4 remote workforces keeping company retreats alive

Buffer company retreats

Company retreats aren’t as common as they used to be. After all, startups tend to keep things agile and lean, and the bigger corporate entities have been known to get some flack when their executives get a little too lavish.

But the company retreat is very much alive, thanks, in part, to a specific subset of the world of work: the remote workforce.

“Team retreats are an incredible way to bring a company together,” writes Megan Berry, vice president of product at Octane AI. “If you are an all-remote company . . . I would say they are even essential.”

That’s the refrain we’re hearing again and again: when your team is even partially remote, it’s crucial that you get everyone together at least once a year for some face-to-face bonding, no matter the cost.

Want some more proof? Here are four remote companies singing the praise of the company retreat.

Octane AI

Back in October, the chatbot creation platform Octane AI had its first-ever company retreat to bring together its 16 remote employees.

“The one thing you don’t have with a remote team is the ability to build strong in-person connections with your coworkers,” writes Berry. “This is where a team retreat is invaluable.”

One of the biggest challenges of a remote company retreat is timing. Six months in advance, Octane shortlisted a bunch of dates, and then sent out a survey to employees to find the week that work best for everyone. “As new employees joined after the dates were set, we told them the retreat timing during their onboarding so they could mark their calendars and make plans with their families,” writes Berry.

Choosing the date first also allowed Octane to narrow the list of location and venue options (they eventually chose Park City, Utah). The organizers wanted everyone to have two things: their own room, and had a little free time.

Octane AI company retreatsHaving a schedule is important, but not every moment should be scheduled. Give people time to bond on their own or take some time to recover,” writes Berry.

In fact, only half the retreat was devoted to work activities, like company mandate presentations, cross-departmental brainstorming sessions, and goal-setting. The rest of the time was for ziplining, hiking, swimming, and other team-building activities.

The results were extremely positive: “We ran an anonymous post-retreat survey and asked employees on a scale of 1 to 10 how much the team retreat facilitated team bonding,” explains Berry. “70% said 10, 30% said nine, no one put anything lower. Can you think of any other activity companies do that have such universally positive results?”


We’ve heard remote management tips from Wade Foster of app integrator platform Zapier before. He’s a staunch believer in company retreats – he tries to get his 95-strong team together twice a year.

“Some things are just better done in person. For instance, it’s hard to have an impromptu, deep conversation with a teammate over Google Hangout about their kids, some random idea you’ve had improving a secondary process in the company, or company values,” writes Foster.

“All those things tend to naturally happen in person, while they don’t happen in a remote team, unless you force it.”

Through trial and error, he found that a six-day trip (five work days and one fun day) with two travel days book-ending the trip best suited his team. “People with family and kids aren’t too inconvenienced and it’s long enough to do something meaningful.”

In terms of location, he’s found the best retreat venues are close to the airport and big enough to hold everyone, with plenty of activities nearby. “Some of the best activities we do are mostly unrelated to work,” he says.

This includes playing party games, singing karaoke, and other events (like a Game of Thrones viewing party!), as well as hiking and swimming (outdoor activities seems to be a trend at these retreats). In terms of work-related activities, Zapier usually pairs mini-conference with a hackathon.

An event like this isn’t cheap, but to Foster, the comradery it fosters is invaluable.

“Obviously cost is a big consideration for doing a trip like this,” says Foster. “Retreats aren’t cheap, but what’s even more expensive is having a remote team that doesn’t work well together. Ultimately, the cost of the trip is well worth it in my mind, but you have to make that choice based on the constraints of your own business.”


Once a year, web development company Automattic brings their team together for what they call “Grand Meetups.” So far, they’ve hosted retreats in Mexico, Hungary, Canada, and several locales across the U.S. They also set up smaller team meetups for strategy brainstorming sessions throughout the year. “If you join our merry band, expect to travel three to four weeks per year,” says Automattic.

Automattic company retreatsAt the grand meetup, the goal is on connecting with each other, and the main activity is a week-long hackathon.

“We’ve always spent a good portion of the week co-working on projects and launching them at the end of the week,” explains team lead Toni Schneider. “With a small team it was everyone working on tasks from our then current to do lists. As our group got bigger, we started having more planned out projects for multiple teams. The projects are designed to be interesting to the group, have components that everyone can contribute to, and be small enough so they can be launched quickly to get a sense of achievement and completion.”

There are the usual activities – everything from skydiving to Wii marathons – but there’s another always-present event: flashtalks. Every team member gives a short talk to the group on a topic of their choice.

“The rules are simple: Present to the group, five minutes maximum, any topic, everyone has to give a talk,” says Schneider. “The talks end up being a fascinating mixture of people talking about hobbies, families, work habits, diets, books, things they’ve recently gotten passionate about, and much more.”


Social media management platform Buffer also does retreats for its remote staff twice a year – they have gone everywhere from New York to Reykjavik (shown above). And at their recent Hawaii retreat, significant others and kids were invited too (the company footed half their bill), which meant a guest list of upwards of 90 people. They even allow each employee to book their own plane ticket (it gets expensed, of course) to ensure that everyone can travel on their own terms.

While on retreat, employees stick to a rough nine-to-five schedule for work-related activities, and then the afternoons and evenings are filled with optional group activities, like surfing lessons or sightseeing tours – not to mention lots of informal events like board games and yoga. As the team gets bigger and bigger, they organizers have also started to add an orientation day off the top to keep everything organized and make sure everyone is meeting everyone else.

Buffer is up-front about the challenges of whisking away the whole company for a whole week, twice a year. For example, handling customer service can be an issue, and the cost is always growing (the budget for Hawaii was about $400,000).

“Between costs, time zones, visas, Buffer babies and kids, our actual work, and many other factors, it’s quite a challenge to pull off an event like this twice a year,” writes Courtney Seiter, Buffer’s director of people. “But there are so many more moments of joy, serendipity and learning together that make it all worthwhile.”

See also:
8 expert tips for managing remote workers
Going the Distance: How to hire and manage a virtual team


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