Driving Disruption: Ranmali Bopitiya Of Oscar Health On The Innovative Approaches They Are Taking To Disrupt Their Industries

An Interview With Cynthia Corsetti

Be a connector. The world is increasingly connected, but healthcare remains very fragmented. Many of us have had the experience of taking a sick parent or child to different providers, who each prescribe a new medication or treatment, leaving us feeling overwhelmed and lacking clear direction. This fragmentation causes real burdens for people. Oscar is designed to create a flywheel based on connecting patients and their network of providers with the right information at the right time. I believe we can work in a more integrated, seamless way — powered by AI and our tech stack.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes, but driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth, and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they are taking to disrupt their industries. As part of this series, we had the pleasure of interviewing Ranmali Bopitiya.

Ranmali Bopitiya is the Executive Vice President and Chief Legal Officer at Oscar, where she oversees the company’s Legal, Risk and Government Affairs functions.

Ranmali has an extensive background in healthcare and is passionate about driving innovation that creates access to high-quality, affordable care. She joins Oscar from Everside Health, one of the largest direct primary care providers in the U.S., where she served as Chief Legal Officer and oversaw the legal, compliance and risk management functions. Before that, she served as Vice President and General Counsel for Colorado Permanente Medical Group of Kaiser Permanente. Before joining Kaiser Permanente, Ranmali led the legal function of a high-growth start-up within Stanford Health Care and worked for multiple law firms advising health systems, provider groups and innovative care companies.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’m one of those lucky people who found my path to meaningful work early in my career. I am passionate about making care more accessible and affordable, and that energy comes from my family’s story. My parents had the opportunity to immigrate to the U.S. because my dad is a physician. During my childhood, we visited Sri Lanka regularly, which was embroiled in a horrible civil war, and I had a profound gratitude for having the opportunity to grow up in America. I also grew up listening to my dad tell stories of his solo medical practice. He was determined to ensure every patient who came to him could get care — that meant making calls and asking favors to try to ensure all his patients could get follow-up care when they could not afford it. I was raised hyper aware of this dichotomy — that this is the world’s most prosperous country and yet Americans can be left vulnerable when they get sick. It has always been clear to me that America needs a better way. So, I focused my education and career on helping clients navigate the complicated regulatory landscape to innovate a better way in healthcare.

What do you think makes your company stand out? Can you share a story?

Oscar was built on first principles: People deserve a good experience in healthcare. And if you deploy technology well, we can make it so. It’s been infused in Oscar’s DNA by our co-founder Mario Schlosser. Oscar’s culture pushes people to question assumptions and to “make it right.” The “why” behind that pushing is clear — it’s in service of improving the member experience. And through the years, Oscar attracted additional first principles thinkers into the company.

For example, Oscar plunged headfirst into the Affordable Care Act when it was brand new. The marketplaces were uncharted waters. If you lack clarity on your principles, it’s easy to get unmoored from your purpose. Oscar had to navigate a myriad of challenges facing a nascent company in a quickly evolving market. I don’t think Oscar would have survived if it had not clung to its raison d’etre. Ultimately, through Oscar’s early years amidst legal challenges to the ACA, competitors entering and exiting, and high levels of uncertainty, Oscar remained focused and built the foundations of a product that members love.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I love that I get to be part of a community at Oscar of people who are smart, hard-driving and care about the mission. A few of the traits that I believe are key to our growth are the following:

  1. Be intellectually curious. I think that’s always been a bit of my inclination. I’ve never been content to just swim at the surface. I’ve always tried to dig deeper into the “why” to better understand the greater connections between what’s going on and what is at the root of any challenge. I recognize that curiosity in our leadership and my teams. We’re surrounded by high-integrity, crazy smart people. It’s a special place to be.
  2. Work hard. I was raised to value hard work. I come to work every day and spend time with others who want to innovate, do things differently and shift paradigms. I think real change requires rolling up your sleeves and doing the work. The best ideas are just that — ideas — until you put in the work to convert those ideas into action. At Oscar we say, “no genius without grit.” Our team’s hard work is at the center of our innovation, entering new counties and new states, and taking new products to market.
  3. Be personally invested. I care about the people I work with and the work we are doing together. I am deeply motivated to try to create teams where people of all backgrounds have a sense of belonging. In doing so, we can collectively do right by our members. Change and disruption is hard, and when you’re going through hard moments you want to do it with people who put their heart in it.

