Portfolio Holding

McCaulley.Org

Portfolio of Companies

Companies

Two distinct ventures under active development and operation — systematic trading and AI-first security.

OR

Options Roamer

Algorithmic Trading · Fintech

AI-driven investment clearinghouse. Real-time signal processing, ML regime detection, and conviction scoring — combined to generate and execute high-quality options trades autonomously. Built for precision at the speed of markets.

TS

Trailhead Security

Cybersecurity · AI Pentesting

AI-first penetration testing platform. Autonomous assessments powered by Cairn — web, cloud, Active Directory, and API attack surface coverage with CISSP-backed reporting. Professional-grade security made accessible.

Principal

Operator and builder. Two companies, one direction.

Brendon McCaulley

Brendon McCaulley

CISSP MBA Fintech Security

Builder and operator with a background spanning financial technology and cybersecurity. Founded Options Roamer to apply institutional-grade systematic trading methods at a private scale, and Trailhead Security to democratize professional penetration testing through AI-augmented tooling.

Active in the North Texas security community. Approach: systematic, data-driven, AI-augmented — across both domains.