Community Spotlight: Dawn Owens on When It’s Time to Take a New Hill

Dawn Owens laughs when she describes herself as change-averse.

New wallpaper? She doesn’t like it. Different flowers in the garden? Not her favorite either.

Yet over the course of her career, she has repeatedly embraced some of the biggest professional transitions imaginable. She has changed companies, functions, industries, and leadership roles. She has led turnarounds, guided organizations through transformation, and most recently helped lead the evolution of TripleTree’s private equity business into what is now Truehelm.

The irony isn’t lost on her.

“Change is inevitable,” Dawn said. “It will either be pushed upon you, or you can embrace it and use it to create momentum.”

Her Early Start in Healthcare

Like many successful leaders, Dawn’s early career did not unfold according to a carefully scripted plan. But her interest in healthcare started long before her first job.

Her mother was a nurse, her uncle was a physician, and she grew up believing healthcare was a place where people could make a meaningful difference in the lives of others. At various points, she even considered becoming a physician herself.

“Healthcare is a sector where you can make a difference and where you can solve big problems, whether they be for patients or for the system itself,” Dawn shared. “It is an industry that needs to continue to change to create sustainability, and where you need people who are problem solvers. There’s a tremendous amount of opportunity.”

After college, she joined Aetna and quickly found a company she loved. “I felt convicted that this was a place I was going to retire from,” she recalled. She began her career in sales, helping employers design and implement employee benefits solutions. Starting with small and middle-market businesses, she gradually expanded her responsibilities to larger and more complex self-funded employer groups. Along the way, she discovered that she loved solving problems, building relationships, and helping organizations navigate complicated decisions.

Just as importantly, she found herself in an organization that invested heavily in developing its people. Aetna provided opportunities to learn, grow, and take on increasing responsibility. The culture reinforced a lesson that would stay with her throughout her career: growth comes from being willing to stretch beyond what feels comfortable.

What she could not have known at the time was that the young salesperson learning the fundamentals of healthcare benefits would one day run the entire business.

Inflection Points

One of the first major inflection points in Dawn’s career came when Aetna acquired U.S. Healthcare. The strategy of the organization changed, and with it, the future she had imagined for herself. For the first time, she found herself facing a decision that would become a recurring theme throughout her career: stay with what was familiar or pursue a new opportunity.

Rather than holding on to what had been, Dawn made a move that would ultimately shape the next fifteen years of her career, joining United Healthcare, then a much smaller and less established competitor. At the time, United Healthcare was a regional HMO, far from the healthcare powerhouse it would eventually become.

What drew her wasn’t the title or the certainty of the opportunity. It was the vision. “I was drawn to what they were trying to build,” she said.

That decision would become the first of many moments where she chose growth over comfort.

What followed was an extraordinary period of growth. As United Healthcare expanded, so did Dawn’s responsibilities. She quickly developed a reputation for taking on assignments others avoided, embracing difficult challenges, and stepping into opportunities that stretched her beyond her experience.

“It was a time when if you were willing to raise your hand, there was tremendous opportunity,” she reflected.

Over the course of fifteen years, she moved through a variety of leadership roles and eventually found herself running the very business where she had started her career. By then, it had grown into a multi-billion-dollar operation. By almost any measure, she had achieved what many executives spend an entire career pursuing.

And yet, something was missing.

Trading Comfort for Challenge

By almost any measure, Dawn had achieved what many executives spend an entire career pursuing. She was running a successful multi-billion-dollar business and had risen through the ranks of one of the fastest-growing healthcare companies in the country.

But she was restless. “I was bored,” she admitted.

She wasn’t searching for a bigger title or a larger organization. She was searching for an opportunity to learn something entirely new.

That search led her to become Chief Marketing Officer of Ingenix, a technology business within UnitedHealth Group that would later become Optum Insight.

On paper, the move looked like a step backward. She was leaving a business she was running to take on a functional leadership role in a business that was less understood and less celebrated within the organization.

