Five years of corporate introspection, customer research and owner input readied this 75-year-old beachfront stalwart to take to the world stage.
For Outrigger Hospitality Group President and CEO Jeff Wagoner, the acid test for corporate strategic planning comes down to one simple question: Is this the company we want to go into the future with?
“I think we all know the answer to that,” he said.
That was the topic on the table in 2018 when Wagoner as the newly named head of this resort legend gathered “a highly diverse group of individuals” with a wide range of expertise to talk strategy. The task at hand was to develop a way forward that would meet new owner KSL Capital Partners’ challenge to not just modernize this what was then a 70-year-old icon, but to future-proof its upside for global growth and maximized enterprise value.
What and how to build a roadmap for change was complicated by the company’s already sterling reputation based on more than seven decades of success, concerns about alienating a worldwide customer base of high-spend travelers who did not want their expectations or experiences reimagined and sensitivity to the carefully crafted relationships that engendered loyalty among both team members and community members.
The first steps in laying the foundation for the new era of Outrigger covered the fundamentals: gaining comprehensive knowledge about the brand and the business; learning how “things were done” and determining what drove the decision-making process for everything from development to design to sustainability.
“Before we could even think about a growth strategy, we had to understand what we had and establish the corporate pillars that described ‘who’ Outrigger is. Only then could we start to explore how to create a vision for the future that’s relatable and makes sense from an acquisition and monetary perspective,” said Wagoner.
“What our leadership team saw was that we had a company with a tremendous history, and we wanted to preserve that. But a lot changes over what was then 70 years, and we knew we’d have to do things differently to compete in an evolving business climate,” he added. “That’s where the planning discussion shifted from, ‘How was this done in the past?’ to ‘How do we move forward?’ ‘How can we take each decision a step further?’”
Work on Outrigger’s corporate transformation started at its very foundation with a name change from Outrigger Enterprises Group to Outrigger Hospitality Group to better convey its targeted business focus. The team made it easy for customers to “see” that step forward with the launch of a new logo and fresh company colors. Taking advantage of Covid-induced downtime, Wagoner and his team used the business slowdown to dig deeper, hiring a marketing firm to craft a voice and imaging that would project the company’s contemporary identity alongside consultants to take a deeper dive into research among owners and customers.
Match growth with mission, metric
Then came the even more challenging work: Revamping and modernizing its assets. “Future-proofing growth and portfolio management requires contextual thinking. Before we seriously consider a deal, we have to ask ourselves, ‘Does the quality of the asset(s) or the company meet the marketing message and voice we're trying to portray?’” said Wagoner. “It was important that our strategy was not only marketing – the look and feel and sexiness of the company – but also literally that all of our properties would match our vision. That's the path we're on today.”
That path has turned into a fast-track for portfolio growth. Outrigger Hospitality Group’s June 22, 2023, announcement of the planned acquisition of the 350-room, barefoot luxury Kaua’i Beach Resort & Spa in Līhu’e, Kaua’i, is the latest return on the company’s half-decade-long investment in comprehensive self-improvement.
Coming just weeks after this Hawai‘i resort icon made headlines with plans to acquire Maui’s 432-room Kā’anapali Beach Hotel, this news marked Outrigger’s seventh purchase in the last two years, joining another newly added property its core Hawai‘i market as well as three resorts in southern Thailand and one in the Maldives. It also served notice that this renowned beachfront resort expert has emerged from its stem-to-stern brand modernization as a nimble, aggressive contender in the upper-upscale resort market.
The company is reviewing existing and newly acquired properties to ensure consistency and spark innovation across its 26-hotel portfolio. The Outrigger Reef Waikiki Beach Resort and Outrigger Waikiki Beachcomber Hotel have already been completely renovated, as have the three Thai properties acquired during the pandemic. The Outrigger Kona Resort & Spa is currently under renovation and will be completed at year’s end while the OHANA Waikiki East just began its makeover.
“Now we're in the execution phase,” said Wagoner. “That entire plan of the transformation of this company is actually happening.”
Think “identity,” not identical
As Outrigger continues to refine its existing portfolio, the company is keeping a sharp eye on future acquisition opportunities as it looks to further cement its hold on upmarket beachfront leisure. For both new hotels and old, Outrigger continues its brand revitalization with changes from technology to shop-local business strategies, a commitment to sustainability and character-enhancing design.
Sustainability has a major role to play, both in development and brand growth. “It’s something we have to lean into. It’s an intuitive piece of decision-making for Outrigger,” Wagoner said. From the choice of building materials to the selection of reef-safe sunscreens, the group is using its strategic corporate direction as well as its on-property operations approach as platforms to educate guests about the importance of caring for the land and the ocean. “This is a critical issue for us. We may be out in front of some of our customers on the urgency of sustainability, but, for us, it’s something that needs to be addressed at every opportunity.”
Wagoner explained that the installation of a whole ecosystem of new tech tools in each hotel is just part of the transformation. Rather than pursue a uniform brand-standard look and feel in each hotel, Outrigger is seeking opportunities to collaborate with local artisans, vendors and musicians in all facets of each hotel to add the crucial element of authenticity.

Before we seriously consider a deal, we have to ask ourselves, ‘Does the quality of the asset(s) or the company meet the marketing message and voice we're trying to portray?’
Jeff Wagoner
“When we buy a property, we want to make sure it's not cookie cutter,” said Wagoner. “Authenticity is a huge part of each property. One example is the Outrigger Reef, which is all about the ‘voyage.’ To support that theme, we brought in famous Hawai‘i artists to create paintings and rope sculptures that would not only beautify the interiors but also inform guests and immerse them in a sense of place.”
Outrigger also ran with that concept for its Outrigger Waikiki Beachcomber Hotel, creating the Beachcomber Originals, a team of advisors to help curate the property, including local musicians, brew masters, underwater photographers, influencers, and more. This hand-picked art, music, food and culture were then embedded in all facets of the hotel, with each floor’s decor designed to be unique.
“I'm getting goose bumps just talking about this,” said Wagoner. “It's what makes us special as a company, now. There's been a DNA within the company for many, many years. We really are enhancing that today and building a brand around the history of the locations where we're already operating and the future of the properties we acquire.”
Brendan Manley is a writer, editor and digital marketer specializing in hospitality content creation based in Warrensburg, New York.
The views and opinions expressed in this column do not necessarily reflect the opinions of Hotel Investment Today or Northstar Travel Group and its affiliated companies.