With more than 30 years of experience in healthcare, Janet brings deep expertise in driving growth, embracing new technology, and creating consumer-focused solutions – all in pursuit of better health for our members. We sat down with Janet to learn what makes Oscar’s culture stand out, how listening closely to members can inspire products like HelloMeno (opens in new tab), and why she believes curiosity is one of the most valuable qualities an emerging leader can develop.
What makes Oscar such a special and unique place to work?
What stands out to me is the people who are drawn to Oscar because of the mission. There’s a real focus on making healthcare easier for the people we serve and removing some of the friction they experience along the way.
You feel that sense of purpose in meetings, at company events, and in conversations with people across Oscar. There’s this shared belief that the work we do can make real-life moments better for our members. That energy is incredibly inspiring, and I think it’s a big part of why people choose to come here and why they stay.
And, of course, if you’re in our New York office on a Tuesday, the dogs don’t hurt either.
Oscar launched HelloMeno to better support women experiencing perimenopause and menopause. Why was that important for Oscar to take on?
HelloMeno is a great example of what can happen when you really understand your customers and listen to what they need.
Women make up a significant portion of our membership, including many women who are 45 and older. When we looked closely at their healthcare needs, we saw an opportunity to improve access to care and coverage for women navigating perimenopause and menopause.
That led us to create HelloMeno, with benefits and services designed around this stage of life. It’s also part of a broader philosophy at Oscar: healthcare shouldn’t be one-size-fits-all. We have an opportunity to understand the distinct needs of the populations we serve and design experiences around them.
We’ve done that in other ways as well. Buena Salud (opens in new tab), for example, was designed to create a more culturally concordant experience for Spanish-speaking members. Spanish-speaking care guides and clinical team members can help people navigate complex benefits, find doctors, and better understand their care and coverage.
RetireEase and Complete Care (Dental/Medical/Vision all in one premium) are two new products being launched in 2026.
Oscar talks a lot about making healthcare more consumer-driven. What does that actually look like for a member?
At the heart of it is the idea that healthcare should reflect personal choice. We believe your health insurance should be portable. Changing jobs or employers shouldn’t necessarily mean starting over with your healthcare. People should have greater choice in who their doctor is, what kind of coverage works for them, and what works for their family.
Then we have to make that experience easy to navigate. That means giving members intuitive digital tools, access to information when they need it, and people who can help when healthcare gets complicated.
You can see that across the Oscar experience – from our app and shopping experience to Oswell (opens in new tab), our virtual care capabilities, care guides, case managers, and clinical teams. Technology is important, but so are the people behind it. Ultimately, all of those pieces should come together so the member feels supported throughout their health journey.
You’ve had a long career as a leader. What advice do you find yourself giving early-career leaders again and again?
Stay curious, and raise your hand.
Most of us start in our first role by chance, become a subject-matter expert, and can eventually feel defined by the job you’re doing today. One of the best ways to grow is to look for opportunities beyond the boundaries of your day-to-day responsibilities.
Volunteer for a committee. Get involved in an event. Join a project inside or outside your department. Those experiences allow you to build new skills, meet people you might not otherwise work with, and give others an opportunity to see what you’re capable of.
I’d start by making sure your manager knows you’re interested in growing and taking on new assignments. Be clear about your interests, and look for ways to be of service to your leader and your team.
But don’t stop there. One of the things I appreciate about Oscar is the accessibility of our leaders. Reach out to someone whose career interests you and ask for 15 or 20 minutes. Learn about their experience. Tell them what you’re interested in. Ask where you might be able to contribute.
Those conversations add up. They expand your network, give you visibility into different parts of the organization, and help you build a reputation that extends beyond your immediate role.
For someone who finds “raising their hand” intimidating, how do you suggest taking that first step?
Start small and be genuine.
You don’t need to walk into a conversation asking someone for a job or a major opportunity. You can simply say, “I’d love to learn more about your career and hear your advice about areas I could explore.”
Curiosity is a very natural way to build relationships. Over time, people learn what you’re interested in and what you can contribute.
And take advantage of the informal moments, too. A company event, an employee group, a conversation in the office – those interactions are opportunities to meet people outside your immediate team. Your career doesn’t have to be defined by the handful of people you work with every day.
Switching gears: If you had 10 minutes to give a TED Talk on anything, what would you talk about?
Solo travel in New York City. I travel quite a bit for work, and I’ve been spending a lot of time in New York. Of all the places I’ve traveled, I think New York is an especially welcoming city for a woman in her fifties traveling solo.
There’s so much you can experience at your own pace and never feel alone. You can find a great restaurant and sit at the bar, where you’ll often meet a friendly bartender or strike up a conversation. There’s incredible theater, public art, vintage pop-ups, pickleball clinics, and so much happening outdoors. You can be surrounded by people without feeling like you need to be with anyone.
I think my TED Talk would be “Traveling Solo - Top 10 experiences in New York City” Essentially, how to embrace the city on your own.
Is there one New York experience you’d put near the top of that list?
Joe’s Pub at The Public Theater. It’s such an intimate experience, and there’s a wonderful mix of performers and local talent in comedy, music, theater, just all kinds of performances. You can sit down, have dinner, watch a show, and feel like you’re part of the community even if you arrived by yourself. That’s what I love about New York. There are so many places where being on your own doesn’t mean feeling alone.
One final thought for people building their careers?
Stay curious about the company, the people around you, and what you might be capable of doing next.
Some of the most meaningful opportunities in a career begin because you volunteered, introduced yourself, or asked someone for 20 minutes of their time. Be willing to explore beyond the role you have today.
The people who contribute to a company’s culture aren’t necessarily doing it because it’s written in their job description. They do it because they care about the community they’re part of and they choose to participate in it. That’s something I really value about the people at Oscar.
(Editor’s Note: The interview was edited for clarity and brevity.)
Disclaimers:
This presentation is intended for informational purposes only. It is not intended to be a substitute for professional medical advice, diagnosis or treatment. Always seek the advice of your physician or other qualified health care provider with any questions you may have regarding a medical condition or treatment and before undertaking a new health care regimen, nor should you disregard professional medical advice or delay medical treatment because of the information being provided here.
Oscar Medical coverage is underwritten by Oscar Insurance Company and its affiliates. Administrative Services for all plans provided by Oscar Management Corporation. All insurance policies and group benefit plans contain exclusions and limitations. This advertisement may be broadcast in states where policies and plans are not sold. For availability, costs, and complete details of coverage, contact Oscar at 855-672-2788.
The Women’s Health with Menopause Benefits Plan is available to all eligible persons, and is most suitable for women who are experiencing, or have experienced, natural or forced menopause. This plan is available in AZ, FL, GA, IA, MO, NC, NE, OH-B (Buckeye), OH-C (Cleveland), OK, TN, and TX. Plan names vary by state: Silver Simple Women's Health with Menopause Benefits and Silver Simple Women's Health with Menopause Benefits Guided Care.
Elektra Health is available to all eligible persons enrolled in the HelloMeno Plan in the following states: AZ, FL, GA, IA, MO, NE, OH (Buckeye), OH (Cleveland), OK, TN, and TX. Clinical cost share including virtual care, personalized coaching, prescriptions, and labs follow the member’s medical plan option. See your policy for further details. HelloMeno Plan members in OK are not eligible for Elektra Health rewards.
Buena Salud plans are available in Arizona, Georgia, Illinois, and Texas. For availability, costs, and complete details of coverage, contact a licensed agent or Oscar sales representative.
