Executive TPM - Cloud Cutover & Readiness Lead

The Judge Group; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job description

A leading financial services organization is seeking an experienced Executive Technical Program Manager to lead the final production cutover from a legacy clearing platform to a new cloud-based environment.

This is a high-impact leadership role responsible for planning and executing a complex enterprise migration, ensuring all production, infrastructure, data, resiliency, and operational readiness activities are successfully completed before go-live. We're looking for a hands-on leader who can build detailed cutover plans, lead command center activities, manage risk, and provide executives with confidence that the transition is fully tested and ready.

Key Responsibilities

• Own the end-to-end cutover strategy, governance model, execution plan, and command center operations.
• Lead production data migration, reconciliation, validation, and readiness activities.
• Coordinate infrastructure, application, networking, security, monitoring, and operational transitions.
• Develop detailed runbooks, go/no-go criteria, rollback plans, and contingency procedures.
• Lead cutover rehearsals, mock conversions, disaster recovery testing, and operational readiness assessments.
• Manage risks, dependencies, executive reporting, and decision-making throughout the migration.
• Drive post-go-live stabilization, hypercare, incident management, and transition to steady-state operations.

Required Qualifications

• 15+ years of experience in technical program management, infrastructure, cloud transformation, release management, or enterprise modernization.
• Proven success leading large-scale production cutovers, cloud migrations, platform replacements, or mission-critical go-live events.
• Deep understanding of cloud infrastructure, distributed systems, databases, networking, middleware, security, monitoring, and disaster recovery.
• Strong experience with data migration, production validation, reconciliation, rollback, failover, and resiliency planning.
• Advanced Jira and integrated program management experience.
• Exceptional executive communication and stakeholder management skills within highly regulated environments.

Preferred Experience

• Financial services, capital markets, clearing & settlement, payments, banking, or exchange platforms.
• Cloud-native technologies including Kubernetes, Kafka, CI/CD, backup and recovery, and multi-region architectures.
• Experience presenting readiness recommendations to executives, regulators, audit committees, or board-level stakeholders.