Groupon layoffs hit HR, customer service and tech teams amid AI restructuring

Groupon is cutting up to 400 jobs worldwide across human resources, customer service, software engineering and operational functions as the company accelerates a sweeping artificial intelligence-led restructuring effort aimed at rebuilding the business around automation and AI-driven workflows.

According to a filing submitted to the US Securities and Exchange Commission and statements shared with the Chicago Tribune, the Chicago-based online marketplace expects most of the workforce reductions to be completed by the end of the third quarter.

The layoffs represent nearly a quarter of Groupon’s global workforce.

The company said the restructuring is expected to generate annualised savings of roughly $25 million, with as much as half of the savings being reinvested into AI infrastructure and automation capabilities.

The latest move marks one of the clearest examples yet of a consumer internet company openly reshaping operational teams around AI adoption rather than positioning automation purely as a productivity enhancement tool.

AI overhaul expands beyond engineering teams

While technology companies have increasingly introduced AI tools across coding, analytics and customer support functions, Groupon’s restructuring extends into several business operations simultaneously.

Mike Tepeli, spokesperson for Groupon, told the Chicago Tribune that the layoffs were global and operational in nature, adding that the company wanted to remain “at the forefront” of AI transformation.

According to Tepeli, the company plans to use AI systems across multiple commercial and operational areas, including:

• Identifying local merchants likely to use Groupon’s platform
• Automating lead sourcing and outreach
• Supporting customer engagement workflows
• Streamlining operational tasks across HR and customer service
• Improving software engineering productivity

“We are not fully replacing our sales team,” Tepeli told the publication. “We are building in AI layers.”

The company also stated that AI agents would increasingly handle operational work end-to-end, allowing employees to focus more on strategy, judgement and relationship management.

Workforce reductions continue years-long restructuring

The layoffs add to a decade-long workforce contraction at Groupon.

Once one of Chicago’s most prominent technology companies, Groupon expanded rapidly after launching in 2008 with its discounted local deals business model. At its peak, the company employed more than 11,000 people globally and became one of the most closely watched internet companies during the early daily-deals boom.

However, slowing revenue growth, mounting operational losses and shifting consumer behaviour steadily weakened the business over the past decade.

Key workforce and operational changes include:

• Groupon employed 1,734 workers globally at the end of 2025
• The Chicago headquarters had 377 employees at year-end 2025
• The company previously reduced staffing from over 11,000 employees to fewer than 2,000
• Groupon exited its large River North headquarters in Chicago during cost-cutting efforts
• In 2024, the company moved into a smaller office at the Leo Burnett Building in downtown Chicago

According to the report, the Chicago office will also be affected by the latest layoffs, although Groupon did not disclose location-specific reductions.

The restructuring comes shortly after Dusan Senkypl, Groupon’s largest shareholder and controlling investor since 2023, intensified efforts to reposition the business around AI-enabled commerce operations.

AI becomes central to Groupon’s turnaround strategy

Groupon’s management is framing the AI push as a proactive transformation rather than a defensive cost-cutting exercise.

In a May 7 earnings release cited in the report, Senkypl said the company was rebuilding Groupon as an “AI-native company” capable of operating at the speed required for “agentic commerce”.

The company believes automation can help solve scaling challenges that previously depended heavily on labour-intensive sales and operational models.

According to company statements:

• Groupon expects $5 million in net savings in fiscal year 2026
• Net savings are projected to rise to $7.5 million the following year
• Up to 50% of restructuring savings will be reinvested into AI infrastructure
• Earnings guidance has been raised following the restructuring plan

Tepeli also acknowledged that Groupon had historically lagged behind previous technology transitions, including mobile, cloud computing and operational streamlining.

“The AI-native shift is happening now,” Tepeli told the Chicago Tribune. “We are choosing to move while the window is open.”

Revenue pressure continues despite signs of recovery

The restructuring follows mixed financial performance for Groupon.

After years of decline, the company recently showed signs of stabilisation through a renewed focus on local experiences and hyperlocal commerce offerings.

According to company figures cited in the report:

• Groupon generated $1.67 billion in billings last year
• Revenue reached $498 million
• First-quarter global revenue this year remained flat year-on-year
• Billings declined 1% compared with the previous year

The company had previously issued a “going concern” warning in 2023 after warning investors that Groupon could face severe financial pressure within a year without operational improvements.

At the same time, Groupon’s leadership changes continue alongside the restructuring. The company disclosed that Jiri Ponrt, chief operating officer and partner at Prague-based investment firm Pale Fire Capital, plans to step down in July.

The broader restructuring reflects a growing shift across the technology industry, where companies are increasingly redesigning workflows around AI systems while reassessing hiring needs, operational structures and workforce composition.

For Groupon, the latest overhaul represents another attempt to revive a once high-flying internet business now betting heavily that AI can help restore operational growth and competitiveness.