Work Hard, Play Harder: Upside Team Days Are a Step Back from the Day-to-Day

Danielle Mitchell
Upside Team Blog
Published in
4 min readOct 3, 2019

All work and no play is not how we operate at Upside. Although we’re constantly moving at a fast pace, we understand the importance of taking a break, and one way we do that is with a Team Day. I just experienced my fourth Team Day at Upside and it happened to be one of the more memorable ones I’ve attended. Team Days give our people the opportunity to step back from their day-to-day jobs to spend time getting a deeper understanding of aspects of our business, as well as to participate in team building activities. This year, Upside put four Team Days on the calendar, so once a quarter all Upsiders get to spend the day with colleagues they don’t normally work with, while engaging in activities that promote teamwork and peer-to-peer education.

Our Team Days typically start with an educational component that leads into fun games or challenges with small teams and ends with an all-company social component. Our most recent Team Day ended with a large slip and slide setup in our kitchen, which led to a plethora of hilarious videos and pictures that came from watching colleagues, leadership members and our leadership team participate.

Our Chief People Officer, Cristyn Girolami, shared her thoughts with me on the importance of Team Day by saying, “Since the start of the company, Team Days have been a great opportunity for our entire team to get together and break out into smaller groups to learn about the business, focus on our goals and have a lot of fun along the way. We all get the chance to step away from our day-to-day focus and spend some time and get to know others we don’t normally get to work with every day. It is an AWESOME way for the team to connect and get excited about what we are working on and still need to achieve.”

There’s a ton of planning that goes into organizing a team day, and part of my role is to ensure everyone knows what they’re doing, where they’re supposed to be and that they’re having a great time. It starts with finding volunteers to be on the committee, bringing them together weekly in the months leading up to Team Day, and making sure they have everything they need to run a learning or team building session.

There’s a certain level of pressure that comes with involving the entire company in an event. All eyes are on you if something goes wrong, and you have to remind yourself that it’s not the end of the world when something does go wrong. Overall, it’s a fun day filled with learning, laughing, friendly competition and hopefully making a new friend(s) in the company.

Here at Upside, we work hard to provide amazing events, activities and workshops for our people, and it’s one of my favorite things about working at this company. Adding a slip and slide to an already busy Team Day was a challenge of its own. We utilized our Culture Crew to help plan, implement and execute a slip and slide in our space with minimal mess and cleanup. It was such a fun way to end an eventful day, and seeing everyone’s reactions and smiling faces made the day even more successful.

I love that our leadership encourages more balance between work and life. Team Days are a mental break that we all need, where the two main themes are learning and having fun. Seeing my teammates take a needed break and enjoy each other’s company reminds me of why I enjoy working at Upside so much. I like who I work with and I’m not the only one. I look forward to seeing what we come up with for our next Team Day!

Do you want to be a part of our next Team Day? Upside is hiring! Check out our careers page to see our open positions.

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