GTM AI Specialist

Groupon, Inc.

Job Overview

Location

Chicago (35 W. Wacker Dr.); Remote - United States

Job Type

Full-time

Full Job Description

📋 Description

• GTM AI Specialist at Groupon is a hands-on builder role focused on creating AI agents that transform the sales organization from the ground up, directly reporting to the CSO and owning end-to-end development of autonomous and assistive AI systems that drive real merchant outcomes.
• Day to day, you will build and iterate across two layers of AI agents: Layer 1 for autonomous sales motions (outbound, lead prioritization, reactivation) and Layer 2 for rep enablement (context surfacing, deal history, next-action suggestions), while identifying high-value problems, proposing solutions, testing with real merchant data, mining call transcripts for insights, and documenting performance trails.
• You’ll join a bold, AI-first culture at Groupon — a marketplace connecting 16M customers with over 1M merchant partners — where innovation, speed, and extreme ownership are non-negotiable, and your impact is immediate due to scale and autonomy despite the company’s size.
• In this role, you’ll rapidly advance your ability to ship production AI systems, connect technical work to gross profit outcomes, refine commercial judgment, and master end-to-end agent lifecycle ownership — all under direct mentorship from the CSO as you help define Groupon’s AI-powered sales future.

🎯 Requirements

• Degree from an Ivy League or equivalent top-tier university in computer science, data science, economics, mathematics, or a systems-thinking discipline
• Proven experience building and iterating on a real AI agent or automated workflow (not a class project) that you designed, shipped, and improved based on real-world behavior
• Technical ability to work with LLM APIs (OpenAI, Anthropic, etc.), design prompt architectures, and integrate systems using Python or equivalent to build working AI agents independently
• Strong commercial curiosity — instinctively linking technical builds to business outcomes like conversion, revenue, or merchant success
• Rigorous approach to data: questioning sources, building custom measurement frameworks, and refusing to accept metrics without understanding their origin

🏖️ Benefits

• Competitive salary range of $70,000 – $110,000 based on experience, plus eligibility for performance-based bonuses
• Comprehensive health benefits including medical, dental, vision, EAP, life and disability insurance, and FSAs
• Retirement and financial benefits: 401(k) match, employee stock purchase plan (ESPP), and flexible PTO

Skills & Technologies

Python

Remote

$70k-110k

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Groupon, Inc.

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About Groupon, Inc.

Groupon is a global e-commerce marketplace connecting consumers with local merchants by offering activities, travel, goods and services at discounted rates. Founded in 2008, the company operates primarily through mobile and web platforms, serving millions of active customers across North America, Europe and other international markets. Groupon generates revenue by selling vouchers and deals on behalf of third-party businesses, taking a commission on each transaction. It also provides advertising and promotional tools for merchants to attract new customers and grow sales. The company is headquartered in Chicago, Illinois and is publicly traded on the NASDAQ under the ticker GRPN.

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