I led the cloud strategy and business case engagement for a $4B specialty insurance holding company planning a full datacenter exit across the US and UK. The scope covered 226 applications running on 1,100+ servers, with a dual cloud evaluation against AWS and Azure. I built the complete financial model, facilitated discovery and Value Stream Mapping workshops, and delivered the 6Rs classification of the full application portfolio — including 16 SOX-regulated apps requiring sequenced migration planning.
The engagement concluded with a recommendation for AWS as the primary platform based on total cost of ownership, ecosystem fit, and available incentives. I structured the business case around ~$14M in 5-year savings with a 12-month payback period, unlocked ~$2M in AWS MAP credits, and drove the engagement through to SOW signature for Phase 2 migration execution.
Discovery & Inventory
Used Flexera One to extract server inventory, application dependencies, and utilization data across US and UK environments — forming the basis for rightsizing and TCO modeling.
Dual Cloud TCO Model
Built a detailed financial model comparing AWS and Azure across 3-year and 5-year horizons, including compute rightsizing, reserved instance pricing, licensing adjustments, and migration costs.
Value Stream Mapping
Facilitated VSM workshops with business and IT stakeholders to map current-state delivery processes, identify cloud readiness blockers, and define future-state capability targets.
Application Classification
Led the 6Rs classification of all 226 apps — assigning Rehost, Replatform, Refactor, Repurchase, Retire, or Retain disposition with SOX sequencing constraints applied.
16 SOX-regulated applications sequenced as the first migration wave to ensure compliance controls were established before dependent workloads migrated.
| Evaluation Dimension | AWS | Azure |
|---|---|---|
| 5-Year TCO | Lower — ~$14M savings vs. on-prem | Higher — Azure licensing premiums for Windows stack |
| Migration Credits | ~$2M MAP credit package structured | Limited ACE credit commitment at evaluation stage |
| Ecosystem Fit | Strong for insurance workloads; mature data lake capabilities | Strong Azure Active Directory alignment (existing M365 tenant) |
| Windows Workloads | Supported via BYOL and Windows AMIs | Native licensing integration; Azure Hybrid Benefit |
| Managed DB Services | RDS, Aurora — mature managed SQL and NoSQL options | Azure SQL MI — strong but higher licensing overhead |
| Compliance (SOX) | Extensive SOX-specific reference architectures | Comparable; requires additional configuration |
| Recommendation | Primary platform — AWS recommended | Secondary / hybrid option for M365-adjacent workloads |
Foundation & SOX Applications
AWS account structure, network foundation, and security baselines. Migrate the 16 SOX-regulated applications first to establish compliance controls for all subsequent waves.
Core Business Applications
Rehost and replatform migrations for core insurance operations, underwriting, and claims systems. Target 100+ apps across this wave with active workload validation at each stage.
Complex Workloads & DC Exit
Refactor candidates, legacy integrations, and the final UK datacenter exit. SaaS substitutions complete. On-premises retained systems confirmed with appropriate connectivity in place.
Current State — Key Findings
- Manual server provisioning lead time: 6–8 weeks via ITSM ticket workflows
- No self-service capability for infrastructure — all requests routed through central IT
- Release cycles averaging 3–4 months due to shared environment constraints
- Limited observability — reactive incident management, no proactive monitoring
- Duplicate toolchains across US and UK teams with no shared standards
Future State — Cloud Enablement Targets
- Infrastructure-as-Code provisioning reducing lead time from weeks to hours
- Developer self-service through AWS Service Catalog with guardrails
- CI/CD pipeline standardization enabling monthly or more frequent releases
- Unified observability stack: CloudWatch + centralized log aggregation
- Cloud Center of Excellence (CCoE) to govern multi-team cloud adoption
Financial Modeling
Built the complete dual-cloud TCO model: server rightsizing, reserved instance pricing, licensing adjustments, migration costs, and 3/5-year NPV comparisons for AWS and Azure.
AWS MAP Credit Negotiation
Structured the MAP credit application, qualifying ~$2M in incentives by mapping the migration scope to AWS program eligibility requirements and aligning the timeline with program gates.
App Portfolio Classification
Led the 6Rs classification of all 226 applications — combining Flexera data, stakeholder interviews, and dependency mapping to produce a migration-ready disposition for each app.
VSM Facilitation
Facilitated Value Stream Mapping workshops with IT and business stakeholders — translating current-state pain points into cloud readiness blockers and future-state capability requirements.
SOX Migration Sequencing
Identified the 16 SOX-regulated applications and designed a compliance-first Wave 1 migration sequence, ensuring internal controls and audit trails were validated before dependent workloads moved.
SOW Closure & Handoff
Drove the engagement from assessment to commercial closure — aligned on Phase 2 scope, pricing, and timeline with stakeholders on both sides, resulting in a signed Phase 2 SOW.
| Deliverable | Description | Format |
|---|---|---|
| Cloud Business Case | Dual-cloud TCO model, NPV analysis, 5-year savings projection, and recommendation narrative | PPTX + XLSX |
| AWS vs. Azure Evaluation Matrix | Scored comparison across 12 dimensions including TCO, compliance, ecosystem fit, and credits | XLSX |
| Application Portfolio Disposition | 6Rs classification for all 226 apps with Flexera data, dependency mapping, and SOX flags | XLSX |
| Migration Wave Plan | 3-wave migration schedule with SOX Wave 1 sequencing, resource requirements, and milestones | PPTX + XLSX |
| Value Stream Maps | Current-state and future-state VSMs for IT provisioning, release management, and incident response | Visio + PPTX |
| AWS MAP Credit Package | MAP application documentation, eligible workload scoping, and credit milestone tracker | DOCX + XLSX |
| Cloud Readiness Assessment | Skills gap analysis, governance maturity, and organizational readiness findings | PPTX |
| Executive Summary Deck | C-suite readout: recommendation, financial rationale, risk register, and next steps | PPTX |
| Phase 2 SOW | Migration execution scope, pricing model, and timeline for Phase 2 delivery | DOCX |