Executive Team
Chief Executive Officer
Gordon McClendon
Gordon McClendon began his journey with the Miami-based software company in 2000 in its Systems Products division. After serving as Vice President for 21 years, he was named SPI’s CEO in 2022. During Gordon’s decades of service, he has distinguished himself and SPI Software, generating recognition within the vacation ownership industry as its preferred software developer. Under his guidance, SPI’s ability to remain the leader in vacation ownership software – since almost the beginning of the industry itself – has been achieved by maintaining close contacts with clients from all corners of the globe and adapting their software to keep pace with constantly evolving industry changes.
Gordon’s leadership journey with SPI Software has been marked by numerous achievements. In 2024, Gordon was recognized with a prestigious Lifetime Achievement Award at the GNEX conference in Miami Beach. This honor acknowledged McClendon’s exceptional leadership of SPI Software and his significant contributions to the advancement of the timeshare industry. He has overseen the company’s steady growth and expansion, successfully navigating the company from a privately held business to a fully owned subsidiary of the NYSE-listed Kingsway Financial (KFS).
He began his career as an actuary and holds a degree in mathematics from Blackburn College in Carlinville, Illinois. Gordon is active with the American Resort Development Association and served on the Board of Directors of the Canadian Resort & Travel Association. Earlier, he ran a major financial derivative trading firm – with offices from New York to Tokyo – and was a founding board member of the after-hours trading system, Globex. He was in a leadership position at Chicago Mercantile Exchange for many years, having the distinction of being elected to the board by the highest vote total ever.otal ever.
President
Drew Richard
Drew Richard joined Kingsway in the summer of 2022 as an Operator-in-Residence. In 2023, he led the formation of Vertical Market Solutions LLC (“VMS”) and its subsequent acquisition of SPI Software (“SPI”). He currently leads strategic growth for SPI and the VMS platform.
Prior to joining Kingsway, Drew worked in a variety of roles at Chevron Corporation, most recently as Corporate Negotiator. Prior to Chevron, he worked in investment banking and intelligence analysis. Drew began his career as an officer, platoon leader and Apache helicopter pilot in the US Army.
Drew graduated with an MBA from Harvard Business School and a BS with honors in Engineering Management from the United States Military Academy at West Point. He is a CFA charterholder.
VP, Business Analysis and System Implementation
Kyle Oliver
Kyle Oliver is a key executive at SPI Software, serving as the VP of Business Analysis and System Implementation. She joined the company in December 2004 as a Senior Systems Analyst. She and her team are responsible for system setup, conducting user training, providing quality assurance testing and analysis, writing business requirements and functional specification documentation and system support at SPI. Kyle has extensive experience in technology, including thorough knowledge of timeshare business IT, Help Desk operations, and project management. Prior to joining SPI in 2004, she served as a Business Consultant for Interval Software Services, the software division of Interval International. Kyle has over 20 years of experience in the timeshare industry and holds an MBA from the University of Miami with specializations in Computer Information Systems and Finance. Previously, she was in the scientific field.
Vice President of Engineering
Farzin Zaker
As Vice President of Engineering, Farzin Zaker is instrumental in driving innovation, enhancing operational efficiency, and delivering exceptional value to SPI’s global clients. Zaker joined SPI after more than 22 years of experience in software development, including 15 years of leadership in managing and scaling high-performing engineering teams. His strategic visionary skills –combined with his ability to align technology initiatives with business goals – has made him a highly respected leader in the software industry.
Farzin previously served as Vice President of Engineering at IgniteTech, where he managed a broad portfolio of software products, while streamlining operations for improved efficiency and customer satisfaction. He has a proven track record of driving innovation through AI/ML solutions and building high-performing engineering teams. His ability to mentor and develop top talent has been instrumental in creating a culture of excellence and continuous improvement.
Farzin holds a Ph.D. in Computer Science from York University of Toronto, Canada, and both a Bachelor and Master of Science in Software Engineering from Shahid Beheshti University of Tehran, Iran.