Healthcare entrepreneur Andrea Ippolito on leadership: Don’t get bogged down by the small stuff

Biomedical engineer Andrea Ippolito’s career has wound through private industry, government, academia and entrepreneurship. The through line has been her drive to solve difficult problems, at scale.

Ippolito, 40, is founder and CEO of SimpliFed, a maternal health platform providing breastfeeding counseling and support via telemedicine. It costs patients nothing, thanks to a provision in the Affordable Care Act that requires insurers to cover it. Roughly 16,000 patients were referred to SimpliFed last year, she says. The company has a staff of 13 and a nationwide network of providers.

Ippolito, 40, earned undergraduate and graduate engineering degrees from Cornell University. A junior-level job at medical technology company Boston Scientific taught her “that I was a very average scientist. … What I really enjoyed was being in leadership and the business side of technology.”

That led to more graduate school at MIT, studying system design and management; co-directing the MIT Hacking Medicine group; and co-founding a medical scheduling application later acquired by athenahealth. Then it was on to a graduate assistantship for the Chairman of the Joint Chiefs of Staff, where Ippolito helped develop a telemedicine strategy for counseling active-duty military returning from Iraq and Afghanistan by tapping less busy providers at bases whose soldiers were away on deployment. In 2014, Ippolito became a Presidential Innovation Fellow, assigned to the Department of Veterans Affairs. She dropped her Ph.D. studies to continue working for the federal government, overseeing the Innovators Network, a pathway for VA employees to develop new approaches to better serve veterans and their families.

Ippolito joined the Cornell faculty in 2017 to teach engineering management. She and her husband settled in Lansing.

“Fast-forward, I had my first daughter. I saw how hard baby feeding was, and I saw how deeply connected it was to my baby’s health, how deeply connected it was to my physical health and mental health,” she says. SimpliFed grew out of her desire to provide a high level of support to breastfeeding moms, no matter where they live. And they have a right to it, whether they know it or not.

Our conversation has been edited for length and clarity.

How did you become interested in engineering?

I grew up outside of Boston, the daughter of two engineers, Mary and Steve Ippolito. I get choked up thinking about it. My mom was an electrical engineer in the early 1980s. She was the daughter of coffee shop owners in New Haven. She went to Cornell, [as] a textiles major. She then went on to design spacesuits. … She was one of the only women on the team [working out] how female astronauts go to the bathroom in space. She decided she liked the technical side. So, she went back and got her electrical engineering undergraduate and master’s degrees. She had me two-thirds of the way through it. With two engineering parents [her dad is a mechanical engineer], not shockingly, I became an engineer. It is a good example of the Marian Wright Edelman quote, “You can’t be what you can’t see.”

It’s 2025. Are we still talking about women in engineering?

It still is a thing. Institutions like Cornell have done such a great job. We’re at gender parity at the undergraduate level. The gap is in leadership. A Cornell alum, Claudia Goldin, won the Nobel Prize in Economics in 2023. She showed that what’s holding women back is it’s not necessarily a pipeline problem. There are pipeline issues, but the biggest gap is when women start having kids. And I’ve had three daughters. But I digress.

Were you in leadership roles growing up?

I was a very nervous person, but I was an extremely hard worker. … On one side of my family, I’m the granddaughter of Italian immigrants. That hustle is baked in you. I’m also a very mission-driven person. If not me, then who? I am attracted to leadership roles.

Over time I had to build my confidence and now I’m in a much better place. That came from making a lot of mistakes, learning from them. I used to play ice hockey. I was not a very good ice hockey player, but I was very scrappy and always willing to get back up. You just have to keep getting back up.

What do you wish you’d known before starting a business?

I wish I had known that there were going to be mistakes along the way and you just have to treat them as learning moments and not get bogged down. I heard another entrepreneur say this, and I agree: You can’t be fully naive to the challenges you’re going to solve, and you almost don’t want to be so embedded that you can’t see around those boulders. I feel like I had the right amount of knowledge ahead of time. I just wish I had given myself some more grace along the way.

This is your third startup. Does it get any easier?

You develop the foundational skills and the confidence, and it doesn’t necessarily get easier. The goal post changes.

I want to solve this problem and be the category leader because that is what I believe is going to create the most impact. … Our goal is to elevate this specialty so that it’s part of the maternal experience and so it becomes the standard of care. That is my expectation. When you have high expectations of yourself and your team, you can’t rest on your laurels of the experience you had before. You need to be pushing the boundaries and the status quo to make a difference in people’s lives.

Do you consider yourself a visionary?

I consider myself someone who is not happy with the status quo … who is not willing to stand by the sidelines and accept the status quo. I am a problem-solver. I’m an engineer at heart and I have a ferocious attitude toward solving problems at scale.

Is there a decision that you wish you could take back?

No. Every part of my career trajectory, every part of our company’s trajectory, has been a huge learning moment and an opportunity to get better and stronger. … Everything that might have been a mistake or a misstep allowed us to get to where we are today.

