricks there? How do you go about identifying and hiring the right people?


Dawn Owens  4:04

It’s probably one of the hardest things for anyone to do well and consistently. You have to recognize that sometimes you’re not going to get it right and be willing to deal with that as well. As it relates to building your team, one of the things I’ve evolved in my perspective over the years is not everybody is like me and not everybody has to be like me. In fact, I am better when I’m surrounded by people who not only bring different experiences, perspectives, or skill sets functionally but also as it relates to personality and style. Now, we all have to be on the same page as it relates to the mission, to the strategy, and to the culture but, as you think about those other things, you are much stronger with a mosaic of diversity that is less about how you look and is more about what you bring to the table within an organization. That’s been super important. Secondly, within that, think about the elements that are most important in the role you’re hiring for. I have a particular leader in our organization and we couldn’t be more different as it relates to how we like to work, how we like to prepare, and even our risk tolerances, but we complement one another exceptionally well. When we first started working together, it was a very bumpy road. We really struggled because I did not provide her with what she needed to feel comfortable and successful and I would be frustrated by her because she was always a speed block as it related to what we wanted to do. We, however, recognized the strengths we each brought to the equation. We worked really hard to seek to understand one another, what each other’s needs and expectations were so we could shift the way in which we worked together to get the best out of each other so we could drive the business forward. We have become a really strong team. In fact, the other day I said to this person, “I want you to continue to challenge me. I want you to continue to tell me the things I don’t necessarily want to hear. That’s what I need from you, but what I also need from you is trust in me that there are going to be times where I can take that advice and we can run down that path that you’re suggesting. Other times, you’ll have to trust me that I know it, I’ve got it covered, but we’re going to go in a different direction.” The more you recognize that, as you say to your children, “you don’t need to just talk louder to be heard, you need to be wiser about what you’re saying so you can be heard and understood.” That’s been a really important ingredient in learning as it relates to building a team, finding the right people, and being the right leader so those people can thrive and excel.


Gary Bisbee  7:13

It also speaks to your confidence as a leader, Dawn, because a lot of people kind of mouth the words, “Yeah, sure, you can challenge me,” but a lot of people really don’t want that. In your case, it sounds like you actually seek it out.


Dawn Owens  7:27

It speaks to knowing what you’re good at, where your blind spots are, and areas you’re not as strong in. As you ascend into general management roles and leadership in a general management arena, you don’t know everything. You can’t know everything. In an industry that is highly regulated, where compliance is a really important element of what we do, I am not the expert in that, so I have to be (1) a very effective communicator about what we’re doing as a business so the right people are aware of all the things that are going on. Then I also need to listen to them around how we calibrate our strategies and activities to satisfy the various requirements that are put upon our business. It’s really important, especially as you ascend into executive leadership positions, to know what you’re good at and where you need help.


Gary Bisbee  8:31

Tell us about the young Dawn, particularly in terms of leadership. At what point did you discover you were a good leader and enjoy doing it?


Dawn Owens  8:41

The young Dawn, and the Dawn of today still, is passionate about helping individuals solve problems, helping organizations solve problems, and being a part of the solution (hopefully not a part of the problem). That is what drove me very early on in my career. I love to learn so I loved to understand the detail and—at that point in my career—be the expert, be the person who knew more than anyone else and was able to take that knowledge and apply it to problem-solving. That made an environment where I was able to apply that and be very successful, first as an individual contributor. In most organizations—if you’re good at something, passionate about something, and you do it well—as an individual, you tend to start to have the opportunity to lead small teams or have other people be a part of that at different functional leadership levels. One of my blind spots as I started to take on functional leadership positions was that I thought everybody was motivated by what I was motivated by. I thought everybody wanted to do the job the way I wanted to do it. I also did not have an appreciation for how people’s lives and their life stages affected how they approached their work. I was young, I was single, I didn’t have anything to do other than work, so I put everything into work and I put everything into learning. I was optimistic and all of those things, and that can be really powerful as a leader, but it also can only take you so far. I wasn’t sympathetic to the guy who wanted to catch one of his kids’ soccer games and wanted to pick up the work afterward. I was not as open-minded or tolerant of those types of things. I was focused in a way that was good, but also really limiting as it related to my effectiveness in being a leader. I’ll never forget the “first half” of my leadership career lifecycle. I had taken over a team that was an average team, let’s call it. I was establishing myself in a very new industry for me with a new team and I was getting to know this guy, we were talking about what he was doing in it. At some point in the conversation, I said, “You know what? That’s just not acceptable. That just doesn’t work.” The guy comes back to me and he looks at me and says, “You say that way too much, and you know what? That doesn’t work with me, so we’re going to have to figure out how this works differently.” It was a good wake-up call for me that not everybody’s the same, that I have to flex my style, that I have to flex my— not expectations because you still expect excellence, but how you get it is different. What you expect of a person based upon who they are and what their expectations are shapes how you lead and manage.