Leadership often entails making difficult decisions or hard choices between two good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Recently, the Centers for Medicare & Medicaid Services (CMS), announced its intention to limit non-standard plans that carriers can offer on the ACA Marketplace. This was a huge strategic hurdle for Oscar because we’re built on the principle that innovative, member-centric plans tailored to the unique needs of individuals are essential to better care. I had to decide what to do about it. As a leader we constantly make choices on how to spend limited resources. Oscar is still a relatively small player in healthcare (where the scale of legacy players is huge). And our regulators are juggling their own priorities. We had to decide whether this was an issue where we wanted to concentrate our finite influence to try to punch above our weight.

We know that one-size-fits-all care plans aren’t working, but we had to invest time and resources into making our case. On the one hand, we invested in relationship building — meeting regularly with regulators at the state and federal levels. On the other hand, we invested in data. We beat that drum. We took data demonstrating what consumers want and what consumers choose. For example, Oscar offers personalized plan designs for members who suffer from chronic illness including Diabetes Care, to support diabetic members, and Breathe Easy, which addresses the needs of individuals with COPD and asthma. We know that, because of their unique needs and preferences, consumers tend to choose non-standard plans when given the choice. Approximately 88% of Oscar’s members nationally enrolled in non-standardized plans in plan year 2023.

In the end, we influenced CMS ensuring there will be an exceptions process to bring these innovative plans to market. We built credibility with our regulators, we pushed for policy that serves the interest of members, and we are ensuring access to plans that are more personal and relevant to their needs. I’m incredibly proud of my team for their leadership on this issue. It’s also a validating decision that we should spend our energy on the things that have the deepest impact on our customers. When we do that, succeed or fail, we can at least ensure there are no regrets.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. In the context of a business, what exactly is “Disruption”?

For me, disruption means being unafraid to challenge the current system.

How do you perceive the role of “disruption” within your industry and how have you personally embraced it? Is it a necessity, a strategy or something else entirely in your view?

At Oscar, it started with a basic premise. We think the healthcare experience is broken, and we believe our technology and our focus on wanting to deliver a great customer experience can lead to something better. And we’ve stayed laser-focused on that.

The growth followed. Whether it’s through our AI integration or our customizable plans, we ask ourselves what’s our hedgehog principle? What’s the thing that we can do better? It’s that first principles thinking that enables us to be super disruptive in a highly regulated and complicated industry.

What lessons have you learned from challenging conventional wisdom and how have those lessons shaped your leadership style?


Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition and what advice would you give to others in a similar situation?

There are a lot of fears and misconceptions about the role of AI in healthcare, and for that reason, there is confusion and resistance. Given the rapid development of AI, policymakers are unsure how to proceed. Consumers are nervous about what AI means for them. And nobody wants a situation where there are 50 or more different frameworks regulating AI.

When we started developing our first generative AI features, we set up an AI Governance Committee to vet use cases and set guardrails, using a risk-based approach. Leveraging relationships we had with others in the industry and our experience building effective governance over AI tools, we worked with other payors and providers to come up with a set of healthcare AI commitments. Our efforts paid off. Late last year, 27 forward-thinking payers and providers co-signed a pledge with us, supported by the White House, that commits to developing AI solutions that are safe, secure and trustworthy. The commitments are intended to build trust with consumers and policymakers by, for example, informing users if content is largely or exclusively AI generated and not subject to human review. Each organization committed to effective governance, risk mitigation and responsible development.

My team was instrumental in developing these commitments, and we have continued to see more organizations sign onto these commitments. You can read these commitments in full at healthcareaicommitments.com.

As for advice, lawyers are conservative by nature. It is much easier to follow established precedent. My advice is to know your goals — where are you trying to go as a business and then focus on how you can make it possible.

What are your “Five Innovative Approaches We Are Using to Disrupt Our Industry”?

