Group Director, Product Management - Last Mile Optimization & AI

Position Summary...

Last Mile Delivery sits at the center of how we win with customers-and it's undergoing a fundamental transformation. As expectations for speed, precision, and reliability rise, and the gig economy continues to evolve, we are re-architecting delivery from the ground up using advanced optimization, real-time decisioning, and applied AI at massive scale.

We're looking for a Group Director of Product Management to lead Last Mile Optimization & AI-the intelligence layer that powers every critical decision across our delivery ecosystem. This leader will own the platforms that determine how work is created, priced, matched, routed, and fulfilled-continuously balancing speed, cost, and experience across millions of real-time decisions. Unlike traditional marketplaces, this system must also incorporate real-time store operations-where variability in picking, readiness, and substitutions directly impacts delivery performance.

This role requires evolving a live, large-scale system-improving cost, reliability, and speed today while re-architecting for the future through better optimization, data foundations, and decisioning systems.

This is a high-impact, high-visibility role at the intersection of marketplace dynamics, large-scale optimization, and operational complexity.

What you'll do...

* Define the future of last mile:
Set and drive the vision and strategy for optimization and AI across pricing, matching, batching, routing, and store-aware decisioning-incorporating real-time operational signals from stores and drivers.

* Own the intelligence layer:
Build and scale horizontal AI platforms that power real-time, high-stakes decisioning across the entire ecosystem, including the underlying data foundations, consistent metrics, governance, and shared signals that ensure reliable and aligned decision-making across systems.

* Operate and evolve a live system:
Improve cost, reliability, and speed in an already scaled system-balancing short-term performance with long-term architectural evolution, while accounting for real-world variability in store operations.

* Partner to push the frontier:
Work closely with Engineering and Data Science to deliver scalable, explainable, and continuously improving optimization and ML systems in production environments.

* Balance a dynamic marketplace:
Optimize a complex, multi-sided ecosystem across customers, drivers, and store operations-balancing driver earnings, cost efficiency, and service reliability.

* Lead at scale:
Grow and develop a high-performing team of product leaders, raising the bar on product craft, clarity, and execution.

* Create alignment in complexity:
Drive focus and prioritization across Product, Engineering, Data Science, Operations, and Business teams.

* Solve at massive scale:
Tackle challenges like real-time responsiveness, signal quality, and marketplace volatility across millions of daily decisions-including working with noisy or incomplete data, non-stationary demand, and tightly coupled system dynamics.

* Drive high-stakes prioritization:
Make clear, high-quality tradeoffs between foundational improvements, optimization gains, and new capabilities in a highly constrained and dynamic environment.

* Influence the business:
Partner with senior leadership to shape investment strategy, articulate tradeoffs, and guide one of the company's most critical growth engines.

What You'll Bring...

* Deep product leadership: 12+ years in product management, including leading leaders and scaling large, high-impact teams.

* Marketplace & optimization expertise:
Experience building or operating systems with tight coupling between supply, demand, and operational constraints (e.g., logistics, marketplaces, or retail operations).

* Experience with imperfect, real-world systems:
Proven ability to design and operate systems where inputs are noisy, incomplete, or rapidly changing-and where human behavior impacts outcomes.

* Strong AI & data partnership:
Proven success working with data science on optimization models, experimentation, and economically driven decision systems. Deep understanding of model limitations in production and the ability to design systems that account for feedback loops and unintended consequences.

* Strong product strategy and prioritization:
Demonstrated ability to define clear direction, sequence investments, and make difficult tradeoffs in complex, ambiguous environments.

* Strong cross-functional leadership with operations:
Experience partnering closely with operations teams to ensure systems reflect real-world constraints and drive measurable execution improvements.

* Comfort with ambiguity:
Ability to navigate and lead in environments where tradeoffs between speed, cost, and experience are constant and dynamic.

* Executive presence:
Exceptional communication, influence, and cross-functional leadership skills.

* Sharp product instincts:
Systems thinker with strong judgment and the ability to translate complexity into clear, actionable strategy.

Why This Role…