This post is by request from Baron Schwartz who has written about forming connections within his company, Vivid cortex

I have been at SendGrid for nearly 7 years now and have been working remotely for 4 of those years. While SendGrid is not a ‘remote first’ company, it was distributed in multiple locations from the very beginning. Since the early days, leadership at SendGrid believed that we needed a way to form human connections as a team across the different office locations. Here are how this evolved over time and what things have remained the same.

In the early years this was an annual event. But we were also a small company focused on growth so we had a very informal travel policy, there was very little resistance to anyone booking a trip to Colorado or California and visiting an office then later expensing that trip. As we grew larger, the inter-office travel budget grew dramatically. At about 4 years ago, with these full company all hands already happening twice a year, it was time to set some guidance around inter office travel. While office visits outside the semi annual all hands can still happen, they need to have a justified business reason in

It was important for us to make at least one of those all hands away from all the offices. Yes it is more expensive. But I have found that I created the strongest bonds with coworkers not in my local office in those ‘off the grid’ multi day all hands where I get to have dinner with new coworkers, get to exchange inside stories of issues we are facing, projects in progress. I have more than once formulated plans to deal with issues in those evening conversations with coworkers I had not met in person yet until these gatherings. Our early year kickoffs have been mostly in Mexico where it is actually pretty well priced getting all inclusive accommodation for everyone with many nearby options for team building outings when the schedules have allowed. Travel time became a concern though as the company size grew and flying so many people became a scaling problem (yes that is a theme when you work at SendGrid, scaling) so now we have made one of the all hands local in the US but not in any of the offices and one of them near our HQ in CO the latter still has plenty of social events in the evening for those coming in from out of town to still socialize.

The schedule of these events is an area that has changed dramatically over the years. The early day kickoffs used to have only one day of planned meetings and the rest was left unscheduled. The idea there was to encourage socializing, leave room for teams that might be distributed to plan team building events. But as the company grew, the unscheduled time became just lounging by the pool, hanging by the pool bar time and while those are fun too, it is hard to justify for an entire day and a half for a company of a few hundred people. Now our kick offs are more structured. We still have the full first day of presentations from all parts of the organization, recapping the past year and presenting goals for the new one. The second full day is spent in breakout sessions which vary from brainstorming sessions to start the planning of the new year goals, to teaching sessions where principal engineers can do what very much resembles conference talks, showing the newer engineering team members the thought process behind some of our architecture, best practices, how to use certain tools, etc.

When SendGrid had its first kickoff, the company was 65 people. Total. We are now approaching 500 employees. Like everything we do, these all hands gatherings had to also scale. Let me start by saying that I am always in awe of these events at the skill and hard work by our office managers team , corporate IT and internal event planning teams who start planning these many, many months in advance. Scouting locations, securing necessary internet infrastructure which was crucial when these events used to be in Mexico and as the company grew it became necessary to cater all the meals and that became part of the planning too. I work with an amazing event planning team and I am always in awe of what they accomplish planning these gatherings for an ever growing number of people.

One of the things that did not change is one rule. No family members come on these trips. We have other social events that are open to all (summer picnics, holiday parties) but this semi annual all hands is about company strategy and team building and those work best without the added work of traveling with one’s family. It’s a difficult choice and I’ve had to miss some of these events due to prior family plans but ultimately i do get the greatest benefit and come back more energized for our plans when I’ve enjoyed the informal chats with coworkers. But like everything, absolutes are not effective. So when people have to miss these events due to any number of reasons, we keep recordings of all the large strategy meetings and post them to the company drive along with slide decks.

You may think that this post contradicts previous writing by me about how I view distributed teams and the word ‘Remote employee’. I would say this is actually the other side of that story. I have always valued these gatherings when I still worked in The Grid’s SoCal office but I have seen the value in them even more when life required me to move away from a daily commute to the office. I do not take credit for any of planning or execution of these events but it is the investment the company puts in them and constantly improving them with team alignment in mind that has made my journey as an employee who is not in the office everyday not just continue but thrive in more responsibility, more involvement in project planning and more leadership within the company. These connective tissue exercises, with deliberate schedules and thought behind every one of them, are very important for rejuvenating connections for all employees and even more valuable when we do not have the day to day human connection we all crave.

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Silvia Botros



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