Three Lessons from the Underdog.io Team on Building Remote Company Culture

October 24, 2022

After a hectic morning of navigating NYC traffic, our team huddled around a tiny Avis rental car office in Midtown Manhattan. For the first time in almost a year of remote collaboration, our sales, marketing and candidate success teams finally had the chance to meet in person. Between clumsy handshake-hug hybrids and height assessments, the temperature in the room warmed as we remembered that after months of Zoom calls and Slack messages - we do in fact know our coworkers. 

A chalkboard with the words "Welcome Team Underdog"

In-between weekly all-hands meetings and Slack huddles, we had learned enough about each other to feel comfortable being ourselves almost immediately. We told jokes, recalled shared stories, and settled into the knowledge that we were all on the same team moving towards a shared goal. 

Company culture is already a strangely intangible phenomenon, but when transported to an entirely virtual setting it's even more difficult to wrap our heads around the concept. Against all odds, the Underdog.io team has been able to build and maintain a unique remote company culture that encourages both flexibility and collaboration. In this very special blog post, we’ll share a bit about our team, our company culture, and three lessons we’ve learned about crafting a remote team built on trust. 

Lesson One: Culture is in the details

Company culture is a catch-all term for ‘how things work here’. While most employees probably could not describe their company’s culture, they can easily recognize implied value systems and norms in water cooler talk, decisions made, rules bent and so much more. For the Underdog.io team, defining our culture for our team’s specific needs has allowed us to tailor norms and policies that put people at the forefront.

To better understand our company culture, I asked my team members to tell me a bit about  what company culture means to them. 

Alison, our amazing Customer Success Manager, describes company culture saying, “It's how I feel about work on Sunday night - am I walking into an environment week after week where I feel supported through challenges? Are my colleagues people who value ownership in their roles? Do we genuinely enjoy each other?” 

Lauren, our favorite Account Growth Representative, calls it “the shared philosophies and practices that exist within a team.” Instead of the static, measurable metric many HR teams point to.

Andrew, one of our amazing Business Development Representatives, names company culture as something “both consciously cultivated and accumulated over time as a result of mutually-agreeable decisions.”

Lesson Two: Work hard but play harder

Hot take: Playing as a team is just as – if not more important than – working collaboratively. Obviously we all have responsibilities that require us to work, meet, and create in order for the business to grow. But having fun with teammates helps to craft a more trusting, creative, and innovative environment, which allows us to work better together. Communication between team members becomes smoother and more honest. Problems are noticed and called out quicker. Brainstorming becomes easier because team members trust that they’re all on the same team. 

At Underdog.io, we make sure play is an active part of our team cadence. Whether it's our monthly game night (where the team takes turns losing to me – our brave and fearless Growth Marketer) or the weekly ‘Fun Stuff’ segment that closes out our weekly All Hands meetings – fun is a fundamental part of the way things work around here. 

After working remotely for over a year, our recent company offsite was another opportunity for our team to foster a culture of trust and creativity. We spent a week together in the Catskills petting llamas, enjoying five star meals and sharing stories over a campfire. We asked the team about their favorite part of the offsite.

Andrew’s favorite part was “the bonding that takes place when you're sitting around a campfire at night and trading stories” Oh and of course “whiskey tasting in the garden!”. 

Julia, our amazing Account Executive, loved “the fun dinners and fire side chats.”

Lauren loved “every activity and was living (her) best life,” but her favorite part was “bonding with coworkers that (she) did not often have meetings or conversations with” For her, hearing her coworkers talk about their work was “really educational” and allowed her to “understand the work that each person is doing behind the scenes to create the results that we share in meetings.” The offsite’s focus on non-work downtime not only allowed the team to bond but for Lauren in particular, it “gave (her) a new level of respect for everyone”.

Lesson Three: Build culture together

Culture is how a company collaborates, communicates, creates, innovates, makes decisions. None of this happens in a vacuum and no leadership team – regardless of how great they are – can craft company culture on their own. It is an evolving, living, breathing reflection of the individuals on the team so everyone should play a part in building it. Whether you are an individual contributor, a people manager, or a director – we should all be aware of the ways in which we may be positively or negatively impacting the larger company culture.

We asked the Underdog.io team about how they think they impact team culture. 

Andrew “considers (himself) very lucky to be part of a team that encourages communication and values transparency.” He mentions that he impacts team culture by “sharing feedback or making suggestions…because everyone is accessible and receptive to new ideas.” 

Lauren “brings energy and action.” She understands that while “everyone may not see or understand the strategy behind (her) actions,” they can see “the energy and boldness (she) brings to set things in motion.” 

Allison tries to “focus on the positive even when things are crappy.” Finally Chris, one of our co-founders and a proud member of the late night crew, impacts team culture by “staying out of the way and letting our culture bend and shape on its own as new folks join the team.”

With all of the challenges that appear with virtual collaboration, it can feel daunting to build a strong remote company culture. By setting clear expectations, putting people first, and prioritizing a fun and productive work environment, a great remote company culture is within reach. When your team lets its guard down and agrees to work toward a shared vision, your company culture will blossom into something everyone on the team can be proud of. 

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