Sheryl Vieira

Sheryl Vieira 

Vice President of Marketing & Communications

Sheryl Vieira is a senior executive and CMO-level marketing leader at Caldwell Trust Company, responsible for the strategic direction of the firm’s brand, communications, and business development initiatives. As Vice President of Marketing & Communications, she plays a vital role in advancing the company’s mission, driving growth, and strengthening relationships with clients, partners, and the broader community.

Since joining Caldwell in 2011, Sheryl has led transformative marketing strategies that helped scale the company’s assets under management from $400 million to over $2 billion. She spearheaded Caldwell’s digital modernization, developed multichannel campaigns that elevated brand visibility, and launched long-term initiatives reinforcing the firm’s reputation for trust, innovation, and legacy planning. She also led milestone efforts for Caldwell’s 25th and 30th anniversaries and oversaw the publication of its historical brand book.

Sheryl is a nationally recognized communications professional. She was named a finalist for Marketer of the Year by PR News, is a multiple Silver ADDY Award winner for excellence in advertising, and was recently honored with the FPRA Pinnacle Award for Corporate Communications Team of the Year. She currently serves on the Board of Directors for the Florida Public Relations Association’s Central West Coast Chapter and is a past president of the chapter. She is also a graduate of FPRA’s Leadership Program (Class V).

With more than 20 years of experience spanning financial services, luxury real estate, hospitality, and nonprofit sectors, Sheryl brings a rare combination of creative insight, business acumen, and strategic vision. She is known for building strong internal cultures, forging lasting community partnerships, and aligning marketing with enterprise-wide objectives.

Sheryl's community involvement reflects her deep commitment to regional impact. She has co-chaired numerous nonprofit events and supported organizations such as All Faiths Food Bank, Marie Selby Botanical Gardens, Taylor Emmons Scholarship Fund, Children First, and the Boys & Girls Clubs of Sarasota County. She has been honored with the President’s Volunteer Service Award from the President’s Council on Service and Civic Participation.

Prior to Caldwell, Sheryl held senior marketing roles with Signature Sotheby’s International Realty, MPR Luxury Real Estate, and the Cystic Fibrosis Foundation. Her marketing career in Sarasota began in 1999 after relocating from New York to consult with RHI Group, Inc. Her first Florida client—acclaimed Chef Paul Mattison—sparked a lasting passion for culinary marketing, leading to her leadership at Mattison’s Culinary Group and involvement in wine dinners, Italian culinary tours, and the regional TV show What’s Cookin’ on SNN6.

Her executive competencies include enterprise brand strategy, corporate communications, financial services marketing, omnichannel campaign execution, public relations, executive visibility, and stakeholder alignment. She is experienced in leading high-performing teams, managing multi-million-dollar marketing budgets, and driving business objectives through measurable marketing performance.

Sheryl’s approach is guided by a clear mission: to position Caldwell Trust Company for sustainable growth, client-focused innovation, and generational impact.