Celebrating 20 Years of Dedicated Service

Kyle Oliver Global VP of Operations

For the past two decades, Kyle Oliver has served as a driving force behind SPI Software’s continuous development of cutting-edge software and technology solutions for the vacation ownership industry. In this role, she has nurtured, developed, and mentored a management team that averages over 20 years of industry experience. She has guided the development of software solutions that streamline operations, enhance guest experiences, and optimize profitability for timeshare operators. As SPI enters a new chapter as a subsidiary of Kingsway (NYSE: KFS), Kyle reflects on the evolution of the industry and her vision for the future.

Q: After 20 years at SPI Software, please share your thoughts on how the industry has evolved?

A: When I joined SPI in 2004, the focus was on traditional “legacy” ownership models with marketing primarily via onsite presentations. Today, the timeshare industry has experienced a significant transformation with a greater emphasis on flexibility of use and catering to diverse customer needs. We have witnessed the rise of points systems, fractional ownership, the integration of vacation rentals and Club offerings, all fueled by the desire to provide a wider range of vacation ownership options.

Q: Reflecting on your career at SPI, what memories stand out?

A: The exciting thing about SPI Software is that we have a fantastic team of true visionaries that are always working on something new. Our product evolution is driven by the needs of our clients and industry partners and made possible by the ingenuity of our team. It is our team members and clients that drive our growth, innovation, and success. I genuinely appreciate the professional and personal relationships I have developed over the years with such a talented group of people built on respect and collaboration.

Q: Now that SPI Software is part of the Kingsway family, how do you see this impacting the company’s future?

A: The Kingsway acquisition is a thrilling development. Their global reach and financial strength will be instrumental in accelerating our growth. We can now invest even more heavily in R&D, expand our product offerings, and reach a wider audience within the timeshare industry. It is a win-win for both companies, and ultimately for our clients. We recently expanded our development and operations teams and are expediting numerous product enhancements for our clients.

Q: We understand you are a devoted dog lover. Tell us about your furry companions?

A: I have two Labrador Retrievers, Stevie, and Sammie. They are a constant source of laughter and entertainment. Labs are such intelligent and playful dogs; they brighten up the most hectic days that we all have in our fast-paced industry. Very few can resist the charm of a chocolate lab.

Q: What do you envision for the future of the timeshare industry and how will SPI Software be involved?

A: I believe SPI’s role in the future of the timeshare industry lies in developing technologies that drive efficiency and success while maintaining personalization and an enhanced user experience. Customers increasingly expect seamless digital interactions, flexible ownership options, and a focus on experiences, not just ownership. SPI Software is well-positioned to address these needs. With Kingsway’s support, we will develop innovative solutions that create a more dynamic and customer-centric timeshare experience. We are looking at AI-powered tools, mobile app development, and enhanced data analytics to personalize offerings and optimize marketing, sales and operations for both resorts and owners. I am optimistic about the future. Our CEO and my mentor Gordon McClendon – along with our new President, Drew Richard – are phenomenal leaders committed to driving a brighter future for our industry, one innovation at a time.

Q: Speaking of clients, SPI has an international presence, can you tell us about your experience with global clients?

A: Visiting and collaborating with our clients in locations such as Finland, Malta, Great Britain, Canada, Mexico, and the Caribbean has given me a deeper appreciation for the diverse needs of our global clientele. We are truly an international business both in terms of where our employees are based and originate from and where our clients are located and their nuanced operational needs.