Application Security Cannot Remain a Periodic Exercise
OpenAI’s Astra announcement is a capability warning. The enterprise response is a governed verification loop across code, identity, configuration and running systems.
Writing
Field notes from the CTO job.
I write about applied AI, connected products, infrastructure and the day-to-day work of technical leadership.
01 02 When AI Shrinks the Team, the CTO Job Expands
Small AI-enabled teams can carry much larger delivery surfaces, but only when the organization redesigns ownership, verification, specialist access and learning around them.
03 Beyond Cloud by Default: What the 37signals Exit Actually Teaches
A CTO reading of the 37signals cloud exit, with a practical test for deciding when managed cloud has stopped buying enough advantage to justify its permanent premium.
04 Applying the AWS AI Security Framework to Agentic Workflows
How we translate AWS guidance into practical controls for identity, data, tools, authorization, observability and recovery across an agentic workflow.
05 Own the Boring, Rent the Weird: A Workload-Level Infrastructure Strategy
How I choose between cloud, owned infrastructure and a deliberate hybrid one workload at a time.
06 How Technical Ownership Scales Beyond the CTO
How I distribute technical judgment through strong leads while keeping cross-team decisions, interfaces and escalation clear.
07 Building an Agentic Support System for Complex Connected Products
How I structure support agents to investigate product evidence, use tools carefully and hand useful work to a person when the case needs one.
08 Evaluate Agents Against Historical Work, Not Demo Prompts
How to turn historical work into leakage-aware agent evaluations that test decisions, tool use, escalation and recovery as well as the final answer.
09 Human Baseline Blindness: Why We Forgive Human Errors We Condemn in AI
How to compare AI systems with measured human work, then set a higher standard where scale or consequence demands it.
10 When Software Meets the Physical World, the CTO Job Changes
Connected products expand the CTO boundary from software delivery to lifecycle, industrialization, field conditions and long-term system operation.