Defining Moments of a Female Pioneer

Mar 22, 2022

During Women’s History Month, Fairfield County’s Community Foundation is profiling pioneering Women leaders who have made a mark on our community. Throughout the month, we’ll be sharing stories of these important figures and showcasing their work to make Fairfield County and our state a stronger, more equitable community.

Mayor Caroline Simmons

Stamford Mayor Caroline Simmons’ career has been shaped by two touchstone events.

The first occurred when she was in high school on a Tuesday morning in September 2001.

“Sept. 11 was a moment of inflection for me,” Simmons said. “After that day, I knew I wanted to dedicate my life to creating a positive impact through democracy by helping as many people as I could.”

But for Simmons, creating that positive impact didn’t actually begin in the political arena; it all started with pursuing a career in the CIA.

While she didn’t ultimately make the final cut for becoming a member in the elite group of CIA operatives, she did go on to work in the Department of Homeland Security.

“I’m personally very proud of the hard work that we did during my time in Homeland Security, but it was also an eye-opening experience in realizing how I could actually create an even larger impact by serving my fellow citizens at the state level,” Simmons said. “So I moved back to my home state of Connecticut and decided to run for the state legislature.”

But as soon as she made the decision to go back home in pursuit of serving the people of her home state, a second touchstone event occurred: the Newtown mass shooting.

“Coming off of the Newtown shooting, the core issue of my legislator campaign was gun violence prevention,” Simmons said. “And after several years of working diligently on this most important issue, along with passing other major legislation, such as addressing family paid leave, I once again realized that I could have an even greater and more immediate impact by working at the local level.”

Standing Up for Stamford
A career in politics is not for the faint of heart.

All politicians face criticism from opponents and the media. But as the first woman to be elected as Mayor of Stamford, the critiques have often been loaded.

“On the really hard days, I always try to remind myself of the ultimate mission, which is to make our government work better for the people of Connecticut,” Simmons said. “Only 19 percent of our country’s mayors are female. Only 25 percent of women hold positions at the federal legislative level.”

“Women, and especially for women of color, don’t have enough seats at the table,” she added. “And we all know too well the great benefits that our society could have if we had equal representation in terms of both gender and race across all industries.”

But rather than focusing on what the critics say, Simmons defines her success as the ability to build a more inclusive, equitable and prosperous city for all residents, no matter their Zip code.

“That means that the people of Stamford not only feel welcomed and included, but that our entire community is connected and all residents can have access to the services they need, when they need them,” Simmons said. “This city has given me so much, and I’m so honored to have this opportunity to serve the people here and to make our city a more equitable place.”

Blazing a Trail for Others
With such a small percentage of women holding political positions across the country, being the first female mayor of Stamford comes with the unspoken responsibility of lighting the way for future female leaders.

Simmons recognizes this inherent influence that she holds and offers this advice:

“For all the women and girls who have never seen someone who looks like them in a position of power, please know that you can be anything that you want to be,” Simmons said. “You have to believe in yourself, despite the obstacles that lay ahead. Work hard, don’t be afraid to ask questions, find a mentor and do not be afraid to fail. If you’re passionate about something, keep trying, no matter what.”

Join us in person at the Greenwich Hyatt or virtually via our livestream for our Fund for Women & Girls 2022 Luncheon! Get inspired by keynote speaker Anita Hill, learn about our newest signature initiative, and support women and girls across Fairfield County in achieving their best lives. Learn more: