Kerry Sain Of Oscar Health: How AI Is Disrupting Our Industry, and What We Can Do About It

An Interview With Cynthia Corsetti

Employ an agile and robust AI governance process, which includes regular checks on the accuracy and performance of our models and a diverse leadership committee that provides consistent, well-rounded inputs.

Artificial Intelligence is no longer the future; it is the present. It’s reshaping landscapes, altering industries, and transforming the way we live and work. With its rapid advancement, AI is causing disruption — for better or worse — in every field imaginable. While it promises efficiency and growth, it also brings challenges and uncertainties that professionals and businesses must navigate. What can one do to pivot if AI is disrupting their industry? As part of this series, we had the pleasure of interviewing Kerry Sain.

Kerry Sain is the Executive Vice President of +Oscar, where she oversees the go-to-market strategy for Oscar’s platform business.

Kerry is a seasoned business executive and experienced board member with over 30 years of proven results globally and has developed a track record of maximizing customer value and driving unprecedented levels of sustainable growth with a people-centric focus.

Kerry most recently served as the Chief Commercial Growth Officer for Aetna, Inc. In this role, she was responsible for managing all segments across the company’s extensive commercial markets medical business. Prior to this position, Kerry held a variety of senior positions, including President and Executive Managing Director of 13D Global Strategy and Research, Chief Revenue Officer at SAP America, Inc., CEO and President of bswift (part of CVS Health), as well as a Senior Partner at Mercer.

Kerry is passionate about bringing people, processes, and technology together to create the very best outcomes in work and life. She is a strong advocate for mentoring today’s talent to become tomorrow’s leaders, building team cultures focused on inclusivity and integrity, and leveraging her broad expertise to enable the success of companies spanning all types, sizes, and maturities.

Thank you so much for joining us in this interview series. Before we dive into our discussion our readers would love to “get to know you” a bit better. What do you think makes your company stand out? Can you share a story?

Since its inception, Oscar has been focused on making a healthier life affordable and accessible to all. We invested early on in building our own technology stack, allowing us to create a health insurance company that fits around the consumer and not the other way around. We value the experiences our members have with their healthcare and seek to make every step of the process as smooth and affordable as possible.

I’ve been in the healthcare space for many years. None of what has been rolled out over the past 20 years has been effective in bending the cost curve. Actual health — which is a meaningful and accessible experience between individuals and their healthcare providers, at a reasonable cost — is what will help empower people to take proactive steps towards their well-being. It sounds basic, but it isn’t.

I have followed Oscar for a long time. Oscar’s use of innovative technology to analyze and understand our members, to be more caring and personalized, sets us apart from other health insurers. I wanted to be part of this journey. I also believe powering as much of the healthcare ecosystem as possible will be a game changer that positively impacts people’s lives. There’s something special here.

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

The challenges facing today’s business leaders are dynamic and complex ― and that requires us to be growth-oriented and adaptable. While there are many different traits that leaders bring to the table, four that rise to the top for me include:

  1. Grit. I tend to be a pretty relentless person; relentless in my commitment to being part of the solution to drive change, even when it is a struggle. Oscar has a value, “no genius without grit” that really resonates with me. To me, “no genius without grit” is about change, embracing what it takes to get there and an attitude to keep learning. A lot of people talk about change, but few talk about the grit and the pain (and the joy!) required to actually effect it.
  2. Adaptability. Executing a plan and having a vision is essential, but we can’t predict the future. Change is constant. Our capacity to adapt, embrace and effectively manage change not only elevates our leadership but also empowers us to guide our teams toward greater heights.
  3. Being team-oriented. One of my favorite things about Oscar is that everyone jumps in to get “it” done. I love seeing the startup mentality remain. We haven’t lost the scrappiness and tenacity. Being part of a team working from the ground up is thrilling. This mindset has always been part of how I view the world.
  4. A sense of humor. Don’t take yourself too seriously. Being approachable and human impacts your team’s mojo and energy.

Let’s now move to the main point of our discussion about AI. Can you explain how AI is disrupting your industry? Is this disruption hurting or helping your bottom line?

As a tech-driven insurer, Oscar has a unique purview on AI. We believe large language models provide a once-in-a-generation opportunity to drive the change we want to see in healthcare. AI can help streamline and simplify processes that have historically made the healthcare experience cumbersome and costly — resulting in an easier, more pleasant and more engaging experience for every person navigating the healthcare system.

We are unique in having built a proprietary tech stack that we believe will enable us to make use of large language models across every aspect of healthcare. This can become a competitive advantage for us and Campaign Builder, our engagement and automation platform. AI continues to be a part of our overall strategy to ensure our technology can deliver a superior member experience, improve health outcomes, meet provider needs and lower costs — and we continue to incorporate AI use cases across Oscar and +Oscar.

Can you share a pivotal moment when you recognized the profound impact AI would have on your sector?

