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Dr. Jessica Grossman: “Not everyone is going to like you”

Not everyone is going to like you. This is so important for women to hear, because many of us tend to be “people-pleasers”. I used to work way too hard to make sure that everyone was happy. Pleasing everyone is exhausting, and impossible! I remind myself of this constantly. As a part of our series […]


Not everyone is going to like you. This is so important for women to hear, because many of us tend to be “people-pleasers”. I used to work way too hard to make sure that everyone was happy. Pleasing everyone is exhausting, and impossible! I remind myself of this constantly.


As a part of our series about strong women leaders, I had the pleasure of interviewing Jessica Grossman, MD. Jessica is the CEO of Medicines360. Dr. Jessica Grossman has dedicated her career to women’s health and building communities of women who can empower one another through their healthcare choices. She is working to ensure that all women have access to the most effective forms of birth control — no matter where they live, how much they make or if they have insurance. A trained OB/GYN, Dr. Grossman chose to follow a less-traditional path and pursued a career in medical technology and entrepreneurship. That bold change in direction empowered her to become one of the few female CEOs in the male-dominated Silicon Valley.


Thank you so much for doing this with us! Can you tell us a bit about your “backstory”? What led you to this particular career path?

I always had my heart set on being a doctor. However, during my OBGYN residency I realized I could do more in different ways. I witnessed firsthand the failings in women’s healthcare that led to a lack of effective birth control options and high rates of unplanned pregnancies. I was passionate about women’s health, but I wanted my focus to be on finding evidence-based solutions to these issues. I also felt drawn to technology, so I took my training as an OBGYN to Silicon Valley, where I started my first company. At Gynesonics Inc., I focused on minimally invasive surgical solutions for women’s health. This experience confirmed my love for transforming the current state of women’s health. Since then, I’ve led multiple organizations focused on addressing issues in women’s health. This all led me to Medicines360, where I am channeling my passion to bridging the gaps in women’s health with innovation.

Can you share the most interesting story that happened to you since you began leading your company?

When I became the CEO of Medicines360, I wanted to understand the organization from every angle. So, I spent my first year out in the field with the sales team. This experience showed me firsthand what practicing physicians were saying and thinking about our product and the current state of women’s health through the eyes of their patients. I learned that low cost and low price doesn’t necessarily drive adoption of a product, which I didn’t expect.

I learned that physicians are constantly bombarded with information, and those I spoke to in that first year opened my eyes. They made me realize that physicians don’t have time to change their practice parameters, which enabled me to adjust our business model to better meet their needs and those of their patients. I learned how to share information about our product and our groundbreaking clinical trial in a quick and easily digestible way. Taking time to listen and understand how to make our mission and clinical data matter was essential to my current success as Medicnes360’s CEO.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

There is one funny, albeit disheartening, mistake that has occurred several times in my role as CEO, but it wasn’t me who made it. I attended a meeting with a male colleague who worked for me when I first started at Medicines360, and the team we met with spent all their time and energy addressing him. At one point, he stopped them and said, “Why are you focusing all your energy on me? She’s the CEO.” They were extremely flustered and apologized for the confusion.

For women in leadership positions, especially in a male-dominated industry like medicine, this is a regular occurrence. I’m sure many women executives have similar stories.

OK, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO that most attracted you to it?

I was always drawn to leadership, and I feel comfortable working in leadership roles because I am decisive. I enjoy a challenge. So, navigating complex issues and pulling my resources to keep the company moving in the right direction is thrilling for me.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

What separates a CEO from other leaders is that the CEO must think about the health of the entire organization, not just one department or one line of business. The health of the organization encompasses quite a few things: human resources, morale, and all of the employees. A CEO has to think about the organization like an organism: for an organism to be healthy, every single part of that organism has to function properly.

Another important role of being a CEO is managing the board of directors. This role can be underestimated as “managing up,” and managing a board can be very challenging. You must simultaneously take the counsel of the board of directors into account and work to align them with your vision for the organization. It can be a tricky balance, because the board is likely made up of other experienced and decisive leaders.

What is the one thing that you enjoy most about being an executive?

I love the fast pace that comes with being an executive, but what I enjoy most is being a connector. As CEO, I put “the pieces of the puzzle” together by making connections between people and projects that align with one another.

What are the downsides of being an executive?

