Austin Wright ran into the same coworker three times on his vacation in Barcelona. Then he ran into another one.
Your coworkers may be the last people you’d expect to see on your summer vacation, but ever since Lose It! hired Wright in March, he’d been looking forward to it. The Boston tech company has an annual tradition of flying its entire team and their families to a far-off destination to live and work for up to a month.
This year, it was the Catalonian city known for its beaches and extravagant architecture.
“It wasn’t until my last interview that the company dropped this perk on me,” Wright said. “I was like, ‘Wait. That makes no sense. I don’t understand’”
Call it a twist on a family vacation. While other Boston companies might arrange an outing to a Red Sox game or bond over drinks and lobster rolls at The Barking Crab, Lose It! takes its staff and their families on an all-expenses-paid retreat.
Last year, employees worked and sipped wine under the glow of the Eiffel Tower. This summer’s trip included mystery dinners, castles, an exclusive vineyard tour, and, well, all of the tapas.
To Lose It!’s leadership, the ‘family vacation’ is more than just a standout perk — it’s an opportunity to foster connections that go beyond team roles and to explore life outside of work.
Here’s How it started
Lose It! CEO Charles Teague came up with the idea for a company-wide overseas retreat two years ago. He wanted to see the world with his family without having to take weeks off of work to do it, and he felt that his employees should have that same opportunity.
The trip itself can be the experience of a lifetime for most, but it is also a concrete way to demonstrate the key values that drive the company.”
Over the years, Teague said, Lose It! had fostered a culture that prioritized personal growth as much as it did productivity. For the most part, that’s played out through common perks like flexible remote work policies, unlimited PTO and balanced workloads that let employees further their education outside of work. The retreat represented the perfect way to advance those values while also providing an experience employees wouldn’t get anywhere else, Teague said.
“The trip itself can be the experience of a lifetime for most, but it is also a concrete way to demonstrate the key values that drive the company,” Teague said.
After talking it over with the management team and a few key leaders at Lose It!, they decided to make it official.
Employees Plan their own itineraries
For each retreat, Lose It! comes together as a staff to vote on where they want to go. This year, the staff chose Barcelona over Copenhagen, Denmark and Banff, Canada.
The company then provides each employee, as well as their spouses and children with stipends. While the company did not disclose how much they provide each employee, the money is enough to cover flights, food and boarding for up to a month. Employees can make their own itineraries and budgets, choosing whether to spread it out over the entire month or spending it all in a week of extravagance.
Having that flexibility to choose what you want to do had a huge role in making this a success.”
The goal is to make the trip accessible for all employees, whether they have a family or not. Everyone on the trip is given the freedom to explore the city on their own, but they are expected to work during the week — with Fridays off as part of Lose It!’s summer Friday policy. Meanwhile, those who can’t go or choose to skip the trip are able to work from home and enjoy summer Fridays.
“We carefully plan the trips in locations and with schedules that are designed to give employees the opportunity to have a transformative personal experience without having to stop working to get it,” Teague said.
This year, about 40 employees and 15 family members made the trip. Product manager Austin Wright, who joined the company in March, flew to Barcelona in mid-June with his wife, their 6-year-old twins and 2-year-old daughter. They booked an Airbnb blocks from Barcelona’s famous Las Ramblas street.
Wright worked Monday through Thursday until 4 p.m., and then spent the evenings and weekends exploring the city with his family. They rode trains through the Spanish countryside, introduced paella and tapas to their kids, and road tripped the French Riviera. It was an experience he never imagined having with his family.
“A year ago, we didn't think we were going to live in Boston, let alone to be able to explore the French coast,” Wright said. “Having that flexibility to choose what you want to do had a huge role in making this a success.”
But for all the personal opportunities to explore, the trip also created a unique way for coworkers to bond.
Creating connections beyond work
During workdays, Lose It!’s Slack channel was filled with photos and stories from that day’s adventures.
Some employees roomed together, and others chose to meet for drinks, explore the city together or take weekend trips to Madrid. While Wright stayed with his family, he enjoyed the serendipity of running into the same coworker three different times in Barcelona. With everyone traveling the city at the same time, it broke down the group silos and in-jokes that can often develop in an office setting.
“Because the communication was constant, we felt like one massive group,” Wright said.
The company did gather for one week during the retreat for a planning session and a few planned outings. Lose It! took everyone on a behind-the-scenes tour of a vineyard, and several employees coordinated and hosted mystery dinners. Wright volunteered to host one of these dinners, which included a gondola ride to the top of Montjuïc where they ate dinner at a cafe.
Having the team experience new cultures and new experiences is a great way to change perspectives, build relationships and encourage creativity.”
According to Wright, those shared experiences have led to more meaningful conversations between employees and brought the team closer together.
“Having the team experience new cultures and new experiences is a great way to change perspectives, build relationships and encourage creativity,” added Teague.
do ‘out there’ perks work?
For Lose It!, the retreat has been helpful in retaining and recruiting employees.
As a mid-size app developer, Lose It! is often competing for talent against much larger companies that can offer higher salaries, and with smaller ones that can provide future equity. The culture retreat not only provides a unique life experience for an employee, but it also emphasizes the company’s commitment to enjoying life outside of work.
The key is to find benefits that are both hard for employees to find elsewhere and that are an honest reflection of how the company thinks about employees.”
From a work standpoint, the company has experienced spikes in productivity and improved communication across teams while working in Barcelona, according to Wright. The team also returns more refreshed and ready to tackle their work in Boston.
While Teague knows not every company can replicate an annual retreat, he believes every company can benefit from offering a unique perk like this.
“The key is to find benefits that are both hard for employees to find elsewhere and that are an honest reflection of how the company thinks about employees,” Teague said. “If you find that for your company, it will help you attract talented and like-minded employees.”
