Chicago (Hybrid) or New York City (Remote) · Global remit · Full-time, permanent

About the role

Help shape how Groupon’s marketplace performs for customers, merchants and the business. Working with senior leaders across Groupon, you will identify high-priority opportunities, determine where to focus and lead initiatives through measurable results. Your work could range from improving merchant supply in high-demand markets to strengthening deal quality and evaluating pricing and take-rate trade-offs. You will combine independent problem-solving, rigorous analysis and cross-functional leadership to turn important commercial questions into changes that improve the business.

This is a hands-on leadership role: you will personally lead the analysis and work with senior functional partners to turn recommendations into measurable results.

Key Responsibilities

You’ll report to the VP of Marketplace Strategy & Operations and work across Sales, Product, Marketing, Finance, Analytics and Operations. You’ll spend your days in the data, in the numbers, and in rooms with senior leaders getting to a decision. You will lead implementation with the relevant teams and make sure the improvements become part of how the business operates.

With a global remit and direct access to senior leaders, you will move quickly from analysis to decisions and implementation.

Concretely, you will:

• Identify and prioritize opportunities. Diagnose marketplace performance, size the opportunities, and determine where Groupon should focus across merchant supply, customer value, sales productivity and operating efficiency

• Own initiatives from diagnosis through results. Define the problem, establish the business case, decide the course of action and lead implementation with the relevant teams

• Use analysis to guide decisions. Build and pressure-test models, investigate the underlying data, and evaluate commercial trade-offs

• Lead decisions across functions. Bring senior stakeholders to agreement on priorities, trade-offs, responsibilities and delivery commitments. Resolve obstacles and keep implementation moving.

• Establish how success will be measured. Define baselines, targets and expected impact, then track whether the change delivered and adjust when it doesn’t

• Test, launch and scale improvements. Design and run pilots, measure results and refine the approach. Turn successful changes into repeatable processes and tools, with clear ownership for ongoing operation.

• Use AI to go faster. Investigate, prototype and automate recurring work; and know when to distrust what it gives you

Role level and scope

Both levels own complex initiatives from diagnosis through implementation and measurable results. Senior Director candidates should bring experience leading a broader or more complex commercial agenda, with greater independence in shaping priorities, resolving trade-offs and securing commitments across functions. This role leads through cross-functional influence and has no direct reports at hire.

Key Requirements

• Bachelor’s degree, and 8+ years in Strategy & Operations, business operations, consulting, corporate strategy or another analytically demanding operating role

• For Director: you’ve owned complex initiatives end to end — including the implementation and the measurable result, not just the recommendation

• For Senior Director: you’ve owned a comparable business or agenda at scale — a P&L, a function, a multi-year commercial agenda — where you carried the decisions and the outcome, and settled trade-offs directly with senior leaders

• Strong analytical and commercial judgment: comfortable working directly with data, quick to challenge assumptions, able to decide with incomplete information

• You learn unfamiliar areas quickly and move from ambiguity to grounded decisions at pace, with the judgment to know when an 80/20 answer is sufficient and when deeper work is required.

• A track record of leading work across functions and influencing senior stakeholders without reporting-line authority

• AI fluency is a baseline here, not a bonus. You already use AI to investigate problems, prototype and automate; and you validate what it gives you

• Clear executive communication: concise recommendations, explicit trade-offs, constructive challenge

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

What Success Looks Like

• Measurable improvement in the marketplace metrics you take ownership of

• Priority questions reach a grounded, evidenced decision in days, not weeks

• Priority initiatives progress against clear delivery milestones and deliver measurable business results

• Improvements become embedded in how the business operates and continue to deliver results.

• Your recommendations shape important marketplace decisions and lead to action.

We Are Interested In

• How you spot important business problems and take ownership of solving them.

• If you know when an 80/20 answer is sufficient and when deeper analysis is needed.

• People who enjoy turning analysis into changes that improve business performance.

• How you build practical solutions that teams can adopt and sustain.

How We Operate

At Groupon, we build on five principles: Extreme Ownership, Speed Over Comfort, Impact Obsessed, Simplify to Scale, and Disciplined. These aren't values on a wall — they're how we expect everyone to show up.

In this role, these principles mean:

• Extreme Ownership — you carry a problem from an ambiguous question through to an operating change, including the parts that sit between functions and belong to nobody.

• Speed Over Comfort — you move priority questions to grounded decisions in days rather than quarters, and you'd rather test a view early than protect it.

• Impact Obsessed — you measure yourself on whether the change delivered, not on the quality of the analysis behind it.

• Simplify to Scale — you leave behind a repeatable process with a named owner, rather than a dependency on you.

• Disciplined — you set the baseline and the targets before you start, and hold yourself to them afterwards.

The comp

• Base: DOE $190,000–$280,000

• Target bonus: 35% at Director, 45% at Senior Director

• Target total cash compensation, including base salary and annual bonus: approximately $257,000–$406,000

• Annual equity award

• Chicago: hybrid out of our 35 W. Wacker Dr. office. New York City: remote, as we have no local office

• Travel: approximately 10%

The compensation range covers both Director and Senior Director levels. Your offer will reflect the level of the role and your relevant experience.

What else you get

• Benefits from day one of the month after you start: medical, dental, vision, life, disability, FSAs, EAP, 401(k) match, and ESPP

• Direct exposure to senior leadership across the business, and the AI tooling to work at a pace most companies can’t

Why now?

Groupon is rebuilding how its marketplace works, and the decisions being made this year will define what the platform becomes. This role sits at the centre of that — close enough to the VP and the functional leaders that your recommendations become operating changes rather than filed analyses, and clear enough in its remit that you’ll be able to point at the numbers you moved.

Groupon is an AI-First Company

We’re committed to building smarter, faster, and more innovative ways of working and AI plays a key role in how we get there. We encourage candidates to leverage AI tools during the hiring process where it adds value, and we’re always keen to hear how technology improves the way you work. If you’re passionate about AI or curious to explore how it can elevate your role you’ll be right at home here.