How Wild Moose Turned a Tokyo Offsite Into a Breakthrough Week for Team Connection and Collaboration

Wild Moose is an early-stage startup building AI systems that help engineers debug production issues faster. With team members spread across New York, Tel Aviv, and other locations, bringing everyone together in person is a priority.

This year, the company chose Tokyo for its annual offsite. We spoke with Tom Tytunovich, VP of R&D and one of Wild Moose’s co-founders, about why the team picked Japan, what made the week so impactful, and how Retreat helped make a complex international offsite feel seamless.

About Wild Moose

Wild Moose is a team of around 10 people building AI systems that help engineers identify and fix production issues. The company is U.S.-based, with its R&D team in Tel Aviv, Israel. Tom is VP of R&D and one of the company’s three co-founders.

Why Tokyo

Because Wild Moose is a distributed company, the team tries to gather in person at least once a year. Previous offsites were usually held in New York, where the company already had an office. This time, the team wanted to try something different.

Tokyo stood out for a few reasons. Tom had worked in Japan before and remembered it as a place that was not only exciting, but also highly practical for getting real work done. It offered the infrastructure of a modern city and the energy of a destination filled with unique shared experiences. That combination made it ideal for an offsite that needed to balance focus and fun.

For some employees, this was their first time visiting Japan. For others, it was a chance to return with coworkers and experience the city in a new way. By the end of the trip, many people were already saying they wanted to come back next year.

Balancing work and bonding

One of the biggest goals of the offsite was to make the work itself part of the bonding experience. Instead of simply working side by side on separate tasks, the team designed each workday like a mini hackathon. The goal was to move one feature or product area forward from start to finish in a single day.

That structure created a different kind of energy. People were making decisions in real time, helping each other directly, and solving problems together in the same room. Tom said it created a true startup feeling: not a group of individuals working through isolated tickets, but a team building something ambitious together.

At the same time, Wild Moose did not want the week to become all work. The team also wanted experiences they could only have in Japan—moments that would help people open up, relax, and build real relationships outside the workday. In practice, those two goals reinforced each other. The more comfortable people became with one another socially, the easier it was to collaborate deeply during the day.

The moments that mattered most

One of the clearest highlights was karaoke night. At that point in the week, some team members had only known each other for a couple of days, and one employee’s first day at the company was actually at the offsite. At first, the evening felt a little awkward. By the end, everyone was singing, laughing, and staying longer than planned. Before heading to karaoke, the group stopped at Don Quijote and gave each person a snack budget, then brought everything back to share. It became one of the moments that most clearly broke the ice.

Other activities stood out as well. Team members loved teamLab, and the tea ceremony and wagashi workshop made a strong impression because they felt so different from everyday life. A local festival ended up being another major highlight. For the team, it felt like the kind of experience they never would have found on their own: lively, local, and full of food stalls, games, drinks, and spontaneous interactions.

There were also unplanned moments that became memorable, like ending up in a small local bar and discovering that the owner had gone to high school with one of Wild Moose’s investors. Those unexpected experiences gave the week a sense of discovery that stuck with the team.

What changed after the offsite

The impact of the trip continued after everyone went home. Tom described a clear difference in how easily people communicated once they had spent a week working and exploring together. One engineer based in Seattle, for example, had previously spent months working with the R&D team remotely. After Tokyo, communication suddenly felt natural. Reaching out no longer carried awkwardness or hesitation because people no longer felt like strangers.

That change mattered beyond morale. In an early-stage startup, communication is tied directly to ownership. Wild Moose wants employees to understand context, think end-to-end, and make decisions with the full picture in mind. The offsite made that far easier by lowering the friction of asking questions, sharing information, and collaborating across locations.

The experience also changed how the company thinks about structuring work. After seeing what happened when everyone aligned around the same shared goals in person, the team came away more convinced that collective momentum matters. According to Tom, some employees even said they could have worked together remotely for years and still not reached the same level of trust and connection they built in a single week in Tokyo.

How Retreat helped

Tom said the value of Retreat went far beyond logistics, though those mattered too. Coordinating restaurants, activities, and workspace options for a group of 10 from abroad would have taken a huge amount of time—and, more importantly, carried a lot of uncertainty.

The biggest benefit was confidence. Even for someone already familiar with Japan, planning a company offsite is very different from planning a personal trip. Tom said he knew places he personally liked, but he did not know which restaurants actually worked for a group of 10, which activities fit a team offsite, or what hidden constraints might come up.

That peace of mind turned out to be especially valuable with the workspace. Left on its own, Wild Moose likely would have chosen a standard corporate coworking option like Regus, simply because it was familiar. Tom said that would probably have cost four or five times more than the workspace Retreat found. Instead, the team ended up in a spacious, comfortable workspace in a quieter area they would not have chosen on their own—and it turned out to be perfect for the kind of collaborative work they wanted to do.

Advice for other startups

Tom’s advice to other distributed startups considering Tokyo was simple: do it.

He recommended giving the trip as much time as possible, especially if the goal is to combine work with local experiences. For Wild Moose, around nine days felt like the minimum. He also recommended looking beyond the obvious attractions. The famous spots were great, but many of the most meaningful moments came from more local, less predictable experiences.

For Wild Moose, Tokyo was not just a backdrop for an offsite. It became a place where the team could work intensely, connect personally, and come back stronger. As Tom put it, some team members called it the best professional experience of their lives.