After more than a decade in the tech world, Darryl transitioned into hospitality nearly three years ago. The move came unexpectedly, following the closure of a startup he had joined, but the timing aligned with Omni’s growing need to modernize its digital capabilities.
“I oversee email, SMS, gift cards, and social media, as well as a couple of strategic projects around loyalty and how we engage with customers at the front desk and beyond,” Darryl explained. “We’re really focused on bringing Omni Hotels to life across our digital channels.”
His role focuses on connecting strong hotel operations with smarter digital tools—especially in loyalty and guest engagement, areas he believes are ready for modernization.
One of the biggest shifts Darryl experienced moving from tech to hospitality was the intent behind digital experiences. “I think a lot of people, especially over the last couple of years, have entered into almost an adversarial relationship with technology,” Darryl noted. “It seems like all of these websites and apps are trying to squeeze you for more.”
Hospitality, by contrast, flips that dynamic. “Through our digital channels, we’re focused on making a guest’s stay more comfortable—whether that’s delivering amenities that feel personal and special or ensuring the experience from check-in to check-out is seamless,” Darryl observed.
That mindset shows up in the details. When Darryl first joined Omni, many loyalty processes were still handled manually. By digitizing and automating those workflows, Omni has strengthened delivery on core loyalty promises such as water at check-in, upgrades for higher tiers, and late checkout.
“There’s a lot happening behind the scenes,” Darryl added. “Our goal is to make it easier for associates to know what’s happening, what they need to do, and what the system is designed to handle—so they’re not relying on memory alone,” Darryl added.
At Omni, loyalty and customer engagement are structurally linked, and that matters. “Kind of uniquely at Omni, they’re rolled into one organization,” Darryl explained.
That structure reinforces Omni’s strategy. With roughly 50 properties rather than thousands, Omni cannot rely on sheer presence. “We really have to make the experience special for everybody when they come in for the first time,” Darryl emphasized. Otherwise, customers default to brands that are everywhere and heavily incentivized by points and miles.
Of course, Omni is also investing in its loyalty program. While much of the hotel industry has devalued loyalty programs, Omni went in the opposite direction. “We’re making the program more rewarding, more expansive, giving you more ways to earn, more ways to redeem,” Darryl said.
“Building value isn’t enough if guests don’t know it exists,” he pointed out. “By showing up consistently on channels like social media, email, and SMS, we strengthen brand awareness and make sure people understand everything Omni has to offer,” he pointed out.
When the discussion turned toward the operational and data challenges behind the strategy, Darryl pointed back to a lesson from early in his career. “The biggest thing goes back to something I learned when I first started my career at Amazon, which is you always start with the customer and then work backwards,” Darryl said.
That philosophy shapes everything from seasonal activations to cross-functional planning. Even a simple idea—like Omni’s Tiki Social summer pop-up, a poolside experience featuring a new tiki bar—requires early alignment across operations, food and beverage, and hotel leadership. “If you align everybody at the very beginning, it then becomes a lot easier to seamlessly execute when you go from planning in January to launching in May,” Darryl explained. The same thinking applies to data. While Omni, like most companies, still has work to do, progress is tangible. “We’ve actually made a lot of strides onboarding a customer data platform,” Darryl shared.
That work has also positioned Omni for what comes next. “We’ve begun playing in the AI space, but our approach started with a focus on business fundamentals rather than chasing hype,” Darryl reflected.
One of the most visible outcomes of Omni’s data work has been a complete redesign of its Select Guest loyalty program. Since its inception, Select Guest has rewarded free nights after a fixed number of stays.
That structure made it difficult for most guests to reach higher status or earn free nights. To address this, Omni rebuilt the program as a hybrid points-and-nights model, with a key new capability underneath. “For the first time, if you charged a restaurant bill or a round of golf to your room, we were able to capture it and turn it into an additional way to earn rewards,” Darryl explained.
This shift drove engagement quickly. “We saw many more people moving through the tiers,” he said. “We noticed people actually asking, ‘Is my balance up to date? Can I get this applied to my room?’” The confidence gained from that success unlocked bigger ambitions, from new redemption options to deeper personalization.
As Omni’s data became more connected, the team fundamentally shifted how they approached activation. “In the past, every single communication would have been, ‘Hey, we’ve got a promotion or a new opening that we want to put in front of everyone,’” Darryl said.
That approach, he explained, was highly top-down. But as data capabilities improved, Darryl and his team began looking for more customer-led opportunities hidden within behavior patterns.
One of the first actionable use cases centered on guests who reliably booked with Omni every year. For many hospitality brands, repeat guests still book through paid search or third-party travel platforms, triggering commission fees or media spend that cuts into margins. From Darryl’s perspective, that created both a cost challenge and a strategic opportunity.
By encouraging guests to book through direct channels, Omni reduced reliance on external booking platforms. But Darryl emphasized that the benefit wasn’t just financial. “It also gives guests the chance to explore all of our offers and packages and enjoy a more personalized experience,” he explained. “Now it’s an own-booking, where they see everything we have to offer.”
Other activations included reminders for people who started a booking but did not complete it, and cross-property recommendations, such as introducing convention guests to resort destinations. “It’s with these more customer-centric things that we said, ‘Okay, here are the quick wins,’” Darryl noted.
Omni’s omni-channel strategy focuses on restraint as much as reach. “A lot of it is very subtle,” Darryl said. Loyalty members might see a slightly different email header or a reminder of their current Omni Credits balance, small touches that reduce friction.
Another example is timely account summaries. “We’re pushing that out days after the accounts close every month,” he explained, rather than weeks later, keeping loyalty top of mind.
Some of the most creative ideas are also the simplest. Darryl highlighted a favorite automation tied to weather. “When it rains in L.A., we say, ‘Why don’t you go visit our Palm Springs Resort,’” he said. While the audience is small, engagement is consistently strong. “It plants that seed that we’re always trying to find ways to make the experience a little better for a guest,” Darryl added.
Looking two to three years out, Darryl sees major opportunity in moving beyond campaign-level optimization. “At Amazon, you could be eligible for hundreds of campaigns at once, but you only get one per day,” he said, describing a system that optimized at the individual level rather than the campaign level. “You’re completely re-imagining the way you think about campaign structure and cadence,” Darryl said.
Another major area of focus for Darryl over the next few years is analytics, particularly as Omni moves closer to individualized orchestration. He explained that deeper personalization depends on stronger analytical foundations. “That does get us closer to the super personalized world where you’re only getting the most relevant email, or in some cases no email, that applies to you in that moment,” Darryl added.
But today, bandwidth remains a constraint.
For Darryl, the challenge is twofold. First, how does he carve out time for his team to think more strategically instead of constantly executing campaigns? And second, how can AI help accelerate that shift? “So how do I get my team to build in more time for themselves to focus on analytics and strategic thinking? And or how do I get something like an AI analytics agent to do some of that for us?” he asked.
He envisioned a future where AI could process massive amounts of behavioral and transactional data and return structured, actionable recommendations. “Okay, I’ve combed through three terabytes of data. Here are 10 campaign ideas that you can action on,” Darryl said, describing the kind of output he would like to see.
Ultimately, Darryl sees Omni moving toward a next-best-experience model that blends data, automation, and human service. “If you’re really competing in this kind of upscale luxury space, you’re always anticipating the guest’s needs,” he said.
That could mean suggesting spa appointments before arrival, booking tee times automatically, or removing the administrative burden that often eats into a guest’s stay. “So that when they get there, they’re not spending an hour in their room planning,” Darryl said. “They can really get to the point of what they’re doing, which is having a relaxing vacation.”