Q2 2026 Team Roadmaps — All team kickoff summaries: June 1st deadline, safety pivot, cross-team dependencies
Sitemate Farewell Learnings — Honest lessons from the Sitemate CTO chapter: Q126 sequencing, 6-month Slack overlay, what the chapter delivered, the velocity-of-adaptation gap
CTO Operating Doc Template — Forward-looking template for next chapter: proximity contract, trigger conditions, pace check, day-one application
Org Design in the AI Era — Why hierarchy persisted 2,000 years, why AI changes it; Block’s capabilities/world-models/intelligence/interfaces model; DRI + player-coach roles; Diana Hu / YC closed loops + queryable company + token-maxing
Engineering in the AI Era — Macro thesis on where the bottleneck moved, re-deriving “good code”, comprehension debt, skill atrophy (Anthropic RCT), 80% problem (Osmani), creative destruction (McCabe), AI software factories
Forward Deployed Engineer (FDE) — Vasuman synthesis: intelligence is commoditising → deployment is the edge; Palantir SOF origin; Audit/Evals/Deployment anatomy; six pillars of production agents; AI labs’ “million-dollar hire”; distinct from Hartley’s internal Forward Deployed flow