Jon Henley, Founder & Principal Consultant
A career built where technology, security, and business change meet.
Jon Henley has spent more than 25 years operating at the intersection of enterprise technology, cybersecurity, and large-scale transformation.
He began his career in application development at Countrywide Financial, building and managing software systems that supported enterprise call center and knowledge management operations. When Bank of America acquired Countrywide, Jon stayed and continued to grow inside one of the largest financial institutions in the world. Over the next 12 years, he rose to SVP of Technology Infrastructure Services, holding global accountability for end-user computing, branch and campus infrastructure, service desk operations, and knowledge management across Consumer Banking in the U.S., Canada, and the U.K.
During that period, Jon held leadership positions through major acquisition integration efforts involving Countrywide Financial and Merrill Lynch, helping align infrastructure, identity controls, service operations, and security posture into a more unified operating standard at scale.
After Bank of America, Jon served as Interim CTO at Prospect Mortgage, leading the full technology stack through an M&A transition, including infrastructure, applications, data management, security posture, and the people and operating model required to reach Legal Day 1. A consulting engagement at The Walt Disney Company followed, focused on third-party security assessments and GDPR compliance.
Jon then spent seven years at Amazon as an Information Security Technical Program Manager, running program and operations responsibility across Application Security, Incident Response, Insider Threat, Third-Party Security, GRC, Red Team, and Penetration Testing, while building AI-assisted analytics and executive reporting workflows that foreshadowed what he would build next.
In 2026, Jon founded Henley Technology Consulting to take his enterprise experience independent, helping organizations turn technology strategy and transformation vision into practical, governed, working capability.