Fractional CTO & CAIO Services

Bridging strategic vision with technical execution through flexible, high-impact technology leadership.

Fractional CTO

Strategic technology leadership without the full-time commitment. Guide your team, architecture, and roadmap.

Fractional CAIO

AI strategy, model selection, fine tuning, and tactical oversight. From AI readiness assessments to holistic implementation.

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.

Comprehensive technology leadership for modern enterprises

Bridging strategic vision with technical execution through flexible, high-impact technology leadership.

Technology Leadership

Fractional CTO

Strategic technology leadership without the full-time commitment. I serve as your trusted technology executive, providing board-level guidance, team leadership, and architectural oversight.

  • 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
AI Strategy & Integration

Fractional CAIO

Navigate the AI landscape with confidence. From strategy to implementation, I help you identify genuine business value and build sustainable AI capabilities.

  • AI roadmap & use-case prioritization
  • MLOps/AIOps infrastructure guidance
  • Model governance & ethics framework
  • Pilot design → production scaling
  • Team training & capability building
Technology Consulting

Enterprise Modernization

Transform legacy systems into modern, scalable platforms. I've led multi-million dollar modernization initiatives for Fortune 500 companies—bringing that expertise to your organization.

  • Legacy system assessment & modernization roadmap
  • Mainframe exit strategies & cloud migration
  • Replatforming & technology stack evaluation
  • API & integration architecture
  • Critical path analysis & risk mitigation
Technical Due Diligence & Scaling

Startup Advisory

For investors evaluating acquisitions or startups scaling engineering teams. I provide the technical expertise needed to make informed decisions and build foundations for growth.

  • Technical due diligence for investors
  • Code & architecture quality assessment
  • Scaling engineering teams & processes
  • Product-technology alignment
  • Fundraising technical decks & materials
Custom to Your Needs

Flexible Engagement Models

Multiple engagement options designed to fit your timeline, budget, and objectives. From short-term workshops to ongoing fractional leadership.

  • Retainer (fractional ongoing)
  • Project (fixed scope & timeline)
  • Advisory (board-level guidance)
  • Workshops (1-3 day accelerated)
  • Sprint/Discovery (30-90 days)

Deliverables & Outcomes of the Fractional Approach

From strategy to execution, the fractional CTO / CAIO approach delivers tangible results.

Services
Key Deliverables
Business Outcomes
Fractional CTO
  • 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
Fractional CAIO
  • 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
Enterprise Modernization
  • 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
Startup Advisory
  • 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

Proven Track Record

Decades of Fortune 500 experience. Millions saved. Teams led. Engineers inspired. Delivering results that make a real impact.

$100M+

Saved through M&A due diligence

$20M+

Multi-year projects delivered

30+

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.

"Artificial intelligence machine learning models can be very effective - you just have to take baby steps to engage this area."

Shawn Livermore
Senior Consultant, Product Perfect

"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 exceptionally gifted, and works within a trusted network of diverse talent -- highly recommended."

Steve Orgill
Chief Technology Officer, LERETA

"Shawn works at an extremely high level and I trust his work implicitly within a trusted network of diverse talent -- highly recommended."

Steve Orgill
Chief Technology Officer, LERETA

“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.”

Paul Larkin
Former Chairman of the Board, LERETA

Shawn’s implementation teams are, without exception, the best designers and developers we’ve ever worked with.”

Audrey Bridges
Treasurer, Bloom Benefits Association

“Bringing Shawn Livermore in to help us refine our software applications was one of the best decisions we ever made as a company.”

Marshall Cook
CEO, Balance Genics

“The consultants from Shawn Livermore were able to understand our industry well and design a great user experience as a result.”

Erin Fergus
Accounting Manager, PRAM

Ready to Transform Your Technology?

Whether you need strategic CTO guidance, AI implementation, or enterprise modernization—let's talk.