How Grouparoo works as a team

When Brian, Evan, and I first talked about starting a company, we already had some ideas in mind about what we might want to do differently from our past roles. The three of us had all worked together before at TaskRabbit, but since we were starting a brand new company, we decided to approach how we would work from a first principles approach. I thought we’d share some tidbits about how we work right now.

Remote-first and asynchronous-first

We view these two principles as distinct, but how these two principles interact is often intertwined. We decided to make the company remote-first for a few reasons. First, the three of us all live in different areas (ok, Brian and I are both in the SF Bay Area, but we’re easily 60 minutes apart so let’s just say we’re in different areas for convenience’s sake 😅). Additionally, we believe that there is good talent everywhere, not just around the major tech hubs or cities. We’d all had varying degrees of experience working remotely, but few of us had done so from the start. Starting remote from the beginning of the company actually wasn’t too challenging. We’d all used Slack, Google Meet/Zoom, Github, and various other tools for our past roles, so the tools weren't particularly new to us. We’ve also been very happy with Tuple, a screen-sharing tool made specifically for pair programming. The ability to use someone else’s mouse and keyboard remotely really approximated the pair-programming experience we were used to (sidenote that we're still bummed that Slack bought ScreenHero and did approximately nothing with that product before shutting it down).

The trickier part for us was moving to asynchronous working. We were mostly used to sitting in the same room as our colleagues. Often with the tap on the shoulder or a slack message, you can pull their attention away. Many studies have shown that getting into a flow-state (having uninterrupted time to focus) improves people’s satisfaction with their work as well as their work output. One of the many cultural practices that I loved from my time at Stripe was how nearly every decision or idea was written in a document. Writing your thoughts in a document both helps you think through what your ideas are, and then additionally, having a document gives people time to digest and respond. We've adopted this practice here at Grouparoo, and it's worked pretty well for us so far. That isn’t to say writing docs is the best approach for all instances, but it’s a solid default stance to take.

We do still meet synchronously when it’s warranted; we have daily “stand-ups” in a video chat, and we have a weekly planning meeting on Monday and a weekly demo/retro. If we ever chat in Slack and there’s a fair amount of back-and-forth, we’ll propose we jump into a call in case that could help eliminate confusion about our discussion.

Meeting IRL is great (when it can happen)

While our default is async and remote, meeting in-person is still very important to us. Before COVID, we would meet in-person once a month for a day-long “on-site”. During those days, we’d brainstorm our plans for the month, discuss strategy and the roadmap, goals, and have a team dinner (and maybe a team game of Civilization).

While we haven’t been able to meet IRL since March 2020, we’ve moved these full-day “on-sites” online. That said, they haven’t taken the same form. Attending a full-day on-site IRL can be draining; attending a full-day online on-site is mind-numbing. We’re now spreading them out into a few 60-90 minute meetings across a couple of days, and doing more pre-work so the discussions can be more focused. I wouldn’t say we’re 100% nailing this process, but we’re still learning and evolving with each month.

Since we aren’t able to meet IRL, we’ve taken to playing games online for some non-work activities. Most recently we played some Settlers of Catan!

Default to open

When we decided to build an open-source product, we found ourselves asking over and over again “should this feature be open-source/free or paid?” Asking that question for every roadmap item could get exhausting, so we decided to take a framework-approach to how we’d think about open-ness. We landed on, by default, everything we do will be open, from our core project, our roadmap, and even our marketing site. That said, there are some artifacts that we don't keep open, such as pay and our longer-term strategy. That said, we have all of those docs available privately to all of our team members (in Github, of course).

Snapshot

Most of what I shared is just a snapshot of how we work right now in October 2020. One of the most exciting parts about growing the team is that the culture and practices of the company will (and should!) change and evolve. We don’t presume to have the answers to everything, so we’re very excited to bring in new team members and for them to contribute ideas to how we can work better together. We’re hiring!