Why We Take Team Retreats at ConvertKit

The team at our January 2017 retreat to Oceanside, San Diego

The ConvertKit Team is entirely remote. That means that we work from our home offices, our bedrooms, our vans, coffee shops, co-working spaces, or airports most days. There are a lot of benefits to remote work, but there are pitfalls too. One of them is the absence of in-person connection.

I’m an extrovert (I know because the ConvertKit team all took 16 personalities to find out) which means I get my energy from other people. Day to day, I can get this on customer calls, team calls, and meetings, but I start to feel drained after going several months without seeing my team in person.

We had our first retreat in August of 2016, in McCall, Idaho. I was 10 months into my role at ConvertKit and desperate to meet my team face to face and find out how tall everyone was. More than that, as a company we were facing some pretty serious stability issues. Our app was crashing a lot, and erroring out. Our customers’ emails weren’t delivering like they should. ConvertKit customers were understandably pretty unhappy, and we had some serious work to do to improve their experience and gain their trust.

The word “retreat” makes it sound like we all went to Bali for a 10 day yoga-and-juice cleanse. It doesn’t really paint the picture of 20 people sitting in the biggest living room you’ve ever seen, working furiously on their laptops.

Writing code, answering support emails, sharing customer feedback and pain points in real time. Growing as humans and pushing our teammates through unsolicited feedback. Setting the product roadmap for the next six months. And yes, taking some time each day to have amazing adventures like paintballing, escape rooms, paddleboarding, and surfing the Pacific Ocean!

At the first retreat, we set our company vision: to legitimize blogging as a valid career and income source. This was the why behind hosting our first conference, Craft + Commerce.

The second retreat was the first time some Visual Automations wireframes and logic was shared with the greater team, and we spent over an hour mapping out what this feature could look like. Now, it’s in beta and soon to be released to all ConvertKit customers!

Here’s a video from our second retreat in Oceanside, CA.

As a remote worker, I don’t often get to reproduce a bug with an engineer watching over my shoulder. And I’m often not included in conversations about the best way to fix it. But at retreats, I get to do it all in one conversation. It takes 5 minutes to come to a solution for a customer and get it added to the priority list.

Here’s how Ashley, our Director of Operations, benefits from our retreats:

I love learning more about why teams operate the way they do and what that means for the business. Things like how the database is set up, different programming languages we use & how they interact w/ each other, why we run our ads the way we do, or how we help individual customers have better deliverability.

And Matt, our Onboarding Lead (you may have seen his face in your welcome video!) can tell you why he loves team retreats in his vlog from our last retreat.

Matt Ragland’s take on why team retreats are so important

Barrett, on the marketing team, is an extrovert like me. He loves the retreats for similar reasons:

After so many days and months of working alone at home, I get a chance to have in-person, synchronous conversations with my teammates. We have time to really connect and understand how each of us are doing as people. But most importantly, we get to dream together.
Remote work is wonderful because we get to work with amazing people from more than 15 cities and 5 countries around the world and we get to do it on a schedule that works for each of us. But working alone can be hard. Retreats are like a chance to recharge my batteries and fill up on encouragement, connection and inside jokes to hold me over until next time.

At ConvertKit, we retreat to work together in person and to set the pace and strategy for the next 6 months. We retreat to continually grow as individuals, teammates, and as a company.

But most of all, we retreat to continue making it easier and more fun to earn a living from your blog. Because without our customers, we don’t get to do any of this work that matters to every one of us.