Profile
“Being true to who we are is key; we are purely a referral-based business. There is zero marketing or advertising”
Adam Rakowski,
Ortus Financial
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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“You can’t control the outcome, but you can always control what version of you turns up every day”
Adam Rakowski,
Ortus Financial
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
Milestones
ELITE WOMEN 2024 JUDGE
“You can’t control the outcome, but you can always control what version of you turns up every day,” he says.
While at the helm of a rapidly growing business and a family that includes two young children at home, Rakowski has learned to manage what he calls a “never-ending list of commitments” that consists of a new team member each month, a new interstate office and two to three new referral partners monthly.
“Our business is a human business, so investing genuine time in every person can be draining on a personal level. Balancing it all is a challenge,” he says. “Simply put, do what you say you will do, and act at all times with honesty and integrity, being respectful and empathetic. The financial outcomes are a byproduct of the human interactions we have.”
Attracting, retaining and delivering exceptional client outcomes and service starts with a sincere interest in their journey and remaining relevant to them as their lives and needs evolve, notes Rakowski. He points out that he and his team put in most of the work upfront in building meaningful relationships, which is a testament to its 99% client retention rate.
He says, “We are clear in the types of clients we work best with and our value proposition. We also look for a cultural alignment with all of our referral partners, and we are acutely aware of our strengths and how different we are from our industry peers.”
Rakowski recently opened a Queensland business and plans a foot in every other capital city. He strives to establish the brokerage as a national business with on-the-ground representation in every state by the end of 2025.