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Marriott Vacations Worldwide with President and COO Mike Flaskey
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Mike Flaskey is President and Chief Operating Officer of Marriott Vacations Worldwide, the Orlando-based vacation company behind roughly 120 vacation ownership resorts and about 700,000 owner families. Appointed in February 2026, he sets the company's commercial strategy and oversees all brand, commercial and operating functions, with a mandate to sharpen sales and marketing execution and grow the lifetime value of owners through an experience-based model.

Flaskey brings more than 25 years of leadership in vacation ownership and hospitality. He was Chief Executive Officer and a board member of maritime hospitality company Hornblower Group from August 2024 to December 2025. Before that he spent more than a decade at Diamond Resorts International, serving as Chief Executive Officer from 2017 to 2021 and leading a transformation, including several strategic acquisitions, that culminated in the company's sale to Hilton Grand Vacations. Earlier in his career he held senior executive roles at Starwood Vacation Ownership and Fairfield Resorts (now Travel + Leisure), building expertise across brand, sales, marketing, operations and resort management. He serves on the board of Invited Clubs and previously served on the board of Holiday Inn Club Vacations.

This episode of The New Normal was recorded in Florida with Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide. Ruben Harris is joined by co-host Jeff Herzfeld, OutRival's Head of Travel. The company has 120 resorts around the world, more than 37,000 rooms, 23,000 associates and 700,000 owner families across the Marriott, Westin, Sheraton, Ritz-Carlton, St. Regis and Hyatt vacation ownership brands. Flaskey joined in February after CEO Matt Avril, a colleague from their Starwood Vacation Ownership days, asked him to come in as president.

Flaskey walks through the full owner journey. Marriott Vacations Worldwide sources first-time buyers from the Marriott Bonvoy and World of Hyatt databases with a $199 preview stay in exchange for 90 minutes of their time, and about two in ten purchase. Those who are not ready can take the Explorer trial package. Owners use a points product that works like a currency across resorts, unit sizes and lengths of stay, and the average owner buys three to four times over the life of their ownership. Half of the roughly 500,000 annual tours are existing owners, yet they account for 70% of sales, which Flaskey credits to the housekeeping, engineering, front desk and activity teams who deliver the dream. Inner Circle, launched in June, adds curated experiences in music, culinary, television and sports for small groups of owners.

On AI, Flaskey is direct that the company is in the top of the first inning. The one application in production is Tour Logistics, a proprietary algorithm that ranks each of about 1,400 sales associates by tour type and routes tours three times a day so the best performers get the most at-bats. He sees digital workers helping next with learning why first-time guests leave without buying, hearing from owners at scale, collections, loan servicing, contact centers and preparing each stay before arrival. His position is that AI makes the team smarter and does not replace the person who welcomes an owner home.

Key Takeaways

  1. Loyalty is the growth engine. Half of the roughly 500,000 annual tours are existing owners, yet they account for 70% of sales. Mike credits the housekeeping, engineering, front desk and activity teams who "deliver the dream."
  2. Experiences keep owners in the system. Inner Circle brings the kids and grandkids of longtime owners back, and it also draws younger families who would once have chosen an Airbnb.
  3. The best AI win so far is matching. Tour Logistics ranks every sales associate by tour type and routes tours three times a day. Like a batting order, it gives the best performers the most at-bats.
  4. The next opportunity is reach. Surveys only capture part of the picture. Mike sees digital workers learning why 70% of first-time guests leave without buying, hearing from owners at scale, and preparing each stay before arrival.
  5. Efficiency does not mean eliminating jobs. Mike sees the value in doing both things at once: lowering costs and improving the metrics that matter. Leadership and the face-to-face moment stay human.
  6. Experiences are moving from luxury to necessity. This was Mike's answer on the new normal in travel.
120
Resorts
Around the world, across the Marriott, Westin, Sheraton, Ritz-Carlton, St. Regis and Hyatt brands
37,000+
Rooms
Who account for 70% of annual sales by buying more of the product
700,000
Owner families
Who account for 70% of annual sales by buying more of the product
23,000
Associates
Including about 1,400 sales associates handling roughly 500,000 tours a year
Pull Quotes
MARRIOTT VACATIONS WORLDWIDE · EPISODE 11
“AI tutors alone haven’t moved the needle in education. The real opportunity is using AI to reach learners proactively, support the people building courses, and remove the barriers that keep students from completing them.”
You don't have the reach that these digital workers do. This is not a hotel. These folks have committed money, real money, to own with us, so we welcome them home. We have a sales and marketing team that sells the dream. But what really matters is when our owners show up, are we delivering the dream. What technology can't tell you is the human nature. So you have to have human beings. You gotta eat it a bite at a time. What you don't wanna do is make the big mistake.
Mike Flaskey
President and COO, Marriott Vacations Worldwide
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