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.
"I've leveraged Shawn and his company in multiple engagements over the last ten years. They have a trusted network of diverse talent and operate with integrity -- highly recommended."
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
What would a fractional CTO do for my business?
Assess all technology & create a roadmap
A thoughtful, right-sized technology roadmap gives executives a clear way to plan around — and engage with — the technology that powers their business.
- Thoughtful, clear, and right-sized roadmaps help executives plan and engage with the technology that powers their business.
- I assess the existing technology footprint and show the AS-IS versus the TO-BE in a single visual diagram.
- I help executives forecast thoughtful technology decisions on a five-to-ten-year time horizon.
Create slide decks & presentation materials
Board-ready materials turn complex technical decisions into something executives, investors, and acquirers can act on with confidence.
- M&A narratives, technical roadmaps, product visions, migrations, consolidations, and everything in between.
Automate business processes with AI agents
A clear AI strategy — proliferated across every department — turns agentic automation into durable efficiency instead of scattered experiments.
- Create an AI strategy for the organization to adopt, then help proliferate it across every department and initiative.
- Define, document, and implement agentic platforms.
- Lead developers to grow into the AI- and agentic-first era.
- Oversee development of all agentic workflows and ensure they fit the long-term enterprise architecture strategy.
Design & build custom software
Custom software — designed, architected, and launched with executive oversight — becomes a measurable driver of impact and company valuation.
- Design the software user experience in Figma and work through the nuances with the business.
- Architect the code and database, and oversee development of custom applications across web, iOS, desktop, and kiosk.
- Integrate custom software with existing applications and consolidate those integrations for oversight and architectural compliance.
- Oversee and direct the launch across the entire organization for maximum impact and valuation increase.
Oversee technology
When every vendor, developer, and IT decision rolls up to one accountable technology leader, the business makes informed, future-proof choices and finds real cost savings.
- Vendors, software developers, AI automation integrators, and IT staff roll up to a technology leader who makes informed, thoughtful, future-proof decisions for the business.
- All code, data, designs, and infrastructure are overseen and scrutinized for cost savings across platforms, channels, and departments.
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.
"Shawn was exceptionally helpful to our business. He understood our industry well and delivered on the promise of transformational results."
"Shawn's work touched numerous areas of the company. His intellectual capacity and technical maturity exceeded expectations."
"Shawn analyzed our systems, then designed, built, and scaled our flagship application from the ground up."
"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."
"Shawn is razor sharp and expert-level. Can't say enough good things about his work."
"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."
