From Medieval History Grad to CISO | Kevin O'leary | Be Fearless Podcast EP 4

Be Fearless Podcast by SquareX

In Episode 4 of the Be Fearless Podcast, our teammates from the Founder’s Office Audrey and Aleksandra interviewed Kevin O'leary, who’s acted as CISO for some of the most iconic global brands such as HP, General Electric and most recently JP Morgan.
Hear directly about Kevin’s journey from medieval history graduate to CISO, what fractional CISOs can offer enterprises and more!
0:00 Kevin’s cybersecurity journey and his thoughts on the CISO role
7:48 Kevin's proudest CISO moment and the importance of teamwork
16:33 On AI in cybersecurity
23:59 The evolution of the CISO role
32:55 Dealing with third party risks
36:42 Pros and cons of SASE/SSE solutions
41:23 “Creative” attacks Kevin has seen
45:00 On Fractional CISOs and their role
54:15 Rapid fire questions and some fun facts about Kevin
🔔 Follow Kevin, Audrey and Aleksandra on:
https://www.linkedin.com/in/kboleary/
https://www.linkedin.com/in/aleksandra-melnikova-1012/
https://www.linkedin.com/in/audrey-adeline/
📖 Episode Summary:
In this episode of the Be Fearless podcast, Kevin O'Leary, a seasoned CISO with experience at HP, General Electric, and JP Morgan, shares his journey in cybersecurity. Kevin began his career in an era when cybersecurity did not exist as an industry. With a background in medieval history, he initially worked in various IT roles before moving into cybersecurity. Kevin discusses the evolution of the CISO role from a technical position to one that includes risk management and organizational leadership, emphasizing the importance of soft skills and aligning with business outcomes.
Kevin also discusses current cybersecurity trends, highlighting the importance of managing third-party risks, especially in the financial sector. He explains how modern tools like SASE and SSEs have improved security but also points out their limitations. He underscores the need for continuous adaptation and vigilance in cybersecurity, discussing the role of AI in both attack and defense. He also shares his perspective on the evolving landscape of cybersecurity roles, including the benefits of fractional CISO positions for smaller organizations and startups.

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Kapitel

1. Kevin’s cybersecurity journey and his thoughts on the CISO role (00:00:00)

2. Kevin's proudest CISO moment and the importance of teamwork (00:07:48)

3. On AI in cybersecurity (00:16:33)

4. The evolution of the CISO role (00:23:59)

5. Dealing with third party risks (00:32:55)

6. Pros and cons of SASE/SSE solutions (00:36:42)

7. “Creative” attacks Kevin has seen (00:41:23)

8. On Fractional CISOs and their role (00:45:00)

9. Rapid fire questions and some fun facts about Kevin (00:54:15)