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In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.

Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.

The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.

Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.

Episode Chapters:

02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide

10:06 - How Marriott Vacations Worldwide thinks about loyalty

11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings

18:53 - What vacation rental operators can learn from timeshare

19:30 - How brand standards help build guest trust

28:20 - Why lifetime value matters in the customer journey

29:00 - Viewing vacation ownership as a subscription business

31:09 - Using experiences to strengthen loyalty and engagement

40:11 - How Marriott Vacations Worldwide is using AI in sales training

41:41 - How AI is changing digital search and hospitality marketing

47:52 - Why prepaid vacations create resilience

51:43 - What is ahead for Marriott Vacations Worldwide

Connect with Mike:

LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094

Instagram: https://www.instagram.com/thevacationdr/reels/

Connect with Marriott Vacations Worldwide:

Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/

Westin Vacation Club: https://www.instagram.com/westinvacationclub/

Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/

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#vacationrentals #shorttermrentals #timeshare