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 two transformative decades
Led numerous digital transformation projects for fintech/banking/tax sectors
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, and many others. Built reputation as trusted enterprise architect.
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
Specialized expertise in FinTech, real estate, mortgage, and enterprise SaaS—industries where technology decisions have significant financial, regulatory, and operational consequences.
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.
"Artificial intelligence machine learning models can be very effective - you just have to take baby steps to engage this area."
"I’ve worked with Shawn in multiple engagements over the last fifteen years. Shawn has a trusted network of diverse talent and always operates with integrity -- highly recommended."
"Shawn is exceptionally gifted, and works within a trusted network of diverse talent -- highly recommended."
"Shawn works at an extremely high level and I trust his work implicitly within a trusted network of diverse talent -- highly recommended."
“LERETA envisioned revamping its flagship product offering, giving it a new look and feel... We had a very positive experience working directly with Shawn, with very tangible results.”
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“Shawn’s implementation teams are, without exception, the best designers and developers we’ve ever worked with.”
“Bringing Shawn Livermore in to help us refine our software applications was one of the best decisions we ever made as a company.”
“The consultants from Shawn Livermore were able to understand our industry well and design a great user experience as a result.”
Let's discuss your technology strategy
Ready to transform your organization's technology and AI capabilities.