SPI Software’s Drew Richard…a Lesson in Leadership

SPI’s new President, Drew Richard, and the rest of the executive team are in the middle of a jam-packed week in Vegas catching up with current customers and introducing themselves to prospective new ones.

“Last week, we were in Miami meeting with a large customer. This week we’re in Vegas,” Drew tells me. He doesn’t list the dozen or so other places his team have already been to or will need to visit before the end of a tour which puts Taylor Swift to shame. Generously, however, Drew has broken away from his whirlwind of meetings for his Resort Trades interview with me.

“We’re increasing our engagement; it’s a key part of our strategy…meeting people face-to-face,” he says, alluding to the numerous site visits the Vegas trip entails. It’s a sure-fire way to grow your business. Coupled with sponsorship of events that include this past spring’s ARDA Timeshare Together Conference, the ARDA ROC TBMA conference coming up in September, and presenting a strong front at the DC 2024 ARDA Leadership & Policy Forum in November, Drew and team are intent upon doing just that.

Heart for the Independent Resort

“We are all-in on supporting the ARDA-ROC & TBMA initiatives. Frankly, from a software point of view, it seems like no one’s been able to find a solution that meets unique-to-each-property needs and that can be delivered cost-effectively. We think we can offer one and we’re so excited about this opportunity!”

Richard grew up vacationing with his family at their timeshare property on Hilton Head. He has personally experienced and appreciates the value of a getaway for three generations to be able to create memories together. “We see a lot of these resorts that are just loved by the family. Owners enjoy going there year after year, right? But many have challenges when it comes to collecting maintenance fees. Or, maybe they need help managing their rental programs and helping owners rent their unused weeks.

“We know we can create something for them—repackage software for this audience of owners who love their vacation ownership—and that will enable resorts to quickly get up to speed. They don’t have a whole army of IT staff who can quickly customize systems that will work seamlessly. They need something that can be readily understood and implemented. We really see that as a huge opportunity for us.“

SPI’s corporate culture of concern for smaller, independent resorts is evident from Richard’s interest in protecting and preserving them. He emphatically states SPI’s understanding and appreciation for the importance of serving the larger, healthier timeshare companies while, at the same time, supporting these smaller entities.

18 Months in an Army Hospital

My interview begins with the typical question, “Tell us about yourself.” Richard’s story is not what I expected, however. After earning a degree from West Point, he began his military career as an Army helicopter pilot. At age 25, he was already leading a helicopter platoon in Afghanistan. He was at the top of his game when his aircraft crashed while on a combat mission.

“I was very lucky,” he remarks. “I was evacuated to Bagram AFB. From there, they flew me to Germany and then ultimately to San Antonio, Texas, where I spent the next 18 months.”

During his year-and-a half of recovery, he had plenty of time to think. He had a military career all planned out. After West Point and the additional commitment of flying helicopter missions in the war, he figured he’d have a career of at least ten or more years in the Army. His combat injuries didn’t change the fact that his military career and doing what he loved best were over.

“I had been expecting to serve for at least several more years.” He doesn’t discuss the painful journey of physical and emotional recovery, but clearly, he had to have gone through an uphill climb. “You’d never know by looking at me what the extent of my injuries were.” And it’s true. You’d also never guess how much trauma he’d experienced from his positive, enthusiastic demeanor. We’ve heard the phrase ‘a walking miracle,’ and here was a legitimate one.

“I talked to a lot of folks who made a similar transition. And one mentor of mine, my first commander, had gone to a full-time MBA program. That just sounded really cool,” he grinned. “I thought going back to school? Why not! So I put my efforts into applying to some MBA programs. Of the five or six schools where I applied, Harvard Business School (HBS) was the one that actually came through!”

Next Steps

HBS came through more than just academically, as it turned out. It was there that he met his future wife. “Yes, in 2013, I met my wife, Sarina, on Day One of school. We got married in 2017.”

HBS gave Richard a chance to explore some different career options. Coming out of the Army without business experience, he was open to exploring everything in sight. He is much too modest to boast of his obvious intelligence, but his first job after getting his MBA was in Chevron’s elite leadership development program. As it turns out, his background in the Army gave him the broadest imaginable experience in leadership.

“To go through a life-and-death situation, to be in charge of people and very expensive machinery without a command structure, but actually assuming a lot of autonomy was a big opportunity for growth.

“Most of all, I learned that leadership is all about serving others. I found that the Army officers I admired the most were the ones who really cared about people. At its core, that is what I took away from my experience coming out of the Army.