Gary Bisbee  12:01

What about your parents? Did you pick up any of your leadership traits or characteristics from your parents?


Dawn Owens  12:07

My mother was a nurse and practiced medicine in a number of different environments. My father was a teacher who became a union manager organizer, so what I picked up from my parents was grit, determination, and that they expected a lot of me. I had a lot of responsibility. My parents were divorced when I was very young, so I was super independent very early on, probably in ways that today everybody would be horrified by. My parents expected a lot from me and assumed I could do it all. They kind of said, “You can do whatever you put your mind to.” What they didn’t do—and I don’t fault them for this, it was just the environment I grew up in—they didn’t paint a picture of what that could mean from a professional perspective, from a career perspective. Business was not something that was really in our orbit of understanding, so I had a pretty narrow view of the world and what a professional journey might look like as I grew up. Obviously, it worked out fine, but they gave me important characteristic elements that shaped who I was, how I believed, what I could do, and what I could accomplish.


Gary Bisbee  13:30

We’re all interesting situations relative to our parents and others that influenced us through the years. About half of the viewers of this show are up and comers in their 30s and 40s. You’re obviously a tremendously successful leader. Off the top of your head, what advice would you give up and coming leaders?


Dawn Owens  13:56

A couple of things are really important. First off, there’s a lot of wisdom, if you allow there to be, that you capture in your career as you journey through your life and your career. Careers are not straight lines, they zigzag, and your passions about things zig zag, your satisfaction, your trajectory can change over time. Having someone in your professional orbit who can act as a mentor to you to help you keep things in perspective, to help you look around the corner, who can help you navigate internally or externally in an organization is a very important relationship. It doesn’t have to be formal, like in a mentorship program, but that’s a really important person or people to have in your life professionally. I probably didn’t value mentorship as much as I should have or could have early in my career, but I see the power of it today, so that’s number one. Second is, not only does your career zigzag, your life zigzags. I talked about who I was as a leader when I was early in my career when I had nothing to do but work. I poured so much of my energy into work. Time went on, I got married, I had kids, and my priorities evolved, so be realistic about your career goals, life goals, and how you reconcile those things, and how you make those things work. You have to make choices and sometimes there are trade-offs. If I wanted to go to every kid event that exists with my children today, I probably couldn’t do the job that I do, especially when we start back on airplanes. It’s been a little nice with COVID because I’ve been able to do more of that, given not traveling. My husband and I have had to make choices around how he spends his time personally and professionally and how I spend my time personally and professionally to make my ability to be the leader I am and the demands that require work in our family to have the family cohesion that we expected. If I expected that I had to do all of that and be the leader that I am, I would be crushed. I wouldn’t be able to do it for the long haul. Those choices matter a lot as well. The final thing is I would focus less on “I want to get to this place and what are all the steps to get there?” I would focus on what you’re passionate about, what gives you energy, and be willing to not over-focus on the optics of what the world is going to say about the decision you just made about your career but how are you going to feel? Are you going to be satisfied and fulfilled? When those things come together, generally, you can be exceptionally successful career-wise.


Gary Bisbee  17:04

Let’s turn to your professional career. You’ve been in healthcare for almost all of it. How did you become interested in healthcare?


