[sethammons]

SendGrid famously had our annual full-company trips to Mexico. We kept this going for (I think) 7 years. Eventually, it became impossible to get everyone to the same place around the same time.

The goals were team building (esp. with folks you don't see every day) and company alignment. As we got larger, it was harder and harder to get to know everyone; however, the first couple of years, you came back knowing just about everyone in the company. This was great and helped interacting with people over chat and in meetings. As we continued to get larger, you just couldn't meet everyone, but you could strategically find folks from teams you work with from other locations. Getting aligned on the company direction for the upcoming year always stayed really solid. The trips were more and more jam-packed with meetings each year. Whole day meetings are hard, but it was nice to unwind with coworkers for a few hours each night.

Good times.