Proven track record of technology leadership
For nearly 3 decades, I have brought strategic technology solutions to Fortune 500 companies across numerous industries.
I help growing and established companies navigate complex technology and AI transformations. I bring AI strategy and legacy modernization expertise within a fractional CTO model.
Nearly 3 decades of technology leadership
From Fortune 500 enterprise architecture to complex fintech startups, I've built a career solving complex technical challenges at scale. My approach combines strategic vision with hands-on execution—ensuring technology decisions deliver measurable business results.
Fortune 500 to Startups
Led transformations at LERETA, First American, Carvana, H&R Block, Pacificare, & 30 others.
Hands-On Technical Skills
Extremely technical, hands-on architect, developer, to mentor teams all the way from inception to execution.
Industry recognition and professional achievements
Hands-on developer and project management certifications; accelerator participation for growing startups
Technology leadership journey across nearly 3 decades
Carrying the AI and technology vision for organizations who need a fractional CTO or fractional CAIO.
2024 - 2026
Now leveraging AI and nearly 3 decades of senior level technology leadership experience to help businesses as a fractional CTO and fractional CAIO.
2020 - 2024
Sr. Enterprise Architect | LERETA
Led $20M modernization for 2nd largest US property tax processor ($18B annually). Managed 30+ developers across 2 flagship product rebuilds.
2017-2020
Principal Architect | Simpluris
Chief architect for class action settlement administration company. Full solution design, architecture, and team leadership.
2016-2017
Inventory Data Team Lead & Solutions Architect | Carvana
Architected vehicle inventory data systems processing for $2B valued company. Supported IPO process and partner integrations.
2011-2016
CEO & Founder | Ziptask
Built SaaS platform from $0 to $2M revenue. Raised 6 rounds of venture funding. Complete platform architecture and business development.
2009-2011
Chief Enterprise Architect | First American Title
Saved the client $120M through M&A technical due diligence. Led architecture for world's largest title insurance company with ~900 engineers and 770 applications.
2006-2009
Enterprise Architect | Oakwood Worldwide
Oversaw all IT architecture for 3,000-employee global organization. Integrated 80+ applications across multiple continents.
2000-2006
Solutions Architect | Multiple Fortune 500s
Led technology implementations for H&R Block, Kelley Blue Book, WellPoint, CompUSA, PacifiCare, Blue Shield of CA, and many others. Built reputation as trusted enterprise architect.
“Watching Shawn come alongside our team was awesome. He really carried the project forward.”
Full-spectrum technology leadership
From board-level strategy to hands-on architecture, and now including an emphasis on AI transformation & AI migrations, I bring hands-on technical expertise across the complete technology leadership spectrum.
Strategic Leadership
Executive-level technology guidance for boards, C-suite, and investors. From fractional CTO services to M&A due diligence, I provide the strategic clarity needed for confident technology decisions.
- Fractional CTO & CAIO Services
- Technology Strategy & Roadmapping
- M&A Technical Due Diligence
- Enterprise Architecture
- Team Building & Leadership
- Board-Level Technology Advisory
Technical Execution
Hands-on architecture and implementation across modern technology stacks. I don't just strategize—I design systems, review code, and guide teams through complex technical challenges.
- AI Strategy & Implementation
- Legacy System Modernization
- Cloud Migration (Azure, AWS) Software
- Architecture & Design
- Full-Stack Development
- Integration & API Design
Industry Expertise
Deep domain knowledge in high-stakes industries where technology complexity and regulatory requirements demand specialized experience and proven patterns.
- FinTech & Payment Processing
- Real Estate & Mortgage Technology
- Title Insurance Systems
- SaaS Platform Development
- E-commerce Architecture
- Regulatory Compliance (HIPAA, EDI)
AI Jumpstarts & Transformations
Structured approaches to architecture, project management, and delivery. I bring battle-tested frameworks that accelerate execution while reducing risk.
- Rapid AI pilots and AI prospectus docs
- Setting up AI models
- Background setup for AI LLM training/tuning
- LLM definition and investigative efforts
- Self-tuning training systems
- AI-first UX design mentoring and creation
Proven Methodologies
Structured approaches to architecture, project management, and delivery. I bring battle-tested frameworks that accelerate execution while reducing risk.
- Agile & Scrum Facilitation
- PMP Project Management
- DevOps & CI/CD
- Architecture Patterns (DDD, MVVM, SOA)
- Data Modeling & Database Design
- UX & Interface Design
Industry expertise
Organizations in mortgage, real estate, financial services, healthcare, logistics, and government often face legacy overload and modernization opportunity. If your environment looks like one or more of these, modernization work becomes a multiplier for business value.
Delivered secure, high-reliability software and system integrations for mission-critical operations.
Architected digital and data platforms for leaders like Carvana and Kelley Blue Book.
Modernized financial systems to enhance scalability, compliance, and operational transparency.
Led enterprise integration projects balancing modernization with strict regulatory compliance.
Built HIPAA-compliant platforms improving interoperability and patient data management.
Developed secure class action and claims administration systems for national legal firms.
Designed enterprise platforms optimizing data flow and coordination across global supply chains.
Rebuilt large-scale mortgage and property tax systems processing billions in transactions.
Delivered compliant data systems enhancing operational visibility and reporting accuracy.
Engineered modernization frameworks for top real estate and tax processing enterprises.
"Shawn is razor sharp and expert-level. Can't say enough good things about his work."
“Shawn Livermore understood the pharmaceutical industry well and built a beautiful, custom platform that integrated seamlessly with our vendors and partners.”
“Shawn Livermore was amazing. He was able to articulate a thoughtful vision for our technology platform and how that vision connected to our broader organizational strategy.”
Let's discuss your technology strategy
Ready to transform your organization's technology and AI capabilities.