Dawn Owens  17:15

My mother was a nurse, my mother’s brother was a physician, so at a very young age, I wanted to be a physician. For many reasons, I didn’t become a physician. I joked around when I was at OptumHealth leading OptumHealth, I would say, “I may not be a physician, but I play one on TV,” meaning I could speak credibly about clinical things, but I was not a physician. My sister is now a nurse, so I was surrounded by healthcare. I graduated from college with a degree in German and international business, so you can see I’m really using that. Also, another lesson: those things don’t matter as much as you start your professional journey. It happened pretty naturally. Once I got into the business of health care, I realized how vast and diverse and dynamic it was. I started selling health plan benefits to employers and that was my world. That was my narrow view of healthcare. As I grew professionally and applied my skills into other parts of UnitedHealth Group—which was a wonderful place to grow professionally because it was such a diverse set of businesses—I realized just how big the healthcare marketplace is and how many different facets there are. It was a very natural progression to a place where there’s so much greatness in our healthcare system but yet so much opportunity to continue to evolve and change and grow that need to be met at a personal, individual, patient-level and a systemic level.


Gary Bisbee  18:58

You’re currently the CEO of TripleTree Holdings, and we’ll ask you in a minute to share more with us about TripleTree Holdings, but I’d like to ask the question regarding when you went to TripleTree. You went as the president, but you left the OptumHealth CEO job, so CEO to President. You made the point earlier about your passion as opposed to what people are going to think about the job, but a lot of people would be concerned about giving up a CEO title for president’s title. How did you work your way through all that?


Dawn Owens  19:36

A couple of things. First off, it was the second time I had made a transition like that where, on paper, it didn’t make sense from a title and scope and even from the size of the organization. I was the CEO of OptumHealth, a 5+ billion dollar, multi-line business at the time. I was the CEO and doing well and very successful. Now, look at TripleTree, a merchant bank in healthcare, meaning we focused on health care. By all definitions, TripleTree is a small business. I had 1,000s, 10s of 1000s of employees internationally at OptumHealth, I had less than 100 employees at TripleTree. I was the President. I was moving into an industry where I knew a lot about the business’ area of focus but in an industry I had never been a part of and, on the surface, was not equipped to be the CEO by any means. I made that transition because of the themes I spoke about: what am I passionate about? I’m passionate about health care, solving problems, growing and learning, learning being a really important part. I saw this. I had plenty of opportunities when I left UnitedHealth Group to pursue a career path that would have gotten me in that CEO chair and would have been very comfortable as it related to the type of business I would be leading because I had led businesses like that before. I saw this career moment as an opportunity to take a risk, to see if I could apply who I was as a leader into something different and continue that growth journey that I had throughout my career. I thought it was a really exciting opportunity to learn a new industry and to become a new in a fairly senior position but yet still be an expert able to contribute and so forth. It played out beautifully, obviously, as I sit here today as a CEO of that business and successfully navigated a founder transition, which was part of that plan. I had to be willing to focus on those things that were my true north, as opposed to “the world’s optics” of judging me on what I should be doing.


Gary Bisbee  22:08

How did you manage going from a huge organization to a smaller company like TripleTree?


Dawn Owens  22:18

We have two parts of our business: investment banking and principal investing, and in principal investing we run private equity funds, early-stage growth equity funds. We’re always looking for people to come into these young businesses that we are investing in that know the domain and can help advance that business. We see a lot of people come out of large corporate America (like I did) and want to go into that private company space, smaller company, entrepreneurial company. The biggest question we have to figure out for those people is not whether they have the knowledge, but whether they can apply that knowledge into that smaller company context. It’s hard because, the reality is, you don’t fully appreciate the abundance of resources you have in a large company perspective. You also have Matrix and you probably don’t own exactly quite as many things. With smaller company contracts, you own it all. The buck truly stops with you. You have to rely upon your team and you have to have a team of people with diverse experiences. You have to do much more yourself. You have to be much more creative around how to get things done. You need to manage cash in a much different way. There are lots of different things that are different. You have to recognize and be willing to work within those trade-offs to be successful in that smaller company, more entrepreneurial, private company context.


