How We Run Blue-Green Deployments
The first time I ran a blue-green deployment in anger, it was 6:40 on a Friday evening and the payment authorization service had been down for eleven minutes....
9 min613Read →
Blog — Page 3
Practical notes on engineering leadership, fintech, and building at scale.
How to Let Someone Go With Dignity
The first person I ever let go, I did badly. It was 2011, I was a newly minted team lead, and I had rehearsed the meeting so many times in my head that when he...
10 min577Read →
The Case for Boring Technology in Fintech
A few years ago I sat in a postmortem for an outage that cost us most of a business day of failed settlements. The root cause was not a bug in anything we had...
10 min806Read →
The Two-Pizza Team Rule, Revisited
The first time I heard the two-pizza rule quoted back to me in a planning meeting, it was being used to justify keeping a team at four people while they owned...
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Building a Rules Engine You Can Actually Maintain
The worst rules engine I ever inherited had 1,847 rules in a single database table, evaluated top to bottom, and the order they ran in was determined by the...
10 min504Read →
Running Sprint Planning That People Respect
The worst sprint planning meeting I ever sat through ran for three hours and ended with nobody able to say what we were actually building that week. Fourteen...
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What a Decade in Fintech Taught Me
When I started in fintech, the word itself still carried a faint whiff of novelty. We were the upstarts, the people building software around the edges of banks...
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Designing Safe Database Schema Changes
Of all the operational risks I worry about as a CTO in regulated payments, the one that keeps recurring in postmortems is not a fancy distributed-systems...
11 min354Read →
The Habits of Calm Engineering Teams
I have managed engineering teams through payment outages on the busiest shopping day of the year, through regulatory audits that arrived with two weeks notice,...
11 min761Read →
Observability Beyond Logging
For the first decade of my career, observability meant one thing: logs. When something broke, you SSH'd into a box, tailed a file, and grepped for the word...
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When to Build vs Buy
Every engineering leader I know has a build-versus-buy decision sitting in their backlog right now, and most of them are getting it wrong in one of two...
10 min735Read →
Handling Timezones and Dates Correctly
Of all the categories of bugs I have seen ship to production over a twenty-year career, the ones rooted in date and time handling are the most insidious. They...
11 min970Read →