Kerri Shields knows that success isn’t just about chasing milestones—it’s about staying grounded in who you are. As the President and Co-Founder of Playeasy, she shares her purpose-driven leadership journey, reflecting on what it means to build a meaningful career while celebrating small wins, staying present, and embracing the messy middle. From startup lessons to personal rituals, Kerri’s story is a powerful reminder to lead with intention and live fully, no matter where the road leads.
When you think about living a life that you love, what is it that you picture?
I have always made a conscious effort to surround myself with good people. I get a lot of fulfillment from people who make me want to be better, who love and support me—not just me as a professional or what’s going on in my life at that point, but me as a person.
I love to laugh and have a good time, and I really try to fill my cup by surrounding myself with people who make me feel like my best self but also challenge me to be the best version of myself. I feel incredibly lucky to have a great family and friends who have supported me through it all. For me, living a life I love doesn’t mean having it all figured out—it means being intentional. It means showing up fully, surrounding myself with people and work that light me up, and finding joy and purpose in the process.
Life will always evolve, but as long as I’m growing, connected, and grounded in the things that matter most, that’s a life I love.
How do you balance your ambition with life?
I’ve really tried to strike a balance between ambition and living a fulfilled life. This is something I learned early on during my time as an athlete at Boston College. When you’re playing sports, you’re always working towards a goal. One thing that taught me—specifically my college experience, because there was a lot of change that was out of my control—was to expect and plan for uncertainty. I had three coaching changes, a ton of transfers, and all kinds of things that I had no control over. I don’t think I took enough time to enjoy the journey and be present while striving toward that goal, but that is something I am really working on doing now.
Co-Founding a company has probably been the hardest thing I’ve ever done. I’ve tried to celebrate the small wins—because the small wins are big wins. A small win today would have been the biggest we could have imagined five years ago. But that goalpost keeps moving forward. It’s constant and never-ending. So I really try to take time to be proud of what we’ve accomplished and enjoy more of the day-to-day.
I’ve also been intentional in finding things outside of work that really make me happy. I love spending time with the people who bring a lot of joy in my life, being active, going to the beach and traveling and exploring new places and meeting new people. I’m working out daily. I love yoga, I love reading, I love going for walks. I’m doing everything I can to fill my cup and be more present in this journey.
How has community been a part of your journey to this point in your life?
Community has been everything—both professionally and personally. My first community and biggest support system is my family, but my parents always encouraged us to meet all different types of people. And since then, I’ve been surrounded by people who believed in me, challenged me, and showed up for me—whether that was my family, my teammates, mentors, or now the incredible people I get to work with. Through every step in my journey I’ve relied on the community I’ve built. Never in a million years did I think I would start a business, but I wouldn’t have gotten to the next step in my journey without my community.
Now, I work remotely and have traveled a lot, and it can be hard to find a work community because we’re a small team and our customers are all over the country. Part of what I’ve done is seek out mentorship within my professional career. I just got back from a women’s conference at the Women’s Final Four, and these spaces allow me to grow my community with like-minded individuals.
What are those habits that have allowed you to get to where you are today?
I’ve always been an active person. Before I can do anything professionally during the day, I need to take care of myself. That’s something I’ve really invested in—doing the little things that make me happy every day. That includes working out, going for walks, listening to podcasts, listening to good music, reading—things I know will put me in the right mental space to be the best leader I can be.
I started journaling recently, and that’s been really helpful in reminding myself of my why. When we first started, it was easy for me to lose sight of the end goal. I’d ask myself, Why did I want to invest so much time and energy into building something? It’s because I believe in the power of sports and the power of connection. I truly believe in the impact both can have—on an individual, an organization, a community, or a city.
Personally, it comes back to the people I surround myself with and how I take care of myself. Life is a roller coaster. There are highs and lows, and I’ve learned that I can’t pour from an empty cup. I try to make sure I’m grounded and taking care of my own well-being before I give too much of myself away.
That’s taken a lot of intention—and honestly, it’s still a work in progress. But I’ve come to believe that prioritizing your own health and surrounding yourself with the right energy isn’t selfish, it’s essential.
What do you think the key is to getting women to stand in their confidence and lean into their potential?
I was recently talking about the first time I read the book Lean In when I was deciding whether or not to go abroad, and it really impacted my decision in the best way. I was scared and nervous to enter something completely new in a place where I knew no one. That book encouraged me to lean in—to have confidence in the unknown. That experience of living and learning and playing abroad is something I credit a lot of my success to.
A lot of my confidence comes from experience. If I hadn’t put myself in uncomfortable situations, situations where I had no idea what would come of it, I wouldn’t have learned as much. I’ve pushed myself into situations that were uncomfortable, uncertain, and sometimes intimidating—and those moments have taught me the most. I’ve leaned into every opportunity to grow, even when it’s uncomfortable, and that’s helped me become a better leader.
I don’t lead with ego. I’ll do whatever it takes to get the job done, and I don’t pretend to have all the answers. I encourage women to lean in, especially because, now that I’m at the executive level, I’ve realized: no one has all the answers.The more experience you get, the more confident you become. Be a sponge. Stay curious. Learn from every experience, conversation and challenge you face. That’s how I’ve been able to build my confidence.
If you were to rewrite a rule for women, what’s one you might edit?
I was raised to believe that with hard work, anything was possible. My parents instilled in us that we could become whoever we wanted to be—as long as we were willing to show up, do the work, and stay true to ourselves. My mom has worked full time my whole life—she is my biggest role model and inspiration. She showed me what it means to lead with strength, empathy, and grit.
Because of that, I grew up never questioning whether I could lead, build something, or chase big goals. And that’s one of my greatest privileges: I didn’t let barriers define what was possible for me.
That confidence, that permission to lead authentically—it isn’t always given. So if I could rewrite a rule, it would be this: there are no rules. You don’t have to lead a certain way or fit a certain mold. I want more women to feel empowered to lead as they are, not as who they think they’re supposed to be.
What legacy do you hope to leave?
I would like my legacy to be rooted in authenticity—someone who empowered others and made people feel like the best version of themselves. I hope to be someone who didn’t just talk the talk but walked the walk and lived with purpose.
That I worked hard, but never let that stop me from being present, enjoying the moment, and finding joy in the everyday. I want to be known as someone who brought energy, laughter, and light to the people around me, even during the most challenging times. Leading professionally is one thing, but I’ve learned the importance of leading with honesty, too. I’ve let go of the pressure to be perfect, and instead, I focus on being real with the people around me. That shift has allowed for deeper connection, stronger trust, and more authentic leadership. I want my legacy to be that of someone who lived authentically, led with heart and genuinely cared about others.
Kerri Shields is the President and Co-Founder of Playeasy, the leading digital platform for the sports event and tourism industry. A graduate of Boston College, former Division I basketball student-athlete, and MBA holder, Kerri is passionate about the power of sports to create connection, impact, and community. She also hosts The Playeasy Warmup podcast, where she shares the inspiring stories of people making a difference through sports.