But Dawn saw something else. “It was less about career advancement and more about wanting another challenge,” she explained. The experience exposed her to entirely new parts of the healthcare ecosystem, expanded her understanding of technology, and ultimately prepared her for her first CEO role. Looking back, it was one of the most important decisions of her career.

Taking the Hill

That first CEO opportunity wasn’t a victory lap. It was a turnaround.

The business was struggling, expectations were high, and the pressure was real. “My first year, the company didn’t hit its plan,” she recalled. “Every day I woke up and thought I was going to get fired.”

But Dawn stayed focused on what mattered. Rather than running from the challenge, she and her team focused on rebuilding the fundamentals of the business, restoring growth, and creating the conditions for future success.

One lesson from that experience continues to shape how she thinks about leadership, investing, and change. Sometimes growth requires leaving. Sometimes growth requires staying. Sometimes the answer is not working harder, but approaching the problem differently.

Meaningful progress often requires leaders to rethink assumptions, build new capabilities, or pursue a strategy that feels uncomfortable at first.

Looking back, Dawn realized that every major transition in her career had something in common. None were driven primarily by titles or compensation. They were driven by the opportunity to learn, solve bigger problems, and take on challenges that stretched her capabilities.

In other words, it was time to take a new hill.

From Operator to Investor

After decades leading businesses inside some of the largest healthcare organizations in the country, Dawn found herself drawn to another challenge. An opportunity emerged to join TripleTree, a healthcare-focused merchant bank and investment platform known for its deep sector expertise and strong relationships across the healthcare ecosystem. While Dawn knew healthcare intimately, private equity was a different world.

Once again, she found herself stepping into unfamiliar territory. The transition required learning a new language, developing a different perspective, and understanding how investors evaluate opportunities, create value, and partner with management teams.

For many executives, moving from operator to investor can be difficult. Operators are accustomed to making decisions, owning outcomes, and living with the consequences every day. Investors must learn how to influence, advise, and support while allowing management teams to lead.

Dawn embraced the learning curve.

What made the move appealing wasn’t just the opportunity to invest. It was the opportunity to work with multiple businesses, multiple leadership teams, and multiple healthcare subsectors at the same time. “I’ve always loved learning,” she shared. “And this gave me the opportunity to continue learning while helping companies grow.”

Her years as an operator ultimately became one of her greatest advantages. Having sat in the CEO seat herself, she understood firsthand the challenges management teams face. She knew what it felt like to navigate uncertainty, manage through difficult decisions, and balance short-term pressures with long-term growth. That perspective shaped how she approached investing.

“The best investors ask great questions,” she said. “They listen. They learn. They understand what management teams are trying to accomplish.”

Over time, she grew from investor to leader within the organization, helping guide the firm’s evolution and growth. But one of the most significant chapters was still ahead.

In 2021, TripleTree sold its investment banking business to Capital One, marking a major milestone for the firm and creating an opportunity to reimagine the future of the private equity platform. While the investment team and strategy remained intact, the transaction prompted an important question: Who did they want to be going forward?

More Than a Rebrand

Following the sale of TripleTree’s investment banking business to Capital One, the private equity firm faced an important opportunity. How should it define itself going forward? For Dawn and her team, the answer wasn’t about becoming something new. It was about more clearly articulating who they had always been.

The firm spent time gathering feedback from portfolio company executives, investors, colleagues, and industry peers to better understand the characteristics that consistently defined the organization. The same themes surfaced again and again: collaboration, humility, partnership, culture, and a hands-on approach to helping companies grow.

“We wanted to affirm the things that have always been true about us,” Dawn explained. The result became Truehelm, a brand designed not to reinvent the organization but to clarify its identity and vision for the future.

She described a culture that values curiosity, collaboration, and continuous growth. “If you love making a difference, you would love working at Truehelm.” While private equity is often associated with sharp elbows and aggressive competition, Dawn believes one of the firm’s defining characteristics is its commitment to partnership.

“We are low ego,” she said. “We’re not the sharp elbows of the coasts.”

