Transitioning out of your Startup as a Founder

In tech we call our companies "start-ups" which I think is an apt name because a lot of the sweat and tears occurs in this stage of just figuring things out. For most companies the act of starting up actually takes years and is filled with many reformulations and relaunches until things start working. It's feels a lot like you are tinkering away in a toolshed, building a machine, hoping that your work will lead to it actually booting up.

Less discussed is the stage of voluntarily moving on from your startup and have it continue without you. This is clearly not a stage everyone faces, but I think enough do that it's worth sharing my experience.

Yesterday, was my last day at Cody /Alo Moves, a company I co-founded seven years ago. Believe it or not this whole process of moving on kicked off nearly a year ago. It takes a long time for a founder to unwind him or herself from a company. I wanted to share some of the steps I took as part of this process.

Before I jump in a little context about our company: We were acquired about 1.5 years ago by Alo Yoga. As part of the acquisition, we kept our HQ in Seattle and increased our team headcount from about 20 to 25 FTEs. Our acquirer is an apparel company and we're a tech / media company so there was some, but not full overlap in our respective disciplines.

So with that context, here's how the whole thing went down:

  • Talk early with your co-founder(s): Before my mind was really made up on moving on I had a series of chats with my co-founder, Paul. I made sure to have these talks outside of the office, in the evening, away from the usual hustle and bustle of the office. I felt like a calmer environment was critical to just have an open voicing of where I was at – particularly since I wasn't sure what I wanted.
  • Plan out your org chart for the transition: Once it became clear what I wanted to do and Paul and I digested it, we turned our attention to the org chart. My responsibilities spanned product (which I directly managed), marketing (we had a lead but I was heavily involved), and operations (HR, office, accounting, legal). After listing out all my responsibilities, we realized we needed at least 2, and ideally 3 people to replace me, as well as shifting some of my other responsibilities to existing team members. This is pretty common for founders. We tend to do many disparate things and given our understanding of the business can do them efficiently.
  • Back into a timeline: Given where we needed the org chart to go, and that some hires should be sequenced we decided that 9 months would give us enough time to make this transition with high-confidence. This also got us through the holiday / new year season which is our biggest and most intense. By leaving in March, the business would be better situated to deal with any bumps. This turned out to be just enough time so I'm glad we picked a long runway. On the otherhand, I have to say that personally dealing with such a long period of transition ended up being draining for me. More on that later.
  • Determine a communication plan: Once we knew my timeline, we had to think through who to tell and when. What we quickly realized is that there would be a lot of questions from opening some of the job roles we had earmarked so we should communicate early. We decided to tell the team in September that I was leaving in March, so a six-month heads up. Partly we felt that such a long heads up would emotionally dampen the news. I decided to do this communication in the days just before our annual retreat, to give me plenty of time with the team afterwards to work through the news. We anticipated it being unnatural to share this news and then just get right back to the regular work week. So on a Tuesday afternoon, I called the founder of our parent company and shared my intention. The next morning I sent an email to the entire team, and held an all-hands a few hours later to talk through it face-to-face. The next day we went on our retreat and I had a number of 1:1 chats during all the fun. All in all, this rollout went very well.
  • Strategically disengage: This was probably the hardest thing I did, and I'm not 100% sure it was for the best. Even before I communicated to the team, I made the decision to increasingly take a backseat in the org as this transition unfolded. My thinking was that rather than suddenly disappear one day, its better if the team just learns to push on their own while I'm still there. This was really hard as I tend to be pretty vocal and hold strong views in meetings. Suddenly I was holding my tongue constantly. In time, I started not attending almost all my regular meetings other than our weekly leads meeting and the product meetings. I can say for sure this made the transition a smooth one, as when I left the teams were already self-sufficient but it was hard for me to be so passive for the last 6-9 months. If I had to do it again, I would've started this process maybe with just 3 months to go.
  • Take a supportive role in recruiting: One of the areas that was especially awkward in this period was figuring out how to best be involved with recruiting. As a founder, I was traditionally very involved and had multiple touch points in the pipeline. But now it felt weird as I didn't want to hold back on the fact that I was months away from leaving. So in the end I decided that I would be involved only in the middle of our process. This is where we give folks a project to do and review over the phone. Candidates would work with other team members for the initial phone screens and in the final interview loop at the office. In this way, I still could gauge the skillset of the candidate and give my opinion but I wasn't a "face" of the organization that they had spent a lot of time with.
  • Spend your last month completely away from the office: While yesterday was my last day, we actually had my farewell party and all last month. With a new product manager on board, Paul and I agreed that it would be best for me to just get out of her way. So after three weeks together, I stopped going into the office. For the past few weeks I've been helping Paul with transition, mostly just doing calls and meeting up with him outside the office. This has been nice as many things only come up only after you're gone. Also, on a practical matter there were several services and payments that I hadn't fully transitioned that we caught during this phase.

I hope this was helpful. If anyone is starting down a path like this and wants advice please feel free to reach out.

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