Sheryl Vieira

Sheryl Vieira 

Vice President of Marketing & Communications

Sheryl Vieira is a senior executive and CMO-level marketing leader at Caldwell Trust Company, where she oversees the strategic direction of the firm's brand, communications, marketing, and business development initiatives. As Vice President of Marketing & Communications, she plays a key role in advancing Caldwell's mission, strengthening client relationships, driving growth, and enhancing the firm's reputation as one of Florida's premier independent trust companies.

Since joining Caldwell in 2011, Sheryl has led transformative marketing and communications strategies that have supported the company's growth from approximately $400 million to more than $2 billion in assets under management. She has spearheaded Caldwell's digital modernization, developed integrated multichannel campaigns that elevated brand visibility, and launched long-term initiatives that reinforce the firm's commitment to trust, innovation, and legacy planning. She also led an award-winning marketing campaign supporting Caldwell’s market entry into Vero Beach on Florida’s east coast in 2025, expanding the firm’s geographic footprint and brand presence. In addition, she directed branding and communications efforts for Caldwell's 25th and 30th anniversary celebrations and oversaw the publication of the company's historical brand book.

A nationally recognized communications professional, Sheryl has earned numerous industry honors, including recognition as a finalist for PR News' Marketer of the Year, multiple Silver ADDY Awards for advertising excellence, several Florida Public Relations Association (FPRA) Golden Image Awards recognizing outstanding public relations programs and communications excellence, and the FPRA Pinnacle Award for Corporate Communications Team of the Year. During her presidency of FPRA’s Central West Coast Chapter, she established the Community Liaison role to strengthen strategic partnerships and enhance organizational engagement. She also created the Mission Mavericks initiative, a professional development and thought leadership platform designed to inspire innovation and elevate the practice of public relations, as well as the Caldwell Cares PR program, aligning corporate social responsibility efforts with community impact and brand storytelling. A longtime leader within FPRA, she previously served as President of the Central West Coast Chapter and as a member of its Board of Directors. She is also a graduate of FPRA's Leadership Program (Class V).

With more than 25 years of experience spanning financial services, luxury real estate, hospitality, and nonprofit sectors, Sheryl brings a unique combination of strategic vision, business acumen, and creative leadership. She is known for building high-performing teams, fostering strong organizational cultures, creating impactful community partnerships, and aligning marketing initiatives with enterprise-wide business objectives.

Her community involvement reflects a deep commitment to regional impact and philanthropy. She has co-chaired numerous nonprofit events and supported organizations including Easter Seals, All Faiths Food Bank, Marie Selby Botanical Gardens, the Taylor Emmons Scholarship Fund, Children First, and the Boys & Girls Clubs of Sarasota and DeSoto Counties. In recognition of her volunteer service, she received the President's Volunteer Service Award from the President's Council on Service and Civic Participation.

Prior to joining Caldwell Trust Company, Sheryl held senior marketing positions with Signature Sotheby's International Realty, MPR Luxury Real Estate, and the Cystic Fibrosis Foundation. Her Florida marketing career began in 1999 after relocating from New York to consult with RHI Group, Inc. Her first Florida client, acclaimed chef Paul Mattison, inspired a lasting passion for culinary marketing that led to leadership roles with Mattison's Culinary Group, participation in international culinary tours and wine events, and involvement with the regional television program What's Cookin' on SNN.

Sheryl's executive expertise includes enterprise brand strategy, corporate communications, financial services marketing, public relations, executive visibility, omnichannel campaign execution, stakeholder engagement, and performance-driven marketing. She has extensive experience leading cross-functional teams, managing multimillion-dollar marketing budgets, and driving measurable business outcomes through strategic marketing leadership.

Her guiding mission is to position Caldwell Trust Company for sustainable growth, client-focused innovation, and multigenerational impact while preserving the values of trust, service, and stewardship that define the organization.