Gary Bisbee  24:04

When you became CEO, you followed the founder of the company. You moved to Chairman, but there are bunches of stories about people who have followed founders. It can be a really difficult transition. How has that gone? How have you managed that?


Dawn Owens  24:21

It can be a challenging transition. I would say it takes two to tango, it takes two to make that transition work well, and it starts with the founder. In this instance, the founder of TripleTree, Kevin Green, had been doing a lot of soul searching, thinking, and talking to executives who had made that transition of what went right, what went wrong, what would they do differently? How would they benefit others from the journey that they had been on? Through that, Kevin realized what was important in the characteristics of a person coming into the business to potentially be that founder, and it wasn’t preordained. He needed to see if the vision of what could be actually played itself out. Coming in, he and I had really good alignment around what we would both need to be comfortable and satisfied with to know whether that transition was something that was going to work. How would we develop the trust, the knowledge, and the ability to work through that transition? We did it. It was hard. We had to take that trust and apply it to communicating about what was going on and how he was feeling through that transition, areas where I was not as sensitive to a founder’s point of view and the absolute care and passion and sacrifice that had been made on a journey of 20 years. I needed to reframe my mindset around what success looks like, just like I had early in my career around how it wasn’t just about being the expert, it’s about navigating that expertise with sensitivity (culturally, relationally, etc.) that allowed us to succeed. It started with him because he had a clear vision of what he wanted to do and was really thoughtful about it. The journey involved a commitment to communication and talking about the good and the bad and the challenging, and commitment to solving through those things together. It forced me to make sure I was putting myself in his shoes to be sure that I was navigating that transition in a way that not only worked for the business (because that was fine) but worked for him. I would say today that, not only was it a successful business transition, we are partners, we are friends, we are committed to the success and the generational opportunities for the business in a way that, had we not done this, could not have been fulfilled.


Gary Bisbee  27:08

Good for both of you. It is tricky. Particularly in that line of business where relationships are so important, that’s a tough transition. Give Kevin my best. He’s a great guy. How did things go in 2020? Or even up through now in terms of the pandemic? How did that affect the business and how were you able to adjust?


Dawn Owens  27:33

2020 was a tense and challenging year for everyone. There was not a business that wasn’t touched by the pandemic, and we were certainly not immune to that. The investment banking business, which is where the business started when Kevin founded it 22+ years ago, is a transaction business. You need to help a company sell itself or get more capital to create a transaction. When you do that, you get paid. That doesn’t happen, you don’t get paid, not dissimilar to elective surgeries. You don’t do that advertisement, you don’t get paid for that service. When the pandemic hit, the markets froze up and there was no transacting. That’s where a large portion of our cash flow comes from, so we knew we needed to manage cash. We also knew we had a great business that was very strong and we wanted to continue to invest in growth and prepare for when the market eventually opened up. It required a shift of priorities. It required a focus on how to use that time when we weren’t transacting to continue to build our business. It required keeping our people-focused and informed and secure and inspired. It required us to continue to be present in the marketplace, albeit in a virtual way. We were able to do all of those things so well that, when the lights came back on, our business was super well prepared to take advantage of a market that was very active. I’m talking about investment banking. The story is a similar arc that just plays out differently on the investing side. As a result of that, both parts of our business had the best years in our company history as we went through the pandemic, but only because we were able to be really intentional about how we navigated through the journey. We’re a people business. We don’t succeed because I’m all that great. We succeed when we unlock the talent, the team, and the individuals that make up our organization to deliver great outcomes for our clients, for our investors, for our portfolio companies that were invested in. I’m really pleased and fortunate and honored to say that we were able to do that through the 2020 season.


Gary Bisbee  30:17

Congratulations. When did the lights come on, by the way? Was it third quarter, fourth quarter?


Dawn Owens  30:24

The third quarter. We prepared for this, but we did as much business in our fourth quarter as we did in the prior year, so just jammed a lot in, but we did a lot of work to get to that point. We didn’t wait until the lights came back on. On the investing side, our pace of investing changed because we were focused on our portfolio companies that are healthcare services and technology companies and helping them navigate through what happened to their market dynamics. Was the market buying more of their services? Companies that supported virtual health were on fire, so it was, how do they hire enough people? How do they continue to scale and deliver and take advantage of that environment to others that were providing services where there wasn’t as much demand? How do you navigate that, focus on those things, but also focus on monetization, liquidity events, investing, etc. We were able to strike that balance as well, so it turned out well.


