My CIO Career: How Dan Regalado Uses His Relationship Skills to Deliver Great Customer Experiences at Wynn Resorts

Working as the North America-based CIO at Wynn Resorts comes with some enviable perks: experiencing the company’s trendy Las Vegas and Boston restaurants, shows such as Awakening, events like Formula 1 Las Vegas Grand Prix, Concours, the Netflix Cup golf competition, and the Kansas City Chiefs Super Bowl championship celebration party.

For Dan Regalado, the opportunity to be part of all that excitement carries strong appeal. But what really drew him to the company, he says, was Wynn’s authenticity in caring for its guests and employees and providing the exemplary and luxury experiences.

Talk to Regalado and you would understand why. He strives to make the most of every day. At work, his focus is on guests and employees. Regalado commits himself and his team to Wynn’s everyday mission of delivering memorable experiences to every guest.

That is all on top of his spare-time pursuits: training for Ironman triathlons and making memories with his family.

Regalado, the Wynn CIO since November 2023, oversees all IT operations for Encore Boston Harbor and Wynn and Encore Las Vegas properties, as well as shared services, including cybersecurity, for Wynn Macau, Wynn Palace Cotai and the planned Wynn Al Marjan Island in the United Arab Emirates. He is focused on using technology as an enabler to corporate strategy and articulating how IT will help shape the company’s future. His overarching mission: to use technology in enabling amazing experiences for every guest and provide best-in-class technology products and services to the company’s employees.

“We have a short stint in this world and an even shorter stint professionally. I want to be part of a team and a company that is a beloved brand. I feel the pride of being part of that,” says Regalado.

Before joining Wynn, Regalado held IT leadership positions at the global pharmacy retail company Walgreens Boots Alliance and Banfield Pet Hospital, one of the largest pet care companies in the U.S.

In this April 2024 interview, Regalado details what defines a top-shelf guest experience, how he builds strong relationships, and how being an Ironman triathlon competitor shapes his outlook on work and life.

Mary K. Pratt: What is Wynn’s vision for enhancing the guest experience?

Dan Regalado: When I interviewed with our CEO Craig Billings, CFO Julie Cameron-Doe and COO Brian Gullbrants, I felt their excitement of onboarding a CIO to help accelerate Wynn’s technology agenda.

They are excited to use data and artificial intelligence to personalize even more of the interactions we have with our guests. We want to leverage data, AI and other technologies, responsibly and ethically, to push the envelope on what an amazing and delightful experience could be. By leveraging data, we will create highly personalized guest experiences versus treating every customer the same way. Our guests have options, but they choose us because they expect us to be the best. It is exciting for me to think of how we can use technology and data to create even more fun for our guests than they anticipated.

Can you give me an example of an “amazing” guest experience you are working to create?

That personalized experience at every touchpoint and moments that matter… over the phone, in our amazing properties, or at our digital channels (i.e., website and mobile) – we should know you as our valued guest.

And as long as our guests allow us, we should know their preferences such as room types, floors, temperature, favorite activities, and restaurants, and then help them enjoy our property as frictionlessly as possible: “Hi, Mr. and Mrs. Smith, thank you for coming back, I see you were with us in July. Your room is ready and at 70 degrees. And by the way, it is on the 57th floor facing the golf course and the Sphere like you prefer. Would you like us to book your favorite restaurant for dinner? SW is available tomorrow at 7. I can book that outdoor seating for two.” That is the kind of frictionless and delightful experience we consider amazing.

What have you found most exciting about your position?

One is our teams – from the hotel and casino staff all the way to the executives. There is no shortage of excitement for how technology can become an ingredient to our continued and elevated success. This is exciting for me as CIO, because my team can focus on execution and shipping quality products with speed versus spending significant amount of energy convincing others what tech can do.

It is also exciting to come into a company that is experiencing significant growth. That shows that the people who are steering the ship are doing the right thing. We know what the strategy is, and we know how to execute against that strategy.

The third exciting and fun piece is the people coming to us, and coming back to us, because they love the Wynn experience and the events we are hosting. I have never been with a company with back-to-back-to-back events. We were a major part of the Formula 1 Las Vegas Grand Prix race in 2023, and it was a smashing success. Then we hosted the Super Bowl in Las Vegas, and, as our Super Bowl guests were leaving, thousands of convention attendees and guests were arriving the same day. Our collective teams were relentless as we executed flawlessly to ensure our guests, whether they were leaving or checking in, were taken care of. Our systems held up, too. Our teams will be seen with a smile through all of these because we take pride in what we do.

