It's nearing a month since my last day at
Checkout.com. I'm wearing the hoodie as I write this.
Checkout is the scale-up that opened the doors of opportunity for me. The day my offer came through I knew it was the one to accept - marking the start of a cherished journey that helped me witness what it takes to operate and work with great minds in a growing and competitive landscape.
It is not a sleeping giant, it is a Goliath. Who appears to David as a towering figure but is a man nonetheless. A champion, larger than most startups ever will be, but most importantly a living company like any other.
To mark 1 month here's a little high-level reflection.
people produce products
Being personable (and/or smart) fosters good teamwork, which creates positive outcomes, which can attract more great talent... but being candid is the real fuel. I'm very grateful to have been on (in my opinion) one of the best teams for this; where even when demoralized, candor and transparency kept us from going insane.
No amount of product innovation, engineering expertise or management jargon can drive the car if you don't know when the tyres need air.
do it right
There's a lot on the internet (especially in the world of programming) around "doing it right" or "failing fast". Firstly, these are not exclusive and secondly they can apply to any business function. By observing staff engineers and other senior product people it became very clear the value in architecting and planning well. I'll save you the why.
Witnessing transactions per second increase 10x as a result of rethinking problems made every tech article make sense.
In the past (working and hearing from friends at megacorps) I heard just "get shit done" - then either too much time was wasted overanalysing details, or solutions had to be hacked together before quickly spiralling into maintenance hell. Viewing things from goliath's shoulders showed little ol' me
how valuable efficient prep can be.
and do it fast
The part I continue to learn over the years is the speed component. Sure i've built things (courses, educational youtube, mobile apps) generally very quickly, but it was always internal motivation. To "get it done", to snatch some first-movers advantage or something else.
It's increasingly clear that controlling the thermostat is better than sitting on the fire. Doing things fast means feedback... and feedback means knowing your next move - this is why doing it fast is necessary. Controlling the temperature gives us versatility.
Slowness is the shortcoming that killed Goliath and a struggle most people (and all companies) have to face, but
avoiding it doesn't mean being the fastest... just be fast.
For much of this month i've been busy. We had the Anthropic AI hackathon, the Gaza hackathon (due to the genocide & humanitarian crisis) plus a small side project all in a short burst.
Still many times I found myself very grateful for my time at Checkout. I truly learnt something from everyone,
from the good experiences and the bad. I got to see how decision making impacts people (which means outcomes) at scale.
A single post isn't enough for me to share my technical and operational learnings with the 🌍 but it can cement my thanks to those with who I crossed paths (in London and beyond).
