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Jon FennerJF

Jon Fenner

Fractional CTO | vCISO | FDE | AI/LLM Platforms

£1,000/day
1 project
Burlington, US
15+ years

Average response time: 1 hour

About Jon

I help companies scale from MVP to 100,000+ users by architecting secure, AI-powered platforms that drive real business outcomes. With 20+ yearsleading technical transformations, I specialize in healthcare technology (FDA/HIPAA compliant), enterprise B2B systems, and cutting-edge AI/ML implementations.

What I bring to your team:
  • Proven scaling expertise - Built remote patient monitoring platform supporting 100K+ patients from ground up
  • Full-stack architecture - Expert in AWS, React/React Native, Node.js, Python, and modern cloud infrastructure
  • AI/ML integration - Implementing LLMs, deep neural networks, and autonomous systems for real-world applications
  • Security-first approach - Certified Ethical Hacker ensuring bank-grade security without sacrificing performance
Projects I deliver:
  • Healthcare platforms - RPM systems, EHR integrations (Epic, Meditech, Cerner), telehealth solutions
  • Enterprise transformations - Microservices migrations, legacy modernization, cloud architecture
  • AI-powered applications - Intelligent automation, predictive analytics, computer vision systems
  • Startup MVPs - From concept to production in 3-6 months with scalable architecture
  • Technical due diligence- M&A assessments, architecture reviews, security audits
Recent successes:
  • Led 38+ engineers building healthcare platform from zero to acquisition
  • Analyzed and recommended changes for PepsiCo's global B2B platform across multiple markets
  • Developed autonomous drone systems for emergency response
  • Reduced time-to-market by 50% through optimized CI/CD and team processes
I combine deep technical expertise with business acumen to deliver solutions that not only work but drive measurable ROI. Whether you need to build from scratch, scale existing systems, or modernize legacy infrastructure, I bring the experience to make it happen.
  • English

    Native or bilingual

Can work on-site
Burlington (up to 50km)

Experience

  • PROJECT X0 S.R.L.
    Malt logoOn Malt
    JENESI - First Fractional Phase Scope
    DIGITAL AND IT
    March 2026 - May 2026 (1 month)
    Technical Strategy and Vendor Vetting for an Advanced AI Platform
    • Client: JENESI, a European tech founder launching an AI/NLP platform to execute complex user instructions with verified proof over existing ecosystems.
    • Challenge: Establish non-negotiable architectural constraints and a robust framework for vendor evaluation to de-risk the core value proposition: utility, trustworthiness, and safety.
    • Role: Fractional Technical Advisor, hardening the founder's technical vision and managing the project scope for vendor handover.
    Key Results
    • Architecture: Defined three non-negotiable architectural "Gates" (Usefulness, Trustworthiness, Safety) for the system.
    • Integrity Mandate: Enforced strict four-boundary data isolation and required proof of transactional idempotency ("zero double-send").
    • Scope Control: Finalized the Prove-It MVP scope, successfully deferring aspirational features and escalating critical flows to formal PASS/FAIL acceptance blockers.
    • Vendor Vetting: Created a decisive technical evaluation filter focused specifically on agentic system design depth and QA strategy.
    Outcome


    Provided a fully hardened technical specification and a complete vendor package (Technical Brief and D1-D4) to successfully launch the Request for Proposal (RFP) process.
    artificial intelligence Digital Transformation IT Architecture IT-Security
  • OnwardAir
    Senior Research And Development Engineer
    AVIATION AND AEROSPACE
    September 2023 - Today (2 years and 11 months)
    Houston, TX, USA
    • Driving innovation in software development, firmware optimization, and IoT hardware integration to enhance the performance and reliability of our aerial systems.
    • Collaborating with cross-functional teams to design, test, and implement cutting-edge solutions that push the boundaries of drone and aviation technology.
    • Utilizing my expertise in Python programming, drone piloting, IoT, and Amazon Web Services (AWS) to develop scalable and efficient systems.
    • Leveraging artificial intelligence (AI) to create intelligent, autonomous flight systems and improve data analysis capabilities.
    • Conducting rigorous research and testing to ensure compliance with industry standards and regulatory requirements, ensuring safety and effectiveness in all developed technologies.
    Internet of things artificial intelligence aviation
  • Sidelight AI
    Head of Engineering (fractional)
    LEGAL
    June 2023 - Today (3 years and 2 months)
    London, UK
    • Architecting AI-powered solutions that streamline legal and medical data analysis, improving accuracy, efficiency, and decision-making for legal professionals and healthcare experts.
    • Developing and maintaining secure, scalable backend systems to support medico-legal applications, ensuring compliance with industry regulations and data security standards.
    • Collaborating with cross-functional teams to design technology solutions that enhance case management, expert testimony preparation, and forensic analysis.
    Implementing DevOps best practices to ensure seamless deployment, continuous integration, and optimal performance of AI/ML-driven applications.
    • Driving innovation through Agile project management and enterprise architecture, ensuring that technology solutions align with industry needs and regulatory requirements.
    artificial intelligence IT Architecture Amazon Web Services Machine learning Forward Deployment Engineer

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Education

  • Private Pilot License
    Private Pilot License
  • Part 107
    Pilot Institute
    Part 107

Skill set

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