By the way, even though we are smiling, that does not mean the job is easy. Our tech team and partners put so much preparation into these events to make sure that the technology stack holds up. Operationally, imagine turning over most of the 4,000-plus rooms through the transition of the Super Bowl to the conference crowds in the same day. Our guests were greeted with surgically clean property and rooms. That is not an easy feat, and I give credit to all our staff and the leadership team for relentlessly pursuing excellence!

In this case, my team was committed to making sure that our housekeeping team had their technology tools working flawlessly, our front desks were equipped with a stable platform to check our guests in and out, and all our tech ecosystem, whether supporting the restaurants, spa, gaming platforms, in-room tech, Wi-Fi, etc., were working flawlessly.

Your biography highlights your relationship-building skills; how do you approach building relationships?

The first step of relationship building is establishing trust, and knowing that trust is earned, not given. I know that I have to earn the trust of my constituents – the CEO, resort presidents, COO, CFO and other leaders – by being transparent, reliable and proactive.

I earn the trust of my team by having their back, enabling them, recognizing great work, and embracing failure so long as we are failing forward. Of course, accountability is enforced, and my team understands this well. My team knows I have their backs, as long as they do their best to deliver our commitments to our guests, partners, and employees.

And I earn the trust of my vendors by viewing them as my partners. I get to know them. I also establish an objective relationship with them, so we can measure the performance of each of them on well-established best practice metrics such as meantime to resolution, availability, and delivery excellence.

How did you develop your relationship skills?

I watched peers and leaders who were skilled in building relationships and those who were not. I saw what worked well for others and for me was being a fair and a good human being. In my experience, this approach brings out the best of my team, my business partners, and service providers, plus they tend to go above and beyond. There is a chance that others will take advantage of that, and in these cases I would employ a different approach altogether. But seeing many react positively to this approach is rewarding. We achieve more together while having fun versus having challenging relationships.

Can you share an example of how this approach delivered a better-than-expected return?

One example was our points of interest were wrong on Apple and Google maps and had been wrong for a long time. Soon after I joined, I personally got lost following the directions on my phone, which to our guests would not be a good first impression trying to get to our property.  With the partnership approach we were able to fix them within a couple of weeks.

Another example: We initiated a virtual war room anchored on a “one-team win and lose together” approach and within a couple of weeks we found a nagging issue causing one of our data-driven products to show inaccurate results. It was in one of our partner’s products and we have since fixed it. We are well underway in re-launching the product, this time with accurate results that the business and guests can trust.

I have seen this work repeatedly. It is easy to go in with the stick approach, but that is not my style. It has its place when the relationship approach fails to deliver.

You identify yourself as a servant leader. How do you define that leadership style?

Servant leadership, in my view, means dedicating myself to enable my team and our extended teams – such as our teams on the floor and our hotel employees – to delight the guests every day.

My view of servant leadership is I work for them. I always ask: What do you need from me or my team to be successful? How can I help you do your job and have fun at the same time?

Servant leadership means being a good listener. I do a bit of that so that I can make informed decisions and be a reliable servant leader to them.

Do you recommend others adopt this leadership style?

To each his own on this topic. I just happen to subscribe to this type of leadership. It may or may not work for other executives. I came from a humble home with pretty much nothing, and I try to keep myself grounded. My folks taught me to never forget where I came from. That influences my servant leadership.

You also call yourself a “disciplined health and wellness enthusiast.” How does that influence your leadership?

I advise my team to dedicate at least a few minutes to their wellness every day. You need to take care of yourself first so you can take care of others. Do something for yourself every day that takes good care of your body and mind. Maybe it is meditation or yoga. Maybe it is stretching or lifting weights, or swimming, biking, or running.

You have competed in 12 Ironman triathlons, which require a 2.4-mile swim, a 112-mile bicycle ride and a 26.22-mile run. How did you become involved in such rigorous races?

Twelve years ago, I could not run a mile without stopping, and even though I grew up in the islands of the Philippines, I did not know how to swim.

But I put it in my mind that I want to do this, so I registered six months ahead of a half Ironman Triathlon. I used that short timeline to pressure myself to train and to learn to swim – or at least to survive in the water. I watched YouTube videos and some friends to learn.

The experience taught me that nothing is impossible if you put your mind and your body into it.
I apply what I have learned from that training to my professional career. I tell my team that work has a resemblance to doing an Ironman. It can be very overwhelming to think about what we are trying to accomplish, so keeping our focus on the ultimate goal without overlooking the smaller milestones. There will be troubles along the way. A swell during the swim may sweep you off course. Pause and re-orient your direction, then keep going. You may get a flat tire. Try not to get discouraged, stay composed and focused, fix the flat, fix the issue, keep going. Put one foot in front of the other on that long run and soon enough you will be at the finish line.

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