Fractional CTO
Experienced fractional Chief Technology Officer and Chief AI Officer, delivering strategic technology solutions for forward-thinking businesses and startups
When technology becomes a business-critical driver, leadership matters.
Organizations bring me in when they need more than engineering management—they need strategic technology leadership.
- Align product, engineering, and business priorities under one strategic vision.
- Modernize legacy platforms and prepare systems for scale.
- Drive performance, delivery speed, and accountability across teams.
- Lead transitions during M&A, early-stage buildouts, funding rounds, or leadership shifts.
- Offer objective insight on technology investments and vendor selection.
A clear path from technical complexity to business clarity.
Technology Strategy & Roadmap
Aligning tech investments with measurable business outcomes.
Engineering Leadership
Building efficient teams and defining effective delivery frameworks.
Architecture & System Design
Creating scalable, cloud-native systems that grow with your organization.
Modernization Guidance
Transforming legacy systems into resilient, maintainable platforms.
Executive Reporting & Board Support
Translating technology progress into clear business value.
Vendor & Partner Evaluation
Ensuring third-party technology aligns with core goals.
What can a fractional CTO provide?
High-Caliber Communication
- Clear, responsive, and transparent across every channel
- Executive-ready docs and updates — no noise, no fluff
- Weekly summaries and monthly executive briefings
- Highly responsive throughout the engagement
Board-Room-Quality Output
- C-level slide decks, technology roadmaps, investor materials, migration plans, project plans, and everything in between
- Visual assets that clarify complexity for any audience
- Deliverables that withstand investor and due-diligence scrutiny
Strategic, Expert-Level Input
- Architecture, AI, data, design/product, and software
- Translating business goals into pragmatic technology direction
- Objective counsel on vendors, hiring, and product strategy
- Constantly refining process, automation, and reporting
Continuous Improvement
- Bringing new AI-driven tools and efficiencies into your workflow
- Committed to long-term impact, not short-term optics
Operational Leadership
- Hands-on technical involvement — code, database, architecture, infrastructure
- Oversight of dev teams, sprint process, CI/CD, and quality
- Focus on velocity, reliability, and measurable outcomes
Partnership & Integrity
- Aligned with your business goals, not vendor interests
- Transparent about trade-offs, risks, and ROI
- Treating your company as if it were my own
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.
"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."
Flexible leadership designed around your organization’s needs.
Each engagement is tailored to fit your stage, goals, and technical maturity.
- Strategic Advisor – I provide high-level guidance and architectural oversight.
- Fractional Chief AI Officer – I act as your senior-most technology/AI executive, covering you at every angle.
- Transformation Lead – I lead modernization or re-architecture initiatives hands-on.
Note: Every engagement begins with a discovery phase to assess current systems, teams, and strategic gaps—delivering a clear action roadmap before execution.
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.
Practical leadership that blends vision with execution.
As a Fractional Chief AI Officer, 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.
“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.”
What modern enterprise software looks like
High-fidelity interfaces and intuitive workflows built alongside architectural leadership — enterprise platforms where design quality is as deliberate as the technical architecture underneath.
Frequently asked questions
What is a fractional CTO and how does an engagement work?
A fractional CTO provides part-time technology leadership — typically a few days per month — covering strategic planning, architecture decisions, team leadership, and executive reporting. Engagements begin with a current-state assessment, then move into defined cadences aligned with the organization's roadmap.
What size companies benefit most from a fractional CTO?
Mid-market companies (50–500 employees) and growth-stage startups are the most common fit. These organizations have outgrown ad-hoc technology decision-making but cannot yet justify a full-time CTO at a $300K–$400K salary. Fractional leadership provides the same strategic capability at a fraction of the cost.
How long does a fractional CTO engagement typically last?
Most engagements run 6–18 months. Some are scoped for a defined project — a technology assessment or roadmap development — while others become ongoing strategic retainers as the organization scales.
What is the difference between a fractional CTO and a technology consultant?
A consultant delivers a report and leaves. A fractional CTO takes ownership — attending leadership meetings, making architecture decisions, managing engineers, and being accountable for outcomes. The distinction is embedded leadership, not advisory.
Related Reading
What Is a Fractional CTO?
The definition, the scope, and when the model applies — explained plainly for founders and executive teams.
How Much Does a Fractional CTO Cost?
Rate ranges, retainer structures, and the pricing variables that determine what you will actually pay.
When to Hire a Fractional CTO: 5 Signals
Five clear indicators that fractional CTO expertise is what your business needs right now.
Do You Need a Fractional CTO?
A fit assessment — not a cost calculator — across the technical leadership gap, stage and complexity, decision quality, team maturity, and strategic pressure.
Take the assessment →