John Gillespie

About John Gillespie

Chief Technology Officer at FreightVana, where we\'re perfecting Power-Only freight through transparency, trailer technology, and data-driven logistics. I lead technology strategy, architecture, and engineering for a Phoenix-based logistics company redefining how shippers and carriers work together. FreightVana is a three-time FreightTech 100 honoree with proprietary platforms all built to make freight more predictable, more visible, and more valuable for everyone in the network. Over 17+ years, I\'ve built and led technology organizations across logistics, healthcare, and banking. As CTO at MegaCorp Logistics, I helped scale the business from $350M to $1B in revenue while keeping IT spend under 2% and driving a 6% reduction in cost-per-load through automation, cloud modernization, and AI-enabled forecasting. Before that, I led enterprise architecture and governance at American Savings Bank and served as technical lead for enterprise applications at Kaiser Permanente. Between roles, I founded Outer Kai Technologies to advise CEOs and boards on technology strategy, AI readiness, and operating model design. My focus areas: • Cloud-first enterprise architecture (Azure, Entra ID, Fabric, OneLake) • AI strategy and responsible adoption (NIST AI RMF, ISO/IEC 42001, EU AI Act) • Data modernization, analytics, and intelligent automation • Cybersecurity, governance, and regulatory alignment • Building high-performing, values-driven teams Based in Wilmington, NC. Always happy to connect with operators, builders, and leaders in logistics and enterprise tech.

Experience

1. Chief Technology Officer

   FreightVana

   Apr 2026 — Present · Phoenix, AZ, US

   Leading technology, engineering, and data strategy at FreightVana — a three-time FreightTech 100 honoree perfecting Power-Only freight.• Own the full technology organization and roadmap, reporting directly to the CEO• Advancing the next phase of FreightVana\'s proprietary tech stack across carrier, shipper, and trailer platforms• Driving AI adoption, data platform maturity, and engineering excellence in support of continued national scale• Partnering across executive leadership to align technology investment with growth, safety, and customer outcomes

Education

• University of North Carolina at Charlotte

  Public Health

  2007 — 2008

• University of North Carolina Wilmington

  Political Science and Government

  2002 — 2008

Skills

• Customer Service
• Technical Support
• Computer Hardware
• Security
• IT Operations
• Computer Network Operations
• Training
• IT Solutions
• Networking
• Computer Security
• Computer Maintenance
• Printer Support
• Microsoft Office
• Sales
• Information Security
• Software Installation
• Leadership
• Printers
• Information Technology
• IT Strategy
• Computer Repair
• Disaster Recovery
• Network Administration
• Management
• Team Building
• Wireless Networking