Gary Bisbee  31:28

If I could follow up on an earlier point you made about diversity and the fact that you look for that and count on that and design your team to be that, healthcare and finance are two areas that have not been very good about gender diversity. I’ve seen numbers in healthcare that 80% of the workers are women and 20% of leaders are women. Probably that or maybe even worse in finance. Here you are in both healthcare and finance. Have you had to make any adjustments through your career due to the fact that you’re a woman? How do you think about that, Dawn?


Dawn Owens  32:16 

As I stand back, I’ve been very fortunate. I do not feel that I’ve had to not be genuine, not be me to be successful. Every person—no matter your gender, no matter the color of your skin, etc.—needs to understand how they show up as a leader, as an individual, and make sure how they show up is how they need to show up to be successful in that context. How I speak to you or how I lead you or navigate a situation isn’t just dependent upon me. It takes two of us. Being mindful about who I am, my style, how I communicate, how I lead, how I manage, and what the other party needs is super important. I’ve had to make adjustments along the way in my career. I don’t look at that as a female issue. Even though some of the ways I show up style-wise might be because I’m a woman, I don’t think I need to do that because I’m a woman. I think a man needs to do it, everybody needs to do it. However, there are self-expectations as far as what life should look like. For women who want to have families, who want to be involved with their children, who have certain priorities that are wonderful priorities, important priorities, it is harder to navigate those priorities and take on executive leadership roles in any industry. It’s hard. It’s a hard balancing act. I believe that in life there are always trade-offs, so what does that look like? In our family, it’s meant that I am the career professional and my husband is a career professional applied into our family, meaning he is the one who’s there at all the parent/teacher conferences, driving the kids back and forth to school, meeting with the teachers, and helping them as they go through their life journey when I’m on the road traveling or doing what I need to do professionally. You need mentors personally and professionally. It doesn’t have to be in the context of a marriage. For us it is. That true partnership where you can together approach those goals you have and how it plays out, plays out. If you’re not realistic about that, irrespective of who you are, you set yourself up for challenges and disappointments and burnout in ways that don’t help you be the best you, whatever that means as far as your goals. Diversity is critical. Having the right team is critical. When those two things come together, it’s magical, but I don’t approach diversity for diversity’s sake. I approach diversity because it makes me and the organization better.


Gary Bisbee  35:53

That’s a terrific view, a very balanced view. It’s an important topic. What’s the trend from your observation? Are we making progress in this area?


Dawn Owens  36:03

In a lot of ways, we are. There is an organization called 50/50 Women On Boards that focuses on getting women into board positions with public and private companies, a lot of them focus on the public side. If you look at what raising awareness of the importance of diversity has done, you’d say we’re making progress. It’s hard-fought progress. It needs to start with developing professional women and men with diverse backgrounds and so forth that ascend into leadership because leaders then become board members. There’s progress being made and there are good professionals providing the mentorship and support, helping people understand and navigate what they need to do to reach those milestone levels. That is an important piece. We have to be careful not to judge. If a person may have every ability to be an executive leader but chooses a different path, that’s not a failure of the system. We need to honor that choice, too. We need to celebrate that choice, too. We want more diversity. We want more women leaders, we want more diversity ethnicity-wise, but we also need to honor the choices people are making and not look at it as a failure when they don’t pursue that.


Gary Bisbee  37:39

Dawn, this is a great place to land and absolutely terrific interview. We very much appreciate your time. Thanks for joining us today.


Dawn Owens  37:47

My pleasure. It’s been great. Thanks, Gary.


Gary Bisbee  37:50

New episodes will debut every Thursday. Join me in conversations to gain advice and wisdom from CEOs, presidents, and healthcare experts. Health care leadership is hard work, but it becomes more manageable as we learn from the remarkable lives and careers of our guests. I’ll see you there.

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