Given the speed of AI, we believe constant experimentation, learning and sharing is the best way to navigate the technology. We call this approach a “continuous hackathon,” and it enables us to iterate and constantly improve. We have had numerous AI-themed hackathons at Oscar, and it’s through this forum that you see how significant this technology really is, and the impact that it can have on our business.

How are you preparing your workforce for the integration of AI, and what skills do you believe will be most valuable in an AI-enhanced future?

Machine learning used to be the domain of data scientists and a highly trained set of people. Today, large language models are broadly available, and anyone can now be their own data scientist. It’s a matter of training people to use these models (and in the case of healthcare, doing so safely) and rebuilding workflows so more people can participate in the creation, experimentation, learning and sharing at the pace AI development requires.

In an AI-enhanced future, in addition to familiarity with AI tooling, employees will need to possess strong critical thinking and problem-solving skills to interpret AI-generated insights, assess their implications and make informed decisions. This involves the ability to ask meaningful questions, evaluate evidence and adapt strategies based on changing circumstances. We’re helping develop these skills by investing in our people and providing everyone in our tech organization access to HIPAA-compliant AI tooling — so everyone can test out ideas, immediately, from big, radical ideas to small but clever productivity hacks.

What ethical considerations does AI introduce into your industry, and how are you tackling these concerns?

AI can drive powerful outcomes, but companies need to leverage it responsibly. The stakes are incredibly high with Artificial Intelligence. Oscar is extremely sensitive to the fact that AI can perpetuate disparities and include biases that contribute to incomplete data sets.

Last year, we got together with 27 of the most forward-thinking payers and providers and the White House to figure out how we leverage frontier AI models to drive the change we want to see in healthcare. We collaborated on a set of voluntary commitments to guide the use of frontier AI models in healthcare delivery, administration and payment.

These commitments include:

  • Developing AI solutions to optimize healthcare delivery and payment by advancing health equity, expanding access, making healthcare more affordable, improving outcomes through more coordinated care, improving patient experience and reducing clinician burnout.
  • Working with our peers and partners to ensure outcomes are aligned with fair, appropriate, valid, effective and safe AI principles.
  • Deploying trust mechanisms that inform users if the content is largely AI-generated and not reviewed or edited by a human.
  • Adhering to a risk management framework that includes comprehensive tracking of applications powered by frontier models and an accounting for potential harms and steps to mitigate them.
  • Researching, investigating and developing swiftly but responsibly.

We are continuing to see more payers and providers sign on to these commitments, which you can read in full at

Internally, we developed an AI governance process and acceptable use policy to ensure we leverage AI in a responsible, safe and secure way. Our cross-functional governance committee of lawyers, engineers and clinicians is tasked with developing and maintaining Oscar’s AI use policy and its guardrails. The committee signs off on features before they go into production and ensures companywide adherence to best practices, regulations, ethical standards and other rules for working with generative AI.

Our guiding principles in utilizing AI include:

  • Safeguarding our member and provider data
  • Upholding our standards for quality, safety and accuracy
  • Continuously providing a positive experience for members, brokers, providers and internal users of our technology

What are your “[Five] Things You Need to Do, If AI Is Disrupting Your Industry”?

For those in industries experiencing a sudden surge of AI, I would advise what we at Oscar are actively doing each day:

  1. Focus the power of AI in “no regret” areas to streamline backend processes.
  2. Carefully launch any feature that impacts member care and/or experience.
  3. Commit your organization to continuous learning.
  4. Employ an agile and robust AI governance process, which includes regular checks on the accuracy and performance of our models and a diverse leadership committee that provides consistent, well-rounded inputs.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

There’s a quote by Dr. Maya Angelou I always think of when discussing the impacts of mentorship and interactions with people along the journey, “I’ve learned that people will forget what you said, people will forget what you did but people will never forget how you made them feel.”

Mentorship and the meaningful act of dedicating time to others have been pivotal themes throughout my career. Mentorship has been something I’ve always been passionate about, especially for women early in their careers and young girls. I have always wanted my daughters — and others I’ve mentored — to know that humility, empathy and compassion as a female do not make you a weak leader or employee. Lead and work in a way that’s true to who you are. All of us can have an impact on something or someone.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Am I moving fast enough, am I being open and receptive to continuously learning? How that influences my actions is to periodically press pause and purposely reengage in embracing new ideas.

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. 🙂

Giving people your time and undivided attention is so valuable. We’ve become much more siloed in our own little bubbles. Bringing back the deliberate, yet casual, “fireside chats” where everyone has a voice and there is no hierarchy or agenda, would reinforce how important connectivity with others is. No one has conversations anymore; it’s a lost art!

I believe it’s important to impart lessons and share failures and learnings with the next generation. Through human conversation and giving of your time, we all have an opportunity to impact someone’s life — no matter where you are in your career.

How can our readers further follow you online?

LinkedIn —

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.