§ 01 — Field Notes, Rev. 2026.05

Will Macdonald

MedTech Advisor  ·  Chicago, IL  ·  AI on the Line

Notes from the seam between AI models and the workflows they get bolted onto. Mostly manufacturing and healthcare. Mostly what breaks in the second month, after the demo is over.


§ 04

Notes in the margin.

Field Annotations — TIL

Better agent control using hierarchical agent.md/claude.md file structure:

#ai #agents
DEC 8 Source →

DSPy's BootstrapFewShot optimizer can learn from user feedback to improve prompts automatically - no manual prompt engineering needed.

#ai #dspy #prompt-engineering
NOV 30
§ 05

Standing order.

About
Will Macdonald

MedTech advisor in Chicago. Most of my work sits at the seam between AI models and the workflows they were bolted onto — manufacturing operations, regulatory and compliance, supply chain, and the long tail of things that quietly break in the second month after a pilot ships.

The coding here is so I understand the boring half of generative AI well enough to advise on it. I work on agentic systems, eval harnesses, and the integration plumbing that decides whether a pilot survives past the demo. When the model is the easy part, I'm interested in the rest.

When I'm not coding or advising, I'm in the kitchen, in the workshop, or behind a camera lens.

willmacdonald
Rev. 2026.05  ·  Chicago, IL