Yusuke Otsuka

Executive compression is happening faster than anyone expected. Workday's CTO took "Member of Technical Staff" at Anthropic. Atlassian's CTO took "Business Lead" at Stripe. Mike Krieger went from CPO to MTS on the Claude Code team. Instagram cofounder voluntarily dropping "Chief" from his title to write code. Four senior executives in six months all made the same bet: get closer to the work. AI tools are collapsing the ratio of managers to makers. One senior IC with Claude Code and deep domain knowledge is starting to outproduce a 15-person team with three layers of oversight. The management layer that made sense when shipping software required 200-person orgs is compressing fast. When that happens, the value of "Chief" anything drops and the value of "person who actually builds" spikes. A CTO managing 500 engineers is less differentiated than an engineer who can ship with frontier models. The smartest executives in tech are dismantling the ladder and moving to the floor where the work happens. The org chart of 2030 is going to look nothing like today, and these moves are the first draft.

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