For Dawn, some of the most rewarding feedback comes from executives who choose to partner with the firm multiple times throughout their careers. It reinforces the idea that Truehelm brings more than capital. The firm strives to help leaders grow, solve problems, and create lasting value.

The process also reinforced several of Dawn’s core beliefs about leading through change. First, leaders must be clear about what should remain constant. While strategies, structures, and even names may evolve, the organization’s values, purpose, and culture must remain at the center. “You need to keep your eye on what matters,” she said.

Second, successful change starts long before the announcement itself. “If you wait until you’re announcing the change, you’re already multiple steps behind.” For Dawn, change is most successful when people understand not only what is changing, but why.

The Truehelm rebrand was not about creating a new identity. It was about clarifying an existing one and ensuring that the firm’s culture, mission, and values would continue to guide the organization into its next chapter.

Great Investors Ask Great Questions

Today, Dawn leads a healthcare-focused private equity firm investing in founder-led companies that are ready for their next phase of growth. Her path from operator to investor gives her a unique perspective. She believes one of the biggest mistakes investors can make is underestimating how difficult it is to run a business.

“The best investors do their homework,” she said. “They are really good listeners and they ask phenomenal questions.” Likewise, she believes many operators don’t fully understand how investors think, how they measure success, or how they evaluate opportunities. The strongest partnerships happen when both sides invest the time to understand one another.

That idea extends beyond investing. It is also Dawn’s best business development advice.
Do your homework. Ask thoughtful questions. Understand the person sitting across from you.
Because business, at its core, is still deeply personal.

Purpose Over Networking

One of the most surprising moments in our conversation came when Dawn admitted that networking has never felt particularly natural to her. She is comfortable speaking on a stage. One-on-one networking has always required more intentional effort.

Over time, however, she has reframed what networking means. Rather than viewing it as a task, she views it as an opportunity to learn, help, and build genuine relationships. Her favorite conversations are the ones where she can add value, solve a problem, or help someone think through a challenge.

“I like the engagement being purpose-driven versus the purpose being networking.” It is a subtle distinction, but one that says a lot about how she approaches leadership and relationships.

Seeing People as People

When asked what habit has contributed most to her success, Dawn’s answer had nothing to do with productivity systems, strategic frameworks, or leadership books. Instead, she talked about people. She talked about remembering that every employee, founder, investor, executive, and colleague is first and foremost a human being.

“Once you get away from seeing people as people, you lose perspective.”

It is a simple idea, but one that has shaped how she leads teams, evaluates opportunities, navigates difficult decisions, and builds relationships.

A Reminder That Small Actions Matter

When asked for a book recommendation, Dawn didn’t immediately point to a leadership book, business strategy guide, or private equity classic. Instead, she shared a recent favorite: Theo of Golden.

What resonated with her most was the book’s reminder that small acts of kindness and human
connection can have a profound impact on others.

The story follows an unlikely friendship and explores themes of purpose, compassion, and the ripple effects of showing up for people in meaningful ways.

For Dawn, the message aligns closely with how she thinks about leadership. Whether leading a turnaround, guiding a rebrand, investing in a founder, or mentoring a colleague, she believes the most meaningful impact often comes through everyday interactions rather than grand gestures.

“It’s a reminder that you never fully know the impact you can have on someone else’s life,” she shared.

The recommendation feels fitting from someone whose career has been built around helping organizations grow, supporting leaders through change, and never losing sight of the people behind the business.

Final Thoughts

Throughout the conversation, Dawn returned repeatedly to the same idea: growth rarely comes from standing still. Whether leading a company, investing in a founder, or navigating a career transition, there comes a moment when the current path is no longer enough.

The challenge is recognizing it.

The courage is acting on it.

And the opportunity is finding the next hill worth taking.

Throughout her career, Dawn has repeatedly chosen vision over certainty, growth over comfort, and purpose over predictability. Looking back, those decisions became the very moments that shaped her career and leadership journey.