I came in when it was still scrappy, growing rapidly and when decisions got made over Slack, and I left after the IPO, when there were investors and analysts and a stock ticker attached to things I used to just go build. Five years at a startup is a long time in startup years. It's long enough to learn about how real rapid growth actually happens, and I picked up quite a few lessons along the way.
A key lesson is simply to treat execution as a hypothesis. You have to experiment faster than feels comfortable. Not recklessly, just faster.
Before my startup adventure, I spent years handling state government technology. In that life, I was used to timelines where it could take literally years before anything new was actually developed and deployed, especially when we were tackling full-scale migrations of massive, legacy systems. When you are dealing with decades-old infrastructure, the default assumption is that every single detail must be perfectly mapped out in a massive project plan before anyone makes a move.
But stepping into a fast-paced environment forced me to unlearn everything. What I ultimately discovered is that you can still experiment, even if you are attached to age-old code and clunky systems. You don't have to wait for a grand, multi-year migration to be complete just to test how users actually want to interact with a new application, workflow or process.
I learned to stop waiting for a plan to be perfectly airtight. Instead of spending three months internally polishing a guess about what a solution should look like, it was always better to spin up a rough prototype or a wireframe and put it in front of real users, and let their behavior tell us where our assumptions failed. 99% of the time we got something wrong. Getting comfortable with being wrong was hard. But I always learned something so that we could quickly pivot or improve the experience, which was a thousand times better than waiting for years just because it wasn't considered "finished" yet.
Small businesses can learn this. Big enterprises can learn this. Government can learn this. It isn't about moving recklessly fast on things that deserve care. It's about noticing which decisions are actually high stakes and which ones just feel that way because nobody's tried moving faster on them before. It's about being open to testing your ideas, getting feedback quickly and pivoting or improving on the original concept.
If you're sitting on an idea, waiting until it's ready, I get it. I spent years learning that ready is a moving target, and the only thing that actually moves it is doing the thing.