“I had leadership and people management skills, but really no business experience. So, going into Chevron, which is a phenomenal, very large global company, gave me lots of opportunities to learn. I had a total of eight jobs within the six years I was there. It was truly a crash course in business. Plus, I got to live in several different cities, including the San Francisco Bay Area, Australia, and Houston, Texas; be in a lot of different groups and teams and different parts of the business; and work with a lot of really great players to solve interesting problems.”

The Entrepreneurial Path to Acquisition

“There was a course at HBS called ‘Entrepreneurship Through Acquisition.’ Meeting people within that ecosystem was my first exposure to this concept that becoming an entrepreneur was a goal I could reach. Many people, including myself at the time, consider entrepreneurship to be a couple of brilliant Silicon Valley engineering minds taking an idea from zero to one then raising venture capital to swing big and scale fast. That is one form of entrepreneurship I very much admire. But that was not me.”

“I had an entrepreneurial drive, and HBS helped introduce the possibility that one can go out and acquire an existing business that’s already established and then make it better. I felt like the time was right in my personal family life as well as in my professional skills and experience. I was getting to the point where I had one child and a second one on the way. With the support of my wife, who understood this was a dream of mine, I was ready when the opportunity came up to go make it happen.”

Drew’s parents were very supportive of his venture into the timeshare industry segment since they had, themselves, owned and enjoyed vacation ownership for many years. “Often, the loudest voices have produced negative connotations about the industry, despite customer surveys revealing high satisfaction.” But the Richards’ positive experience as a family enjoying their summers together showed him the value.

Partnering with Kingsway

Richard’s entrepreneurial ambition led him to connect with a prominent investment firm, Kingsway Financial (NYSE: KFS). He and the Kingsway team began searching through hundreds and hundreds of opportunities for companies that would meet their criteria.

“Kingsway is a really excellent partner. Essentially, we have the support of having the capital to go out and hire a great small business. The criteria are pretty straightforward: we look for established companies in growing industries, with a history of profitability underpinned by high-quality, recurring revenues. You might be surprised at the difficulty of finding opportunities that check all those boxes. ”

The team was very pleasantly surprised by the potential for growth of SPI Software. They saw the consolidation by larger players as a plus. “They’ve really been a part of pushing the industry forward and appealing to a younger generation.”

Related: Become Referable: The Ultimate Strategy for Sustainable Success

Richard and the team at Kingsway determined that with the emergence of Millennials and Generation Z, not only as customers but also through employment, “this would be a great industry to be in. Particularly in the larger companies. They are attracting professionals with strong educational backgrounds and who have a positive, good outlook on life, too.

“That’s one thing that keeps me very happy to remain in the timeshare industry. I have a great deal of respect for the operators of resorts, and they are committed to delivering great vacations. You’ve got to love the people in the industry. They work very hard and have the right kind of business mindset. It’s also just a fun industry. It’s resorts and vacations.”

During our interview, we touch briefly on the SPI team, including CEO Gordon McClendon and VP of Sales David Callaghan. Many executives in the timeshare industry were acquainted with SPI’s founder, the highly intellectual and well-respected Karl Lange, whose company has continued to grow and thrive even after his death in 2019. Resort Trades published a biography about Karl six years ago: https://resorttrades.com/holding-strong-for-almost-half-a-century.

“Yes, the team is absolutely phenomenal. It’s a tribute to Karl that the company he built 45 years ago continues to develop its technology, serve its customers, and acquire new clients. It’s a result of the quality of the team and a corporate culture that demands excellence and pursues continuous improvement.”

Plans for Growth While Retaining Quality

Richard is just the guy to continue SPI’s upwards trajectory. “So, our plan is to grow exponentially. Five, ten, twenty years from now, we will be a substantially larger software company and will continue to adhere to our standard of excellence. That growth is not going to come at the expense of our sacrifice of any kind of quality or service.”

“We’ve all seen companies trying to scale very rapidly at the expense of quality or loss of focus. Our approach is to double down on understanding the best possible solution for our customers. Focusing on the team and the customer is how I see us achieving this goal.”

ABOUT DREW RICHARD

Richard, an Army veteran with a MBA from Harvard Business School, lives in Austin, Texas, with his wife, Sarina, and two children. Contact him at Drew.Richard@spiinc.com.

ABOUT SHARON SCOTT WILSON, RRP

Sharon Scott Wilson, RRP, publishes Resort Trades magazine and oversees digital marketing. Ideas for an article in The Trades? Write to sharon@thetrades.com, Request a Media Kit for advertising information from marla@thetrades.com or call her at 931-484-8819.