Team Member
I'm Jesse James Richard. I've spent more than twenty years building companies' software from the first line of code — four companies' worth. This site is where I write about how.
What this blog is
The build log. Giant Context was built by one architect conducting a crew of AI agents, and this blog is the technical history of that build: the architecture decisions, the war stories with surprising root causes, the methodology that emerged from working this way, and the infrastructure underneath it all.
No product pitches. The interesting parts of building software are the parts that surprised you.
What I'm looking for
What I'm looking for is an early engineering seat at a company building developer infrastructure, API platforms or AI application tooling, where one person is trusted with the architecture end to end. Remote, on Pacific time, full-time or contract. I've reported to founders and to a board and I'm fine doing it again. The record of changing course on evidence is in the log: permissions borrowed from Amazon and Google rather than invented, 179 of them restandardised on Google's notation, a rule layer I built and then deleted, a polyrepo reversed to a monorepo.
I live in Canada with my family. I play hockey, walk my dog a lot, read more than most people think is reasonable, and write almost as much as I code.
You can reach me at j@jessejamesrichard.com.
Contact
...origin story
It started with a video game written in Pascal at a University of Calgary programming camp when I was twelve. The thing on the screen did what I told it to do, and that was it — hooked.
Passportal: co-founded around 2010, a password management and IT documentation platform for MSPs. I wrote all the software — the LAMP stack, the mail servers, the DNS, the integrations. I was the initial architect, then a minority shareholder and a board member, and when I moved from the engineering seat to the board the direction changed and I was no longer the one setting it. It grew until SolarWinds acquired it.
Made Live: six years on an AI-assisted children's storybook publishing platform. It didn't survive contact with its market, and that tuition — everything about making AI-generated work trustworthy enough to publish under your own name — is baked into everything I've built since.
ManaJing: a Microsoft Sentinel management platform, full Azure stack, production. And now Giant Context — an AI marketing platform on GCP, and the first company where I do all of it: code, infrastructure, product, pricing, and the marketing copy that explains it.