While growing our startup from initial success with a team of 6 to a headcount approaching 100 we faced many hurdles that come with scaling up an engineering team. We're dealing with technical, team structure, and knowledge sharing challenges. All of these require tradeoffs as we're building out the system, while running it 24/7.

I will cover some of the specific challenges faced when things don't scale well, how we moved past them, and lessons learned.

The problems we faced ranged from technical, like how early choices in a growing code base painted us into a corner later, to how a growing user base coupled with growing system complexity lead to difficult tradeoffs for deployments, and making sure a growing team speeds up, rather than slowing down.

Crucially, you can't scale up the last man who knew everything (me), and expect the engineering team and output to scale up while he is in the centre of it all and not sharing knowledge.