Monday.com's AI Pivot Just Cost It the Executive Who Ran the AI Platform
Monday.com spent the summer telling 620 employees their jobs no longer fit the company's future. This month, four of the executives who were supposed to help build that future are heading out the door themselves — including the one who ran the flagship product the layoffs were meant to pay for.
Calcalist's CTech reported October 17 that Orly Stern Izhaki, the company's VP of AI Work Platform, is expected to leave within a month. So are Sergei Liakhovetsky, VP of R&D, and Seetvon Amir, VP of Product. Lior Zagury, a six-year veteran serving as senior director of Global IT & Workforce Technology, is set to depart at the end of October. A fifth R&D VP, Liron Shtraichman, left the company last month, meaning monday.com has now lost five VP-or-above leaders inside roughly six weeks — one of them the executive most directly identified with the strategy the company bet its restructuring on.
Monday.com's statement to CTech attributed the exits to a mix of "company management decisions and individual executives' personal choices," without specifying which departure fell into which category. The company did not name successors for any of the roles.
A restructuring that already cost 620 jobs
The departures land squarely inside the aftershock of monday.com's July 22 announcement that it would cut about 20% of its global workforce — roughly 620 to 630 people, including some 350 in Israel, about half the headcount at its Tel Aviv development center. Co-CEOs Roy Mann and Eran Zinman framed it at the time as the company's largest product change to date: a shift from software that helps people manage their own work to a platform where AI agents and employees work the tasks together. The company was explicit that it did not consider the move primarily a cost-cutting exercise or a case of AI directly replacing workers — but it was equally explicit that the org chart built for the old product no longer matched the one the new, AI-centered strategy required.
Roy Mann and Eran Zinman, monday.com co-CEOs, July 22 letter to staff: "This is the most painful decision we have made since the founding of monday... We are not making this change to protect what we have."
The numbers since then have been mixed enough to keep the pressure on. Second-quarter revenue came in at $364.6 million, up 22% year over year and ahead of analyst estimates, with AI-product annual recurring revenue doubling quarter over quarter and accounting for 17% of net-new ARR. But the stock has still lost more than a third of its value this year, restructuring charges are running $45 million to $55 million, and management kept its full-year guidance flat rather than raising it on the beat — a signal that investors are still pricing in uncertainty about whether the AI pivot pays off faster than it burns through leadership.
Builders leaving what they built
What makes this month's exits notable isn't the number — four or five departures is a rounding error next to a 620-person layoff. It's who's leaving. A VP of AI Work Platform departing within months of the company making that platform its core strategic bet, alongside two R&D VPs and a VP of Product, reads less like routine attrition and more like the people closest to the pivot deciding not to see it through. Monday.com's own framing — some exits were the company's call, others were the executives' — leaves open whether this is a second, quieter round of restructuring at the top or a leadership team reading the same signals the stock price is sending and choosing to leave on their own terms.
The pattern fits a broader dynamic playing out across the industry in 2026: companies that reorganize around AI don't just cut headcount once and stabilize — they keep shedding the people, including senior ones, who were supposed to run the new structure. Layoffs.fyi data cited by TechCrunch put 2026 tech layoffs above 122,000 as of midyear, with 78% of companies citing an AI-driven refocus as a reason, by far the highest share since the tracker began breaking out causes. Monday.com's executive churn suggests that for at least some companies, the instability an AI pivot creates doesn't end when the layoff announcement does — it just moves up a level.