When Customer.io, a globally-distributed company with 166 employees in 34 countries, decided to bring everyone together for a retreat, they turned to Flok for help deciding on a destination and tackling the end-to-end planning. Even though this wasn’t their first rodeo — they were consistently organizing two retreats a year until the pandemic hit — this was their first retreat with over 100 employees, which made logistics that much more complicated.

We sat down with Alyssa Welch, Customer.io’s People and Culture Specialist, to learn more about how they landed on Greece, what the planning process looked like, and top highlights from the experience.

Flok: Why Greece? Did you have that specific destination in mind?
Alyssa: Greece was decided upon by our team because we wanted a destination with outdoor activities so we could be in the fresh air as much as possible (for COVID safety). Activities, sightseeing, restaurants, and stores in Athens are very much open-air, and that felt best for our first in-person retreat since October 2019. We were also drawn to how walkable Athens is and the fact that our large group wouldn’t overwhelm the city. Another consideration was the fact that it’s harder to get certain international employees into the US versus US employees out, so Europe seemed like the perfect option.

Flok: What were you hoping to get out of the retreat? Were your goals specifically focused around team-building? Aligning on a long-term vision? A mix of the two?
Alyssa: The main focus was to spend time bonding since we grew significantly during 2019-2022. At our last retreat, we were a team of around 50 and at this retreat, we were about 160. That meant more than half of our team had never met in person before. We also mixed in some presentations about the future and set aside specific team time to work on projects. There was cross-team collaboration, and we celebrated our 10-year company anniversary too!

Flok: What was the highlight of the experience?
Alyssa: It was an amazing moment when we all toured the Parthenon together and took a huge group photo in front of it. That was the first time we had everyone in one place, and it was incredible to look around and see our size and everyone’s smiling faces.

The other highlight was the volunteer activity at WeNeedBooks with the help of PercentPledge. Being able to give back to the community that we were visiting and staying in for a week was a really rewarding experience for our team.

Flok: Anything you would change if you could do it again?
Alyssa: If anything, I would probably lighten our agenda a bit. We wanted to take full advantage of the amazing sights, history, and culture, but I think we were all really tired by Thursday!

Flok: How do you perceive the return on investment in company culture?
Alyssa: Retreats give us the space to recharge our trust batteries and build connections with each other. Spending time together exploring, working, and sharing meals allows us to really get to know one another on a more personal level and, as a result, work and collaborate together better throughout the year.

Getting together in person is more than just making personal connections. It helps us attract and retain team members because it shows our commitment and investment in employee engagement and culture.

Flok: For you and your team, what was the primary value add of Flok?
Alyssa: Planning and logistics. No one on our team is a “travel expert” and it was amazing to have a thought partner to guide us through the parts of planning that we weren’t familiar with, especially when it came to communicating with certain vendors. Also, it was invaluable to have Allison (our retreat designer) with us in Greece for help with onsite logistics and things like how much to tip, for example.

Flok: So what’s next for Customer.io? Where do you hope the next retreat will be?
Alyssa: I’m crossing my fingers for something tropical! It was hard for some team members to get into Greece, and we want to be really cognizant of that for the next retreat — so perhaps it’ll be Bermuda or Mexico. We’re also bigger now, so if we opted for an all-inclusive, we’d have a better idea when it comes to cost and budget forecasting.

[Interview edited for clarity.]

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