Carol Rollie Flynn Speaker Biography
Cybersecurity and Leadership Expert, CIA Veteran, and President of a Premier Strategic Intelligence Firm
Carol “Rollie” Flynn is the President of The Arkin Group, a premier boutique strategic intelligence and risk consulting firm based in New York. The firm specializes in delivering high-level geopolitical intelligence, business intelligence, and investigative services to corporate, financial, and legal clients navigating complex global environments. Flynn is widely recognized for her ability to translate national security expertise into actionable strategies for the private sector, helping organizations anticipate risk, protect assets, and make informed decisions in an increasingly volatile world.
Distinguished Career at the CIA
Flynn is a highly decorated 30-year veteran of the Central Intelligence Agency, where she held numerous senior executive roles at the forefront of U.S. national security. Her leadership positions included Director of the CIA’s Leadership Academy, Associate Deputy Director of the National Counterterrorism Center, Executive Director of the CIA Counterterrorism Center, and Director of the Office of Foreign Intelligence Relationships. In these roles, she shaped global intelligence strategy, led interagency collaboration, and advised top U.S. policymakers during critical moments.
Her operational experience is equally extensive. Flynn served as Chief of Station in key posts across Southeast Asia and Latin America and operated undercover as a Clandestine Operations Officer in Africa and Southeast Asia. She is particularly known for her expertise in counterterrorism, intelligence integration, and leadership development under high-stakes conditions, making her a trusted authority on navigating uncertainty and crisis.
Leadership, Academia, and Thought Leadership
Beyond her government service, Flynn has built a respected presence in academia and policy circles. She is President Emerita and a Non-Resident Senior Fellow at the Foreign Policy Research Institute, where she contributes analysis on global security and foreign policy challenges. She has also served as an adjunct professor at Georgetown University Walsh School of Foreign Service, teaching graduate-level courses on intelligence, counterterrorism, and security.
Flynn is an active member of the Council on Foreign Relations and serves on the advisory board of the International Spy Museum as well as the board of the Jamestown Foundation. She is frequently sought out for her insights on cybersecurity, geopolitical risk, leadership, and intelligence operations, and is known for making complex global issues accessible and relevant to business and leadership audiences.
Education and Credentials
Flynn holds a Bachelor of Arts from Wellesley College and a Master of Science in Cyber Security from University of Maryland. She has also completed executive leadership programs at Duke University, Georgetown University, and the Kellogg School of Management. Her multidisciplinary education reflects a career that bridges intelligence, technology, and executive leadership.
Advisory Roles and Industry Impact
In addition to her professional and academic roles, Flynn has contributed to a range of advisory and nonprofit organizations, including service on the Foundation Board of Holy Cross Hospitals of Montgomery County, Maryland. Through her consulting work and board service, she continues to influence how organizations approach risk, governance, and resilience in a rapidly changing global landscape.
Speaking Expertise and Topics
Carol Rollie Flynn provides expert guidance on cybersecurity, intelligence, leadership, and risk management to both private sector organizations and government entities. Her speaking engagements draw on real-world experience from the highest levels of intelligence operations, offering audiences rare insight into how global threats evolve—and how leaders can stay ahead of them. She is particularly effective at connecting national security principles to business challenges, helping executives understand how to lead through disruption, manage crisis, and build resilient organizations.
Why Book Carol Rollie Flynn
Carol Rollie Flynn delivers a powerful combination of real-world intelligence experience, executive leadership insight, and forward-looking cybersecurity expertise that few speakers can match. Audiences gain a behind-the-scenes perspective on global threats, decision-making under pressure, and the leadership strategies required to navigate uncertainty. Whether addressing corporate executives, government leaders, or industry professionals, Flynn provides actionable takeaways grounded in decades of experience at the highest levels of national security. As a proud representative of Carol Rollie Flynn, Speakers.com offers clients exclusive access and unmatched expertise in securing her for impactful engagements—making it the best and most trusted partner to book her for your upcoming event.
Carol Rollie Flynn Speaking Topics
Intelligence and National Security
Sprinkled with anecdotes from her extraordinary experiences as a Chief of Station and an undercover operations officer for the CIA, Ms. Flynn provides an overview of intelligence and how intelligence contributes to our national security. This talk addresses the real “spy stuff” – how the CIA recruits and runs spy networks overseas. This interactive presentation also explores the ethical dilemmas inherent in intelligence operations and current intelligence issues.
Leadership in Crisis
This presentation explores the key attributes and practices of effective leaders in crisis situations. Drawing on her experiences as a CIA Chief of Station, Ms. Flynn relates fascinating anecdotes from her clandestine career to demonstrate the best practices and pitfalls of crisis leadership. This presentation can also be adapted to address the full range of leadership topics: Leading Change and Organization Renewal, Strategic Thinking, Effective Decision-Making, Creativity and Leadership, Conflict Management, Trust and Leadership, Organizational Culture, etc.
Leadership and Cybersecurity
It has been said that there are two kinds of organizations: Organizations that have been attacked by cyber criminals and organizations that don’t know that they have been attacked by cyber criminals. Why did Sony get it wrong and what could they have done more effectively? This presentation explores cyber security from the perspective of corporate leadership teams and examines how organizations and leadership teams should prepare and position themselves to overcome a major cyber incident.
Winning Strategies for Women
This presentation explores how women can succeed in male-dominated fields and let’s face it, many fields are male dominated, especially at the top. Drawing on her experiences as one of a handful of female senior executives in the CIA’s National Clandestine Service, Ms. Flynn provides lessons and anecdotes from her days as an undercover CIA operations officer and Chief of Station to help the audience navigate their careers more successfully.
Executive Presence
Executive presence is a key attribute of effective leaders, and this presentation examines how to develop a more dynamic presence. The audience will have the opportunity to learn skills and techniques to become more charismatic and powerful communicators. This presentation will also feature anecdotes from Ms. Flynn’s extraordinary career as an undercover CIA Chief of Station and clandestine operations officer overseas.
