Richard Fleeman

Senior Director @Fortreum

Denver, CO, US

Senior Director at Fortreum, where I provide executive leadership for enterprise penetration testing, red team operations, and offensive security strategy supporting commercial and federal organizations. Responsible for designing, governance, and execution of adversary-focused security programs that validate not only technical controls, but also detection, response, and organizational resilience. My work bridges hands-on offensive security with executive-level risk management, ensuring security investments translate into measurable reduction of business and regulatory risk.Advise C suite and executive teams on building defensible security programs that withstand real-world threats and authorization scrutiny. I am actively involved in shaping testing strategy, cadence, and success criteria moving organizations from point-in-time compliance testing to mature, continuous security operations.Operate as a strategic partner to leadership and clients alike: mentoring our team, developing scalable offensive security methodologies, and translating technical findings into executive-level insights that inform board discussions, risk decisions, and long-term security roadmaps.Core focus areas:• Penetration testing and red team leadership• Adversary emulation and detection/response validation• FedRAMP and regulated cloud security programs• Security program governance and maturity• Executive, CISO, and board-level security advisory

Regis University

Computer Science