Profile
Maura O’Leary is chief information security officer (CISO) at Ryan Specialty, where she has led the development of an industry-leading information security program since 2018.
As the firm’s first CISO, O’Leary built the infosec function from the ground up, now comprising 24 staff and three managed services. Her strategic, risk-based approach has transformed Ryan Specialty’s cybersecurity practices, implementing 24/7 threat detection, AI-driven email security and robust identity governance, all while achieving 100 percent compliance in access reviews.
O’Leary is a key member of the firm’s AI Governance Board, ensuring secure adoption of emerging technologies, and has pioneered due diligence protocols for mergers and acquisitions, supporting the secure integration of 29 business entities in the past year alone. Her leadership extends beyond the enterprise; she actively mentors students through the R.I.S.E. Opportunity Foundation and speaks at industry conferences, championing women in cybersecurity.
A 2025 Enterprise Finalist in the Chicago CISO ORBIE Awards, O’Leary has been recognized for her innovation, integrity, and impact. She also collaborates with the US Secret Service’s Cyber Fraud Task Force, staying ahead of evolving threats. Through her vision and dedication, she not only protects Ryan Specialty’s digital assets but also uplifts the broader cybersecurity community.
155 N Wacker Dr, Suite 4000, Chicago, IL 60606
(312) 784 6001
marketing@ryanspecialty.com
linkedin.com/in/maura-e-oleary
ryanspecialty.com
Maura O’Leary
Chief Information Security Officer Ryan Specialty
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Bio
Milestones
2018
2019–2021
2022
2023–2024
2025
Joined Ryan Specialty as its first chief information security officer, tasked with building the firm’s cybersecurity function from the ground up
2018
Launched key initiatives including 24/7 threat monitoring, a managed detection and response program, third party risk management, and a company-wide security awareness training program
2019–2021
Spearheaded the creation of comprehensive cybersecurity protocols for vulnerability management and application security and established a structured identity governance practice
2022
As a member of Ryan Specialty’s AI Governance Board, Maura helped institute strict vetting protocols for AI tools and vendors and enhanced due diligence for mergers and acquisitions to ensure secure integration of newly acquired entities
2023–2024
Named a 2025 Enterprise Finalist by the Chicago CISO ORBIE Awards, she was recognized for her leadership and mentorship, including her work with R.I.S.E. and the Secret Service’s Cyber Fraud Task Force
Enterprise Honoree – Chicago CISO ORBIE Award and Top Global CISO Honoree: Maura was recognized by both the ORBIE Awards and Cyber Defense Magazine for building Ryan Specialty’s cybersecurity program from the ground up and leading transformative initiatives that elevated the firm’s security posture and operational resilience
AI Governance Leadership: as a founding member of Ryan Specialty’s AI Governance Board, Maura helped establish rigorous oversight protocols for third-party AI tools, ensuring secure adoption while enabling innovation across the enterprise
2025
Milestones