Transferwise's first org chart
I was doing research for my book, and had the pleasure of chatting with @Nilan Peiris, the first employee and now Chief Product Officer at Wise (formerly Transferwise).
He told me that they have over 90 teams now, but in the early days they only had two:
Team grow quickly
Team don't f*** up
I love this story because startups have a complicated relationship with risk. Some parts of any business, like growth, demand a bold "hold my beer" approach. But other parts, like security, compliance and simply handling other people's money, require flawless execution. These two approaches attract very different personalities, and often work in opposition to each other.
Simple Next Step
Does it make sense to reorganise your entire company into teams based on risk tolerance? Maybe, but that feels a bit, well, risky. Thankfully there's a simpler option to start with.
For each project, have an explicit conversation about the expected level of quality vs. speed and risk. Or to put it simply, divide your projects into "hold my beer" and "DFUs." Make those expectations clear from the outset, and assign the projects to the right people - cowboys (and cowgirls) get the JFDIs and give your DFTUs to the thoughtful methodical types. (And try to keep them from killing each other.) Good luck!