Hayden Brown

Hayden Brown is the Chief Executive Officer of Upwork, the world's largest online freelance marketplace, a role she has held since 2020. She joined Upwork in 2014 as Vice President of Marketing and rose through the organisation, taking the CEO role when founder Stephane Kasriel stepped down. Her background spans marketing, product, and corporate strategy, with earlier experience at startups and growth-stage technology companies.

Brown repositioned Upwork from a consumer gig marketplace towards enterprise talent management during her tenure, targeting Fortune 500 clients seeking on-demand access to senior independent talent rather than low-cost task completion. Under her leadership, Upwork expanded its enterprise contracts and pushed into skills-matching technology. She is one of the relatively few women running a major publicly listed marketplace company.

Her management philosophy has emphasised flexibility and human judgement in building high-performing remote teams — which makes her May 2026 declaration that the 'two-pizza team model is dead' a striking reversal, signalling that AI coordination tools have eliminated the case for small, self-organising human teams as the default unit of corporate output.

On 8 May 2026, Brown announced Upwork was cutting 25% of its total workforce, framing the decision around a thesis that AI tools had made traditional team-based management structures obsolete. Her internal memo, which circulated publicly, declared 'two pizza teams are dead' — a reference to Amazon's small-team philosophy — arguing that AI now handles coordination work that previously required human managers and supporting staff.

The memo positioned AI not as a productivity multiplier for existing headcount but as a structural replacement for certain categories of management and operational work. The declaration from a marketplace CEO built on human flexible work made it one of the most-cited executive communications of the 2026 AI employment wave.