Order Management Cutover Lead

We are seeking an experienced Operational Cutover Lead to support a large-scale Order Management System (OMS) migration. This role will lead the business and operational side of cutover, ensuring multiple teams, stakeholders, and workstreams remain aligned and prepared throughout the transition.

The ideal candidate has experience supporting large, complex, cross-functional system implementations or migrations and is comfortable coordinating multiple teams, managing dependencies and deadlines, providing regular updates to leadership, and driving operational readiness through launch.

This position will partner closely with a Technical Cutover Lead responsible for system, data, and infrastructure migration activities. Together, they will coordinate the end-to-end transition from legacy systems to the new OMS platform.

Key Responsibilities

• Lead the operational cutover plan for a large-scale OMS migration, coordinating activities across multiple business teams and workstreams.
• Partner with business and technical leaders to define activities, dependencies, sequencing, deadlines, and ownership.
• Work closely with the Technical Cutover Lead to align operational activities with system cutover timing, data migration, environment readiness, and go/no-go criteria.
• Keep cross-functional teams on track toward key milestones and proactively identify risks, gaps, and dependencies.
• Provide regular project status updates to leadership and business stakeholders, including progress, risks, decisions, and readiness.
• Translate technical migration activities into clear business impacts, requirements, and operational actions.
• Coordinate readiness across areas such as Customer Care, Fulfillment/Warehouse Operations, Store Operations, Finance/Payments, Digital, and Technology.
• Develop and maintain detailed cutover runbooks, operational plans, timelines, checkpoints, contingency plans, and escalation procedures.
• Coordinate and participate in mock cutovers and dress rehearsals, documenting gaps and driving remediation prior to launch.
• Serve as a key operational leader during the live cutover and command center.
• Facilitate communication between business stakeholders and technical teams during cutover execution.
• Coordinate post-launch stabilization and monitor operational impacts, including order flow, fulfillment, cancellations, and customer contacts.
• Lead operational post-mortem activities and document lessons learned following implementation.

Required Qualifications

• 5+ years of experience in program/project coordination, business analysis, operations, product, or a related function.
• Demonstrated experience supporting large-scale, cross-functional system implementations, migrations, transformations, or launches.
• Proven ability to coordinate multiple teams, stakeholders, workstreams, deadlines, and dependencies simultaneously.
• Experience providing project status, readiness updates, risks, and escalations to leadership and business stakeholders.
• Experience participating in or leading cutover activities for a significant system implementation or migration.
• Strong experience developing and managing runbooks, implementation plans, operational readiness plans, or launch playbooks.
• Ability to translate technical activities and dependencies into clear business impacts and actions.
• Strong risk identification, problem-solving, organization, and stakeholder management skills.
• Excellent communication skills with the ability to remain organized and decisive during high-pressure implementation activities.

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