When Jolene Stevens was looking for a more flexible schedule than her corporate job allowed, she turned to travel advising, specializing in planning Disney vacations. She loved the work so much that she eventually founded her own company helping travel agency owners level up their skills to run successful businesses.
Through her company, Travelland, the California-based entrepreneur hosts events — including Travelland's owners-only ELEVATE conference — on business development topics for travel industry leaders. Subjects at the conference range from the nitty-gritty, like contracts, analytics and branding, to the big picture, such as leadership, mentorship and having hard conversations. While she brings in expert speakers to this in-person annual event, she also makes space for table discussions so fellow owners can learn from one another.
“One of the things that I love about the travel industry, and specifically the owners who come to Travelland's ELEVATE, is that everyone shows up to share and to learn,” Stevens explained. “The comment that I hear most from suppliers and attendees is, ‘There are no egos in this room.’ People are so generous with their knowledge and their experiences and what went right, but they’re also really willing to share what didn’t work and their missteps. That’s an amazing presence to be in.”
Each year, ELEVATE gathers around 50 owners for a two-and-a-half-day event that rotates between Los Angeles and Orlando. On average, owners who attend ELEVATE sell $4 million annually and lead 20 agents. Given her background in event planning at such companies as Segway and Disney, Stevens knows how to keep attendees engaged. She switches up table assignments regularly to make sure everybody expands their networks, rather than only talking to people they already know.
Travelland began during the COVID-19 pandemic as an online community, and as the world opened up once again, Stevens wanted to take the momentum of “curiosity, collaboration and community” to an in-person realm. For details on future ELEVATE events, online resources and coaching opportunities, check out travellandcollab.com.
In 2026, those who join the fee-based Travelland community of agency owners can expect programming on how to integrate Google Classroom into their businesses and how to create separate brands to attract different clients. For travel advisors, Stevens is considering creating an online version of ELEVATE tailored to their needs.
Through her work, Stevens has noticed and appreciated how many women are at the helm of independent travel agencies. “It’s all of these super savvy women who are doing business differently,” she said. “The ideas that are coming from within this group, it’s like they’ve unplugged themselves from the typical idea of ‘this is how you have to do business.’ They’ve opened up a creativity and an approach that is new and fresh. That is so energizing and refreshing.”
As a woman business owner, Stevens, who is a mom, remembers an unlikely place she found business leads: kids’ birthday parties. While the kids played in the ball pit or the bounce house, she chatted with other parents and helped them dream of a vacation escape.
When it comes to driving leads, Stevens recommended thinking about how to widen your own circle of potential clients. When she volunteered at an art museum, she ended up meeting a new group of people — some of whom became her best clients. “Think of where you’re currently not connected and you still have interest, and find ways you can contribute,” she recommended.
Her key advice all goes back to making in-person connections — which is especially important in a world of AI slop and social media overwhelm. “I believe that in this realm right now, the most valuable thing is actually the relationships we are building in authentic ways,” she said. “Marketing in your community is one of the best ways to connect with local clients. Getting out and participating in your community is huge. Connecting personally is still king in my book.”
What’s in Jolene’s Carry-on?
“All the comfort things: Noise-cancelling headphones, a fabulous fiction book and I usually have some sort of nonfiction hard-copy book — my favorite recently was Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts by Annie Duke — plus snacks, a protein snack like Chomps sticks and some sort of chocolate. Good socks: Bombas ideally. And lots of patience and the ability to pivot.”
Originally appeared in the Spring 2026 issue of The Compass magazine
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