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Successful Women In Business Luncheon - September

Thursday, September 17, 2026 (11:45 AM - 1:15 PM) (EDT)

Description

Successful Women in Business (SWIB)
September 2026

Thursday, September 17, 2026 | 11:45 AM – 1:15 PM
Venue: Boca Grove Golf & Tennis Club
(21351 Whitaker Drive, Boca Raton, FL 33433)

Always Evolving: A Fireside Chat on Leadership & Professional Development

Join us for an engaging Successful Women in Business fireside chat featuring four accomplished women leaders from Boston Proper for a candid conversation on leadership, professional growth, business strategy, and the experiences that shape successful careers.

Led by Sheryl Clark, CEO & President, alongside Grace Gamao, VP of Product Creation; Kelly Rains, VP of Merchandising; and Tamara Dougherty, VP of Customer Growth, the conversation will bring together four distinct perspectives from across the organization. From building strong teams and taking calculated risks to navigating change, trusting your instincts, embracing innovation, and continuing to evolve as a leader, the panel will explore the lessons they’ve learned throughout their careers and the decisions that have helped shape their success.

Attendees will hear authentic perspectives on leadership, career development, creativity, customer connection, business transformation, and what it means to keep growing professionally—with meaningful takeaways for women at every stage of their careers.

Featuring Women Leaders from Boston Proper

Sheryl Clark
CEO & President

Grace Gamao
VP of Product Creation

Kelly Rains
VP of Merchandising

Tamara Dougherty
VP of Customer Growth

Sheryl Clark has spent more than 35 years building brands, businesses, and teams across the fashion industry. As CEO & President of Boston Proper, she has led the company through a significant transformation from a legacy, catalog-driven retailer into a modern, digital-first fashion brand while preserving the distinctive identity that made Boston Proper iconic. Her leadership centers on transformation, customer connection, building strong teams, taking risks, and having the confidence to challenge expectations.

Grace Gamao, VP of Product Creation, leads at the intersection of trend, innovation, and design, translating customer insight and brand vision into distinctive products. Her perspective brings creativity, customer-first leadership, recognizing opportunity, and the courage to turn new ideas into something people genuinely want.

Kelly Rains, VP of Merchandising, brings more than 15 years of experience across merchandising, buying, planning, and digital commerce. Her work combines creative product vision with commercial strategy, providing a unique perspective on using both instinct and data, taking calculated risks, making bold career moves, and recognizing when an opportunity is worth pursuing.

Tamara Dougherty, VP of Customer Growth, leads Boston Proper’s customer journey across acquisition, e-commerce, customer experience, retention, and technology. She brings a forward-looking perspective on digital transformation, innovation, customer growth, and using data and technology without losing the human instinct behind great business decisions.

Thank You to Our 2026 SWIB Sponsors

Memorial Healthcare System
Wyndham Boca Raton Hotel
KSDT
Toshiba Business Solutions
SouthState Bank
Florida Power & Light
West Boca Medical Center
Northwestern – Striano Financial
Habitat for Humanity

About Successful Women in Business (SWIB)
Successful Women in Business is one of the Boca Chamber’s most popular monthly programs, created to support and advance women in our business community. Held on the third Thursday of every month, this luncheon series brings professionals together for meaningful networking, inspiring speakers, and empowering conversations that foster growth, leadership development, and lasting connections.

Boca Grove Golf & Tennis Club
21351 Whitaker Drive
Boca Raton, FL 33433 United States
Event Contact
Sarah Vielot
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Thursday, September 17, 2026 (11:45 AM - 1:15 PM) (EDT)
Registered Guests
25
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