Leadership & Staff

Leadership: Board of Directors

Thomas A. James, Chairman: Chairman Emeritus, Raymond James Financial, Inc.
Frank R. Chivas: Owner, Island Way Grill, Seaweed, Rumba, Salt Rock Grill & Marina Cantina
Robert D. Basham: Founder, Outback Steakhouse, PDQ Restaurants
Griffith S. Braddock: Owner and GM, Braddock Metallurgical, Inc.
Ronald Ciganek: Senior Vice President, Commercial & Industrial Banking, Valley Bank
Scott Curtis: President, Private Client Group, Raymond James Financial
Robert Enck: President and CEO, Equinox Fund Management
Glenn "Buck" W. Jones, Jr.: Secretary and Treasurer, New Fintech, Inc.
Bill Josey: William S. Josey, LLC
W. Andrew Krusen, Jr.: CEO/Chairman, Dominion Financial Group
Claude Macari: Retired Partner, KPMG
Jessica M. Majeski: CLU, Wealth Management Advisor, Northwestern Mutual
Julie Mastry: Former Pinellas County School Board Superintendent
Conrad A. Plimpton: Chairman and Owner, Inolex Group
Philip J. Powell, Jr.: CEO/President, C3 Management, Inc. and Powell Holding & Development
Elliott M. Ross: President, The Ross Realty Group, Inc.
Eric E. Stewart: Senior Vice President Manager of Commercial & Business Banking, First Citizens Bank
Joseph H. Varner, III: Partner, Holland & Knight
Fred E. Whaley: Senior VP & Managing Director, North Shore Wealth Management Group, Raymond James and Associates
Bill Wickett: Executive VP Communications, Tampa Bay Lightning

Advisors (non-voting members):
Jon Alexander, Special Projects
Paul Shoukry, Finance
Matt Yost, Special Projects


Leadership: Academy Executive Committee

Elliott Ross, Committee Chair: The Ross Realty Group, Inc.
Scott Brown: Retired
Linda Damsky: Retired
Dan Etlinger: Jennis Law Firm
Carlos Guerrero: Bizco Technologies
Bill Hurter: Hurter & Wilson, P.A.
Andrew Ingersoll: Nickel Plate Properties, LLC
John Kobasic: Retired
Monica Kobasic: Retired
Brian Krostue: Vology
Jessica Majeski: Northwestern Mutual
Chuck McGee: FMGI
Pete Morell: Consultant
Ian Peterson: Dialed In Golf Solutions
Scott Tobe: Bimbo Bakeries USA
Sean Tobe: Brown and Brown Insurance
Richard Wegman: Retired



Cary Stiff, CFRE

Cary Stiff.jpg

Chief Executive Officer

Email: cary@chichi.org, Tel: (727) 726-8829, ext. 202

Born and raised in Clearwater, Cary is a graduate of Largo High School and St. Petersburg College. She is a graduate of Leadership Pinellas and co-founder of Clearwater Jazz Holiday. She joined Eastern Airlines as a flight attendant then returned to Clearwater to begin a real estate practice. After earning her Florida broker’s license, she joined a real estate firm to handle downtown Clearwater commercial leasing and property management. She then formed Cary Management and served as president of the firm.

As a volunteer in 1980 for Chi Chi’s, Cary met co-founders Chi Chi and Bill Hayes, who asked her to join the staff in 1984. She began her non-profit career at the Chi Chi Rodriguez Youth Foundation as Director of Marketing and helped steer the fundraising and growth of the Foundation’s 170-acre McMullen Booth campus for 16 years. In 2000, she accepted the position of Director of Major Gifts for Ruth Eckerd Hall and then served as a Director for the Vincent Reid Foundation for children with disabilities.

In 2006 Cary was invited to return to the Youth Foundation as Senior Vice President and Executive Director of The First Tee. Her goal in returning was to assist the Foundation with its future expansion plans and to position its alternative education program for struggling students as a permanent educational institution in the Clearwater community.

She has served as a chairperson for the Downtown Clearwater Association, an Ambassador for the Clearwater Chamber of Commerce, and a member of both Kiwanis and Rotary clubs. Her recognitions include "Up and Comer" from the Tampa Bay Business Journal, Nominee from the Tampa Bay Business Committee for the Arts, Jazz Hall of Fame Honorary Member, Outstanding Young Women of America, and the Century 21 Gold Pacesetter Award for Top Sales Producer.


James Poulter

James Poulter.jpg

Chief Operating Officer

Email: james@chichi.org, Tel: (727) 726-8829, ext. 215

Born and raised in Derby, England, James studied English Law and Business at South East Derbyshire College.

He moved to Pinellas County in 2003 and started his career in The United States by volunteering at The Clearwater Marine Aquarium and The Chi Chi Rodriguez Youth Foundation.

In the summer of 2004, The Chi Chi Rodriguez Foundation hired James to help run The First Tee of Clearwater’s Junior Golf Summer Camp Program. He has held multiple positions within the organization and is currently the Foundations Chief Operating Officer and Director of Golf Operations. He oversees the management and operations of the Golf Club and Sports Complex, including administration and maintenance.

In his free time, James loves to play golf, attend local sporting events and spend time with his wife Jenny, daughter Lyla and son Luke. 
Since 2014, James has served as the Treasurer for the Safety Harbor Chamber of Commerce and is currently Board Chairman. He loves to promote events and other great local non-profits. Grateful for an amazing group of family and friends, James makes sure to make a difference in our community by building relationships every day.



Al Arrigoni
Director of Golf
Email: al@chichi.org, Tel: (727) 726-4673, ext. 214

Ashley Cimillo
Email: ashley@chichi.org, Tel: (727) 726-8829, ext. 250

Wanda Di Landro
Email: wandad@chichi.org, Tel: (727) 726-8829, ext. 205

Eric Dixon
Golf Course Superintendent
Email: eric@chichi.org, Tel: (727) 723-0516

Mallory Hubbard
Director of Development
Email: mallory@chichi.org, Tel: (727) 726-8829, ext. 246

Josh Meurer
Director, Chi Chi Rodriguez Academy
E-mail: pcs.meurerj@pcsb.org,  Tel: (727) 726-8829, ext. 203

Laura Tobe
Community Liaison
Email: laura@chichi.org Tel: (727) 726-8829, ext. 207

Karen Wise
Program Director, The First Tee of Clearwater
Email: karen@chichi.org Tel: (727) 726-8829, ext. 238

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