How Flywheel Uses to Bring Its Team Together

How Flywheel Uses to Bring Its Team Together


Few things are more important to Flywheel than its quarterly retreats. With more than 50 remote workers spread across the globe, the WordPress hosting company knows how crucial it is to get everyone in the same physical location to foster face-to-face collaboration.

That’s why, four times a year, Flywheel flies every last one of its remote workers to Omaha, Nebraska for a big company retreat. Over the course of several days, team members who may only know each other through email and video chat are able to collaborate in person, share learnings and, of course, have fun.

Over the years, these retreats have become a big part of what makes Flywheel Flywheel: a commitment to culture and team building, carried out in a unique, friendly way.

But there’s a problem.

Navigating a “logistics nightmare”

Trying to get 50 people, from 50 different locations, to the same place at the same time is no easy task.  

“Getting those people to Omaha can be a logistics nightmare,” says Brett Hicks, Head of Employee Experience for Flywheel, and the person responsible for ensuring that 50+ farflung workers make their way to Omaha with as little stress as possible.

Unfortunately, “as little stress as possible” turned out to be quite a lot of stress — both for the travelers and for Brett.

In fact, if anything, “logistics nightmare” is an extreme understatement. If you’ve ever tried to book travel for a group, you know how hard it can be to synchronize schedules. accommodate various preferences, and adapt to travel disruptions. Now imagine doing that for a group of 50. And imagine that these 50 people aren’t coming from the same location, but dozens of locations scattered around the world. And you have to get all of these people to Omaha, Nebraska at roughly the same time.

Not easy.

“If somebody’s flight were to get cancelled, I would find out from the travelers themselves and I would be working nights and weekends trying to resolve these travel problems,” said Brett.

Clearly, this situation was untenable. Brett needed a solution to help her manage this complex travel process and ensure that she could give all the visiting employees a seamless, super simple travel experience — without forcing her to spend countless hours tracking flights and calling into airline support.

That’s when she found

“I can sleep at night now”

After trying a few different corporate travel solutions that didn’t quite fit the bill, Brett came across She was immediately drawn to Lola’s highly rated customer service, beautifully designed app, and intuitive book on behalf functionality.  

“Lola has changed everything for us,” she said. Instead of scrambling to re-book dozens of flights and spend hours on the phone with airlines dealing with missed connections, Brett taps into Lola’s world-class support and lets the experts handle the challenges while she focuses on more important problems.

“Today, I just chat with Lola support and they take care of everything for me,” she said. “I have my nights and weekends back and I’m not sitting on the phone with agents.”

These days, when it comes time to plan a team-wide retreat, Brett finds the process much more manageable. Through Lola, she can be sure that her traveling employees are in good hands, even if they’re not her own.

But there are times when Brett is just as grateful that she can remove herself from the booking process.

“Handing over the reins”

When she’s planning a team-wide retreat, it’s easiest and most efficient to book everything herself so she can keep everything consistent and provide a VIP experience for the company’s remote employees.

But in other instances it’s better for Brett to let employees – typically those who have been with Flywheel for a little while — book their own travel. That way they have more control over their itineraries and they don’t need to bug Brett.

“One of the things I love about Lola is the flexibility in who can do the booking,” Brett says. “So when we fly new hires into Omaha for their first weeks of training, I’m the one who takes care of that, and it’s a streamlined process for me to go in, create a user, and enter their flight information.”

This way she helps new employees ease into their Flywheel career with VIP treatment. But shortly after that, Brett is able to simply give these employees access to the platform so they can book for themselves.

“From that point forward, once they’re kind of established at Flywheel, we hand off the reins to Lola to the new hire themselves,” Brett added. “And our travelers love that because they like the flexibility of being able to book whatever flight they want without it having to go through my approval.”

“It just makes for a streamlined experience for me as the admin, and them as the traveler,” she added.

Whether it’s for a full-company retreat or new hire on-boarding, Lola has completely simplified Flywheel’s process for getting employees in the same place. In fact, Lola’s ability to help Flywheel manage its complex travel needs seemed almost too good to be true.

“I have been through too many scenarios with too many travel providers that overpromise and underdeliver, and Lola is the exact opposite,” Brett said.


About the Author: Mike Baker
Mike was Director of Marketing for and a former journalist, farmer and teacher.