Director / Senior Director, Marketplace Strategy & Operations

Groupon•Chicago, IL

3d•$190,000 - $406,000•Hybrid

About The Position

Groupon is hiring a Director or Senior Director to shape marketplace performance for customers, merchants, and the business. This hands-on leadership role identifies high-priority opportunities, determines where to focus, and leads initiatives from analysis through implementation and measurable results. Areas of work may include improving merchant supply in high-demand markets, strengthening deal quality, and evaluating pricing and take-rate trade-offs. The role works across Sales, Product, Marketing, Finance, Analytics, and Operations, with direct exposure to senior leaders. It combines independent problem-solving, rigorous analysis, and cross-functional leadership to turn important commercial questions into operating changes. The position has a global remit and no direct reports at hire. Senior Director candidates are expected to lead a broader or more complex commercial agenda with greater independence in setting priorities, resolving trade-offs, and securing cross-functional commitments. The position is based in Chicago with a hybrid arrangement or in New York City remotely, and includes approximately 10% travel. The base salary range is $190,000–$280,000, with target bonuses of 35% at Director and 45% at Senior Director, target total cash compensation of approximately $257,000–$406,000, and an annual equity award. Groupon describes itself as an AI-First Company and encourages the use of AI to improve work, while emphasizing validation of AI outputs.

Requirements

Bachelor’s degree.
At least 8 years of experience in Strategy & Operations, business operations, consulting, corporate strategy, or another analytically demanding operating role.
Director candidates must have owned complex initiatives end to end, including implementation and measurable results.
Senior Director candidates must have owned a comparable business or agenda at scale, such as a P&L, function, or multi-year commercial agenda, and carried decisions and outcomes while settling trade-offs directly with senior leaders.
Strong analytical and commercial judgment; comfort working directly with data, challenging assumptions, and making decisions with incomplete information.
Ability to learn unfamiliar areas quickly, move from ambiguity to grounded decisions at pace, and judge when an 80/20 answer is sufficient versus when deeper analysis is needed.
Track record of leading cross-functional work and influencing senior stakeholders without reporting-line authority.
AI fluency, including using AI to investigate problems, prototype, and automate, and validating its outputs.
Clear executive communication, including concise recommendations, explicit trade-offs, and constructive challenge.

Nice To Haves

Marketplace or technology experience is useful.
Prior B2B sales experience is not required.

Responsibilities

Diagnose marketplace performance, size opportunities, and prioritize focus across merchant supply, customer value, sales productivity, and operating efficiency.
Own initiatives from diagnosis through results by defining problems, establishing business cases, determining courses of action, and leading implementation with relevant teams.
Build and pressure-test models, investigate underlying data, and evaluate commercial trade-offs to guide decisions.
Lead cross-functional decisions by aligning senior stakeholders on priorities, trade-offs, responsibilities, and delivery commitments; resolve obstacles and keep implementation moving.
Define baselines, targets, and expected impact, then track results and adjust when changes do not deliver as expected.
Design and run pilots, measure results, refine approaches, and scale successful improvements into repeatable processes and tools with clear ongoing ownership.
Investigate, prototype, and automate recurring work using AI, while validating its outputs.
Lead complex initiatives through measurable results and turn recommendations into operating changes.