You probably didn’t start your travel business dreaming about onboarding packets and staff check-ins. But, once you’ve built a thriving business, making the leap from solo advisor to agency owner is one of the smartest ways to scale without sacrificing the quality service your clients have come to expect.
Simply hiring contractors or employees isn’t enough to build a successful agency, though. It requires a strong, intentional leader to turn a group of individuals into a high-performing team that supports your vision.
You don’t need to go to business school to learn how to build that kind of team, but it does help to hear from travel industry pros who’ve done it themselves. Here’s their best advice for leading with purpose, scaling smart and turning your team into an asset that makes your business better — not busier.
Set Clear Expectations From Day One
Before you even make your first hire, good leadership means getting clear on what success in that role actually looks like. Janelle Grissinger, president at JCo Travel, recommended looking for people who have strengths in areas you don’t.
“I’m great at bringing in ideas and inspiration, but I need help with organization,” she explained.
Carry that self-awareness through to the job description. It should clearly outline what the role entails, which skills are essential and how you’ll measure success. Ángel Sarmiento, chief executive officer at Mita Residential, who manages more than 200 employees, recommended reviewing the job expectations collaboratively with the person you plan to hire.
“Let them know that if they complete this bulleted list from the job description, they will be a successful hire,” he said.
Then, get them started on the right foot with a thorough onboarding package. At JCo Travel, that includes a step-by-step guide for the company’s customer relationship management platform, required legal waivers and instructions on signing up with key suppliers.
Create a Culture of Connection
Culture isn’t just a buzzword at JCo Travel; it’s the reason her agency is on track to sell $50 million in travel in the next two years, Grissinger said.
How she hires is at the root of that culture. From the beginning, Grissinger focused on hiring advisors who were kind, driven and team-oriented — not just those with flashy sales numbers.
“I can teach a lot of things, but I can’t teach heart, and I can’t teach that team atmosphere,” Grissinger said.
Grissinger, who now manages a staff of 17 independent contractors, described her team as driven, but not competitive; accountable, but not too serious; caring and empathetic, but not dramatic.
“Just one person can quickly sour a whole group, so I have to be careful about who we bring in,” she explained.
But just as important as hiring the right people is nurturing that team culture every single day. Grissinger keeps her remote team connected through two constantly active group chats — one for work and one for everything else — and two monthly Zoom meetings to highlight what’s working, recent wins and ways to support each other during slower months. She gets the entire team involved in agencywide projects, like updating photo albums from FAMs and retreats, which helps create a sense of shared ownership and pride in the brand.
She’s also rolling out a new structure that pairs newer advisors with more experienced team members in pods, creating built-in mentorship and smaller support groups within the larger team.
“The mentorship was already happening naturally, but now we’re trying to direct it more into the onboarding process,” Grissinger said.
But even with all these virtual opportunities to connect, Grissinger believes nothing reinforces culture better than being together in person, hence why she hosts an annual team retreat. Nearly everyone at JCo Travel also attends the agency’s signature black-tie gala, which is a fundraiser for the children’s charity she founded, Heart of JCo.
“It’s important to the team and our culture. Everybody on my team is a bleeding heart, especially when it comes to kids,” she said.
Make Feedback a Two-Way Street
Creating space for honest, two-way conversations is one of the most effective ways to uncover solutions you might not find on your own and help your team understand exactly where and how they can contribute. (After all, that’s why you hired them!)
“You should make sure that you have regular feedback sessions that are bi-directional, where you’re not just talking about the business, but sharing actual feedback about each other’s work,” Sarmiento said.
When you’re providing feedback — especially criticism — Sarmiento recommended “staying on your side of the net.” That means stating the behavior you observed and sharing how that affected you, your business or your client. Then, give them a chance to share their side of the story and work toward better outcomes together. Ask them what kind of support they need to improve, and listen with an open mind.
Handle Mistakes With Empathy and Action
Strong leaders know that whenever you add people to the team, mistakes can happen. What matters most is how you handle those mistakes. Your reaction directly influences whether or not your team feels safe owning up to their missteps and if they can trust you for support.
Grissinger recalled a time when one of the advisors on her team missed an attrition date for a wedding she was planning, resulting in a $50,000 charge.
“I didn’t want this to ruin either one of us, so I told her we were going to fix this together,” she said.
Rather than pointing fingers, she got to work asking vendors for favors and ultimately bringing down the balance significantly. Even though the advisor worked as an independent contractor and could have been fully liable for the charge, Grissinger opted to split it with her. She felt it was the right thing to do, and it showed her entire team they could count on her in a crisis. That kind of trust nurtures a team that’s willing to go the extra mile for a business.
“If you put people first for real — what they need and who they are — the numbers will follow,” Grissinger said. “In those moments, you truly have to be about more than just the sales.”
As much as you might wish you could control every detail, that’s just not reality. But you can control how you lead when it counts — and that’s how you turn a group of advisors into a team that’s committed, connected and ready to build something bigger with you.
Orginally appeared in the Fall 2025 issue of The Compass magazine
Joni Sweet
comments