Upwork cuts 25% of staff, as AI pressure reshapes software hiring

Upwork’s decision to cut about 25% of its staff and lower its 2026 revenue outlook to $760 million to $790 million is a blunt reminder that AI pressure is now showing up in headcount, not just product road maps. For a company built around matching people to work, the message is clear: slower growth and automation are forcing management to run leaner, and the same discipline is rippling across software buyers.

That matters inside monday.com because customers are increasingly evaluating tools through a productivity lens. Sales teams are hearing it first. Buyers want proof that a platform shortens cycle times, reduces manual handoffs and consolidates work, rather than adding another layer of software for employees to manage. In that environment, functions built on routine coordination, repetitive routing and manual matching are the easiest to compress. More defensible roles are the ones that shape product, design AI workflows, close complex enterprise deals and translate automation into measurable operating gains.

monday.com has been leaning into that shift while still showing growth. The company said fiscal 2025 revenue reached $1.232 billion, up 27% from a year earlier, and fourth-quarter revenue was $333.9 million, up 25%. It ended 2025 with more than 250,000 customers worldwide, a 110% net dollar retention rate, 4,281 customers spending more than $50,000 annually and 3,155 employees. Those numbers are strong, but they also raise the bar. Investors and customers now expect AI to help sustain that growth with fewer bottlenecks and clearer output per employee.

The company is making that bet directly. On March 23, monday.com launched Agentalent.ai through monday agent labs with AWS, Anthropic and Wix, positioning it as a place where enterprises can discover, evaluate, hire and manage AI agents for operational roles. Roy Mann said every company will soon have a blended workforce of humans and AI agents. That is more than a product slogan. It is a signal that monday.com wants to sit closer to the staffing and operating decisions being reshaped by AI, the same pressure now forcing Upwork to rethink its own cost structure.

The cautionary backdrop is still there. Market coverage in February said monday.com withdrew its 2027 revenue target and issued 2026 guidance below expectations, a sign that AI and slower enterprise spending are changing how software is bought and valued. The company filed its 2025 annual report for the fiscal year ended December 31, 2025, and its next earnings call is scheduled for May 11, 2026 at 8:30 a.m. ET. For monday.com employees, the Upwork cut is the bigger lesson: the winners in this market will be the companies that can prove they make teams faster, leaner and harder to replace.