TBBW names 2026 Women Who Win honorees

Tampa Bay Business & Wealth named the winners of its 2026 Women Who Win Awards during an April 17 gala at The Vinoy Resort & Golf Club in St. Petersburg, recognizing business and community leaders across the region.

The program drew nearly 300 nominations, with an independent panel of judges reviewing more than 150 applications to select finalists and winners based on leadership, professional achievement and community impact.

Janet Stringfellow, president and CEO of Volunteers of America of Florida, was named the overall Women Who Win recipient. She also received the award in the nonprofit large category.

Cindy Hesterman, CEO of Vistage Florida, received the Judge’s Choice Award, recognizing a leader whose influence extends across the business community. Alicia Schulhof, president of Johns Hopkins All Children’s Hospital, received the Icon Award for sustained leadership and long-term impact in the region.

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Jason Baker, president and publisher of Tampa Bay Business & Wealth, said the program reflects the role of women shaping the region’s business community.

“These are the changemakers in this room,” Baker said. “You make this community stronger, and you are a big reason Tampa Bay continues to thrive.”

Michelle Delker, CEO of The William Stanley Group and the event’s presenting sponsor, said the recognition reflects work that often takes place outside public view.

“We see you making the decisions that no one else will,” Delker said. “This moment is hard-earned and well-deserved.”

The event was supported by corporate and community partners, including presenting sponsor The William Stanley Group, nonprofit partner Habitat for Humanity Tampa Bay Hillsborough and diamond sponsor International Diamond Center, which provides the annual award pendant. Additional sponsors included Source 1 Solutions, Cadmus Dental Lab, Brown & Kimpton Law and Port Tampa Bay.

Category winners for 2026 included:

Under 40: Amanda Derby, Florida Avenue Brewing Co.
Business Services: Kelly Flannery, South Tampa Chamber
Entrepreneurship: Kelly Boyd-Rivera, Cadmus Dental Lab
Financial Services: Gwynn Davey, ServisFirst Bank
Health and Wellness: Ano Kashumba, Pioneer Medical Foundation
Legal: Barbara Brown, Brown & Kimpton Law
Nonprofit Large: Janet Stringfellow, Volunteers of America of Florida
Nonprofit Small: Elizabeth Reedy, Frameworks of Tampa Bay
Real Estate: Chelsea Drinkard, Office Space Brokers
Retail and Hospitality: Wendy Camacho, Keel Farms
Rising Star: Monica Quimby, Wheel Together Retreats
Technology: Rebecca Nault, Source 1 Solutions

The annual program recognizes women across industries including healthcare, finance, real estate, technology and nonprofit leadership, with finalists representing organizations shaping Tampa Bay’s economy and workforce.