Fractional CAIO
Whether you’re integrating AI into legacy environments or designing AI-native products, I provide the strategy, governance, and architecture to make it work in the real world.
Discovery Process for AI Model Applicability
Organizations bring me in when they need more than engineering management—they need strategic technology leadership.
- Identify high-impact business challenges suitable for AI-driven solutions.
- Assess data readiness, quality, and accessibility across systems.
- Evaluate the feasibility and ROI of applying AI models to existing workflows.
- Map model capabilities to business objectives and compliance requirements.
- Prototype and benchmark multiple AI approaches to determine the best fit.
- Define success metrics, governance needs, and integration pathways for scale.
Board Level AI Execution Strategy
AI Strategy & Roadmap
Identify, prioritize, and execute high-impact AI opportunities.
AI Architecture Design
Design data pipelines, APIs, and model infrastructure that scale securely.
AI Governance & Compliance
Build frameworks for responsible, explainable, and compliant AI use.
Data Engineering Enablement
Establish reliable data pipelines and model-ready datasets.
Model Deployment & Integration
Integrate ML/LLM models seamlessly into products and workflows.
Change Management & Team Training
Build internal capability and confidence in AI operations.
Fractional AI leadership tailored to your organization’s maturity.
Each engagement is designed around your organization’s readiness and goals.
- Strategic Advisor – Shaping AI vision, policies, and direction alongside executives.
- Fractional CAIO – Providing part-time AI leadership (1–3 days per week).
- Transformation Partner – Leading cross-functional teams through design, deployment, and adoption of AI systems.
Note: Every engagement begins with a Discovery & Readiness Assessment—mapping your data, talent, and infrastructure to a practical AI roadmap.
End-to-end AI leadership across data, models, and adoption.
I specialize in helping organizations establish AI capabilities that drive measurable business value.
- Generative AI Integration
- Predictive Analytics & Forecasting
- Intelligent Automation (RPA + ML)
- NLP & Document Intelligence
- Data Modernization & Infrastructure
- AI Governance & Risk Management
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).
M&A Due Diligence
Prevented costly acquisition through technical evaluation for world's largest title insurance company.
Pre-IPO Technology Leadership
Architected vehicle data systems supporting $225M IPO for disruptive auto e-commerce platform.
"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 with Shawn Livermore, complete with 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.”
Practical leadership that blends vision with execution.
As a Fractional CTO, I focus on aligning technology with business outcomes, building confidence in your technical roadmap, and ensuring your teams can deliver effectively. You’ll get:
- Executive-level direction without full-time overhead.
- Clear, measurable technology strategies.
- Deep, hands-on experience in complex systems.
- Collaboration that drives lasting impact.