Role Overview We are seeking a seasoned Azure Cloud Migration Strategist to lead the development of a portfolio-level migration roadmap and execution planning for a large-scale enterprise cloud transformation initiative. The ideal candidate will bring deep experience in cloud migration planning, application portfolio analysis, and Azure architecture, and will serve as a strategic advisor across business and technical stakeholders. This role focuses on both strategic planning (roadmap development) and tactical readiness and migration design for a targeted set of applications, guiding the transition from legacy hosting models to Azure-based infrastructure. Key Responsibilities Portfolio-Level Migration Roadmap Development - Analyze portfolio metadata (e.g., application groupings, business criticality, system complexity) to define migration - Run discovery tooling to inventory applications, databases, hosts, and dependencies. - Define a prioritization and sequencing framework to align with business goals and product groupings. - Conduct stakeholder workshops to shape migration strategy and sequencing. - Estimate ROM-level migration effort and cost using reference workloads and SME input. - Deliver a comprehensive Directional Migration Roadmap, including: - Migration Timeline - Cost Estimates Strategic Planning Considerations (readiness gaps, tooling dependencies, risks) Learn & Plan Execution - Confirm application list and validate architectural, operational, and SLA requirements. - Lead deep discovery and application profiling using tools such as Azure Migrate Appliance and Azure Monitor. - Develop application-level metrics for performance, storage, and compliance constraints. - Validate Landing Zone readiness for workloads and identify blockers. - Define migration strategies (e.g., rehost, replatform) and document technical migration plans. - Produce Azure resource sizing and cost estimates per application. - Deliver a detailed Migration Plan, including: - Application Profiles and Risk Logs - Roles & Responsibilities Matrix - Migration Schedule and Cutover Strategy Risk Mitigation and Compliance Considerations - Required Skills & Experience - 7+ years of experience in cloud strategy, enterprise IT transformation, or large-scale migration initiatives. - Proven experience in leading Azure cloud migrations from roadmap through execution. - Expertise in using tools such as Azure Migrate, Azure Monitor, TCO Calculator, Azure Cost Management, and Microsoft FastTrack templates. - Strong understanding of Microsoft Azure’s Well-Architected Framework, Landing Zones, and cloud governance. - Experience managing stakeholder working sessions, prioritization frameworks, and executive reporting. - Ability to analyze complex environments and produce sequencing plans, effort models, and migration frameworks. Strong communication and documentation skills for both technical and executive audiences. Preferred Qualifications - Azure certifications (e.g., AZ-305, AZ-700, AZ-900) - Familiarity with regulated environments (e.g., compliance, data sovereignty) - Experience with migration accelerators like Microsoft CAF, Ready Framework, or partner methodologies Experience with integration models, legacy modernization, and hybrid scenarios What You’ll Deliver - Strategic Directional Migration Roadmap for a 70+ application portfolio - Learn & Plan Deliverables supporting confident execution - Business-aligned sequencing and resourcing recommendations - Thought leadership in aligning enterprise goals with cloud transformation paths