You directed Cornell’s engineering management program for a time. What does it mean to be a leader who also is an engineer?

I believe with a lot of gusto that there are no better leaders than engineers because we have that mindset of overcoming problems and developing solutions with stakeholders and customers. That’s inherent who you are after your training. And there’s also an ethical responsibility to that.

Why I loved that program, and still do today, is because it allows people to continue to build those engineering skill sets but also build those management and business skills. You can speak both languages, which allows you to communicate with stakeholders. It allows you to ask tough questions. I always tell my daughters at the end of every week: What good questions did you ask? That’s such an important skill. When you ask questions, it shows that you understand and you’re trying to learn more and you’re curious. When you’re an engineer, you’re inherently curious.

Do you have a theory of leadership?

I’m learning along the way. I absolutely believe in servant leadership. I believe very strongly that you need to … have done the tasks yourself in order to understand the system you’re operating in. I am a big believer in understanding what people value. … I’m not perfect on this, but I think you have to recognize and appreciate people along the way or else you have no hope of tackling whatever mission you’re on. VA Secretary Bob McDonald always said we have no hope of improving the veteran experience unless we improve the employee experience. I believe that to the core.

You have to understand the pain point of your customers. I happen to be a patient on our platform, too, so I do understand. I don’t think that is sufficient. We need to be relentlessly focused on the needs of our customers. Your whole organization should be focused on patients and the stakeholders that you have the privilege and honor of serving.

Do you think women lead differently?

100%! I saw this. First off, let’s talk about it from a return-on-investment standpoint. We know from the data in refereed, peer-reviewed journals that woman-led companies perform better. They return more money, they are more innovative, and they get there faster.

Let’s talk about the qualitative side. [The comedian] Amy Schumer talks about how, in schools, moms are the ones who are always organizing stuff. … What is happening in K-12 schools, behind the scenes, extracurricularly or in kids’ lives, birthday parties, etc., it’s led by moms. Imagine if men were doing all that. It just wouldn’t happen. And yet in the world, in business and in government, it’s mostly led by men. And we wonder why there’s so many bad repercussions right now.

I fully believe that if women were leading many different aspects of our lives, we would perform better, because that’s what the data shows. If we had more women leaders, we’d have better returns, because that’s what the data shows. We’d have more empathic leaders. We’d be getting farther, faster in a way that ensures that we’re working at the highest levels of everyone involved, and people feel respected and recognized.

What’s the best piece of advice that a parent, mentor or boss ever gave you?

My mom got me this little book as a stocking stuffer, “Don’t Sweat the Small Stuff.” In my early teenage years, she could see I was getting activated by really small things. … It goes back to my mindset right now of treating each mistake or sidestep as a learning opportunity. You have to stay focused on your learning and your growth along the way. … In order for us to achieve impact in our lives, you can’t get bogged down by the small stuff. You have to keep pushing.

What advice would you give to somebody who aspires to become a leader?

Find a sandbox environment where you can try on new skills, including leadership skills, for size. … For me, early in my career, that was the Society of Women Engineers, the Biomedical Engineering Society, various professional organizations. I started the women’s network at my first company, Boston Scientific. I did it because, A, I loved it, I was passionate about it, and that’s always got to be your North Star. B, I was looking to try on new skills that maybe I wasn’t getting in my day job. Those [roles] were instrumental for me learning how to speak publicly and for building a team and trying on new skills that I didn’t have.

Find a club or organization that you believe in and are passionate about, and try to find small, medium and large leadership roles with them.

What advice would you give somebody starting a career now?

Don’t try to find the perfect role. ... Don’t overthink it. Just get into the arena. Once you get into the arena, you’re going to see so many different aspects of the world, and the professional world, that you’re going to want to get into. I’ll give you an example. I entered as a scientist because research was all I knew. I got into the arena, and I saw I was pretty mediocre at this. And while I like it, I don’t love it, but I got exposed to a lot.

You also probably don’t know what your strengths are.

Find a career or a pathway where there’s a growing market need, you’re good at it and you’re passionate about it. If you can find the convergence of those three things, that’s where you should focus your effort.

You probably could live anywhere. Why here?

First, quality of life. The lakes, the gorges, and the waterfalls and just everything that’s in Central New York, it’s just a beautiful place to live. That matters.

Second, historically, this region has been at the forefront of so much technological change and pace, and I am a big believer that the plane parts are all here. How do we leverage that know-how?

Third, I have an incredibly supportive partner who believes in me, believes in our work, and is willing to put up with a heavy travel schedule. Having a supportive partner is a critical part of being an engineer. And he’s from Central New York. … It’s an incredibly strong community.

The weekly “Conversation on Leadership” features Q&A interviews about leadership, success and innovation. To suggest a candidate for Conversations on Leadership, email Marie Morelli at mmorelli@syracuse.com. Read previous entries in the series.