Managing Member · Fractional CTO & CIO
Matt Crego is a technology executive and trusted advisor whose career spans three decades in technology — more than two of them leading digital transformation across complex, high-growth, and PE-backed organizations. He has driven multiple turnarounds and guided technology functions through private equity acquisitions, mergers, acquisitions, and divestitures — consistently building the operational and data infrastructure that enables sustainable growth. Matt partners directly with boards and C-suite leadership to translate technology strategy into measurable business outcomes.
Expertise
- Artificial Intelligence
- Data and Analytics
- C-Suite Partnership & Education
- Technology Strategy & Roadmapping
- Digital Transformation
- Private Equity Operations
- Cloud & Infrastructure Modernization
- Cybersecurity Governance
- Revenue Operations
- Customer Success
Graduate of the Chief AI Officer Program, University of Chicago Booth School of Business.
Industry experience
Healthcare & Dental
Directed software development and systems modernization for clinical and administrative platforms, managed HIPAA compliance programs across multi-site environments, and delivered patient-facing digital experiences that improved access and operational efficiency.
Property & Casualty Insurance
Managed large-scale policy administration and claims systems for major insurance organizations, led development of quoting software, and drove end-to-end digital enablement of the insurance lifecycle.
Automotive
Delivered technology across the full automotive ecosystem: digital retail storefronts, advertising and valuation platforms, subscription-based membership organizations, and GPS-enabled dispatch systems.
Education & Edtech
Enabled remote and continuing education across multiple disciplines, built digital asset management systems to support content delivery at scale, and implemented edtech platforms that extended learner engagement.
Technology & SaaS
Built and integrated digital SaaS platforms serving a broad range of industries, developed AI and intelligence platforms, and connected enterprise systems with customer-facing experiences.
Approach
Matt embeds with leadership teams as a hands-on partner — driving clarity, alignment, and execution. He brings a practitioner's perspective to board-level strategy and earns the trust of both technical teams and senior stakeholders. His engagements are designed to build lasting internal capability, not create consulting dependency.
Over three decades embedded with companies, teams, and leaders across industries, Matt has built a broad and active professional network spanning individual contributors, functional experts, implementation partners, and executive advisors. He draws on this network directly — sourcing the right talent, counsel, or capability for the challenge at hand, and extending the value of every engagement well beyond what any single consultant could deliver alone.