I led PlanGrid to $100 million in ARR before stepping down as CEO. I have been studying the mistakes I made with my first startup for a long time.
There are many things that will likely fail, regardless of which industry or location you are in.
Key failure points and what I have learned from them are broken down in this post. I would consider this effort worthwhile if these reflections helped one founder.
We were too innovative with our organizational structure. We bragged that we ran our startup like "Star Trek" because we had a flat management hierarchy.
The cute thing stopped working. If you want to keep great people, you need to care about titles and career paths.
We doubled the team to 180 in Year 3 after doubling the team in Year 2. We went from a high execution team to one that was stuck in molasses. We recruited mediocre managers because we didn't know how to find giants.
I did a poor job communicating the direction of the company to more people. During these years of slow execution, we lost our position in a category we created.
People care about titles and career paths, and if you want to retain great people, you have to care about these things too.
If you want to solve problems for your customer and not about organization structures, you need to be creative. A great HR leader can be hired as a business partner to help recruit and retain the right team. A players can recruit other A players but B players can't.
The hardest point to hit was at 150 people.
A factor is hierarchy. Everyone can report to a founder at any given time. Based on basic management ratios, the frontline team member is separated from the founder by three to four degrees.
When you don't hit revenue targets, you become dangerous. It's easy for those who feel like they're performing to blame everyone else when there's a mismatch on performance. There are tensions between the teams. Communication gets harder, so everything gets magnified.
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