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ChiBrrCon 2027
Friday October 9, 2026 1:15pm - 2:00pm PDT
Limited Capacity full
Cybersecurity is evolving fast and so are the opportunities to enter and grow within the field. But for many, especially those from underrepresented or nontraditional backgrounds, breaking in can feel overwhelming. At the same time, artificial intelligence is transforming the way defenders detect threats, hunt adversaries and build careers.
 
In this session, Rosaileen Iandolo, VP of Cybersecurity, shares her journey from the barrio to leading security operations, threat intelligence, and detection engineering. She will demonstrate how AI-powered tools can accelerate learning, remove barriers, and empower aspiring professionals to carve out a place on blue teams. Beyond the technical, she’ll also explore how AI can boost soft skills, from drafting professional communications to preparing presentations and interviews. 
 
Attendees will walk away with:
  • Practical examples of how AI can support security operations and personal skill-building
  • Ways AI can strengthen communication, confidence, and career mobility
  • A roadmap for using AI not just as a technical accelerator, but as a career elevator
This session blends technical insight with career strategy, designed for students, early-career practitioners, and anyone ready to leverage AI to create opportunities and drive impact in cybersecurity.
Speakers
avatar for Rosaileen Iandolo

Rosaileen Iandolo

Vice President of Cybersecurity, Golub Capital
Rosaileen Iandolo is a CISSP-certified cybersecurity leader with over 15 years of experience spanning the financial sector and government, including 7 years with the FBI. As Vice President of Cybersecurity at Golub Capital, she leads security operations, threat intelligence and detection... Read More →
Friday October 9, 2026 1:15pm - 2:00pm PDT
↙️ 4. Paranoia (Hermann Lounge) Hermann Hall Conference Center, 3241 S Federal St, Chicago, IL 60616, USA

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