Amy Papsun Supports Healthcare in the New Age

Amy Papsun, Oscar Health’s associate general counsel and senior director, is passionate about making healthcare more effective and convenient for clients

Amy Papsun, Associate General Counsel and Senior Director, Oscar Health Photo by Greg Hernandez

When Amy Papsun took her first job in the healthcare field, she had no idea it was the first step in a career she would become so passionate about.

“I was a senior in college who needed a job. I randomly found a job at a health law boutique firm,” Papsun explains. “It was totally by happenstance, and that random thing has proven to be really influential in my life. I found that the work was just super interesting.”

Papsun started out at that firm as a paralegal after graduating from American University. She was good at the job and found the work fascinating, so she returned to school at the University of Wisconsin. There, she earned her law degree and a master’s in public health.

Her career has culminated in her position as associate general counsel and senior director at Oscar Health, a tech-driven health insurance company. She leads a team of attorneys and nonattorney professionals in providing legal advice and identifying statutory and regulatory requirements for business operations teams.

She describes Oscar as “a mission-driven company” whose founders include CEO Mario Schlosser. He was inspired to establish the firm after he and his wife dealt with some typical insurance hassles—such as trying to understand why they were being charged for certain services and receiving paperwork that looked like bills but weren’t—when they were expecting their first child.

“I love it because it’s never static. There’s always something new going on, and everyone always has thoughts and opinions, which is just so interesting.”

“The company was founded by people who were not entrenched in the healthcare system and called out some issues that we have all seen,” Papsun says. “It really defines our work and the employee culture, in terms of working for that common goal to help people live healthier lives and do it in a way that’s easier.”

That has led to numerous innovations. For instance, Oscar created technology platforms that allow clients to access information, such as what they owe or how to get involved in a wellness program, via their smartphones.

“It’s more in line with the twenty-first century life that we’re all experiencing,” Papsun notes.

She also enjoys working at Oscar because of its company values. Two of her favorites are “seek the truth” and “inspire and provoke.”

“The first one is pretty self-explanatory,” Papsun remarks. In terms of the second, she says, “As attorneys, we’re always looking for what our requirements are. Working at Oscar has been super interesting because our legal team is consulted for a variety of interesting and innovative business initiatives.”

Sometimes, when her team is offering guidance on something and they don’t see that it can be done the way it’s being proposed, then new doors are opened for discussions about alternative options.

“In talking about those options, sometimes we come to other ideas or new ways to do something,” Papsun says. “That way, we’re inspiring our business partners to think through things that they can try out.”

In her two and a half years at Oscar, Papsun has grown from an individual contributor to someone who manages a team that works on various initiatives to help the company grow. Among the projects keeping her team busy is Oscar’s new partnership with Cigna, which Papsun says will allow Oscar to bring its experience-focused approach to healthcare to more people.

“It’s such a joy to continue to work with them on this project,” she says. 

“The company was founded by people who were not entrenched in the healthcare system and called out some issues with the system that we have all seen. It really defines our work and the employee culture.”

Oscar is also committed to another issue that Papsun is passionate about: encouraging women to pursue and attain leadership roles.

“In the legal industry in particular, we have an issue where the entry rate for law school between men and women is about equal. But then, as you work your way up the ranks in a firm or in private industry, you see the number of women just dwindle,” she explains. “I find it very important to support women and support paths to leadership so that we have a more diverse company and a more diverse industry.”

Oscar’s initiatives that support women include employee resource groups and policies related to time off, parental leave, and flexible schedules that give employees work/life balance.

Papsun also appreciates that Oscar is a place where employees can freely share ideas and develop innovations. And even though her career in healthcare wasn’t part of a grand plan, it has turned out to be the perfect fit.

“It’s been so interesting, since the passage of the Affordable Care Act, and recently with COVID, to be there at the cutting edge,” she notes. “I love it because it’s never static. There’s always something new going on, and everyone always has thoughts and opinions, which is just so interesting.”


Kennaday Leavitt PC:

“Amy excels in a demanding, highly regulated area of law—healthcare—and works for an innovative, fast-growing company, Oscar. She more than meets those challenges with creative solutions for Oscar and regulators.”


Meenan PA:

Because Oscar is an innovative technology company, rapidly entering new health insurance markets utilizing its online portal to support Exchange or Medicare Advantage plans, Amy always asked cutting-edge compliance questions in need of rapid solutions. It’s always a pleasure assisting Amy in advising her internal clients.”

Joy Moore Ryan, Shareholder