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

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, 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, FinOps, 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 approvals, and regional compliance requirements.

Manage global resource planning and mobilization across onsite, offshore, and in-country teams, including role clarity, capacity, onboarding, knowledge transfer, SME availability, succession coverage, and productivity.

Own program financials, forecasting, commercial tracking, cloud and tool costs, vendor commitments, productivity benefits, change requests, and corrective actions for schedule, quality, or cost variance.

Establish transparent executive reporting through steering committees, program reviews, migration dashboards, decision logs, benefits tracking, quality metrics, and outcome-based status reporting.

Ensure controlled decommissioning of VMware infrastructure after migration acceptance, including dependency closure, data retention, asset and license updates, operational sign-off, and evidence required for audit and compliance.

Drive continuous improvement across the migration factory by standardizing reusable patterns, automation, playbooks, quality gates, lessons learned, and measurable delivery acceleration without compromising operational risk.