Sr Strategy & Planning Associate, Pickup Merchant/GTM Lead

Scaling one of our largest growth bets requires operational excellence, strategic thinking, and rigorous execution. We are looking for a Senior Strategy and Planning Associate to act as the Merchant and Go-To-Market Lead and drive the global Pickup program. In this role, you will serve as the engine room of the team, ensuring our multi-phase growth plans are executed on time across all regions while leading special initiatives focused on improving the overall margin profile and business efficiency.

What you will do in this role includes:

• Managing the core execution plan globally, coordinating closely with regional leads across multiple territories to track progress through key foundational and operational phases.
• Leading targeted projects designed to improve profitability, which includes workstreams centered on reducing unfulfilled order costs, mitigating fraud, and optimizing variable spend.
• Identifying manual processes and partnering with cross-functional teams to build automated, scalable solutions for merchant outreach and operational updates.
• Owning the global governance cadence, including weekly and monthly business reviews, to ensure continuous alignment against Gross Bookings and trip targets.
• Driving cross-regional standardization by sharing best practices, playbooks, and merchant onboarding processes across global markets.

To be successful in this position, you should meet the following basic qualifications:

• Hold a Bachelor’s degree.
• Bring four or more years of professional experience in program management, operations, or finance.
• Demonstrate a proven ability to manage complex, global projects involving multiple stakeholders and timelines.
• Possess strong financial literacy with an understanding of P&L components, enabling you to identify cost-saving opportunities and drive efficiency projects.
• Have a passion for building structure out of ambiguity and creating repeatable, scalable processes.

Preferred qualifications that will help you stand out include possessing a PMP or similar project management certification, experience working with central and regional teams within a matrixed organization, and background knowledge in fraud or risk operations.

Compensation for this role varies by location. For Chicago, IL-based roles, the base salary range is USD $118,000 to $131,000 per year. For New York City, NY and San Francisco, CA-based roles, the base salary range is USD $131,000 to $145,000 per year. Across all US locations, you will be eligible to participate in the company bonus program, may be offered equity awards and other types of compensation, and can participate in a 401(k) plan alongside various other company benefits.

Offices remain key to collaboration and our company culture. Unless approved for full remote work, employees are expected to spend at least 50% of their time working in-office. We are proud to be an Equal Opportunity employer, considering all qualified applicants without regard to sex, gender identity, sexual orientation, race, color, religion, national origin, disability, protected Veteran status, age, or any other legally protected characteristic.