Long Strange Trip: CEO to CEO with Brian Halligan Jack Dorsey: Every Company Can Now Be a Mini-AGI
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Apr 2, 2026 
Roelof Botha, Sequoia partner and Block board member, offers venture and board-level perspective. Jack Dorsey, founder of Twitter and Block, outlines rebuilding a company around an AI intelligence layer. They discuss why hierarchies may be obsolete, a three-role company model, cutting 40% to reboot, AI-native startup advantages, and how CEOs must change to align company intelligence.
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Hierarchy Origin And The Intelligence Layer
- Hierarchies exist primarily to manage information flow across people, a problem now solvable by modeling company artifacts as an intelligence layer.
- Jack argues remote work artifacts (Slack, code, docs) let you build a company world model and query it like a mini-AGI to replace lossy human chains.
Reduce Roles To IC DRI And Player Coach
- Normalize roles down to three: IC (builder/operator), DRI (owns customer outcomes), and Player Coach (teaches by doing).
- Make player-coach a temporary assignment not a reporting line so coaching scales without recreating hierarchy.
Measure And Shrink Org Depth
- Measure organizational depth from CEO to any individual and target reducing max depth (Block aimed from ~5 to 2–3 this year).
- Shorter depth becomes manageable because the intelligence layer amplifies reach and context.
