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, FinOps, and business workstreams. • 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. Roles & Responsibilities • 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,…