Director / Senior Director, Marketplace Strategy & Operations

Groupon•Chicago, IL

1d•Hybrid

About The Position

Groupon is hiring a Director or Senior Director to improve marketplace performance for customers, merchants, and the business. This hands-on leadership role identifies high-priority commercial opportunities, determines where to focus, and leads initiatives from analysis through implementation and measurable results. The work may include improving merchant supply in high-demand markets, strengthening deal quality, and evaluating pricing and take-rate trade-offs. The role reports to the VP of Marketplace Strategy & Operations and works across Sales, Product, Marketing, Finance, Analytics, and Operations. It requires independent problem-solving, rigorous analysis, and cross-functional leadership to turn important commercial questions into operating changes. The role has a global remit, direct access to senior leaders, and no direct reports at hire. Director and Senior Director candidates both own complex initiatives end to end; 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 commitments across functions. The position is based in Chicago with a hybrid arrangement or in New York City remotely. Travel is approximately 10%. The compensation range covers both levels: base salary of $190,000–$280,000, with target annual bonus of 35% at Director or 45% at Senior Director. Target total cash compensation is approximately $257,000–$406,000, and an annual equity award is offered. Benefits begin on the first day of the month after the start date.

Requirements

Bachelor’s degree.
At least 8 years of experience in Strategy & Operations, business operations, consulting, corporate strategy, or another analytically demanding operating role.
For Director: experience owning complex initiatives end to end, including implementation and measurable results, not only recommendations.
For Senior Director: experience owning a comparable business or agenda at scale, such as a P&L, a function, or a multi-year commercial agenda, and carrying decisions and outcomes while settling trade-offs directly with senior leaders.
Strong analytical and commercial judgment; ability to work directly with data, challenge assumptions, and make 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 work is needed.
Track record of leading cross-functional work and influencing senior stakeholders without reporting-line authority.
Existing fluency using AI to investigate problems, prototype, and automate, with the ability to validate its outputs.
Clear executive communication, including concise recommendations, explicit trade-offs, and constructive challenge.

Nice To Haves

Marketplace or technology experience is useful.

Responsibilities

Identify and prioritize marketplace opportunities by diagnosing performance, sizing opportunities, and determining where to focus across merchant supply, customer value, sales productivity, and operating efficiency.
Own initiatives from diagnosis through results: define problems, establish business cases, choose courses of action, and lead 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; track results and adjust when initiatives 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.
Use AI to investigate, prototype, and automate recurring work, while validating its outputs.
Lead work across Sales, Product, Marketing, Finance, Analytics, and Operations to turn recommendations into measurable operating changes.