SPOTLIGHT: CHELSEA ORCUTT
Chelsea Orcutt is a strategy and operations leader specializing in high-growth startups in regulated industries. Currently she is Director of Strategy & Operations at Thirty Madison, a digital health company dedicated to delivering care that is accessible, affordable, and focused on improving outcomes. Chelsea has been a devoted member of NYWICI for more than 15 years and today serves as Chief Student & Early Career Affairs Officer. From building young companies to leading at NYWICI, Chelsea embodies curiosity, mentorship, and a deep commitment to fostering meaningful connections.
You’ve scaled your career in the fast-paced world of startups, what attracted you to that path, and what have you taken away from it?
Throughout my career I’ve been drawn to startup building in highly regulated industries like healthcare and fintech. Joining at the earliest stages and helping develop teams and products from the ground up has been incredibly fulfilling. I’ve had exposure across nearly every part of the business, which gave me an accelerated learning curve and has made me a more well-rounded leader. Working in environments that combine speed with a need for precision has sharpened my attention to detail, problem-solving, adaptability, and risk assessment.
What does leading strategy and operations at Thirty Madison look like, and what inspires you most about your role?
Thirty Madison is focused on making high-quality, affordable healthcare more accessible, especially for women’s health through our Nurx brand. Over six years, I’ve launched new business lines and built teams from scratch. Now, I serve in a hybrid role leading company-wide initiatives while acting as Chief of Staff to our Chief Business Officer. What inspires me most is expanding access to care, whether during the rise of telehealth with the pandemic, or more recent policy changes impacting women’s health.
How did your background in communications shape your approach to strategy and operations, and what advice would you give comms pros who want to think bigger about their careers?
Even though I’m not in a traditional comms role, storytelling is at the core of everything I do, whether I’m creating a business case, presenting an idea, or rallying a team. That foundation allows me connect with audiences and inspire action, which translates directly into strategy and operations.
For comms professionals, my advice is to stay curious and proactive. Learn as much as you can about your business, spot opportunities, and don’t wait to be asked to take on bigger challenges. Establish a reputation as someone who identifies initiatives with real impact and figures out how to deliver them. One way to put that into practice today is by embracing AI tools. Carve out time to experiment with small AI projects each week to help you stay ahead as every industry evolves with the technology.
How did your NYWICI journey begin?
My first introduction was as a scholarship recipient in 2009 and 2010. I was blown away by the generosity of the women I met through NYWICI and the mentorship they offered. From there, I stayed involved through volunteering and eventually joined the board of directors. Now, as Chief Student & Early Career Affairs Officer, it’s a full-circle moment to play a role in shaping the very programs that first introduced me to this community.
What’s the most powerful part of being in the NYWICI network?
NYWICI truly champions women at every stage of their professional journey. From students and early-career professionals, to those navigating mid-career development, and their path to the most senior levels, and even those approaching retirement and seeking a community during that time – NYWICI is a resource.
Careers aren’t linear, and I’m proud that NYWICI is a constant source of support through the highs and lows.
The relationships are equally important. The peers in my scholarship class became lifelong friends, and following each other’s careers has been remarkably inspiring. When I moved to New York after college, that built-in network gave me confidence and made the transition so much easier. The relationship-building opportunities NYWICI provides truly set us apart as an organization.
Mentorship is central to NYWICI. How has it shaped your own career and leadership style?
I’ve been lucky to have amazing mentors at the companies I’ve worked for and through NYWICI. They taught me not only what success can look like, but also the importance of perspective and fostering a fulfilling life outside of work. I’ve tried to pay that forward by mentoring younger professionals, which has been just as valuable for me as I hope it is for them.
Those lessons have shaped my leadership style. Being an effective leader isn’t about having all the answers, it’s about asking the right questions, staying curious, and creating space for the best ideas to come from anywhere. When people feel empowered to contribute, that’s when teams do their best work.
Looking back, can you share a standout moment from your NYWICI involvement?
Relaunching the Communications Career Conference in 2024 was a huge highlight. After a pandemic hiatus, we worked to bring it back and pulled it off in just eight weeks of planning. Thanks to an incredible volunteer committee, we hosted a sold-out event at Spotify’s New York office with outstanding speakers and participant feedback. It was rewarding to revive a beloved program that’s so meaningful for students and early-career professionals, and lay the foundation for its future.
Is there something people might be surprised to learn about you?
I’ve been a figure skater for over 25 years, and these days I skate with Gotham City Synchro, an adult synchronized skating team here in New York. The way I describe it is “the Rockettes, but on ice.” We compete and perform all over the country, and it’s been such a fun way to stay connected to the sport and build community in the city.
Written by Geena Wardaki