Henry Schwartz is SVP, chief information officer at OUTRIGGER Hospitality Group, a Hawai'i-based global hospitality company that operates resorts, condominiums and vacation resort properties in the Asia Pacific, Oceania and Indian Ocean regions. His formal education background is rooted in finance, having earned a bachelor’s degree in accounting and, subsequently, his CPA license. He launched his career in healthcare, working at a large hospital in San Diego. “I would later learn,” Schwartz said, “that hospital operations translate directly to hotel operations. Both are always-on operations, centered on service, safety and the human experience."

Schwartz spent 12 years in public accounting, working in business advisory services. He began consulting in financial systems, then created and managed a computer consulting practice before transitioning to hospitality consulting in 1993. During this time, he managed resort IT systems and supported systems transitions for resort acquisitions.

Schwartz joined the KSL family of companies full-time in 1999 and has been with the organization ever since, having spent the past six-plus years with OUTRIGGER. The company has been on a journey to roll out a modern technology infrastructure that can support rapid growth, enable teams to implement innovative solutions and enhance the guest experience.

In his current role, Schwartz has overseen the adoption of several new technologies, including one that stood out in 2025: the G.hn standard for guestroom networking to enhance the speed and stability of data transmission.

By leveraging the G.hn technology from Positron Access Solutions, they can deliver Gigabit network speeds over a property’s existing coaxial cabling. “We have had good results from this system,” he said, “and are adopting G.hn at properties where re-cabling is not practical.” Other initiatives have included transitioning to a cloud-first strategy, with nearly all the company's systems now in the cloud. In 2025, the team finalized a migration to Microsoft 365, and the Hawai’i portfolio to Opera Cloud.

During the next few years, Schwartz and his team will prioritize the adoption and integration of AI by leveraging opportunities within their existing vendor solutions, with an emphasis on governance and upskilling OUTRIGGER's hosts [employees]. They will continue to enhance identity management and user provisioning, thus optimizing systems access, security and compliance. And finally, “we will roll-out Opera Cloud Central to complete our PMS cloud migration,” Schwartz explained of his team’s near-future goals and priorities.

“I am most proud of my team’s adaptability and growth in embracing new technologies, their attention to detail and their unwavering support for our hosts across the company,” Schwartz said. “Together, we have built a culture of innovation and collaboration that drives success. They truly reflect Ke'ano Wa'a, which translates to ‘The Outrigger Way.’”

Henry's Best:

• Family: Wife of 41 years DeAnn and two sons.
• Hobbies: Being outdoors including triathlons, backpacking and traveling.
• Go-to Periodical or Website: Hospitalityoriented websites including Hospitality Upgrade and AHLA. "I also leverage Info-Tech Research Group, which is our IT research firm."
• Book: Physics of the Future by Michio Kaku.
• Music: "Bands from my favorite genres include: The Beatles, Yes, Rory Gallagher, Talking Heads and The Offspring."
• Travel Destination: New Zealand. "My wife and I love the diverse landscape and friendly people. We’re also Lord of the Rings fans and enjoyed visiting the filming sites."
• Advice to Young People: "Don’t be afraid of failure. Taking chances is what fuels innovation."
• Dinner With: "I would have enjoyed being on the camping trip with Teddy Roosevelt and John Muir, which took place in 1903 and was pivotal for U.S. conservation, leading to the Federal protection of Yosemite."