Christopher J. Woods
AI-Accelerated Engineering Leader
Professional Summary
Engineering leader who accelerates complex systems delivery by combining 30 years of infrastructure expertise with cutting-edge AI and machine learning development practices. Proven track record of identifying technology inflection points early—from pioneering Internet infrastructure (1993) to cloud migration leadership to current MLOps and AI-augmented development adoption—and delivering outcomes 40%+ faster than traditional approaches. Expert in Amazon Web Services (AWS), Infrastructure as Code, and leveraging AI tools (GitHub Copilot, Claude Code, Ollama) to transform enterprise-scale projects.
Core Technical Expertise
MLOps & AI Tools
AI-Augmented Development, GitHub Copilot, Claude Code, Cursor / Windsurf, OpenAI Codex, Ollama, Local LLM Deployment
Cloud & Infrastructure
AWS (Lambda, DynamoDB, API Gateway, S3, RDS, EC2), Infrastructure as Code (CloudFormation, AWS CDK), Docker & Kubernetes, Serverless Architecture, Cloud Migration, Cloud-Native Design
DevOps & Automation
CI/CD (Jenkins, Bamboo, GitHub Actions, GitLab CI), Git & Version Control, Automated Testing & Deployment, Infrastructure Automation, Monitoring & Observability
Programming Languages
Python, Java, JavaScript/TypeScript/NodeJS, Go, Rust
Data & Databases
SQL & Database Design, PostgreSQL, SQL Server, MySQL, Oracle
Enterprise Architecture
Microservices, REST/GraphQL APIs, Distributed Systems, Event-Driven Architecture, Enterprise Integration
Professional Experience
Principal Software Engineer & Technical Lead
Liberty Mutual Insurance
- Leading $8M+ enterprise cloud migration of 1M+ LOC underwriting system with 1TB+ data volume, 8-node WebSphere cluster, and 3,000+ stored procedures from Sybase to SQL Server—on track for Q2 2026 production cutover
- Deployed AI development tools (GitHub Copilot, Claude Code, Ollama) across 9-person engineering team, achieving 40%+ productivity gains in code generation, reducing code review time by 35%, and accelerating sprint velocity by 25%
- Mentored 5 engineers in AI-augmented development practices, resulting in team-wide adoption within 3 months and measurable improvements in code quality metrics
- Architected Infrastructure as Code solutions using CloudFormation for complex enterprise integrations (WebSphere MQ, SOAP/REST services), reducing deployment errors by 60% and enabling rollback capabilities
- Built AI-assisted automation workflows that reduced routine development tasks by 30%, freeing engineering capacity for high-value feature development
Solutions Engineer
Liberty Mutual Insurance
- Technology strategist for Global Risk Solutions ($4B+ portfolio), designed multi-year technical roadmap for modernizing 25+ legacy systems across 9 solution delivery teams, prioritizing $15M+ in technology investments
- Led assessment and planning for 6 enterprise-scale cloud migrations, identifying $2M+ in annual infrastructure cost savings and reducing technical debt by 30% over 18 months
- Developed automation frameworks for effort estimation and technical risk assessment, improving delivery predictability by 45% and reducing project overruns
- Partnered with C-suite executives to translate complex technical requirements into business-aligned delivery strategies, accelerating decision-making by 40%
Principal Software Engineer - Cloud Architecture
Liberty Mutual Insurance
- Architected serverless AI applications on AWS serving 100K+ monthly customer interactions with 99.97% uptime, using Lambda, DynamoDB, API Gateway, Amazon Connect, and Lex—handling 3M+ conversations annually
- Launched mobile auto claims application integrating computer vision ML APIs for automated damage assessment from customer photos—reduced claim processing time while demonstrating that production AI adoption is primarily about intelligent API integration rather than model training
- Implemented production CI/CD pipelines using Infrastructure as Code (CloudFormation, AWS CDK) with automated testing, reducing deployment failures by 75% and enabling 3x more frequent releases
- Built enterprise data integration layer connecting AI applications with real-time customer data via REST APIs, processing 500K+ API calls daily with <100ms latency
- Established security and compliance frameworks for AI applications handling PII and sensitive data, achieving SOC 2 Type II compliance and zero security incidents over 2 years
- Led migration from manual deployments to fully automated Infrastructure as Code, reducing deployment time from 4 hours to 30 minutes (80% reduction) and eliminating configuration drift
Senior Software Developer & DevOps Lead
Liberty Mutual Insurance
- Designed and implemented microservices architecture for customer-facing applications using React, GraphQL, and containerized backends
- Built automated deployment pipelines for AngularJS applications and REST services supporting nationwide agent networks
- Developed proof-of-concept ML data pipeline for automated claims processing using AWS Lambda and computer vision APIs
- Established development team standards for code quality, testing, and deployment automation
Enterprise Systems Engineer
Liberty Mutual Insurance
- Led complex enterprise integrations supporting 3,500+ users using IBM WebSphere, Oracle, and messaging middleware
- Designed scalable architectures for mission-critical applications handling millions of transactions
- Implemented monitoring and observability solutions for production systems using enterprise tooling
Earlier Experience Highlights
Senior Systems Administrator & Software Engineer | Liberty Mutual Insurance | 2005-2008
Enterprise application development and infrastructure automation for insurance platforms. Early adoption of virtualization and automated provisioning, laying foundation for future cloud migration expertise.
Technology Consultant | Independent | 1999-2006
Custom software development and enterprise architecture for Fortune 500 clients including CVS Pharmacy, Sun Microsystems, and Harvard Business School. Recognized early potential of service-oriented architectures and web services, advising clients on technology strategy during the dot-com era.
Internet Infrastructure Pioneer | USAInternet, TIAC, Paladin Computing | 1993-1997
Principal technologist for early Internet service providers during the web's critical adoption period. Designed dialup access systems, built web-based GIS platforms, and deployed foundational internet infrastructure. Recognized the transformative potential of internet technologies before mainstream adoption—same pattern recognition ability I apply to today's AI revolution.
Certifications & Continuous Learning
- AWS Certified Cloud Practitioner (2019)
- AWS Certified Solutions Architect Associate (2020)
- Active in AI/ML Community: Regular user of latest LLM APIs, local model deployment (Ollama, llama.cpp), and emerging AI development tools
- Sun Microsystems Java Certification (1997)
Key Achievements
- Successfully deployed AI development tools across multiple engineering teams, achieving 40%+ productivity improvements and establishing best practices for AI-augmented workflows that are now org-wide standards
- Led three enterprise cloud migrations involving terabyte-scale databases, complex data transformations, and zero-downtime cutovers—delivering projects under budget while handling 500M+ transactions during migration windows
- Designed Infrastructure as Code solutions that reduced manual deployment overhead by 80%, eliminated configuration drift, and enabled teams to ship 3x more frequently with higher reliability
- Mentored 15+ engineers throughout career in cloud technologies, automation practices, and AI tools—with 90% promotion rate and several mentees now in senior technical leadership roles
- Maintained 99.9%+ uptime for production systems supporting millions of customers, processing billions in annual revenue, through proactive monitoring and rapid incident response
Technical Projects of Interest
Custom AI Development Pipeline
Built automated code review and documentation generation using Claude API and custom MCP servers
Enterprise LLM Integration
Implemented secure, compliant LLM workflows for internal development team productivity
Cloud Migration Automation
Developed Infrastructure as Code templates and automated testing frameworks for complex enterprise migrations