Meeting In-Person as a Remote-First Company: Pagos’ First Team Offsite

In late March 2022, we assembled all of our Americas-based teammates for Pagos’ first formal offsite. When we started organizing this meeting several months ago, we’d hoped to get the entire global team together, but weren’t sure how that would play out. We expected pandemic-related complexity of course, but we didn’t anticipate how long timelines for visas into the US would be (e.g. multiple months just for an appointment to request a visa) or how tricky the visa process for some countries is. As a result, we landed on an Americas-only gathering, which roughly amounts to half of our small team. I’m disappointed that we couldn’t get the whole flock together and am looking forward to meeting our colleagues in the EU and APAC as soon as everyone can safely do so, but the meet-up was extremely valuable none-the-less.

The intent for our first offsite was to focus primarily on establishing social connections and  building common context on what we’re aiming toward—and how we plan to get there. Here are some takeaways from that:

Observations

Pro-Remote Doesn’t Equal Anti-Meet-in-Person

Face-to-face experience is the highest fidelity way to connect with your team. Without a doubt, meeting one another in person makes it easier for everyone to build social capital, deepen existing relationships, and resolve conflicts. It isn’t the only way it can be done, but it sure is convenient, especially when establishing a baseline for how to work together. 

It was great to kick off discussions on working across different communication styles and backgrounds (that conversation’s never done!), as well as defining our organization’s guiding principles and what they look like in practice. We also had social activities together which allowed us to shift our attention from work for a bit. Everyone seemed to come away with a better understanding of the humans typically on the other side of a screen!

Double, Triple-Check Your Presentation Setup

Context gaps are a risk even when everyone’s in the same room. We planned to record the week’s sessions to ensure those who couldn’t join us would still have access to the presentations and discussions. And yet:

• In our first presentation, the wifi was weak and resulted in low quality audio capture
• We shifted to a desktop tool for capture to avoid dependency on wifi, and the audio stopped recording altogether
• At this point, we started capturing audio on a phone separate from the video capture of the presentation

So… always have a backup form of media capture for every session, and it doesn’t hurt to have a backup of your backup, too.

Working Cohesively Requires Continuous Effort

We’ve assembled a team of talented, thoughtful, and passionate people. And we each have our own baggage, which means we have to: 

• Actively confront biases we’ve picked up along our paths
• Unlearn old roles, methods, and personas we’ve used in past experiences which don’t fit the needs of our new environment
• Be extra mindful of how past working history with some colleagues gives you an advantage of established trust; there’s a risk of perceived and real “in” and “out” groups, which are counterproductive to trust-building
• Accept that there’s more ambiguity when starting something new than joining something established
• Fight the urge to try and shoulder everything on your own and instead ask for help

Next Steps

We have plenty of work to do as a fast-growing startup if we want to expand our team and products in a way that benefits everyone long term. Through our successful first team offsite, we’ve pinpointed some things to keep top of mind as our organization grows:

• Practice and prepare to give away our legos as we grow; this isn’t easy, and it’s critical that we allow our roles to evolve as the needs of the organization change
• Continue to refine our communication approach, operating asynchronously where possible and making sure to add to documentation for the benefit of the next person who picks that work up (context, context, context!)
• Establish baseline frameworks (e.g. postmortems, code/design reviews, responsibility assignments, demos) for accountability, especially in cross-functional work 
• Create more onboarding structure to better enable and empower the next generation of payments geeks 

It was a great experience, and I look forward to the next time we can get together in person. There’s a lot of get-your-hands-dirty kind of work yet to do. If that appeals to you: we’re hiring!