Jack Dorsey

Cut nearly half of Block's workforce (4,000+ employees, reducing from 10,000 to ~6,000) in February 2026, citing AI replacing human roles. Said "100 people + AI = 1,000 people" and predicted most companies would make similar cuts within a year. Critics and a former exec alleged the cuts were standard cost-cutting disguised as AI transformation.

Block eliminated diversity and inclusion roles as part of its 2025-2026 restructuring. Former head of communications at Square noted that cuts to policy and DEI teams were evidence of "standard prioritization and cost management" rather than AI-driven transformation, per a NYT essay.

Cut 4,000 Block employees in February 2026 citing AI, declaring "AI agents are peers to human employees" and predicting most companies would follow. Posted on X that Block would "use AI to do the work instead" of backfilling eliminated roles. Critics labeled it "AI washing" for financial difficulties; Block stock had fallen 40% since January 2025.

In July 2024, Dorsey sent an internal memo warning a major Block reorganization would feel "big and disruptive or uncomfortable," restructuring Square, Cash App, and other divisions. Block also conducted smaller layoffs throughout 2024 as Dorsey narrowed company focus to Bitcoin and core payments products. Dorsey has acknowledged the difficulty of workforce reductions without the extensive public communication Stripe or Airbnb have used.

Dorsey left Bluesky's board in May 2024, citing its drift toward centralized moderation as incompatible with his free speech values. He endorsed X as "freedom technology" and in July 2025 launched Bitchat, a peer-to-peer Bluetooth mesh messaging app with no central servers, no internet required, and ephemeral encryption — specifically designed to be censorship-resistant.

Criticized Israeli actions in Gaza. Blocked by pro-Israel accounts. Donated to Palestinian relief. One of few major tech figures to take pro-Palestinian stance.