AI’s Transformation of Work — May 24, 2026 Update
A weekly update of companies and workers reporting how AI transforms work
Welcome to the Treeline! The view opens up here. This update adds new entries to my ongoing log of AI’s transformation of work, the good and the bad.
What Is AI Doing to Jobs Right Now?
Cloudflare cut more than 1,100 employees after its internal AI usage rose sixfold in three months, the largest of three AI-attributed cuts announced in a single week. ClickUp eliminated 22% of staff from a position of financial strength. Standard Chartered announced plans to remove 8,000 support roles by 2030. CEO Matthew Prince said, “AI isn’t coming for builders or sellers, but it is coming for measurers.” However, Benjamin Todd’s analysis of employment data through early 2026 found little aggregate displacement. SWE postings rose 10% even as tech layoffs tripled. But there is a distinct reduction signal: a roughly 10% decline for workers aged 22–25 in AI-exposed roles, though those appeared to be offset by gains among older workers.
Bun creator Jarred Sumner rewrote 700,000 lines of code from Zig to Rust in six days with AI assistance, something he said would have been impossible a year earlier. At Every, a 30-person publication, AI now handles 95% of emails while managers commit code and engineers talk directly to customers. Headcount hasn’t shrunk there; output has grown. The Stanford startup trial and the Goldman Sachs platform rollout tracked output rising and headcount holding steady.
Rohit Krishnan argued that AI agents differ from humans in specific, predictable ways, needing purpose-built institutions (roles, ledgers, reputation systems, markets) to coordinate effectively. Smart individual agents do not automatically produce smart organizations. Garicano and Saa-Requejo explained that, beyond intelligence, the hardest parts of implementing AI agents are “the workflow redesign, organizational authority, proprietary data, and the political ability to overcome resistance.” In China, where 85% of survey respondents view AI favorably, the enthusiasm stems from fear of falling behind rather than genuine confidence, a pattern rooted in the 1990s mass layoffs that displaced 24 million workers, explains Zilan Qian writing for Asterisk Magazine.
May 23, 2026 · Bun
Bun creator Jarred Sumner reports rewriting the entire Bun JavaScript runtime from Zig to Rust in six days, converting roughly 700,000 lines of code with AI assistance. The rewrite fixed inherited bugs and produced a smaller binary. A year ago, Sumner says, this would have been impossible.
May 22, 2026 · Benjamin Todd
Labor data through early 2026 shows little aggregate evidence of AI-driven job losses. Tech layoffs tripled in Q1 but SWE postings rose 10%. In highly AI-exposed occupations, wages and employment share remain flat. The sharpest signal: a roughly 10% decline in headcount for workers aged 22 to 25 in AI-exposed roles, offset by gains among older workers.
May 22, 2026 · Silicon Continent
Garicano and Saa-Requejo argue AI model labs sit in a structurally unprofitable position: customers switch providers instantly, and hardware suppliers hold monopoly power. Stanford’s AI Index 2026 finds agent deployment in single digits across business functions. The scarce input is workflow redesign and organizational authority, not intelligence.
May 21, 2026 · Every
Every’s team of 30 uses AI across coding, writing, design, and customer service but hasn’t shrunk. AI now handles 95% of emails; managers commit code; engineers talk to customers directly. The publication argues automation raises productivity expectations, which generates more human work rather than eliminating it.
May 21, 2026 · Cloudflare
Cloudflare CEO Matthew Prince explains cutting 20% of staff while growing revenue 30%+: “AI isn’t coming for builders or sellers, but it is coming for measurers.” AI now audits every business risk continuously, replacing quarterly spot checks by internal audit teams and middle managers.
May 21, 2026 · ClickUp
ClickUp cut 22% of its workforce from a position of strength, restructuring around what CEO Zeb Evans calls a “100x org.” Workers who create outsized output with AI will receive million-dollar salary bands. Evans argues existing workflows create bottlenecks in AI systems and must be rebuilt from scratch.
May 21, 2026 · Rohit Krishnan
Krishnan argues AI agents are becoming distinct economic actors that require formal organizational structures to coordinate. Agents follow instructions literally, prefer independent completion over negotiation, and struggle with institutional awareness. Managing them demands new visibility tools and workflow design, not just better models.
May 20, 2026 · Asterisk
Stanford’s 2026 AI Index shows 85% of Chinese respondents view AI favorably versus under 45% of Americans. But the enthusiasm reflects trauma from 1990s mass layoffs that displaced 24 million workers, not genuine confidence. Over 250,000 Chinese enrolled in AI crash courses in 2023 alone, driven by fear of missing the next technological wave.
May 18, 2026 · Standard Chartered
Standard Chartered plans to eliminate roughly 8,000 support roles over four years, cutting corporate functions by more than 15% by 2030. CEO Bill Winters frames the move as replacing lower-value human capital with AI investment, not cost-cutting. The bank’s own AI usage rose sixfold in three months.
Read all 147 entries in the full log at