The Founder
Brendon McCaulley, CISSP
Brendon McCaulley is a CISSP-certified security executive and the founder of Trailhead Security. He brings more than 20 years of enterprise security leadership experience across fintech, payment processing, and healthcare — industries where regulatory scrutiny, fraud exposure, and uptime requirements demand security programs that actually work.
He has served as 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 — 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 close that gap — combining former-CISO discipline with the Cairn agentic engine to deliver assessments at a speed and price the market has never seen.
"The person who used to hire pen testers — and was frustrated with what he got — is now the one doing the testing."
- CISSP certified
- Former CISO — fintech & payment processing
- North Texas security community leadership (ISSA)
- Speaker at FutureCon
- Texas A&M BBA, SMU MBA