Molly Winding Dewey is the co-founder of Leena AI, a women’s health technology platform designed to help women better understand their bodies and feel more prepared and confident when seeking care. Through Leena, Molly is working to address long-standing gaps in women’s health research by creating a supportive space where women can share experiences, learn from one another, and access clear, trustworthy information. Her work is grounded in a simple observation: many women spend years navigating symptoms without answers and often feel unheard in medical settings. By combining community, education, and thoughtfully designed technology, Leena helps women recognize patterns in their health, prepare for appointments, and better advocate for themselves, while also contributing anonymized insights that can inform future research and innovation in women’s healthcare.
Prior to working on Leena, Molly co-founded Mettacool, a leadership development and coaching company supporting women working in technology, finance, construction, and engineering. Through workshops, coaching, and peer networks, the organization helped women build confidence, strengthen communication skills, and move into leadership roles. Molly’s work extends beyond her company into organizations that support families and community health. She serves on the Board of Directors for both Preschool of the Arts and Planned Parenthood Advocates of Wisconsin, supporting efforts to expand access to education, resources, and advocacy around reproductive and community health. She lives in Madison with her husband, their two kids, and two dogs. Outside of work, she enjoys spending time with her family and traveling.
What does receiving this award mean to you?
It’s incredibly humbling, and honestly, very validating. Much of the work I’ve done since graduating, especially at the beginning, can feel uncertain and sometimes even futile. This recognition is a reminder that those early efforts matter. It also speaks to how impactful the J-School was for me — the skills I built there have shaped the way I think and work ever since.
What is your favorite memory from your time at the SJMC?
Winning the J202 pitch was certainly a highlight — it was one of the first times everything we were learning really clicked and confirmed for me how much I love the challenge of public speaking. But the memory I’ll always come back to is taking J565 with my brother. Being in the J-School with him was one of the last experiences we had together in college before embarking on different paths both professionally and geographically as adults, so that time together is something I’ll always be grateful for.
Who is one SJMC professor who made a lasting impact on your career, and why?
I had Shawnika Hull for J201 and J565 and she really made a lasting impression on me. She had a way of commanding the room that was both powerful and engaging. Even more than that, though, she modeled a level of confidence and clarity in how she communicated that I really aspired to — and she did it all with a sense of style that made her presence even more unmistakable.. She’s someone I’ve thought about often over the years as I’ve developed my own voice and professional identity.
What is one thing you learned at the SJMC that you have carried with you throughout your career?
The biggest thing I took from the SJMC was confidence — arguably maybe even a little overconfidence, but in the best way. It made me feel like I could take on just about anything, even before I fully knew what I was doing. That mindset pushed me to go after opportunities I might have otherwise passed up, and it’s something that’s shaped my career ever since.
What has been keeping you busy since your time at the SJMC?
After graduation, I spent most of my time building and growing a company focused on leadership development, working with women across industries like tech, finance, and construction. That experience gave me the opportunity to create content, lead conversations, and build something from the ground up, which ultimately led to the company being acquired in 2024. Along the way, I’ve stayed close to storytelling — whether through media, brand-building, or helping others find and use their voice more effectively. I also managed to marry someone much smarter and cooler than me and have two very cute kids — arguably my best work. 🙂
What are you currently focused on in your career?
Right now, I’m working on a new venture in the women’s health space — an AI-powered platform designed to help women better understand their bodies and advocate for themselves in a healthcare system that hasn’t always worked for them. It brings together storytelling, community, and technology in a way that feels really aligned with both my interests and the skills I developed at the SJMC. At its core, it’s about helping women connect the dots and feel more informed, supported, and confident in their health.