From Legacy to Modern, Without Breaking What Works

Your legacy system works—it runs your business. But it’s also holding you back: difficult to update, expensive to maintain, hard to hire for, slow to scale. You need modernization, but you can’t afford disruption.

I specialize in pragmatic modernization that protects your business while unlocking new capabilities.

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Recent Innovation: AI-Augmented Modernization

Traditional Approach: Manual analysis, slow refactoring, months of work before seeing results.

Modern Approach: AI-assisted code analysis, automated refactoring suggestions, accelerated delivery.

I’ve achieved 2-3x development velocity through mastery of agentic coding tools:

• Claude Code — Primary tool for code generation and refactoring
• GitHub Copilot — multi-model code development and review
• Warp, Kiro, Antigravity — Specification-driven development (SDD) workflows
• Context Engineering — Structured patterns that make AI tools genuinely useful

This isn’t just faster coding—it’s systematic modernization with AI as a force multiplier.

Example: Refactoring that traditionally took 4 weeks can now be completed in 1-2 weeks with higher quality through:

• Automated code analysis identifying patterns and smells
• AI-suggested refactoring approaches with pros/cons
• Accelerated test coverage generation
• Documentation that updates alongside code

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Service Offerings

1. Legacy System Assessment & Modernization Roadmap

Situation: You have a critical legacy system that is becoming a bottleneck, but you don’t know where to start.

Our Solution: Comprehensive assessment of your existing systems, code, and infrastructure. We identify key pain points, risks, and opportunities.

We Analyze:

• Code Quality — Technical debt, maintainability, test coverage
• Architecture — Monolith characteristics, coupling, boundaries
• Technology Stack — Currency, support status, hiring challenges
• Performance — Bottlenecks, scaling limitations
• Security — Vulnerabilities, compliance gaps
• Team Capability — Skill gaps, knowledge concentration risks
• Business Impact — Where legacy limits business agility

Deliverable: Detailed modernization roadmap with:

• Clear, actionable steps prioritized by impact and risk
• Timeline and budget estimates for each phase
• Multiple paths (big bang vs. incremental)
• Risk mitigation strategies
• Success metrics and measurement plan

Timeline: 2-4 weeks for assessment and roadmap development

Modern Advantage: AI-assisted code analysis can scan codebases 10-100x faster than manual review, identifying patterns human reviewers might miss.

2. Cloud Migration (AWS)

Situation: You want to move your on-premise infrastructure to the cloud to improve scalability, reliability, and cost-efficiency.

Our Solution: Plan and execute seamless migrations to Amazon Web Services (AWS) with proven zero-downtime strategies.

Migration Strategies:

• Lift and Shift — Minimal changes, fast migration, reduce data center costs
• Lift and Refactor — Optimize during migration for cloud-native benefits
• Hybrid Approach — Phased migration with gradual modernization
• Parallel Run — Validate in cloud before cutting over

We Handle:

• Infrastructure provisioning (EC2, RDS, VPC, networking)
• Data migration with validation
• Network configuration and security
• Monitoring and observability setup
• Disaster recovery and backup strategies
• Documentation and team training

Proven Track Record:

• Zero-downtime AWS migration for ShareASale platform
• $1B+ annual transaction volume migrated without customer impact
• 24-minute disaster recovery demonstrated post-migration
• 25% cost reduction through architecture optimization

3. Monolith to Microservices Decomposition

Situation: Your monolithic application is difficult to maintain, scale, and update. You want to move to a more agile and scalable microservices architecture.

Our Solution: Strategic decomposition using domain-driven design (DDD) principles to identify service boundaries and create loosely coupled architecture.

Our Approach:

• Domain Analysis — Identify bounded contexts and service boundaries
• Strangler Fig Pattern — Gradually extract services without rewriting everything
• API Design — Create clear contracts between services
• Data Strategy — Handle data ownership and eventual consistency
• Testing Strategy — Contract testing, integration testing, chaos engineering
• Deployment Automation — CI/CD for multiple services

We Avoid:

• “Big bang” rewrites that fail 80% of the time
• Premature decomposition before understanding domains
• Distributed monoliths (microservices in name only)
• Data integrity nightmares from poor design

When NOT to Use Microservices:

• Early-stage products (premature optimization)
• Small teams (<10 engineers)
• Simple domains without clear boundaries
• When operational complexity outweighs benefits

AI Advantage: Use agentic coding tools to:

• Identify coupling patterns and service boundaries faster
• Generate API contracts and OpenAPI specifications
• Create test suites for new service interfaces
• Refactor duplicated code across services

4. Technology Stack Upgrade & Refactoring

Situation: Your application is built on an outdated or unsupported technology stack (ColdFusion, legacy .NET, older Java, PHP 5.x).

Our Solution: Refactor codebase and upgrade to modern, high-performance technology stack with minimal business disruption.

