Westgate Resorts Executive and Leadership Team

May, 2026

Leadership Overview

Westgate Resorts has 7 executives leading key functions including strategy, finance, information technology, operations, sales, and legal counsel.

Driven by a commitment to exceptional guest experiences, Westgate Resorts provides premium vacation accommodations and vacation ownership opportunities, maintaining a significant presence in the hospitality sector with comprehensive resort facilities and professional services.

Leadership Roles at Westgate Resorts

  • Chief Executive Officer - James Gissy
  • Chief Financial Officer - John Willman
  • Chief Operating Officer - Jared Saft
  • President - Gregg Weida
  • Chief Information Officer - Stacey Jackson
  • Executive VP, Sales - Barry Siegel
  • Outside General Counsel - Michael Marder
  • James Gissy - Chief Executive Officer

    James Gissy, the Chief Executive Officer at Westgate Resorts, directs the overarching corporate strategy and operational vision for the luxury resort collection. Gissy guides the company's expansion and service enhancement initiatives, ensuring alignment with its mission to provide premium vacation accommodations and experiences. Overseeing all major business units, the Chief Executive Officer drives performance across multiple locations, focusing on maximizing guest satisfaction and vacation ownership value. This leadership role involves fostering innovation in hospitality services and maintaining Westgate's significant presence in the sector. By setting strategic objectives and resource allocation, James Gissy ensures the continued growth and financial health of the organization, reinforcing its reputation for comprehensive resort facilities and professional hospitality.

    John Willman - Chief Financial Officer

    John Willman, the Chief Financial Officer at Westgate Resorts, manages all fiscal operations and financial planning for the hospitality group. Willman oversees budgeting, forecasting, and financial reporting, ensuring robust financial health and strategic resource allocation across all resort properties. This executive directs the company's investment strategies and manages relationships with financial institutions, supporting the provision of premium vacation accommodations and vacation ownership opportunities. The Chief Financial Officer plays a critical part in evaluating new development projects and optimizing existing operations for profitability. By maintaining stringent financial controls and identifying growth avenues, John Willman directly contributes to Westgate Resorts' sustained market presence and its ability to offer comprehensive resort facilities and professional hospitality services.

    Jared Saft - Chief Operating Officer

    Jared Saft, the Chief Operating Officer at Westgate Resorts, directs the day-to-day operational execution across all luxury resort properties. Saft oversees the management of resort operations, ensuring the delivery of premium vacation accommodations and exceptional guest experiences. This executive is responsible for optimizing service delivery, maintaining high standards for resort facilities, and managing staff performance to uphold Westgate's reputation in the hospitality industry. The Chief Operating Officer drives operational efficiencies and implements best practices to enhance guest satisfaction and support the vacation ownership model. By focusing on seamless execution and service excellence, Jared Saft ensures that each property provides professional hospitality services, contributing significantly to the company's overall success and market presence.

    Gregg Weida - President

    Gregg Weida, the President at Westgate Resorts, holds a senior leadership position overseeing key strategic initiatives and business development for the luxury resort collection. Weida collaborates with the executive team to drive growth and enhance the company's market position within the hospitality sector. This role involves guiding the expansion of vacation ownership opportunities and ensuring the consistent delivery of premium vacation accommodations across all properties. The President works to foster strong relationships with stakeholders and partners, supporting the company's operational goals. By championing strategic projects and operational improvements, Gregg Weida contributes to Westgate Resorts' ability to offer comprehensive resort facilities and professional hospitality services, reinforcing its commitment to guest satisfaction.

    Stacey Jackson - Chief Information Officer

    Stacey Jackson, the Chief Information Officer at Westgate Resorts, leads the technology strategy and digital infrastructure development for the luxury resort collection. Jackson oversees the implementation and management of all IT systems, ensuring seamless technological integration across multiple locations to support premium vacation accommodations and guest experiences. This role is pivotal in enhancing operational efficiency through innovative technology solutions, including those supporting vacation ownership programs. The Chief Information Officer directs cybersecurity efforts and data management, safeguarding sensitive guest information and company assets. By driving digital transformation initiatives, Stacey Jackson ensures Westgate Resorts maintains a competitive edge in the hospitality sector, supporting comprehensive resort facilities and professional hospitality services through robust and reliable technology.

    Barry Siegel - Executive VP, Sales

    Barry Siegel, the Executive VP, Sales at Westgate Resorts, leads all sales operations and revenue generation strategies for the luxury resort collection. Siegel directs the sales teams responsible for promoting premium vacation accommodations and vacation ownership opportunities across multiple locations. This executive focuses on developing and executing effective sales programs to drive market penetration and achieve revenue targets within the competitive hospitality industry. The Executive VP, Sales oversees the entire sales funnel, from lead generation to closing, ensuring a high level of performance and customer engagement. By implementing innovative sales techniques and fostering a results-driven culture, Barry Siegel significantly contributes to Westgate Resorts' financial success and its ability to provide comprehensive resort facilities and professional hospitality services.

    Michael Marder - Outside General Counsel

    Michael Marder, the Outside General Counsel at Westgate Resorts, provides comprehensive legal guidance and strategic advice on all corporate matters. Marder oversees legal aspects related to the company's operations, including contract negotiation, regulatory compliance, and risk management for the luxury resort collection. This role is crucial in safeguarding the company's interests while facilitating the provision of premium vacation accommodations and vacation ownership opportunities. The Outside General Counsel advises on legal frameworks governing the hospitality industry and ensures adherence to all applicable laws and regulations. By managing legal affairs and mitigating potential liabilities, Michael Marder supports Westgate Resorts' sustained growth and its commitment to offering comprehensive resort facilities and professional hospitality services.

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    Frequently Asked Questions Regarding Westgate Resorts Top Executives and Leadership Team

    Who leads Westgate Resorts?
    Westgate Resorts is led by James Gissy (Chief Executive Officer), along with executives such as John Willman (Chief Financial Officer) and Jared Saft (Chief Operating Officer).
    Who is part of Westgate Resorts’s executive team?
    The executive team of Westgate Resorts includes leaders such as James Gissy (Chief Executive Officer), John Willman (Chief Financial Officer), Jared Saft (Chief Operating Officer) and other senior executives.
    How many executives does Westgate Resorts have?
    Westgate Resorts has 7 executives leading key business areas.
    What roles are included in Westgate Resorts’s leadership team?
    The leadership team of Westgate Resorts includes roles such as Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, President, Chief Information Officer.