How (and why) we spent $60,000 on a remote team retreat

Jilt is a fully distributed team. We inhabit all corners of the globe from Canada to South Africa, from the East Coast of the U.S. to the West, from Europe to Asia. Our twenty team members hail from six different countries on four different continents, so most of the year, we only experience each other via virtual communication tools like Slack and Zoom. But real, live, in-person face time is important for remote teams. It replaces the kind of random collisions and daily team bonding that takes place at water coolers and in hallways at a traditional office.

That’s why at least once per year we get the entire team together for a retreat. Since we did this last—in spring 2017—our team has more than doubled in size. So logistically, this year’s retreat was a whole different animal. Planning and operating in-person retreats for rapidly growing teams is a challenge that many remote companies face. Hopefully, our experience can be helpful to other startups facing the same growing pains.

Here’s how we got the team together this year, and why it was totally worth the $60,000 price tag.

Read the full trip recap on