Technology Transitions:

• ColdFusion → Node.js/Python/Go — Modern languages with strong ecosystems
• Legacy .NET Framework → .NET Core/Modern .NET — Cross-platform, cloud-ready
• Older Java → Modern Java/Kotlin — Language improvements, better frameworks
• Monolithic Frontend → React/Vue/Svelte — Component-based, maintainable UIs
• Legacy Databases → Modern SQL/NoSQL — Better performance, scaling, features

Our Process:

• Incremental Migration — Small, frequent changes rather than big bang
• Test-Driven Refactoring — Ensure behavior doesn’t break
• Feature Parity First — Match existing functionality before adding new
• Parallel Operation — Run old and new side-by-side during transition
• Rollback Plans — Always have an escape hatch

Quality Focus:

• Modern testing practices (unit, integration, E2E)
• Code review culture establishment
• Documentation as code
• CI/CD automation
• Performance benchmarking

AI-Augmented Refactoring:

• 4-6x acceleration of refactoring through AI assistance
• Automated test generation for legacy code
• Pattern detection and modernization suggestions
• Documentation generation from code analysis

5. AI Integration into Legacy Systems

Situation: You want to add AI capabilities to your existing system but don’t want to rewrite everything.

Our Solution: Surgical integration of AI features without architectural upheaval.

Integration Patterns:

• API Gateway — AI services behind RESTful APIs
• Event-Driven — AI processing triggered by domain events
• Sidecar Pattern — AI capabilities alongside existing services
• Gradual Rollout — Feature flags for controlled deployment

AI Features for Legacy Systems:

• Semantic search over existing documents/data
• Natural language interfaces to complex workflows
• Intelligent automation of repetitive tasks
• Predictive analytics for business decisions
• Chatbots for customer support

Recent Portfolio Work:

• Built production RAG systems integrating knowledge bases
• Implemented streaming AI responses in modern UIs
• Created evaluation frameworks for quality measurement
• Deployed across multiple platforms (Vercel, Cloudflare Workers)

Why This Matters: Add AI value without modernizing everything. Demonstrate ROI before larger investments.

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Why Choose Me?

25+ Years of Experience

I’ve been doing this since the browser wars:

• Modernized systems written in ColdFusion, classic ASP, PHP 4
• Migrated monoliths to microservices (when appropriate)
• Led cloud migrations protecting billions in transactions
• Refactored codebases with decades of technical debt

Proven Track Record

ShareASale Platform (17+ Years):

• Zero-downtime cloud migration
• Monolith-to-microservices decomposition
• Multi-year platform consolidation (4 acquired companies)
• Legacy ColdFusion → Node.js/C# modernization
• 99.95%+ uptime maintained throughout transformations

Pragmatic & Business-Focused

I understand that technology is a means to an end:

• Don’t modernize for modernization’s sake — Focus on business value
• Incremental beats big bang — Deliver value continuously, reduce risk
• Protect the business — Zero downtime isn’t negotiable
• Transfer knowledge — Your team needs to maintain it, not depend on me forever

Crisis-Tested

I stay calm when things go wrong:

• Catastrophic data center failures
• Production incidents during migrations
• Unexpected technical debt discovery mid-project
• Stakeholder conflicts requiring negotiation

Modern Development Practices

Current with contemporary approaches:

• Agentic Coding — 2-3x velocity through AI tool mastery
• Infrastructure as Code — Terraform, Ansible, GitOps
• DevSecOps — Security built in, not bolted on
• Observability — DataDog, CloudWatch, custom metrics
• AI Integration — Production RAG systems, LLM APIs

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Technical Capabilities

Legacy Technologies (Modernization From)

Languages:

• ColdFusion/CFML (25+ years expertise)
• Classic ASP, VBScript
• PHP 4.x/5.x
• Legacy Java (pre-8)
• .NET Framework (pre-.NET Core)

Frameworks:

• Legacy Hibernate, Spring
• Classic ASP.NET Web Forms
• jQuery-based monolithic frontends

Databases:

• SQL Server (all versions, expert level)
• MySQL (legacy versions)
• Access databases (!), FoxPro
• Flat files and legacy data formats

Modern Technologies (Modernization To)

Languages:

• JavaScript/TypeScript (Node.js, modern frameworks)
• Python (FastAPI, Django, data processing)
• C# (.NET Core, modern .NET)
• Go (when appropriate)

Frameworks:

• React, Next.js (modern frontends)
• Express, Fastify (Node.js backends)
• .NET Core Web APIs
• FastAPI (Python)

Cloud & Infrastructure:

• AWS (EC2, ECS, Lambda, RDS, S3, CloudWatch)
• Cloudflare (Workers, edge computing)
• Docker, containers
• Terraform, Infrastructure as Code
• CI/CD (GitLab, GitHub Actions)

Databases:

• PostgreSQL (including pgvector for AI)
• SQL Server (modern versions)
• DynamoDB, DocumentDB (NoSQL)
• Redis (caching)

AI/ML:

• LLM integration (OpenAI, Anthropic)
• Vector databases and embeddings
• RAG architectures
• AI evaluation frameworks

