The Team
Who We Are
Gillian Smith
Managing Director
For the past 15 years, Gillian’s career has spanned Human Resources, Business Management & Non-Profit Leadership. Her professional career began in the corporate world in the areas of business and banking; however, after completing graduate school, Gillian struggled with an unsettling desire to pursue more meaningful work that improves the community, with a particular passion for youth and families.
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Thereafter, for 5 years, she served in senior leadership roles with the YMCA of the Cayman Islands. In 2021 - together with her husband Greg - Gillian launched Activate Cayman, a consulting firm which specializes in organizational culture, team dynamics and leadership development.
As a small business, Gillian wears many hats at Activate Cayman, including managing day-to-day operations and accounting, providing support for programming, and consulting with clients in the areas of Human Resources and Non-profit Management.
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Gillian earned her BBA in Human Resources from Temple University in Philadelphia in 2010, as well as her MBA from Westminster Business School in London in 2015.
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Personally, Gillian enjoys traveling and spending time with family; particularly, being an Auntie to 6 little ones and lovingly mothering her Cayman Coconut pup, named Kylie.
(345) 927-8316
Gregory Smith
Consultant & Facilitator
Since 1995, Gregory Smith has been a professional facilitator and trainer in the areas of team-building, strategic planning, leadership development and adventure-based counseling. From youth groups and sports teams to Fortune 500 companies, Mr. Smith has designed and delivered a wide variety of programs that emphasize the importance of relationship building and cultural alignment in the achievement of high-performing teams.
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Recently retiring after a 25-year career with the YMCA, Mr. Smith held a variety of leadership and executive roles within the organization. Most recently serving as the first CEO for the YMCA of the Cayman Islands, Gregory specializes in quality control, operations, team development and training. Prior to his YMCA career, he learned team dynamics as a NCAA football player and served in the U.S. Army on tours in Germany, Kuwait and Saudi Arabia.
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Mr. Smith received a bachelor's degree in Psychology from the University of Central Florida, in Orlando and a master’s degree in Organizational Leadership from the University of South Florida, in Tampa.
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Originally from Northeastern Pennsylvania, Gregory currently splits his time between Florida and Grand Cayman, Cayman Islands. He has also served in professional positions in Sarasota, Orlando, Fort Lauderdale, Clearwater and St. Petersburg, Florida, as well as in Houston, Texas.
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In his spare time, Greg is an avid sports fan who enjoys music, boating, handyman projects, coaching youth sports and assisting with various civic groups and community initiatives.
(345) 928-5987
