A Woman Runs for Mayor – Simmons Builds a Bridge to Leadership

David Langston Free, Your Brand Leave a Comment

Three in the Race

In February 2021 when Caroline Simmons announced her run for Mayor of Stamford CT her only competitor was two-term incumbent David Martin—also a Democrat. By early June hometown hero, baseball player/manager Bobby Valentine was in the race with the support to win. And a contentious primary with Martin was in the offing. Simmons had the experience and passion to be a good Mayor. Her leadership strengths were not clear to the thousands of voters she would need to win over.

Valentine is almost universally known in Stamford CT. Hundreds like to say they know him well. Not only engaging and well-connected Valentine is a successful local entrepreneur. “Bobby” has a lot of Brand Equity here.

In June the people who knew Simmons, often other women and earnest young supporters, believed in her but could see they had a fight on their hands. Enthusiasm for Valentine’s campaign came from every corner of the city and from national media outlets as well. Martin, a career public servant and an adequate mayor had good relations with the city’s diverse cultural communities. Many local Democrats were taken aback by Simmons’ decision to challenge.

Caroline Simmons understood the nature of the race she was in. She was ready to stand and do battle. But she also knew she needed a strong public persona to rally her followers and help her navigate the rapids with these seasoned candidates. She knew she had the brains but not the brand.

Simmons needed her own brand strategy. A positioning purpose-built to highlight her unique value and establish a greater level of authority. A Leadership Brand.

With the support of her campaign manager, Lauren Meyer, Simmons worked with Evoke Communications, LLC to map the partisan landscape dominated by Valentine and Martin.

The agency focused first on codifying the strengths and weakness of all three candidates—the makeup of their leadership brands—with the Vision to ultimately position Simmons as the “Wiser” choice.

Diligence to Differentiation

SWOT analysis of the 3 candidates delivered key insights on Valentine and Martin. They were somewhat monolithic. Neither were farsighted. Martin was touting his credible response to COVID, but Stamford was not prospering. Schools and infrastructure were in decline. Valentine was often promoting a return to the city’s former greatness–rather than how he would move the city into the future.

In July the opportunity for Simmons came into focus. Everyone in Fairfield County knew that Stamford, despite becoming a large and busy city, had not become an ideal place for small businesses and residents to grow. And importantly, a key part of Simmons’ audience proved to be newer-to-town than her opponents understood.

Simmons could rightfully be positioned as a Seer, planner, and inspiring collaborator who got things done. She had a Vision for Stamford’s future. It needed to be clearly articulated. With this core premise in place Evoke worked with Simmons to take the Long ViewTM—and built a positioning strategy designed to serve her for years to come.

An Identifiable Leadership Brand

Simmons’ emerging leadership brand now included value propositions designed to illustrate her strengths. A much stronger Visual Identity program, complete with a new color palette and bold typography, was complimented with photography that now displayed her confidence.

Simmons also worked with the agency on presentation—from confidently displaying her height to pausing to consider responses to delivering clear messages and promises from a cohesive platform. Each public appearance was becoming a non-apologetic presentation of Simmons’ leadership strengths.

As Simmons headed into the primary, new confidence was felt by both the candidate and her supporters. A clear Vision for Stamford’s future was being connected with the enhanced SIMMONS brand.


Simmons’ campaign team delivered a strong grassroots effort. She won the primary. Then she took the battle to Valentine. Unnerved, he lashed out with the wrong statements. Simmons challenged the tenor of Valentine’s personal attacks, displayed confidence and preparedness in both debates—and overcame Valentine in a close election.


Caroline Simmons beat Martin and then Valentine by presenting an identifiable, credible, and mature Brand Identity. That of a strong, prepared, and visionary executive who could lead the city. Valentine might argue he was defeated by a large local partisan movement. But Caroline Simmons built her own unique Brand and crossed that solid bridge to the leadership job she wanted—Mayor of Stamford.

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