Upwork Expands Restructuring to Cut About 37% of Its Workforce

Upwork now expects to cut about 37% of its total workforce, according to an amended filing made Thursday. The figure includes the roughly 24% reduction announced on May 7 and a separate reduction underway at an unnamed subsidiary. The company's board approved the expanded plan on November 10.

The filing gives a percentage, not a head count. That omission matters. Upwork reported about 630 employees at the end of 2025, according to its annual report, and also engaged roughly 1,600 independent workers through its platforms for internal projects that year. A 37% cut, if applied to the employee base, would touch well over 200 positions. Upwork did not publish that arithmetic itself.

What changes in the cost estimate?

The restructuring is getting more expensive. Upwork now estimates total pre-tax charges of $27 million to $37 million, mainly severance and other one-time termination costs. In May, the company had estimated $16 million to $23 million. The revised range is roughly 60% higher at its midpoint.

The company recognized $18.1 million of those charges through September 30. Most of the remaining costs are expected to be cash charges, with the majority booked in the fourth quarter of 2026.

Why does the timeline slip?

Completion now lands in the first quarter of 2027, a quarter later than the previous target of the fourth quarter of 2026. The filing offers no detailed explanation for the delay. A longer restructuring window usually means longer severance payouts and extended uncertainty for remaining staff. Upwork did not address either point.

How does Upwork frame the cuts?

The company describes the plan as building "a more efficient operating model" and positioning the business "for profitable growth as the nature of work evolves." These are the standard phrases of a restructuring filing. They promise efficiency and growth without committing to numbers, dates, or revenue targets.

There is a strategic backdrop, however. Upwork has been reshaping its business around AI work. This week, a study the company ran with OpenAI found that AI-related projects on freelance markets carry bigger budgets and more hours than comparable work. The study is company-sponsored research, not an independent audit, and its methodology received limited scrutiny in coverage. Still, it signals where Upwork sees demand moving.

What is not said?

The subsidiary undergoing its own reduction is not named. The filing does not break down how the 37% splits between the May action, the November expansion, and the subsidiary's cuts. Nor does it state expected annual savings, a figure investors typically use to judge whether restructuring charges pay off.

Upwork also did not say whether the independent contractors it engaged internally — about 1,600 last year — face reductions alongside the employee base. The percentage applies to "workforce," and the company leaves the definition vague.

The expanded plan, higher charges, and delayed completion will test whether the cuts convert into the profitable growth the company promises, with the first quarter of 2027 as the measure of delivery.