  1. Be brave. Rely on your first principles thinking to solve novel problems. Don’t be afraid of things that are new, be curious and figure out how it can work. Oscar has done this over and over, leading into the ACA, AI, and now chartering a path forward on the future of the individual marketplaces and the role for ICHRAs.
  2. Make the complex simpler. It was Mark Twain who once said, “If I had more time, I would have written a shorter letter.” It’s hard to make complex things simpler, and I think doing so is disruptive. It is hard to figure out how to find an in-network provider who can see you or how to find out what your imaging is going to cost you. At Oscar, we’re dedicated to simplifying healthcare. It’s a matrix of regulations, networks and payers, all operating under different sets of rules. We can’t be immobilized by this patchwork — we owe it to our members to simplify their experience.
  3. Focus on the consumer. We believe passionately that people should be able to chart their own way forward in healthcare. The most important thing we have is our health. Consumerization helps us enable members to make their own choices about what works best for them. That’s why we are focused on developing more customized plans that meet the needs of different populations.
  4. Be a connector. The world is increasingly connected, but healthcare remains very fragmented. Many of us have had the experience of taking a sick parent or child to different providers, who each prescribe a new medication or treatment, leaving us feeling overwhelmed and lacking clear direction. This fragmentation causes real burdens for people. Oscar is designed to create a flywheel based on connecting patients and their network of providers with the right information at the right time. I believe we can work in a more integrated, seamless way — powered by AI and our tech stack.
  5. Question assumptions. One thing I love about Oscar is that we question everything. This includes questioning the future of health insurance writ large. What would it look like if providers formed custom, fluid networks around each patient and took risks together? Is there a future world in which we provide the technology and the financing to make that kind of custom care possible? It will never happen if we are too afraid to question how we operate today.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

It’s defined my entire experience. There have been so many times when I made choices that defied conventional wisdom on career paths. When I was young, I wanted to understand the healthcare system better. Instead of seeking a fancy internship, I volunteered at a Ryan White clinic serving HIV and AIDS patients, I got a summer job at a free clinic, and I flew to El Salvador with Nursing Students Without Borders. I got to work with people who were dedicated, making an impact and were serving with humility. This was incredibly inspiring, and those experiences had a lasting impact on me as a leader.

As a dutiful South Asian daughter of immigrants, I was on track to be a doctor. When I was writing my applications for medical school, everything that I wrote was about the system of healthcare and how it’s broken. It made me realize that studying law and health policy was what I really wanted to do. So, after four years as a pre-med, biology major, I decided to pivot and follow my gut.

In law school there are two very well-defined paths for success: First you go clerk and then you go to a white shoe firm. I did neither of these things. I knew what kind of work I wanted to do, so instead I focused on where I could get the most experience, where I could get a breadth of exposure to work that I cared about. I went to a small firm where I got direct experience with smaller clients. But I got more visibility and I saw more issues. I saw how decisions get made and how to influence them. And this set me up to be in-house empowered not just to advise from the side-lines, but ready to roll-up my sleeves and build.

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

I was raised Buddhist. There is a tenet in Buddhism of accepting that the world is ever-changing and that we need to find our peace within a world that is full of tumult. I have so much more work to do on that journey. But in the face of change, I try to ground myself in a practice of gratitude and try to preserve the things that matter most to my heart. I also try to stay open to newness, realizing that while leaving the known behind can be scary, that growth and life is found when we venture into new experiences.

In your role as a C-suite leader, driving innovation and embracing disruption, what thoughts or concerns keep you awake at night? How do these reflections guide your decisions and leadership?

At Oscar, we are conceiving of the future for individual coverage. Our path through life is different than it was 10, 20, 30 years ago. We need to expand the way we think about portability for people so that they can change jobs, have major life events and still keep stability in their healthcare. The American healthcare system was built upon a legacy premise of getting your health insurance as a benefit from your employer. That old premise was built in a day when people picked an employer and stayed at the same company for decades. But does that legacy still serve us as we become entrepreneurs and start business, or work the gig economy when we need flexibility, or we change jobs to find new opportunities? Clearly, no.

As we think of what an alternative paradigm could look like, I worry. What if we push forward with changes and people are harmed? What if the new framework has unintended consequences that worsen instead of improving people’s access to quality coverage? I think it is good to give voice to these worries. In fact, as a leader I would not be doing my job if I didn’t worry about the consequences of our actions. That worry is really a nudge from my moral center saying, “make sure you are doing the right thing.” And I think we should always listen to that voice, and then we should always dig in and ensure we are doing right by the people we serve.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

That’s funny. I certainly do not think of myself as a person of “great influence.” But I do hope to ensure what little influence I do have is meaningful and good. Each of us is on our own journey, personally and professionally. And I think those two things are inextricably entwined. There is a movement, supported by wisdom from Jerry Colona in his book, Reboot, that the work we need to do to become good leaders is actually the work we need to do to become good humans. Kindness and empathy play a role in strong leadership. I think good leaders are good listeners and create teams where people can feel seen and belong. The work we’re each doing on our own personal development, being more centered, more capable to get outside of our heads and really listen, trying to understand people — that’s the work we need to do to be good leaders.

How can our readers further follow your work online?

Honestly, I live my life IRL and have very little social media presence. But if you’re looking, you can find me on LinkedIn: Ranmali Bopitiya

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.