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Executive Team

David Siegel

Founder, CEO & President


A self-made visionary, David Siegel has spent more than thirty years developing Central Florida Investments/Westgate Resorts into the largest privately owned company in Central Florida. To its credit, the Westgate portfolio includes destination timeshare resorts, hotels, restaurants, water parks, spas, apartments, travel services, telecommunications, citrus, insurance, transportation, and other many other ventures throughout the United States.

The Westgate Resorts story began in 1982 when the timeshare titan purchased a prime piece of land in Kissimmee, Florida and transformed it into the Westgate Vacation Villas Resort. Fast forward thirty plus years later and the Westgate empire today boasts over 14,000 villas, 27 stunning resorts in the country’s most sought-after destinations with so much more still to come!

Education & Awards

A former student at the University of Miami, Mr. Siegel studied marketing and management and holds an honorary doctorate from Florida A&M University. He also has been the recipient of countless awards and accolades for his philanthropy, community service, and contribution to the hospitality industry.

Notable Awards Include:

Philanthropist of the Year (Perspective Magazine, 2018)

Induction into the UCF Rosen College Hospitality Hall of Fame (2018)

Dick Pope Legacy Award (2015)

Entrepreneur of the Year (Perspective Magazine, 2015)

CEO of the Year (Orlando Business Journal, 2014)

Induction into the Central Florida Hall of Fame (2013)

Induction into Central Florida’s Hospitality Hall of Fame (2013)

Named Central Florida’s Top 10 Most Influential Businessmen (Orlando Business Journal, 2007)

Distinguished Entrepreneur Finalist (Dynetech, 2004)

Outstanding Volunteer Community Service and Philanthropy (The Heart of Florida United Way, 1999)

Entrepreneur of the Year (1996)

Community Service

An avid philanthropist, Mr. Siegel created the Westgate Resorts Foundation in 2001 with the mission to strengthen families and communities surrounding Westgate Resorts’ properties. Since then, the Foundation has contributed more than a million dollars each year to nonprofit organizations across the country to further this mission.

Mr. Siegel has also earned recognition as an outstanding and committed member of the Central Florida business community, sits on the board of many civic organizations, and has earned the National Community Service Award from the American Resort Development Association (ARDA).

As a response to the opioid epidemic, Mr. Siegel founded Victoria’s Voice Foundation in memory of his 18-year-old daughter, Victoria Siegel, who fell victim to a drug overdose. Since then, Mr. Siegel has worked passionately towards saving lives to prevent the loss of future generations to drug abuse and addiction. Victoria’s Voice Foundation has pursued legislation to encourage safeguards such as locking up prescription medication in homes, providing co-prescriptions for the reversal drug that prevents overdose, Naloxone, whenever an opiate painkiller is prescribed, and implementing random drug testing in educational institutions.

Jim Gissy

Executive Vice President


Jim Gissy began his career in sales at the age of 21 for the American Income Life Insurance Company where he quickly became as the number one sales agent in Northern California. By the age of 22, Jim had become the number one sales agent out of 1,100 throughout the United States. After a family trip to Orlando, Florida in 1983, Jim joined Westgate Resorts in January 1984 as a sales representative. Mr. Gissy’s talent was quickly noticed as he began setting records throughout the company. As a result of his tremendous sales ability and his talent in leading and developing others, he was promoted to sales manager after only eight months. Over the next several years, Mr. Gissy significantly expanded his management responsibilities, culminating in his appointment as Executive Vice President of Sales and Marketing in January 1990. Today Mr. Gissy leads a team of thousands of sales, marketing and operations professionals across Westgate Resorts.

In 1996, Mr. Gissy was the recipient of the exclusive ARDY Award from the American Resort Development Association (ARDA) as the Top Sales Executive and has received numerous other industry accolades and awards over his thirty-year career. In addition to his responsibilities at Westgate, over the past thirty years, Mr. Gissy has amassed a large portfolio of personal real estate holdings and is one of the largest players in the Central Florida real estate market.

Mr. Gissy owns over 70 diverse properties including over 2,500 acres of vacant land mortgage-free across the central Florida area. His personal portfolio and partnerships include over two million square feet of commercial real estate, office & industrial buildings, hotels, RV parks, condominiums, billboards, retail shopping centers and historic Florida landmarks. Some of his prime locations include the Cocoa Beach Pier, downtown Windermere, Gissy Springs, the Sea View Inn – Melbourne Beach, the historic Wells Fargo Building in Cocoa Beach and the historic ten-story SunTrust building on Church Street in downtown Orlando. Mr. Gissy is also the largest private landowner on Florida’s renowned spring-fed Rainbow River - home to the fourth largest natural spring in the state of Florida where he owns thousands of feet of river frontage across hundreds of acres of pristine Florida land.

Jim currently sits on the Board of Directors for the Westgate Resorts Foundation and is a major sponsor of the University of Florida Natural History Museum's efforts to support a Sustainable Florida Aquifer and Spring System. Mr. Gissy is the proud father of three children and grandfather of six.


St. John's River College (General Business)

Community Service

Jim was a member of the Heart of Florida United Way Alexis de Tocqueville Society and currently sits on the Board of Directors for the Westgate Resorts Foundation. He is a major sponsor of the University of Florida's efforts to support a Sustainable Florida Aquifer and Spring System.

