The Founder
Brendon McCaulley, CISSP
Brendon McCaulley is a CISSP-certified security executive and the founder of Trailhead Security. He brings more than 15 years of enterprise security leadership experience from the fintech and payment processing industry — an environment where regulatory scrutiny, fraud exposure, and uptime requirements demand security programs that actually work.
He has served as a CISO and senior security leader at three major organizations:
- Heartland — one of the largest U.S. payment processors, with PCI-DSS compliance and breach response at scale
- Optum / VPay — healthcare payments division of UnitedHealth Group, operating under HIPAA, SOC 2, and financial services security requirements
- ConnexPay (current) — fintech issuing and acquiring platform, serving as CISO and building security architecture from the ground up
After years of managing pen test vendors from the client side, Brendon saw a consistent gap: assessments that were slow, expensive, and delivered reports that sat on a shelf. Trailhead Security exists to change that.
"The person who used to hire pen testers — and was frustrated with what he got — is now the one doing the testing."
- CISSP certified
- Active CISO at ConnexPay
- ISSA North Texas chapter leadership
- Speaker at FutureCon
- Texas A&M BBA, SMU MBA