Groupon cuts 400 jobs as it rebuilds around AI
Groupon is laying off nearly 25 percent of its workforce - up to 400 employees - to restructure as an AI-native company. The Chicago-based online marketplace expects to eliminate most positions by the end of the third quarter, according to an SEC filing.
The company projects $25 million in annualized savings and plans to reinvest half that amount into AI infrastructure. It expects $5 million in net savings in fiscal 2026 and $7.5 million the following year.
Groupon had 1,734 employees worldwide at the end of 2025. The Chicago headquarters, which had grown to 377 employees by year-end, will be affected by the cuts, though the company declined to specify how many positions would be eliminated in each location.
How AI will reshape operations
The company plans to use AI agents to handle routine work across sales, software engineering, customer service, and human resources. The goal is to increase operational efficiency tenfold, according to Mike Tepeli, Groupon's spokesperson.
For sales specifically, AI will help identify local businesses interested in selling through Groupon's platform and automate follow-up communications. "We are not fully replacing our sales team," Tepeli said. "We are building in AI layers."
The company frames this as workflow redesign rather than pure cost-cutting. "This is about how work gets done, not head count targets," Tepeli said. "AI agents handle operational work end-to-end, and people focus on judgment, strategy and relationships."
Context: A company fighting for survival
Groupon's workforce has shrunk dramatically. When Czech investor Dusan Senkypl took control in 2023, the company issued a "going concern" warning, stating it could run out of money within a year. At that point, Groupon had dwindled from its peak of more than 11,000 employees to less than 2,000.
The company cut costs by exiting its massive River North headquarters in 2024 and moving to a 25,000-square-foot sublease in the Leo Burnett Building. The Chicago office had shrunk to 150 employees before rebounding to 377 by year-end 2025.
Revenue ticked up to $498 million last year after bottoming in 2024. But first-quarter 2026 earnings disappointed, with global revenue flat and billings down 1 percent year-over-year.
Senkypl said the company is "rebuilding Groupon as an AI-native company to operate at the velocity the era of agentic commerce demands." He acknowledged that Q1 results don't yet reflect the AI work underway but expressed confidence in stronger performance ahead.
HR implications
HR departments will face significant shifts. Beyond the immediate layoffs, HR teams themselves will be reshaped by AI automation. The restructuring signals how AI adoption affects workforce planning, talent management, and organizational design - challenges that HR leaders must now navigate.
For HR professionals managing this transition, understanding AI for Human Resources and the broader strategic implications is essential. HR leaders overseeing organizational transformation may benefit from an AI Learning Path for CHROs to guide these decisions.
Groupon also announced that Jiri Ponrt, chief operating officer and partner at Senkypl's Prague-based investment firm, will step down in July.
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