Episode 30: Bringing Vacation Full Circle with Billy Owens

Years before helping lead the move into Travel + Leisure Co.’s corporate headquarters, Marla Tichi worked in our very same building. In another on-location episode, she joins Jay and Jessica to talk about the unexpected turns in her career and the ideas behind a space built to reflect the vacation business it supports.

What does vacation ownership look like today, and how is the industry continuing to evolve?On this episode of Work + Wander, Jay Cocorullo and Jessica Badlam welcome Jason Gamel, President and CEO of the American Resort Development Association (ARDA), as their first guest from outside Travel + Leisure Co. Jason shares a behind-the-scenes look at ARDA's role in supporting the vacation ownership industry, from advocating for owners and protecting consumers to helping change perceptions of modern timeshare.They also explore how vacation ownership has evolved to offer travelers more flexibility, choices and experiences, along with a few of Jason's own favorite vacation memories and destinations still on his bucket list.

In this episode of Work + Wander, Jay and Jessica sit down with Larry Lee, Vice President of Sales and Marketing at Club Wyndham Glacier Canyon and recipient of Travel + Leisure Co.’s 2026 CEO Impact Award. Larry shares his journey from sales rep to award-winning leader, his approach to building successful teams, and why putting people first makes all the difference. Plus, memorable family travels, unexpected vacation detours, and a little Suitcase Sprint fun!

What does it mean to put people first as a leader?On this episode of Work + Wander, Jay Cocorullo and Jessica Badlam sit down with Rob Shepard, Area Vice President of Sales and Marketing for Tennessee at Travel + Leisure Co. Rob reflects on a career that began as a sales representative in Williamsburg and the lessons that have stayed with him as he’s grown into leadership, from listening before making assumptions to creating an environment where people have the opportunity to succeed.Rob also shares how his approach to serving guests has shaped the way he leads today, why genuine conversations still matter, and what nearly two decades in the vacation ownership industry have taught him about developing people and building strong teams.

What happens when the vacations you grew up taking eventually become part of your career?On the Season 2 premiere of Work + Wander, Jay Cocorullo and Jessica Badlam sit down with Billy Owens, Owner Onboarding Specialist at WorldMark Indio. Billy shares how growing up vacationing with WorldMark helped bring his family closer, how those experiences now shape the way he connects with new owners, and the unexpected career journey that brought him full circle to Travel + Leisure Co.It’s a conversation about family, career, and the experiences that can shape both.

One year, 29 episodes, and a lot of career stories and dream destinations later, it’s time to celebrate the end of Season 1 of Work + Wander!Jay Cocorullo and Jessica Badlam look back at some of the conversations, career lessons and travel stories that have stuck with them most from the first year of the podcast. They revisit a few recurring themes, reveal some surprising Suitcase Sprint stats and reflect on how a fun idea turned into an opportunity to connect with people from across Travel + Leisure Co.And for the first time, Jessica gets to experience the Suitcase Sprint from the other side of the mic.Season 1 may be wrapping up, but Work + Wander isn’t going far. Season 2 is right around the corner!

What does it take to build a successful career in sales and help others do the same?On this episode of Work + Wander, Jay Cocorullo and Jessica Badlam sit down with Trina Miller, SVP of Sales Training, Development and Programs at Travel + Leisure Co. Trina shares her unexpected journey from human resources to timeshare sales, the lessons that shaped her approach to leadership, and why strong fundamentals and consistency matter when developing great sales talent.Trina also reflects on the role vacation has played in her own life, from discovering a love of travel as an adult to creating family memories with her children and now her grandchildren. It’s a conversation about growth, developing people and the experiences that remind us why putting the world on vacation matters.

What goes into creating the digital experiences that help travelers make the most of their vacations?On this episode of Work + Wander, Jay Cocorullo and Jessica Badlam sit down with Summer Rollins, Director of Consumer Platform Strategy and Outcomes at Travel + Leisure Co. Summer shares how her team transformed a blank slate into the award-winning Club Wyndham app, why curiosity is one of the most valuable career skills, and what product strategy really looks like behind the scenes.Along the way, she reflects on lessons learned from unexpected customer feedback, the importance of designing with the user in mind, and how technology can help create better vacation memories. Plus, in the Wander segment, Summer shares why France stole her heart, how she plans every detail of her trips, and the destination that's next on her travel bucket list.

Episode 26: The Ripple Effect with Adria Van BlarcomWhat happens when one conversation changes the course of your career? In this episode of Work + Wander, Jessica and Jay sit down with Adria Van Blarcom, Director of Travel at Travel + Leisure Co. and a 2025 ARDA Award winner, to talk about the unexpected path that led her into learning and leadership. From building impactful training programs to leading across cultures, Adria shares how curiosity, mentorship, and a passion for developing people create a ripple effect that extends far beyond the classroom. Plus, she reflects on memorable travels, dream river cruises, and why the best journeys often begin with simply saying "yes" to a new opportunity.

Some hidden gems don't show up on a map. They show up in the people who bring them to life.In this episode, Jay and Jessica sit down with Cypress Tucker-Wachholz, Guest Services Associate at Worldmark Clear Lake and ARDA Resort Operations Team Member of the Year. In eight and a half years with Travel + Leisure Co., Cypress has gone from housekeeping to launching a gift shop that blew past its revenue target by 300%, certifying her entire front desk team as county tourism ambassadors, and becoming a trainer for the whole county herself.Cypress shares what hospitality really looks like from the ground up, why community winning is the whole point, and what it felt like to walk across that stage at the Bellagio. Plus — bucket list dreams, a confession about Hallmark movies, and why her name says it all.Browse opportunities at Travel + Leisure Co: https://c.flockity.com/c/TNLworkwander