It truly is lonely at the top. The CEO does not have a peer within their organization — I am either managing up or managing down. It can be difficult to find someone with whom I can have an honest conversation. I also rarely get positive feedback. Usually, those above and below me only share feedback when it is something that needs to be improved. This can make it feel like the negative comments vastly outweigh the positive.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

A lot of people think the CEO only answers to themselves. This is not the case. In fact, it is the opposite — the CEO has to answer to everyone! Like I mentioned, you must work with the board of directors to make sure you are all on the same page. You must also work to ensure that every member of your organization is being heard and is being given the resources they need to succeed. If you answer only to yourself, you will not succeed.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

In general, women must work harder than men to achieve the same level of success. Women also have more self-doubt. We’ve all heard of the imposter syndrome, and this is something women experience much more than men. Compared to men in similar positions, I feel more skepticism directed at me that I have to fight against. Instead of feeling that I am already respected when I walk into a meeting, I feel like I need to earn that respect during the course of the meeting (and often when my male counterparts don’t).

I also see that those within the organization are affected by women’s mood in a way that they are not with men in leadership. If I am ever short, brusque, or aggressive with someone, I get the “bitchy” label that men never get. Nobody calls a male a bitch. Instead, they call him a “go-getter” or a “shark” with positive connotations.

What is the most striking difference between your actual job and how you thought the job would be?

My job is even better than a thought it would be. This is mostly because I have a strong, amazing team of people on my side. I try to let them lead, do what they want, and do what they think is right. Of course, we have worked to build this trust over the years, but I trust them wholeheartedly. I am so lucky to lead a strong, passionate team who does a good job and who has my back.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

To be an executive, you must be comfortable with risk. In my role, I often live with uncertainty and don’t always know what’s coming next. If someone is not comfortable with making decisions and being held accountable, this would be a tough role for them. As an executive, you must live with your decisions and course-correct if needed. A CEO has a lot of responsibility and must take ownership of decisions and be comfortable with being wrong or potential failure.

What advice would you give to other female leaders to help their team to thrive?

My biggest piece of advice is to listen, show up, and do your best. I mentioned the imposter syndrome before, and this is something that is very real for many women. It causes us to “get in our heads” and constantly question how well we are doing. I have to say, our best is often head and shoulders above our male counterparts, even if we ourselves cannot see that.

For your team to thrive, you have to listen. It is essential to solicit feedback and opinions from your team. From there, you need to trust in yourself and rely on your work ethic, and the rest will fall into place.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am lucky enough to have had several mentors throughout my career. At the first company I started, there was a chairman who was extremely helpful mentoring me, explaining things to me, and getting the company off the ground. He was there with me every step of the way.

Later, I had a great mentor while working at Johnson and Johnson. She demonstrated what being in senior leadership at a company looked like for a woman. She let me sit in on meetings and get a glimpse into her world. I also observed the way she interacted with others as a woman in senior leadership, of which there were very few back then. This prepared me for my current role today.

How have you used your success to make the world a better place?

I am very lucky that our product is making the world a better place. Because our organization is mission-driven and our product is literally improving women’s lives, I can make the world a better place just by showing up to work every day and doing my best.

I have also used my position to guide my son. I make sure he knows that moms work, moms travel, go to meetings, and join conference calls, moms are businesswomen. It’s important to me that he knows that I am working to provide a life for him. When boys grow up seeing their moms work and achieve, they grow into men who are allies and support women in leadership positions.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. It’s OK to fail. It is impossible to achieve something great if you don’t take a risk. Taking risks, though scary in the moment, have gotten me to where I am today.
  2. It’s OK to have doubt and not know how to proceed. Like I said, executives must be comfortable with uncertainty. As you chart a path for the company, there isn’t always a road map to follow.
  3. It’s OK to get tired and burnt out. Every day won’t be great, and jobs aren’t always happy, exciting, and fulfilling. I tell myself that having a tough day or tough week doesn’t mean I have a tough life. I’ll get through it and get motivated again, but only if I take the time to recharge.
  4. Not everyone is going to like you. This is so important for women to hear, because many of us tend to be “people-pleasers”. I used to work way too hard to make sure that everyone was happy. Pleasing everyone is exhausting, and impossible! I remind myself of this constantly.
  5. If it was easy, everyone would do it. Being an executive is hard for a reason. Fulfilling jobs are often the ones that carry the most challenges.

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

I am loving the current women’s movements that are happening, and I would like to see more of that around reproductive rights. All women deserve to have full reign over their bodies and sexual health. Part of the way women can be independent is choosing if and when they want to have a baby. Women should have the ability to pursue their own economic stability and economic freedom, and reproductive rights and reproductive health are the way to do that.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote is by Maya Angelou: “If you don’t like something, change it. If you can’t change it, change your attitude.” It sums up both my personal approach and the work of Medicines360. When we see areas in need of improvement in women’s health, we do something about it.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Definitely Melinda Gates. She is a woman of great power, but also of great vision. She is trying to make the world a better place every day, especially in the area of women’s empowerment, and I would be able to learn a lot from her.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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