Roger Wyatt
Managing Partner & CTO · 40+ years
roger@wgaipartners.com · 910-297-0929 · linkedin.com/in/rogerwyatt
Executive Summary
Enterprise Software Engineering Executive and CTO with 40+ years of experience leading cross-functional engineering organizations of up to 200+ professionals to design, scale, and deploy cloud-native SaaS solutions. Proven track record of spearheading massive digital transformations, driving multi-billion-dollar revenue growth, and architecting critical systems for premier organizations including NASA and Capital One. Expert in microservices, event-driven architectures, and implementing cutting-edge AI automation frameworks to drastically reduce operating overhead and accelerate deployment cycles.
Areas of Expertise
Professional Experience
Duck Creek Technologies
2023 – 2026Director of Engineering
- Scale & Leadership: Directed an engineering organization of 75+ developers focused on implementing complex network architectures for core enterprise software products.
- SaaS Transformation: Built a specialized team of 18+ engineers to completely redesign legacy software applications into modern, true SaaS implementations utilizing Kubernetes, Kafka, Argo, Kargo, and MongoDB.
- Efficiency Metrics: Streamlined cross-functional workflows to accelerate customer environment provisioning timelines from 3 months down to 2 weeks.
- Performance Optimization: Achieved a 146X performance improvement in formal testing, slashing response latency from 14 seconds to 400 milliseconds while reducing projected operating costs by over $4MM annually.
- AI Innovation: Drove team integration of Claude Code to elevate engineering quality and spearheaded development of proprietary AI agents to replace legacy coding dependencies.
- CI/CD & Observability: Reduced system deployment windows from 2 weeks to 15 minutes while engineering comprehensive enterprise observability using Grafana dashboards and proactive health checks.
- Incident Response: Commanded incident engineering response for critical SEV1 events via data-driven troubleshooting and control variable testing, interfacing directly with Executive Leadership Teams (ELT) for top-tier global clients.
CarMax
2018 – 2022Director of Software Engineering
- Revenue Growth: Led a 50+ person team delivering 20+ core software products that directly yielded $3BN+ in revenue growth.
- Technical Roadmapping: Formulated the technical product strategy and architectural roadmaps for 10+ internal enterprise tools supporting a user base of 10,000+.
- Architectural Innovation: Engineered parameter-driven, runtime module-loading software architectures, resulting in an organization-wide 50%+ baseline performance lift and specific application gains exceeding 200%.
- Cross-Functional Alignment: Collaborated across 10+ cross-functional business units to identify, address, and capture over $100MN+ in previously unrealized opportunity costs.
- Core Tech Stack: Leveraged C#, MSSQL, NuGet, and Azure web services within an Agile development framework.
Data Globe Group
2017 – 2018Chief Technology Officer
- AI Strategy: Initiated the development and technical execution of an AI-driven financial services platform that generated $1BN+ in revenue.
- Scalable Infrastructure: Authored the engineering strategy and mobile/web roadmaps necessary to scale consumer applications to support 10MN+ active users.
- Organizational Design: Structured, scale-built, and managed an engineering department exceeding 200+ developers, managers, and architects.
- Capital Acquisition: Successfully pitched technical product capabilities to international investor syndicates, securing $10MN+ in early capital commitments.
- Global Enterprise Pitches: Architected and presented a $5BN+ ARR technical framework targeted at the African continent for business magnate Carlos Slim, and designed a $2MN ARR engineering solution for a key German enterprise client.
Capital One
2015 – 2017Senior Engineering Manager
- Executive Solutions: Led a 100+ person engineering group developing strategic, high-visibility software portfolios valued at $50MN for CEO Richard Fairbanks.
- Cost Containment: Architected high-performance systems that realized $30MN in immediate operational savings while driving a 12,000%+ increase in processing speed.
- Robotic Process Automation (RPA): Directed a dedicated 30-engineer RPA task force to implement intelligent automation workflows, securing $15MM in recurring annual savings.
- Talent Acquisition: Recruited, interviewed, onboarded, and mentored 30+ cross-functional engineers and technical leaders.
- Reliability Engineering: Evangelized cutting-edge distributed architectures to minimize system downtime, bolster data integrity, and guarantee platform reliability.
Insignia Technology Services, LLC
2015Deputy Program Manager
- Program Management: Supervised a $12M federal program and a 75-person team comprising managers, developers, QA analysts, and project managers to deliver Identity and Access Management (IAM) software solutions for the Veterans Administration.
- Strategic Staffing: Sourced and hired 40 niche technical experts, establishing a robust leadership pipeline by mentoring team leads to enhance delegation and project oversight.
- Stakeholder Relations: Interfaced directly with Senior Executive Service (SES) leaders within the Veterans Administration to harmonize development velocity with federal compliance priorities.
Anthem
2012 – 2015Technical Architect / Developer Lead
- Enterprise Architecture: Overhauled a massive web services infrastructure supporting 500+ secure endpoints across Medicare and Medicaid operations, securing a $1BN+ business segment.
- Telephony Automation: Designed and executed an automated Voice Response infrastructure capable of managing over 100M+ inbound customer interactions annually.
- Technical Mentorship: Institutionalized modern design principles and Gang of Four (GoF) software patterns across engineering squads to boost code maintainability.
NASA, Langley Research Center
2010 – 2012Software Development Manager
- Federal Project Control: Led the architectural modernization of a critical financial accounting ecosystem tracking $2BN+ in federal assets, directly supporting the presidential directive to phase out the Space Shuttle program.
- Process Engineering: Optimized fiscal year data rollover algorithms, generating $200K+ in direct engineering and operational savings.
- Legacy Modernization: Orchestrated the extraction, transformation, and migration of 2,000,000+ legacy mainframe records into a highly secure, web-based ecosystem.
Tynken Interactive, Inc.
2002 – 2012President
- Startup Operations: Founded and scaled a proprietary LAMP-stack web content management solution (CMS) company.
- Business Development: Negotiated and finalized over $1M in enterprise B2B software contracts.
- Product Lifecycle Management: Directed the end-to-end product roadmap and P&L, executing three core software upgrades that drove a 200% surge in active users.
Early Career
- — Corning Inc. — Software Development Manager (Nov 2000 – Jun 2002)
- — Visionair, Inc. — Integration Technical Director (Mar 1993 – Nov 2000)
- — Energy Services, Inc. / Carolina Software / Piedmont Software — Software Developer (1987 – 1993)
Education & Credentials
- — Clemson University — B.S. in Computer Science
- — Private Pilot License (FAA Third-Class Medical Certified)
Technical Proficiencies
- Cloud Platforms
- AWS, Azure, Google Cloud Platform (GCP)
- Core Systems & Architectures
- SaaS, IaaS, Enterprise Software Architecture, Microservices, Event-Driven Architecture, REST APIs, SOAP, SOA, IAM, RPA, CI/CD pipelines
- Orchestration & DevOps Tools
- Kubernetes, Kafka, Argo, Kargo, Grafana, Splunk, Git, Jenkins, TeamCity, SVN
- Languages
- C#, Java, JavaScript, Node.js, PHP, Ruby, C++, C, SQL
- Frameworks & Libraries
- Next.js, React, GraphQL, Angular, jQuery, ASP.NET
- Databases
- SQL Server (MSSQL), MongoDB, MySQL, Oracle, SQLite, XML
- AI & LLM Integration
- Claude Code, GitHub Copilot, Grok, ChatGPT, OpenCV, FreeTTS
Want this experience on your next modernization?
20 minutes. No pitch. Just questions.