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 Blarcom

What 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

What if the career you're meant for isn't the one you planned?

In this episode of Work and Wander, Kim Marshall, Chief HR Officer at Travel + Leisure Co., chats with Jay and Jessica about how a special project changed the course of her career and led her from public accounting to HR leadership. Along the way, she shares advice on building relationships, staying curious, taking risks, and raising your hand when opportunity knocks.

Plus, Kim shares bucket list destinations, carry on travel strategies, and the surprisingly clever way monkeys in Costa Rica avoid crocodiles.

Come for the career advice. Leave inspired to book your next adventure.

Help us Put the World on Vacation: https://c.flockity.com/c/TNLworkwander

We're kicking off a special Work + Wander series celebrating Travel + Leisure Co.'s outstanding associates recognized at this year's ARDA Awards. In this episode, Jay and Jessica sit down with Dan Williams, Director of the Human Resources Service Center and recipient of the ARDA Human Resources Professional of the Year award.

With more than 37 years at the company, Dan reflects on the career decisions, mentors, and opportunities that shaped his journey. He shares insights on building a culture rooted in respect, leading teams that stay and grow together, and why taking risks can lead to unexpected opportunities. Plus, Dan talks travel, from family vacations at Bonnet Creek to memorable trips to Colorado and the destinations still on his bucket list.

Whether you're just starting your career or thinking about your next chapter, Dan's story offers a thoughtful look at what it takes to build a career that truly lasts.

Browse Opportunities: https://c.flockity.com/c/TNLworkwander

Leah Rossi's career has taken her from an internship in Puerto Rico to leadership roles across the Caribbean, Texas, and South Carolina. Now preparing for her next chapter in Williamsburg, she joins Jay and Jessica to share the experiences that shaped her approach to hospitality and leadership.

Leah reflects on leading through back-to-back Category 5 hurricanes in St. Thomas, the importance of building a workplace culture that feels like family, and why great leaders never stop learning from the people around them. She also shares memorable travel stories, dream destinations, and her philosophy of staying open to wherever life takes you next.

Browse Open Opportunities: https://c.flockity.com/c/TNLworkwander

Elizabeth Johnson has spent 20 years with Travel + Leisure Co. — and somewhere along the way, a podcast in a school pickup line changed everything. In this episode, Liz joins Jess and Jay to talk about her journey from Fairfield Resorts to frontline sales, and the passion project nobody asked for but everyone keeps signing up for: "The Happy Class". Plus, Park City ski runs, a $249 trip to St. Martin, and why "calm" is her one word for the perfect getaway.