GTM AI Associate

About the Role Groupon is rebuilding how it sells — from the ground up, with AI — and the person in this role is part of that build from day one. The vehicle is Project Foundry: a production fleet of AI agents designed to give Groupon a parallel sales force that operates 24/7 and to make every human rep sharper the moment they step into a deal. Two layers: the first runs full sales motions autonomously—outbound, inbound triage, reactivation—so reps receive warm opportunities rather than cold lists. The second equips reps at the handoff point—context surfaced, deal history ready, next action suggested. Reporting directly to the CSO, the GTM AI Specialist learns the full architecture, contributes to both layers, and progressively takes end‑to‑end ownership of agents in production. You are building the system that is the business. There is no playbook. You help write it. North Star Ship AI agents that run on real merchant data, prove their value in measurable terms, and make the sales organization faster and sharper than it would be without them. Every signal, every call, every conversion feeds back into what you build next. What You’ll Do Build agents that run autonomously without rep involvement—outbound sequencing, lead prioritization, inbound triage, reactivation—and gradually contribute to each layer of the fleet. Identify high‑value problems for the sales organization, justify them with structured proposals, and present them to the CSO. Run experiments on real merchant data, measure performance, identify failure modes, and iterate. Every agent you ship has a documented performance trail. Mine call transcripts for agent inputs—extract patterns, category signals, and performance data to inform agent design. Document and maintain what you ship—keep a current before/after record, present it, and own the product beyond development. What You Bring A degree from an Ivy League or equivalent top‑tier university—strongly preferred—computer science, data science, economics, mathematics, or a systems‑thinking field. Experience building an AI agent or automated workflow, not a class project, with a clear explanation of the outcome and iterations. Technical capability: LLM API usage (OpenAI, Anthropic, or equivalent), prompt architecture design, system integration, and proficiency in Python or an equivalent language. Commercial curiosity—understand how businesses convert and why certain ideas succeed or fail. Data rigor—build measurement frameworks and make decisions based on validated numbers. Who You Are Builder first—your instinct is to build, not to ask for permission. AI‑native, not AI‑curious—deep understanding of operational, not just demo, AI systems. Comfortable with ambiguity—act quickly with incomplete information and iterate. Commercially curious—connect technology to business outcomes. How We Operate Extreme ownership— own diagnosis and fix when an agent underperforms. Speed over comfort—ship experiments early and learn from live data. Impact obsessed—every hour connects to a gross profit outcome. Simplify to scale—document builds for reusability; refuse hidden complexity. Disciplined—maintain clean data, rigorous experiments, and up‑to‑date performance logs. How We Measure Your Success Agent shipped: first working agent in production by day 90 with documented hypothesis, performance data, and assessment. Quality of proposals—structured agent proposals ranked by commercial impact, grounded in data, specific about build and measurement. Experiment rigor—every agent deployed has a defined success metric set before go‑live. Learning progression—demonstrated improvement in AI build quality, commercial reasoning, and stack fluency quarter over quarter. Contribution to the fleet—at least one documented insight per month surfaced from call transcripts or agent performance data with recommendation. The Details Base salary: 90k‑120k base + 10% ABP Bonus Location: Downtown Chicago (hybrid, 3 days a week in‑office). Alternate locations: remote for the right fit; NYC strongly encouraged. Benefits: start the 1st of the month after your start date—Medical, Dental, Vision, Life Insurance, Disability, FSAs, EAP, 401(k) match, ESPP, flexible PTO, and more. Employee Resource Groups & inclusive team culture. Groupon is an AI‑First Company We’re committed to building smarter, faster, and more innovative ways of working—AI plays a key role in how we get there. Candidates are encouraged to leverage AI tools during the hiring process where it adds value. If you’re passionate about or curious to explore how AI can elevate your role, you’ll be right at home here. Equal Employment Opportunity Statement Groupon is committed to equal employment opportunity. We do not discriminate based on disability, veteran status, or any other protected characteristic. #J-18808-Ljbffr Groupon