Cloudthread Y Combinator
March 29, 2022

The Contradiction of Building a Remote Team

The new, remote world. Why Cloudthread chose remote-first. The contradiction, and how we plan to overcome it.

Remote World

The remote first trend is increasingly becoming an embraced norm. It allows companies to build incredible teams unrestrained by geographic proximity and allows people to flexibly choose where to live and avoid tedious commutes to an office.

Big tech companies (historically resistant) and startups alike have been embracing the trend. If you think startups can’t grow successfully remotely, look no further than Gitlab - remote first all the way from Y Combinator W15 to their IPO last October.

At Cloudthread we reflected on the choice between a consolidated office and a remote-first team. I don’t think there’s a single right option - depends on where you are, existing team personalities & preferences, type of business, and more.

Ultimately, we went remote first and global for three main reasons:

  • Great talent is distributed globally - being remote lets us radically expand the number of great people we can work with. Where our founders are located isn’t necessarily where we’ll find the most talented people that are excited to contribute to Cloudthread’s mission.
  • Diversity of perspectives - everyone brings their own experience to their work. At Cloudthread the best idea wins, not the loudest voice. This makes diversity of perspectives a super power - people bring the best tools, processes, and ideas from their home context.
  • Personal preference - three nationalities are represented on our founding team which creates both an advantage and a subjective preference for global hiring.

The Contradiction

But there is a contradiction between hiring and talent retention that remote work creates which we’ve been thinking about.

On the one hand, it feels like a necessity to hire remotely. Especially software engineers prefer it and avoid work opportunities that mandate in-office presence. We’ve experienced this during hiring. Apple has employees threatening to quit with a mandate to return to office.

On the other hand, people typically stay at companies because of the sense of community that they create at work. They admire their colleagues, learn from each other, create strong personal relationships, commiserate through highs and lows, laugh together, cry together. These things are facilitated organically at a physical office through spontaneous conversations, lunches, Friday boardgames, etc, etc.

So this is the contradiction: how do you build a remote team and, despite being remote, sustain a strong work community that people want to stay a part of?

How To Foster Community Remotely

At Cloudthread we’ve thought about what important things happen naturally in person, what can be recreated remotely, what needs to happen in person, and how to create a strong sense of community.

It’s a learning process, there’s countless companies globally that are going through it together, and there’s an endless stream of products and services popping up specifically designed to serve remote teams

Several things we’ve embraced which have been working great so far:

Remote happy hour weekly

Remote activities always feel a bit forced and awkward at first. I feel like it’s inevitable. BUT, they almost always end up fun, rewarding, and you feel closer to your teammates afterwards. This is an hour long “meeting” where you’re not allowed to talk about work, it is encouraged to be eating or drinking, and we have a space to unwind as a team. Sometimes this hour is spent chatting aimlessly about anything under the sun, sometimes catching up on each others’ lives, and sometimes it’s spent playing structured games like poker, escape rooms, Pandemic, Chess, Catan, or Thursday.

For now, we’re small enough that this can happen on a single video call and we feel equally a part of the event. When we get bigger, we may have to find options from the new remote socializing platforms (e.g. Gather).

Daily updates

We share more typical sprint standup updates written/async but we still have a daily touch point to chat through any blockers and also to see each other’s faces, say hello, chat briefly. The meeting is brief, it’s not a time suck, but it also creates space to connect consistently.

Team Spirit Check In

Every two weeks we meet to share feelings, not facts. Feelings about how things are going at Cloudthead but also feelings about how things are going outside of Cloudthread. How each other’s lives are going. This is the type of interaction that would likely happen organically working in person but space has to be created for a remote team. Alignment on what you’re working on is essential at a startup but so is alignment on how the team is feeling. Shoutout to Ilia for evangelizing and facilitating!

Create overlap time

Processes, tools, and written communication are all super important for async work (this could be material for another blog post!). That said, overlap time for meetings that need live discussion needs to exist. For anybody that joins the team we create the expectation of several hours where everybody overlaps daily and during that time we prioritize meetings that really need a discussion to arrive at a decision.

In person off-sites

Working remotely is nice, but there’s some brainstorming and personal relationship building that can only happen when sharing experiences together in the physical world. We’ve committed to getting the whole team together in person twice a year for a week of work, hacking, strategizing, and community building - next stop this summer is Mexico!

We’re always excited to learn about new activities or processes that build community so if you come up with something, don’t hesitate to reach out at! Also reach out if you’re curious about tools we use to facilitate remote logistics/collaboration/fun.
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Copyright © 2024 CloudThread Inc. All rights reserved