Micha Kaufman

Micha Kaufman is an Israeli entrepreneur who co-founded Fiverr in 2010 with Shai Wininger, turning five-dollar gigs into a public marketplace that connects millions of freelancers with buyers worldwide. That business model put him on both sides of the AI upheaval at once: the freelance work Fiverr sells is exactly the kind generative AI threatens to automate.

The wake-up call

In April 2025 Kaufman sent employees a memo so blunt it went viral: AI was coming for everyone’s job, including his own, and it did not matter whether you were a programmer, designer, lawyer, or salesperson. Staff who failed to master the tools of their trade would, he warned, “face the need for a career change in a matter of months.” Unlike most AI-mandate memos, Kaufman published his willingly and defended it as honesty rather than threat.

Five months later the other shoe dropped: in September 2025 Fiverr cut about 250 people — roughly 30% of the company — to become what Kaufman called an “AI-first” organization, leaner, with fewer management layers and infrastructure built around AI. Critics, including former staff, accused him of telling employees to upskill and then cutting them anyway; Kaufman argued the reset was survival, telling Fortune later, “Don’t be a cheerleader. If you’re not practicing, don’t preach.” The episode sits alongside Tobi Lütke’s Shopify memo as a defining document of the AI-first management wave.