March 1, 2018. I won’t forget that date any time soon because it was the day I made my first major mistake as COO… and it had taken less than 6 hours in the role to happen. “We can’t keep letting this happen. We just lost one of our largest customers to a completely avoidable […]
How We Structure the 50-Person Team at ConvertKit
As a team grows from the early stages when everything feels fun and crazy into a more mature phase of predictable growth, team structure has to change to support that growth. When I joined the ConvertKit team in 2016, we had about 20 teammates and $3.5M in annual recurring revenue. Today we have almost 50 […]
How to Introduce a Friend or Colleague
“My name is Barrett Brooks. I live in Portland, Oregon with my wife and two dogs. I work at a software company. Really happy to be here.” That’s my standard “humble” self-introduction when I’m not familiar with the people I’m being introduced to. It doesn’t do my work justice. It doesn’t make me more connected […]
If You Want to Succeed in Teams, Learn to Understand the Immoveable Constraints
“What is your biggest concern or fear about working together?” I asked my mentor as we were having a conversation about the possibility of working together. “Well, you have a tendency to find the immoveable constraints and then push on those. I’ve been at this long enough that I know my constraints and I need […]
How We Use Compensation and Benefits to Keep Our Team Happy, Healthy, and Productive
The goal of compensation and benefits is to recruit the very best people onto your team, keep them happy for as long as possible, and unlock their full potential in the process. Many organizations look at this as an opportunity to do the least amount necessary to keep people from leaving. I believe every organization […]
The Communication Tools We Use to Run a 50-Person Remote Team at ConvertKit
We have nearly 50 teammates spread across 39 cities in 7 countries. Our team is 100% remote with no office. This is awesome because it means we can recruit incredible people from all over the world (and we actively do that). This is not awesome because, like any company, it comes with its unique challenges. […]
How I Use Social Media to Build Community
The three things I most want to feel in my life are love, joy, and belonging. Belonging requires a sense of community. And community doesn’t appear out of nowhere. It takes work to build community or to become a part of existing communities. I use my social media channels to foster a sense of community […]
How to Make Decisions When Things Don’t Go According to Plan
We were about to hit a class 3 rapid at the end of our 12 mile run for the day on the McKinzie River. The four other rafts in our group had made it through and had a blast. There was just one problem: our boat was backwards. A class 3 rapid is defined as […]
The First Time is the Hardest Time
The fly landed softly. A quick ripple shot across the water, and the fly was gone. I pulled the floating line in with my left hand. I let the fish run a bit. It was a small one, so there wasn’t much fight. I did, however, feel a nearly endless sense of excitement. I pulled […]
What to Do When You Appear to Be Good at Everything
If you’re a jack of all trades, it probably means you have many talents and are able to master almost anything you put your mind to. That’s great in many ways, but it’s also dangerous if you want to make an impact through your work. It means you can go through life knowing that you […]