Reflections on UpBuild’s First Team Day

One week ago, UpBuild had its first Team Day and it was a pretty big deal. At the start of Month 7 (wow, has it really been that long?) we set aside a full day to get in the same physical space to really get on the same page, work through some tough problems, have fun, and just get to know each other on a deeper level.

Why Team Day?

UpBuild is a distributed team, meaning we all work remotely. We have no office and probably never will. I believe that this allows us to be more flexible in how we work, more agile in how we operate as a company, and more balanced in supporting a happy team.

Being distributed is not without its challenges, but they’ve been fun challenges to work to surmount. I’ve thoroughly enjoyed experimenting with ways we can stay connected, be in-the-know, and feel like part of a team while all being located in different cities or even different states. One proactive step that seemed like it would help is acknowledging that there are some needs that just can’t be fulfilled by remote work environment and doing something about it. Enter Team Day!

What is Team Day?

UpBuild Team Day is twice-yearly event where we fly everyone on the team out to a city (Portland, this time around) and spend a whole day together. For our inaugural event, we had out non-Portland team come out and we rented a great meeting space in the Pearl District. We gave our clients the heads up that we’d be available for critical needs, but otherwise pretty heads-down for the day. We spent a good portion of the day with the following:

  • UpBuild’s First “Company Presentation” – I gave everyone the full history of how we came to be, clearly outlined our vision and guiding ideals, reported on our financial health, and laid out some exciting stuff that the team could look forward to seeing in the near future.
  • Strategic Brainstorming Sessions – The senior team took turns leading brainstorming for each of our clients. Depending on the needs of the account, we figured out ideal roadmaps for the coming months, assessed strengths and weaknesses, or just worked on a specific challenge that the client was having.
  • UpBuild SWOT – As a team, we dug into the strengths, weaknesses, opportunities, and threats that we saw in UpBuild. It was an eye-opener to say the least, a little uncomfortable at times, but possibly one of the most helpful outputs of that day (for me, at least).
  • Team Meals – We got to share two great meals together. Over lunch, we went around the table and each told our story of how we ended up here. It was great to learn about where everyone came from. I think we realized that we all had more in common than we ever thought.
  • Glow in the Dark Pirate-Themed Mini Golf – Because…obviously.


Our first Team Day was an unqualified success. I’m so glad that we did it, and just the fact that we were able to do it was huge. That day was the first time I’d met one of our team members face-to-face, which was crazy to think about since we’d been working together for 6 months.

One big opportunity that our Team Day afforded us was to just “be” in the same space and let unstructured interactions happen. That’s one thing that’s a bit tricky to foster in a remote-only environment. Chatting on HipChat when you’re at your desk is one thing, but there are definitely more opportunities to ask non-work related questions and spark random conversations when you’re face-to-face. That was one of my favorite things that I saw during the day – coming back into the room to see everyone just talking about something completely unrelated to work or just laughing about something ridiculous. Those moments make the cost and logistics of planning a day like this worth it.

Moving forward, I think we’ll be doing these events twice a year. Doing this the first time didn’t shake me from the vision of having a completely distributed team; it made me feel even better about it. Through our fledgling efforts, we’d built a team that felt like they already knew each other upon meeting for the first time. No one felt like strangers.

Rather than being something that highlighted shortcomings of our current set up, Team Day ended up being an awesome supplement to how we do things. It was a fantastic reassurance that we’re on to something here and that there’s absolutely a way to find that ideal balance between remote-first and team-centered.


Written by
Mike founded UpBuild in 2015 and served as its CEO for seven years, before passing the torch to Ruth Burr Reedy. Mike remains with the company today as Head of Business Operations.

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