Kyle Brierley
Kyle Brierley is the founder of TheTechStack and a product leader with experience at Oracle and Tealium. His work spans enterprise AI workflows, customer data platforms, and API integrations. He writes about the decisions teams face when connecting AI to real business processes, including evaluation, permissions, and operating ownership.
How I work
I use AI to assist with research and drafting. I’m responsible for the editorial direction of TheTechStack and for addressing corrections. The articles distinguish documented behavior from interpretation and proposed tests; they don’t imply hands-on product testing unless that work is explicitly described.
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Research and analysis
Inside Glean's knowledge workflow: access, freshness, and answer review
What Glean documents about knowledge sources, document permissions, freshness, and answer feedback—and what an enterprise team should test.
Inside Fin's support workflow: knowledge, actions, and human handoff
How Fin connects support knowledge, external systems, testing, and escalation—and what a team should verify before letting it answer customers.
Inside GitHub Copilot's agent workflow
GitHub's Copilot stack connects retrieval, isolated agent execution, pull requests, policy controls, and measurement into one operating loop.
Before choosing an agent platform, test what survives a failure
A research brief on session recovery, isolated execution, and the questions to bring to an agent-platform evaluation.
What Linear actually runs
The most opinionated product in project management runs a deliberately boring stack — TypeScript, Postgres, GCP — except for the one thing they built before almost anything else: the sync engine.
Stack Moves: Slack kills SSH, Stripe's one-PR TypeScript migration, Anthropic overtakes OpenAI
Slack retires SSH for a REST job gateway, Stripe's 3.7M-line Flow-to-TypeScript PR still the industry's favorite migration story, and Supabase's 2,000-founder survey shows Anthropic overtaking OpenAI as the default model provider.
What Cursor actually runs
A $500M-ARR product built by ~50 engineers on a TypeScript monolith, a Rust orchestrator named Anyrun, and a database migration executed mid-outage.
What TheTechStack actually runs
Our current publishing stack: Astro, Markdown and JSON in git, Vercel hosting and analytics, and browser-side pilot planning.
Planning resources
Start with the AI stack inventory, browse all decision guides, or explore the implementation comparison, pilot evaluation worksheet, and Workbench, or discuss a workflow review.