Director, Operations - Transformation

We're looking for a Director of Transformation & Enablement to accelerate the transformation of Trust and Safety (T&S) across the rapidly growing and evolving Last Mile Delivery platform. This role translates strategic vision and business priorities into an integrated transformation portfolio and drives the planning, execution, and operational readiness needed to deliver change.

The role will lead strategic planning, project management, and operational readiness capabilities that help T&S modernize operations to enable emerging business priorities and scale effectively as the delivery business evolves.

Key Responsibilities

• Accelerate T&S transformation by translating strategic vision and business priorities into plans, initiatives, milestones, and measurable outcomes that enable new or scale existing T&S operations.
• Modernize ways of working by identifying and advancing operating models, industry best practices, and process improvements that increase efficiency, effectiveness, and scalability. Establish clear standards and ways of working that strengthen execution and operational excellence across T&S.
• Govern strategic portfolio planning by developing and maintaining integrated T&S roadmaps and partnering with Technology, Product, Strategy, Finance, and business teams to support unified prioritization, business reviews, AOP and LRP, investment and resource planning, and other program-level planning activities.
• Drive execution and accountability by providing updates on status, milestones, owners, dependencies, and measures of success. Coordinate the tech portfolio and launch calendar with Product and Technology, proactively resolving or escalating risks when there are barriers to execution.
• Lead operational readiness and change management by leading project management, operational readiness, and strategic planning resources and coordinating implementation, testing, stakeholder alignment, communications, training, launch readiness, and post-launch measurement for transformation initiatives and process changes.
• Manage program performance and leadership mechanisms through content aggregation, KPIs, scorecards, portfolio reviews, strategic planning forums, executive reporting, and other business reviews that provide visibility into transformation progress, operational impacts, risks, decisions, and execution health. Develop and aggregate decision-ready content and recommendations for executive level audiences.
• Lead high-priority special projects and rapid-response initiatives, including digital innovation, pilots, task forces, and cross-functional working groups. Manage resources, budgets, timelines, and outcomes and develop recommendations based on results.

Qualifications

• 8+ years of experience in operations, business transformation, strategy, portfolio or program management, operational readiness, or related fields.
• 3+ years of experience leading teams or complex cross-functional programs.
• Demonstrated experience translating strategic vision into transformation roadmaps, executable plans, and measurable outcomes.
• Experience leading strategic and portfolio planning, prioritization, governance, resource planning, and complex cross-functional execution.
• Experience leading operational readiness, change management, and large-scale implementation across business and technical teams.
• Strong business and operational judgment with the ability to evaluate priorities, dependencies, risks, tradeoffs, and performance.
• Experience developing KPIs, scorecards, executive content, business reviews, and other operating and decision mechanisms.
• Strong analytical, communication, and influence skills with the ability to drive alignment and accountability across senior stakeholders.

Preferred Qualifications

• Experience in last-mile delivery, gig economy platforms, marketplaces, logistics, eCommerce, or other high-volume operations.
• Experience supporting Trust & Safety, risk, compliance, fraud, safety, or other risk-sensitive functions.
• Experience leading large-scale operational or technology-enabled transformation.
• Experience enabling new business models, geographic expansion, or significant organizational change.