Program Manager - AI-Led Enterprise VMware Exit to AWS Cloud

Job Description
Must Have Technical/Functional Skills

• Bachelor's degree in Computer Science, Engineering, Information Systems, Business Administration, or a related field; advanced degree preferred.
• 15+ years of technology delivery experience, including 7+ years leading large enterprise infrastructure, data center exit, cloud migration, or modernization programs.
• Demonstrated experience managing multi-year, multi-region VMware or data center exit programs involving discovery, assessment, AWS foundation, migration waves, testing, cutover, stabilization, and decommissioning.
• Strong understanding of AWS cloud adoption, VMware environments, landing zones, migration factories, workload disposition, application dependency mapping, security, networking, resilience, and operations transition.
• Experience applying AI, automation, analytics, and agentic capabilities to accelerate discovery, assessment, wave planning, code and configuration analysis, testing, migration execution, cutover, and governance.
• Proven delivery experience in regulated industries; insurance or financial services experience preferred, with strong awareness of security, privacy, audit, compliance, and regional requirements.
• Strong experience in program financials, commercial management, resource mobilization, vendor coordination, executive governance, risk management, and customer engagement.
• PMP, PgMP, SAFe, Scrum, AWS, or equivalent program and cloud certification preferred.
• Expertise in program governance, integrated planning, migration wave management, critical-path control, dependency management, RAID, change control, release governance, and executive reporting.
• Working knowledge of VMware estate discovery, application and infrastructure assessment, workload disposition strategies, AWS landing zones, account and network foundations, data migration, and decommissioning.
• Understanding of AWS migration and modernization patterns including rehost, replatform, refactor, retire, retain, and repurchase, with the ability to govern disposition decisions and benefits realization.
• Ability to direct AI-led migration use cases while maintaining Human-in-the-Loop validation, traceability, quality controls, security review, and accountable SME decision-making.
• Ability to coordinate application, infrastructure, AWS foundation, network, security, data, automation/IaC, testing, release, change, compliance, operations, Fin Ops, and business work streams.
• Strong commercial and financial acumen, including forecasting, budget management, cloud consumption tracking, productivity commitments, contract obligations, and variance recovery.
• Excellent executive communication, stakeholder management, negotiation, conflict resolution, decision facilitation, and escalation leadership across global and regional teams.
• Own end-to-end delivery of an enterprise VMware/VMC exit to AWS Cloud, spanning mobilization, discovery, assessment, target-state planning, AWS foundation, migration waves, testing, cutover, stabilization, decommissioning, and transition to operations.
• Establish the integrated program roadmap, governance model, workstream structure, migration factory, milestones, regional plans, critical path, dependencies, acceptance criteria, benefits measures, and release readiness controls.
• Serve as the single point of accountability for program scope, schedule, budget, quality, staffing, risk s, issues, assumptions, decisions, dependencies, and customer commitments.
• Lead discovery and assessment governance to create a reliable inventory, validate application dependencies, define workload dispositions, prioritize migration waves, confirm business ownership, and establish executable cutover plans.
• Drive an AI-first delivery approach by identifying and governing appropriate uses of AI and automation across discovery, assessment, reverse engineering, migration planning, infrastructure-as- code, testing, evidence generation, cutover, and operational handover.
• Ensure AI-generated recommendations and automation outputs are reviewed by accountable architects and SMEs, with clear auditability, exception handling, security controls, and fallback procedures.
• Coordinate delivery across AWS foundation, application migration, infrastructure migration, networking, identity, security, compliance, data, automation/IaC, testing, change, release, Fin Ops, decommissioning, and cloud operations teams.
• Partner with customer executives, business and application owners, enterprise architecture, security, infrastructure, AWS stakeholders, vendors, and regional teams to resolve decisions and dependencies.
• Govern migration waves through readiness checkpoints covering application, infrastructure, landing zone, connectivity, data, security, testing, business validation, cutover, rollback, hypercare, and operational acceptance.
• Own RAID and critical-path management, including dependency escalation, scope volatility, environment readiness, third-party constraints, business blackout windows, performance risks, security…