Behind the Scenes at Our Company-Wide Meetup with a 100% Remote Team

Follow Up Boss has been a remote company since day one, so getting our employees together in-person has always been essential for brainstorming, collaboration, and having a little fun. 

Before the pandemic, our company-wide meetups would happen once a year. But like most in-person events the last couple of years, our annual retreat was put on pause…until now. 

Just a few weeks ago, the entire Follow Up Boss team met up in Austin, Texas for our first meetup since 2019. Needless to say, it was pretty dang exciting talking about all the new features and ideas that week plus meeting our co-workers–and for most of us, for the very first time!

We asked Beth Hogan, Head of People at Follow Up Boss, and Casey Blanchette-Phillips, Operations Manager at Follow Up Boss, for a behind-the-scenes look at what it was like planning our 2022 company-wide meetup.

Q: Why are in-person meetups important at Follow Up Boss? 

A: As a 100% remote company, it’s important to provide in-person retreats and gatherings to connect on common goals, prevent a siloed work culture, and boost overall morale.

Q: What are some of the challenges of planning an in-person event for a remote company?

A: One of the most challenging parts was the short planning period this year. We only had about 3 months to pull everything together. 

Developing the retreat content and agenda can also be tricky. Ensuring that we provide captivating material to staff and making sure our customers were taken care of while all staff were on-site. Each of those components took a lot of effort and collaboration to prepare. 

Toss in a pandemic and doubling the size of our team… we are pretty impressed with how it all came together!

Q: What was part of the planning process went the smoothest?

A: Our team’s support and willingness to hop in on anything and everything we needed was a huge help. We also hired a company called Flok to assist with event coordination onsite which really benefited us. Flok helped with a majority of logistics in terms of scheduling transportation, team building activities, retreat meals etc.—the process would not have been as smooth without them.

Q: What does the itinerary look like for a company meetup?

A:  The itinerary was carefully planned and executed with good care. It went through a few variations and stages but ultimately the days were strategically planned to provide a healthy mix of company-focused sessions, all hands-on deck support power hours, and fun group activities and evening festivities to reward our team for their hard work.

This is a guesstimate but about 70% of the day was spent on working 30% on team activities and leisure time. 

Q: We have remote folks all over the country (and some international!) how did you land on Austin?

A: We talked through a bunch of destinations and all the ones we chose were within a 1-hour driving distance to major airports for any and all international folks joining us. Ultimately we landed on Austin as it fit the bill for location and activities. 

Q: What was the theme of the event?

A: FUB to the Future!

Q: How did you land on this theme?

A: As a group we wanted to focus on the future of Follow Up Boss without forgetting where we came from. The idea was brought up on one of our retreat planning calls that that theme could be “FUB to the Future”. We all agreed and jumped right on into that. 

Q: What are your top five tips for planning an in-person event as a remote team?

A: Top five tips would be:

1. Give yourself plenty of planning time and set strict deadlines for planning milestones.  
2. Set expectations and try to plan as much as you can before announcing it to the team.
3. Invest in a local management/planning company that can assist you in hotel and vendor negotiations and help you onsite the week of the event.
4. Make sure you include the folks who can’t travel to the event as much as possible so they still feel part of the team.
5. Clearly define early on in the planning process the goals and key-takeaways you want from this event – it will help you formulate the agenda, decide activities, if you are including families, and ultimately choosing WHERE you should have your retreat. 

BONUS Q: Planning a company-wide event in 3 months is no small feat! If you had to pick a meme to represents the planning process, what would it be?