Fractional CTO & CAIO services
Bridging strategic vision with technical execution through flexible, high-impact technology leadership.
Enterprise Modernization
Transform legacy systems into modern, scalable platforms. Nearly 3 decades of Fortune 500 tech leadership experience.
M & A Advisor
For investors evaluating acquisitions or startups scaling engineering teams. I provide the technical expertise needed to make informed decisions and build foundations for growth.
AI & Modernization Projects
Project based AI implementations or custom software modernization buildouts.
Architecting high-value outcomes
Driving innovation and scalability through enterprise architecture that supports rapid growth, investor confidence, and billion-dollar valuations.
Pre-IPO Technology Leadership
Architected vehicle data systems supporting a $225M IPO and $2B valuation for a disruptive auto e-commerce platform.
"Shawn does amazing work and I would most definitely work with him again."
Deliverables & Outcomes of the Fractional Approach
From strategy to execution, the fractional CTO / CAIO approach delivers tangible results.
- Technology strategy & roadmap
- Architecture governance
- Team org design & hiring plans
- Vendor evaluations
- Board-ready reports
- Aligned technology & business strategy
- Reduced technical debt & risk
- Faster, more confident decision-making
- Improved team performance
- Cost optimization
- AI strategy & use-case roadmap
- Pilot design & validation
- MLOps infrastructure guidance
- Model governance framework
- Team capability assessment
- Clear AI ROI & business value
- Reduced AI implementation risk
- Faster time-to-production
- Sustainable AI capabilities
- Competitive advantage
- Legacy assessment & analysis
- Modernization roadmap
- Migration strategy & architecture
- Risk mitigation plans
- Integration design
- Reduced operational costs
- Improved system performance
- Increased agility & scalability
- Lower maintenance burden
- Foundation for innovation
- Technical due diligence reports
- Code & architecture assessment
- Scaling roadmaps
- Fundraising tech materials
- Team hiring strategies
- Informed investment decisions
- Avoided costly mistakes
- Scalable engineering foundation
- Investor confidence
- Accelerated growth
Client success stories
Proven impact across enterprise modernization, M&A, and technology leadership. From $100M savings to $20M+ transformations—see the outcomes.
Enterprise modernization at scale
Led 30+ developers to rebuild flagship products for 2nd largest US property tax processor ($18B annually).
Holistic Software Architecture
Architected and led development teams for a legal automation software company, aquired for $50M.
Software Product Design for Title Ins Web App
Reimagined and redesigned multiple windows desktop apps into a new design of a single, unified, modern web app.
iOS Web App Design and Webservices
Front-end iOS design and back-end webservices architecture and development to support the new iOS app.
DevOps CI/CD Pipeline Implementation
Helped one of the fastest growing legal processing companies in the United States to automate its continuous integration / continuous deployment DevOps pipelines.
Proven track record
Decades of Fortune 500 experience. Millions saved. Teams led. Engineers inspired. Delivering results that make a real impact.
Saved through M&A due diligence
Multi-year projects delivered
Developer teams led
How we work together
From understanding your unique needs to delivering measurable results, we follow a structured, transparent approach that ensures alignment at every step.
Discovery & Assessment
Deep dive into your technology landscape, challenges, and opportunities. Stakeholder interviews and technical review.
Strategy & Planning
Develop roadmap, architecture, and implementation plan aligned with business objectives and constraints.
Execution & Delivery
Hands-on implementation, team leadership, and continuous guidance through completion.
Measure & Optimize
Track outcomes, adjust approach, ensure sustainable results and knowledge transfer.
“LERETA had a very positive experience with Shawn Livermore, complete with tangible results, following an incredibly important and complex engagement.”
“Shawn Livermore is, without exception, one of the best designers and developers we’ve ever worked with.”
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“We saw the diagrams take shape and quickly realized Shawn Livermore had a great handle on the complexity. Our data project would not have succeeded without his involvement.”
