HeyJaredWork + Wander
Work + Wander is where career stories meet dream destinations. Hosted by Jay Cocorullo and Jessica Badlam from Travel + Leisure Co., each episode features engaging conversations with leaders, innovators, and colleagues about their career journeys — and the travel experiences…
- Indexed episodes, last 90 days
- 7
- Latest publication
- Sep 28, 2026
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- Checking…
- Earliest in this view
- Jul 6, 2026
Latest episodes
Episode 31: Leading by Putting People First with Rob Shepard (opens the original)
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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
Episode 30: Bringing Vacation Full Circle with Billy Owens (opens the original)
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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 conversa
Episode 29: Celebrating One Year of Work + Wander with Jay & Jessica (opens the original)
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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 +
Episode 28: Building Sales Talent That Lasts with Trina Miller (opens the original)
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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 rol
Episode 27: Building Better Vacation Experiences with Summer Rollins (opens the original)
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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
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