Development Tools & Practices

• Version Control: Git, GitLab, GitHub
• Agentic Coding: Claude Code, GitHub Copilot, Kiro
• Testing: Jest, Pytest, MSTest, E2E frameworks
• Observability: DataDog, CloudWatch, Prometheus/Grafana
• Documentation: Markdown, OpenAPI/Swagger, architecture diagrams

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Engagement Models

1. Assessment & Roadmap (Fixed Scope)

Duration: 2-4 weeks
Deliverable: Comprehensive modernization roadmap

Includes:

• Legacy system analysis (code, architecture, infrastructure)
• Technical debt quantification
• Risk assessment
• Prioritized modernization plan
• Budget and timeline estimates
• ROI analysis

Pricing: $8,000 - $20,000 depending on system complexity

Follow-on: Implementation support available

2. Cloud Migration (Project-Based)

Duration: 3-9 months typically
Deliverable: Production system running in cloud

Includes:

• Migration strategy and planning
• Infrastructure setup and configuration
• Data migration with validation
• Zero-downtime cutover execution
• Post-migration optimization
• Team training and documentation

Pricing: $30,000 - $150,000 depending on scope and complexity

3. Modernization (Ongoing Engagement)

Duration: 6-18 months
Time Commitment: Part-time or full-time depending on scope

Services:

• Incremental refactoring and modernization
• Architecture evolution
• Team mentoring and knowledge transfer
• Quality improvement (testing, observability)
• Performance optimization

Pricing: $10,000 - $25,000/month depending on time commitment

4. Consulting / Advisory

Duration: 1-3 months
Time Commitment: 5-10 hours/week

Services:

• Technology evaluation and recommendations
• Architecture review
• Migration strategy consulting
• Team coaching on modern practices
• AI integration planning

Pricing: $3,000 - $5,000/month

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Ideal Client Profile

You’re a good fit if:

• You have critical legacy systems that need modernization
• Business continuity is non-negotiable (no tolerance for extended downtime)
• You value incremental progress over big bang rewrites
• You want knowledge transfer to your team, not permanent dependency
• You’re open to AI-augmented development for faster delivery

You might not be a good fit if:

• You want to rewrite everything from scratch (rarely the right answer)
• Downtime is acceptable to save costs (I optimize for reliability)
• Your legacy system is <5 years old (probably not “legacy”)
• You need domain-specific expertise I don’t have (embedded systems, hardware)

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Risk Mitigation Strategies

Modernization projects are high-risk. Here’s how we reduce that risk:

Technical Risk

• Incremental migration — Small, frequent changes vs. big bang
• Parallel operation — Old and new systems running simultaneously
• Automated rollback — Quick escape hatch if issues arise
• Comprehensive testing — Automated tests for regression prevention
• Feature parity validation — Ensure new matches old before cutover

Business Risk

• Zero-downtime requirements — Architecture designed for no customer impact
• Revenue protection — Migration during low-traffic periods
• Stakeholder communication — Regular updates, manage expectations
• Phased rollout — Control blast radius of changes
• Success metrics — Clear definition of “done” before starting

Team Risk

• Knowledge transfer — Document everything, train as we go
• Pair programming — Work alongside your team
• Code reviews — Teach best practices through feedback
• Gradual handoff — Reduce dependency over time
• Post-launch support — Available after completion

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Case Studies (Brief)

Zero-Downtime AWS Migration

Challenge: Migrate ShareASale platform to AWS without impacting $150M+ in annual partner commission volume.

Solution: Parallel run strategy with safe cut over, extensive observability, automated rollback capability.

Results:

• Zero customer-facing downtime
• 25% cost reduction through optimization
• 24-minute disaster recovery capability demonstrated
• Improved scalability and reliability

Platform Consolidation (Post-Acquisition)

Challenge: Map and bridge the expansive ShareASale feature set onto Awin and migrate customers for a unified architecture and user experience.

Solution: Multi-year incremental migration protecting revenue while consolidating infrastructure.

Results:

• Migrated 260k users with 85% terms acceptance on 1st login
• 99.5% revenue protection during consolidation
• Zero merchant-facing downtime across critical migrations
• Successful team integration across US, UK, Germany
• Significant cost savings through infrastructure consolidation

ColdFusion to Node.js Migration

Challenge: Modernize 15-year-old ColdFusion monolith running critical transaction processing.

Solution: Strangler fig pattern extracting services incrementally, comprehensive testing, parallel operation.

Results:

• Gradual migration without customer disruption
• Improved performance and reliability
• Easier hiring (Node.js vs. ColdFusion)
• Foundation for future microservices

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Get Started

Ready to modernize without disrupting your business? Let’s assess your options.

Contact: Get in Touch · LinkedIn

Portfolio:

• 25+ years modernizing legacy systems
• Zero-downtime cloud migrations
• Platform consolidations protecting billions in revenue
• Modern Development Examples (recent work)

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Note: I’m also open to full-time roles focused on platform modernization or technical leadership for the right opportunity.

Last Updated: December 2025