AI Sales Associate at Groupon in Greater Chicago Area

Summary: Groupon is a marketplace where customers discover new experiences and services every day, and local businesses thrive. The AI Sales Associate will be integral to rebuilding Groupon's sales approach using AI technology, contributing to the development of autonomous AI agents that enhance sales processes. Responsibilities: - Build across both layers of the fleet — Layer 1: agents that run autonomously without rep involvement — outbound sequencing, lead prioritisation, inbound triage, reactivation. Reps receive warm opportunities, not cold lists. Layer 2: agents that equip reps at the moment they step in — account context surfaced, deal history ready, next action suggested. You learn how both layers work and progressively contribute to each - Identify what to build and make the case for it — You are not waiting to be given a task list. You look at the sales organisation, find the highest-value problem an agent could solve, and bring a structured proposal to the CSO. Judgment about what is worth building matters as much as the ability to build it - Test, measure, and iterate — You run experiments on real merchant data, measure whether what you built is working, identify failure modes, and refine. Every agent you touch has a documented performance trail. You do not ship and move on - Mine call transcripts for agent inputs — Process sales call recordings to extract patterns, category signals, and performance data. This is raw material for the agents you build — not a separate analytics workstream. You surface insights from it and design around them - Document and maintain what you ship — Every agent you deploy has a before/after record. You keep it current. You present it. You own what you built — not just while you're building it Required Qualifications: - A degree from an Ivy League or equivalent top-tier university — computer science, data science, economics, mathematics, or a field that taught you to think in systems - You have built an AI agent or automated workflow — not a class project. Something you designed, built, and iterated on because you wanted to see if it would work - You can explain what it did, what broke, and what you changed - Technical capability to build: you have used LLM APIs (OpenAI, Anthropic, or equivalent), built prompt architectures, and connected systems together - Python or equivalent - You do not need to be a software engineer — but you need to be able to build a working agent without asking someone else to write the code - Commercial curiosity. You read about how businesses make money - You ask why something converts and why something else doesn't - You do not need a sales background — you need the instinct to connect what you build to a GP outcome - Rigor with data. You do not accept a number without understanding where it came from - You build your own measurement frameworks when none exist - Builder first — your instinct is to build, not to ask for permission - AI-native, not AI-curious — you have spent real time understanding what these systems can and cannot do - Comfortable with ambiguity — you can start without a complete brief, identify the next right step, and keep moving - You learn faster by doing than by waiting for clarity - Commercially curious — you connect what you build to a business outcome - You ask why something converts and why something doesn't Required Skills: AI agent development, LLM APIs OpenAI, LLM APIs Anthropic, LLM APIs, LLM APIs equivalent, Prompt architecture design, Python programming, Data rigor, measurement frameworks, Sales data analysis, Automated workflow building, Commercial curiosity, Comfortable with ambiguity, Impact obsession, Discipline, Extreme ownership Benefits: Medical, Dental, Vision, EAP, 401(k) match, ESPP, Life and disability insurance, FSAs, Flexible PTO, And more.