I recently stepped down as the CEO of Boardable with Jeff Middlesworth stepping into the role. Here is a recap of the journey.
After we completed our Series A in late 2020 we hit the gas on growing the team. We doubled from 25 to 50 people in about 6 months. It was an exciting time! But I began to see that my talents were more suited for getting businesses up and running than scaling operations and revenue.
Now with 2000 customers and millions in revenue, Boardable had achieved lift off and then some. By the end of 2021 I saw that my time in the CEO role was coming to a close. The business was at a stage where it needed someone who was more comfortable with the road ahead than the road behind. Someone who had “been there, and done that.” Someone with the energy and vision for scaling the business. Fortunately that person was already in the business.
When I first Jeff Middlesworth 4+ years ago I knew I wanted to work with him before we finished our first conversation. The wisdom he had from building and scaling products (Exact Target, Emma and others) over the last 20+ years shone through immediately.
I first engaged Jeff as an advisor before he joined fulltime as our Chief Product Officer in early 2020, right in time for the pandemic. Over the last 2 years Jeff took over more and more of the business. Through our conversations I learned that he was interested in the CEO role.
In January of this year we promoted Jeff to the President role and I began pulling away from the day to day of the business. We made the CEO change in mid-April and announced it to the team. It was an emotional time for me and many others.
I am so grateful to Jeff, Andy Clark (co-founder and COO) and the board for their support during this journey. I never felt threatened or rushed. They let me initiate and lead this process. Not all CEO transitions are smooth and I am grateful to them for a low-drama transition.
I am especially thankful to the Boardable team, past and present. There is something special about the people that work at Boardable. They will always be family to me. Thank you!
Thank you to my wife, Jenny Banner, who supported me through all the emotional ups and downs I experienced while making this decision and going through the changes. I love you Jenny.
Thank you to my coach, Dave Kashen, who lovingly helped me work through the fear and anxiety I had in making this decision and change.
Our Boardable customers deserve a special thank you. From early on, our customers gave us the feedback and support we needed to grow a successful software company. Our customers are kind, caring, and fun. Not every business can say that and we don’t take it granted.
You may be wondering- so what’s next for me? Near term, nothing much, I am in a season of rest. I will stay engaged with Boardable as a founder and continue to help out as I can. After a 20+ year run in CEO/leadership roles I need some serious re-charging. I’m not sure if I will be a CEO again, I’m open to it. But I do want more variety in my life. I’d like to work with 10-15 businesses vs 1. I love advising and mentoring. I love sharing what I’ve learned with others. I love seeing others grow. I love starting new things. I love working with early stage companies and first time entrepreneurs. I love being in nature. I love making music with friends. Maybe there is something out there that overlaps some of these interests? We will see.
Thank you for reading. I would be happy to answer any questions you have in the comments. And if you have been a part of my journey the last 5+ years (or more), thank you! I feel very blessed to be on this journey with yo