Episode 22: Creating Family Wherever You Go with Leah Rossi

Episode 22: Creating Family Wherever You Go with Leah Rossi

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.

Episode 21: Happy Is the Strategy with Liz Johnson on Location

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.

Episode 20: From Needing a Chance to Changing Lives with Aaron Evans on Location

For the first full Work + Wander episode on location, Jess and Jay head to Myrtle Beach to sit down with Aaron Evans, Director of Sales & Marketing. Aaron shares the story of how a $50 interview outfit turned into a life-changing career — and how he now helps others do the same. From leadership to mindset to unforgettable travel moments, this episode is all about what’s possible when you bet on yourself.

Episode 19: On Location in Myrtle Beach with Angela Small

We took Work + Wander on the road. Recorded on location in Myrtle Beach, this episode marks the start of our new “On Location” series. Jay and Jessica are joined by Angela Small for a quick, unscripted conversation covering travel, career, and a fast-paced Suitcase Sprint — all recorded just feet apart for the first time. A short episode, and a preview of what’s to come.

Episode 18: Events, Experiences, and Everything In Between with Louis Acosta

In this episode of Work + Wander, hosts Jessica Badlam and Jay Cocorullo sit down with Louis Acosta, Senior Vice President of Sports, Entertainment, Event Marketing and Sales at Travel + Leisure Co. From launching his career on the beaches of Cozumel to leading large-scale, best-in-class events across the industry, Louis shares how a passion for hospitality turned into a career built on creating unforgettable experiences. The conversation explores what it really takes to design moments that go beyond the expected — from bucket-list events and exclusive partnerships to the idea that “better is better.” Louis also reflects on how travel shapes perspective, why experiences matter more than ever, and how meaningful moments can leave a lasting impact long after the trip ends. Plus, stay tuned until the end for an exciting announcement you won’t want to miss — and hear why the best trip is always the next one. Hot Jobs from your hosts: Jessica: https://c.flockity.com/c/TNLJessica [https://c.flockity.com/c/TNLJessica] Jay: https://c.flockity.com/c/TNLJay [https://c.flockity.com/c/TNLJay]