The Power of In-Person Connection, Even for Remote-First Companies

In October, Teachable announced our decision to become a remote-first company. Today, we have team members across the country, alongside our Hotmart colleagues in Brazil. We have the ability to hire the absolute best talent, as well as added flexibility that allows us all to do more meaningful work.?

And that work is more important than ever. Creators are intent on diversifying their income streams, they want to build enduring businesses, their audiences are willing to pay—and underpinning these changing creator needs is a continued, widespread rise in entrepreneurship.?

Teachable’s power to help creators scale on their own terms is perfectly aligned to the present moment. But in order to bottle and act on the momentum we are feeling around us, I had a feeling we needed to step away from Zoom and come together as a team.?

The result of this decision was Teachable’s inaugural :transform by Teachable offsite. For three days in New York City last week, nearly 200 of us met under one roof to recommit to our mission, align around our goals and objectives for the year, and build a renewed sense of community. I am happy to report we, undoubtedly, made progress on all fronts.

Here are some of my key takeaways from the event:

1. Our employees drive our mission. I always tell people I knew I had found “my people” when I first interviewed at Teachable. As a team, we are here to break down the historical barriers to entry when it comes to teaching and sharing what you know with the world. We do this because we believe it can unlock transformational opportunities for both our creators and their students. Knowledge can be the most valuable business foundation for a creator and the thing that changes the course of a student’s life forever.

Being in person reminded me just how passionate our team is. In fact, some of them are Teachable creators themselves. It’s true we show up and put in hard work every day for our creators, but it takes a team who truly believes in your effort to impact people’s lives to deliver the very best product and experience.

2. Even the best remote-first companies require in-person time. At Teachable, we are continuously working to optimize our operating rhythm to make the best use of meetings, all-company moments, and asynchronous connection. Our output has not wavered, while our remote-first approach helps to increase flexibility. And still, I believe the impact of face-to-face problem-solving and brainstorming is undeniable.

Last week, team members commented on how quickly they were able to wrestle through an idea while sitting next to their colleague. So while our priority is making sure we continue to build a meaningful and effective remote culture, carving out in-person time allows your team to energize one another and head back to their at-home desk in even better shape to go after goals.

3. Let your team carry the agenda. We didn’t want this event to feel like your standard conference, with hours of presentations and very little interactivity. Our sessions were rooted in learning, collaboration, and problem solving. They also each mapped directly to the goals our cross-functional teams are dedicated to this year to ensure that the time felt generative and like it was effectively furthering our strategies.

An agenda like that only works if you allow your employees to bring it to life—by being present, driving the discussion, asking tough questions, and committing to the outcome. Even by the last day, our team was engaging in deeply strategic and thoughtful discussions, and coming up with creative solutions. It was amazing to watch.

4. Challenge your team—and make it fun. It was important to me to put our big challenges on the table up front, and to create a safe environment where the team could think big and boldly. This took the form of an “Idea Storm,” where every single team member helped generate creative ideas to help tackle some of our key challenges.

The groups were intentionally made up of team members from different functions, and the problems they were solving for were outside their day-to-day focus area. It was a real privilege to witness such diverse personalities, skill sets, and creative approaches jump in and reimagine how we can think about our work. At the end of the session, team members voted on their favorite ideas. It was absolutely a highlight of the week.

5. Don’t just talk about your customers’ challenges, invite them into the room. Our customers inspire us each and every day. Their insights guide our decision-making and prioritization. But talking about those successes and pain points is only good enough. With our entire team together in one room—including those without direct customer-facing roles—it felt imperative to bring our creators in.

A highlight for many of our team members, we organized a panel and open Q&A session with creators, new and old. Hearing their stories validated much of the work we are already doing, while also bringing in an essential perspective as we tackle the future.?

An old manager of mine used to love challenging me with new assignments I wasn’t sure I could handle. He would tell me: “You are smart. You will figure it out. We are counting on you.”? I told the Teachable team they should all expect those types of challenges this year—things they might not think they can do at first. I am absolutely confident they can.?

#creatoreconomy #remotework #workculture