​ Groupon Cuts Up To 400 Jobs As Company Pushes “AI-Native” Overhaul
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Another One: Groupon’s AI Pivot Comes With Pink Slips As Company Plans To Cut Up To 400 Roles

Grace L. by Grace L.
May 27, 2026
in Tech
Reading Time: 2 mins read
Another One: Groupon’s AI Pivot Comes With Pink Slips As Company Plans To Cut Up To 400 Roles

Another One: Groupon’s AI Pivot Comes With Pink Slips As Company Plans To Cut Up To 400 Roles

Groupon is trying to sell Wall Street on a comeback story, but hundreds of workers may be paying the first bill.

The Chicago-based deals platform approved a new restructuring plan on May 21 tied to its push to rebuild itself as an “AI-native company,” according to a Form 8-K filed with the SEC. The company said the “initial phase” is expected to include “up to 400 positions globally,” covering both employees and contractors, with most cuts expected by the end of the third quarter of 2026. 

The move is part of Project Foundry, Groupon’s automation-heavy overhaul. In its first-quarter results, Groupon described Project Foundry as a “company-wide initiative to transform our operating model by embedding AI agents into the core of every function,” saying it is “intended to enable the Company to operate with the speed required to succeed in an AI-native world.” 

Translation: Groupon wants fewer bottlenecks, faster execution and more AI doing the work that used to require layers of people. In its filing, the company said the cuts could bring $20 million to $25 million in annualized payroll savings, with $10 million to $12 million expected in 2026. Groupon also said it plans to reinvest up to half of this year’s savings “in marketing, AI infrastructure, and talent density.” (SEC)

The company also raised its full-year adjusted EBITDA guidance from $70 million to $75 million, up to $75 million to $80 million. Investors seemed to like the math: Fast Company reported that GRPN stock jumped more than 9% Tuesday, closing at $20.69, then moved higher again in premarket trading Wednesday. 

Still, this is not Groupon’s first round of painful trimming. TechCrunch reported that the company cut 500 jobs in August 2022, nearly 15% of its workforce at the time, then approved another 500 cuts in January 2023 as part of a multi-phase cost savings plan. 

Now, with AI at the center of the pitch, Groupon is calling this a transformation. Workers may call it something else.

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Grace L.

Grace L.

Hazel L., known as thinktank, is a breaking news and trends writer for Baller Alert, delivering fast, accurate updates on the stories shaping culture and current events.

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