About Jon Fenner

Technology Executive · Certified Ethical Hacker · Expert Witness

Background & Experience

Jon Fenner is a technology executive, Certified Ethical Hacker, and expert witness who brings 25+ years of hands-on experience to complex technology litigation. His career has spanned healthcare technology, cybersecurity, AI/ML systems, and enterprise insurance software — giving him the rare combination of technical depth and industry breadth that attorneys need when technology is at the center of a dispute.

Professional Narrative

Jon’s career reflects a consistent focus on building, securing, and leading technology at scale.

As Chief Technology Officer and Co-Founder of Community Wellness, he architected a HIPAA-compliant Remote Patient Monitoring platform that grew to serve over 100,000 patients across 12 healthcare provider networks in four states. He led the company through SOC 2 Type II certification, implemented EHR integrations with the major hospital systems (Epic, Meditech, and Cerner), and was directly responsible for the security of protected health information across the platform.

For 11 years at Guidewire Software, the dominant provider of core insurance systems for property and casualty carriers, Jon served as Principal Infrastructure Architect. He provided implementation and security consulting to some of the largest insurers in the world, including State Farm, Liberty Mutual, American Family, QBE Europe, and Liberty International Underwriters. His work included conducting penetration testing of customer-facing applications, leading complex multi-system integrations, and managing international implementation teams.

Through his consultancy AuraQuest, Inc., Jon has provided security audits, penetration testing, and technical architecture for clients including PepsiCo, the University of Colorado, National Gift Card, and Gatik AI. He has architected systems supporting 20 million daily requests and data warehouses serving 16 million users.

Currently, Jon leads engineering at Sidelight AI, where he develops AI/ML solutions for medico-legal applications involving medical records analysis. He also serves as a Senior R&D Engineer at OnwardAir, working on AI systems for autonomous aviation, including eVTOL aircraft and drones.

Certifications & Education

Certified Ethical Hacker (CEH) — EC-Council
The CEH certification validates proficiency in penetration testing, vulnerability assessment, and ethical hacking methodologies. Jon has applied these skills in real-world security engagements for clients across healthcare, insurance, education, and financial services.

AWS Certified Solutions Architect – Professional — Amazon Web Services
This advanced certification demonstrates expertise in designing distributed systems and complex cloud architectures on AWS, including security, reliability, and cost optimization.

Private Pilot License — Federal Aviation Administration
Relevant to aviation technology matters, including drone systems and autonomous flight technology.

B.S. Computer Science and Engineering — University of Texas at Arlington

Publications

“Design of an IRFPA nonuniformity correction algorithm to be implemented as a real-time hardware prototype” — Technical publication on infrared imaging system design and implementation.

Expert Witness Approach

Jon approaches each engagement with the same rigor he brings to building and securing technology systems. His process includes thorough review of technical evidence, independent analysis of system architectures and security measures, and the development of clear, defensible opinions grounded in industry standards and best practices.

Having served as a CTO and led engineering teams of 38+ professionals, Jon understands technology disputes from the executive perspective as well as the technical level. He can explain complex concepts in terms that judges, juries, and opposing counsel can understand — without oversimplifying the technical substance.

Jon is available for both plaintiff and defense engagements and provides the same objective, thorough analysis regardless of which side retains him. His rates are the same for every retaining party, and a detailed fee schedule is available on request.

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