Fractional CAIO

I provide AI strategy, AI governance, and AI architectural expertise, bridging the gap for companies looking to expand traditional technology stacks into AI products and services.

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Chief AI Officer

What's a Chief AI Officer

CAIO is the cross-functional senior-most AI leader in the organization that works alongside and within the technology department.

  • Leads the charge across the organization to solidify high-impact business challenges suitable for AI-driven solutions.
  • Positions the organization for AI data readiness, quality, and AI leverage opportunities across systems.
  • Evaluates the feasibility and ROI of applying AI models to existing workflows.
  • Map model capabilities to business objectives and compliance requirements.
  • Prototypes and benchmarks multiple AI approaches to determine the best fit.
  • Defines success metrics, governance needs, and integration pathways for scale.
Impact of a Fractional CAIO

How a Chief AI Officer Impacts the Business

The role firmly establishes a transformation of the organization into the new generation of "AI-first". 

  • Strategic Advisor – Shapes AI vision, policies, and direction alongside executives.
  • Modernization Lens – Envisions and communicates the systems and processes of the organization through an AI-first perspective.
  • Transformation Partner – Leading cross-functional teams through design, deployment, and adoption of AI systems.
What I Deliver

Expert level AI formulation & execution

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AI Strategy & Roadmap

We will identify, prioritize, and execute high-impact AI opportunities and which models fit as a foundational roadmap.

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AI Architecture Design

Your model requirements will dictate the AI architecture, data pipelines, APIs, and model infrastructure.

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AI Platform / Cloud Services

We will work together to outline, map, formulate, and execute the launch of the right AI platform for your business.

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AI Data Engineering

I've defined and prepared large and reliable data pipelines and model-ready datasets for enterprise clients.

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LLM Deployment & Integration

I've integrated ML/LLM models into products and workflows for real-world production systems.

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Automated AI Model Fine Tuning

I have architected, built, and deployed automated AI model fine-tuning batch subsystems.

As a First Step

Creating the matrix of every possible AI opportunity.

One of the key deliverables in the discovery phase of the process is the AI opportunity matrix, which provides a detailed list of each key AI insertion opportunity that exists and its ultimate impact on the financial and operational bottom line.

  • Area, focus, and impact
  • Financial implications
  • Integrations and technical ramifications
  • Ownership, accountability, and expectations
More on the AI Opportunity Matrix

"I have worked with Shawn and I know his talent and leadership can have an enormous impact in a consulting engagement. I have seen it first-hand."

Pete Klein
Software Development Manager, Microsoft
Real-World Client Experience

Automated self-training AI model for content platform

Learn more on a recent engagement, where I architected, built, and deployed an automated AI model training and tuning system for an AI-based content creation platform.

  • Model Selection
  • Model Training Data Formulation
  • Automated Batch Training Data Processing
  • Oversight and Visibility
  • Integration into Developer Routines
More on this AI engagement
AI Model Expertise

Hands-on AI expertise across data, models, and adoption.

I specialize in helping organizations establish AI capabilities that drive measurable business value.

  • Model Discovery, Evaluation, and Deployment
  • Predictive Analytics & Forecasting
  • Intelligent Automation (RPA + ML)
  • NLP & Document Intelligence
  • LLM Training & Fine Tuning
  • AI Governance & Risk Management
"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."
Steve Orgill
Chief Technology Officer, LERETA
"Shawn is razor sharp and expert-level. Can't say enough good things about his work."
Scott DeLong
Executive Team, Confidential Client
"I have worked with Shawn and I know his talent and leadership can have an enormous impact in a consulting engagement. I have seen it first-hand."
Pete Klein
Software Development Manager, Microsoft
"Shawn's work touched numerous areas of the company. His intellectual capacity and technical maturity exceeded expectations."
Paul Larkin
Former Chairman of the Board, LERETA

Client success stories

Proven impact across enterprise modernization, M&A, and technology leadership. From $100M savings to $20M+ transformations—see the outcomes.

$20M+ Project

Enterprise modernization at scale

Led 30+ developers to rebuild flagship products for 2nd largest US property tax processor ($18B annually).

$50M Acquisition

Holistic Software Architecture

Architected and led development teams for a legal automation software company, aquired for $50M.

User interface screens showing contact listings, user profile details, and document workflow in a business application.
Largest Title Insurance Firm in USA

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.

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iOS App

iOS Web App Design and Webservices

Front-end iOS design and back-end webservices architecture and development to support the new iOS app.

Detailed project timeline chart for 2017 showing tasks and dependencies across six projects: Fender, Yellowstone, Brookstone Data, Sequoia, Yosemite, and File Masters, divided by quarters Q1 to Q4 with multiple milestones and timelines interconnected by arrows.
DevOps

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.

Ready to operationalize AI in your organization?

Let’s build a strategy that transforms AI from concept to core capability.

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