Barry Siegel

Executive Vice President

As Executive Vice President of Sales, Barry Siegel oversees Westgate's travel club resort sales & marketing companywide.


Barry Siegel has served in a number of increasingly senior sales leadership roles throughout his career at Westgate Resorts. Barry joined Westgate in 1979 as one of its earliest Team Members and served as Sales Manager, General Sales Manager, Director of Sales, Vice President of Sales, Senior Vice President of Sales and Executive Vice President of Sales during his long and illustrious career. Barry's expertise has been instrumental in leading resort sales operations to record heights. In 1996, Barry received the exclusive ARDY Award, presented by the American Resort Development Association, for his outstanding sales and performance. Prior to Westgate, Barry was a sales manager for The Keyes Company, the largest real estate company in the South.


University of Miami (B.A., Business Administration & Management)

Community Service

Barry is a long-standing member of the Heart of Florida United Way Alexis de Tocqueville Society. He is also on the Board of Directors for the Westgate Resorts Foundation.

Tom Dugan

Chief Financial Officer

As Chief Financial Officer, Tom Dugan is responsible for the company's accounting, tax, financial reporting, information technology, human resources, treasury and mortgage service functions.


Tom brings to our company over twenty-five years of professional and financial management experience. Prior to joining our team, Tom was an audit partner for one of the world's largest accounting firms, KPMG. His experience includes Controller and CFO for multi-national companies, extensive strategic business planning, acquisitions, public offerings, investor relations, systems development and SEC reporting.


  • American Institute of Certified Public Accountants (Member)

  • New Jersey Society of Certified Public Accountants (Member)

  • St. Peters College (B.A., Accounting)

Community Service

Tom is a member of the Heart of Florida United Way Alexis de Tocqueville Society.

Mark Waltrip

Chief Operating Officer

As Chief Operating Officer, Mark is responsible for the continued evolution of the Westgate brand as the industry leader in experience-based, destination resorts. He is recognized as an industry leader in the development and operation of themed destination resorts, and is responsible for the acquisition, design, development, operations, and marketing for Westgate Resort properties. Mark has a very diverse background, including corporate leadership, sales, marketing, real estate development, project acquisitions, construction, resort operations, asset management, procurement services, information technology and human resources. Mark also leads the development and operation of all Westgate non-resort projects, including commercial office space, apartment complexes, land development and a variety of restaurant concepts, retail shops and destination health spas under the brand, Serenity Spa by Westgate.


Mark has a remarkable and diverse career that includes working in the space launch industry where he helped develop the launch facilities for the commercial space program and was an engineer on the launch team for 12 Atlas-Centaur space launches. He served 20 years in the United States Air Force, where he specialized in program management and business reengineering. Prior to joining Westgate, Mark was with Computer Sciences Raytheon, where he supported the development of the space launch infrastructure for the Kennedy Space Center. Mark joined Westgate Resorts in June of 1996.


  • University of Colorado (M.S., Aerospace Engineering)

  • University of Colorado (B.S., Aerospace Engineering)

  • National Honor Society for Aerospace Engineers

  • National Honor Society for Engineers

Community Service

Recognized as an inspirational and tireless leader in the community, Mark serves on the Board of Directors for the Westgate Resorts Foundation and the Central Florida Regional Commission for Homelessness and is a past board member of the Florida Special Olympics with which he is still actively involved. He is also a member of the Urban Land Institute (ULI) and the American Resort Developers Association (ARDA). Mark is the author of "Recipes for Success" and is frequently featured as a guest speaker at industry, academic and leadership conferences across the country.

Michael Marder

General Counsel

Michael is responsible for handling all of Westgate Resorts' legal requirements, practicing in such areas as commercial litigation, real estate law, administration law, timeshare and resort law, and business and corporate law. He has extensive experience with complex financial transactions, and notably completed a successful asset-backed securitization of timeshare mortgages in excess of $1 billion dollars.


Michael was admitted to the Florida Bar in 1978, and has also been admitted to the United States District Court, Southern District, United States District Court Middle District; United States Court of Appeals, Eleventh Circuit, and Arbitrator United States District court, Middle District. He is also the previous Chair and current member of the Judicial Nominating Commission for the 5th District Court of Appeal. In addition, he is a member of the Florida Bar in Sections of Real Property, Probate and Trust Law, as well as in Corporate, Business and Banking Law. The Co-Managing Director of Greenspoon Marder LLP, Michael is a member of the American Bar Association; the Association of Trial Lawyers of America; and the Orange County Bar Association; and a member of the U.S. Supreme Court bar. He is also a trustee and board member of the Board of Directors for the American Resort Development Association and member of the Metro Orlando Economic Development Commission.


  • Stetson University College of Law (J.D., cum laude)

  • University of South Florida (B.A., cum laude)

  • Bar Admissions and Activities

  • The Florida Bar, Sections of Real Property, Probate and Trust Law; Corporate, Business and Banking Law

  • American Bar Association

  • Orange County Bar Association

  • U.S. Supreme Court Bar

Community Service

Michael is a member of the Heart of Florida United Way Alexis de Tocqueville Society.


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