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Block (Square / Cash App)

high confidence · updated 2026-06-06

Fintech holding company led by Jack Dorsey. In 2026 it cut 40% of its workforce and flattened its management structure, with some engineering managers reaching up to 175 direct reports and a stated goal of all employees reporting to Dorsey without a permanent middle-management layer.

Block is a publicly traded fintech holding company led by Jack Dorsey. In 2026 it laid off 40% of its workforce and restructured around a flatter, AI-supported management model in which some engineering managers reached up to 175 direct reports and the company stated a goal of having all employees report to Dorsey without a permanent middle-management layer ('I didn't want to be the guinea pig': inside tech's AI-fueled manager purge (Guardian, May 15 2026)). Block has been described as an operational case of intelligence-replaces-hierarchy.

FieldValue
TypePublic company
Founded2009 (as Square; renamed Block in 2021)
HQOakland, CA
CEO[[entities/jack-dorseyJack Dorsey]]
Board memberRoelof Botha
Primary productsSquare (merchant), Cash App, Afterpay, Bitkey, TBD (Bitcoin)

Workforce reduction and reorganization

In February 2026 Block laid off 40% of its workforce (Source: theguardian.com). Following the cuts, the company moved to a flatter management structure. By May 2026, internal org charts reviewed by the Guardian showed some engineering managers with up to 175 direct reports, compared with roughly 6–12 direct reports previously ('I didn't want to be the guinea pig': inside tech's AI-fueled manager purge (Guardian, May 15 2026)). Block's stated goal was for all 6,000 employees to report directly to Dorsey, removing intermediate management layers.

In a statement, Dorsey and board member Roelof Botha wrote that "there is no need for a permanent middle management layer" (Block, May 2026; Source: block.xyz).

Under the new model, Block split traditional managerial duties three ways:

  1. AI is primarily responsible for sharing information between managers, their reports, and other teams.
  2. Directly responsible individuals (DRIs) — workers who oversee strategy and priorities.
  3. Player-coaches — individual contributors who manage employee growth.

Financial results

Block reported gross profit up 27% in Q1 2026, following the 40% staff reduction, which it attributed to an AI-native cost structure that produced leverage on a smaller headcount.

Reception and concerns

Freeland Abbott, a former Square technical lead laid off in February 2026, said of the 175:1 management ratios that he "doesn't expect those management ratios to last," adding that "companies will recognize the need for more humans even if the role isn't called a 'manager.'" Abbott also argued that off-loading employee development to same-level colleagues "could disadvantage less-experienced and marginalized teams" ('I didn't want to be the guinea pig': inside tech's AI-fueled manager purge (Guardian, May 15 2026)).

Relationships

Sources