In this episode of The New CISO, host Steve Moore speaks with Alex Rice, Founder, CTO, and CISO at HackerOne, about challenging one of cybersecurity's most deeply held beliefs—that security should be the top priority. Drawing from his journey building security programs at Facebook and founding HackerOne, Alex introduces the "safety third" philosophy and explains why accepting that security is never first can actually make you more effective as a leader.

Alex shares his unconventional path into cybersecurity, starting as a 14-year-old programmer in rural Florida and eventually leading product security at Facebook during its explosive growth. He reveals how Facebook ran 70+ penetration tests annually with top-tier vendors and still wasn't finding enough vulnerabilities—until they opened the doors to the hacker community and received over 300 valid findings in a single weekend. This experience became the foundation for HackerOne's bug bounty platform.

The conversation tackles critical leadership challenges facing modern CISOs, including the toxic tendency toward victim blaming when breaches occur, why security teams struggle with customer-centric design, and how to avoid becoming the team everyone knows only for blocking work and sending phishing tests. Alex argues that security professionals must stop drinking their own Kool-Aid and recognize that usability and business outcomes will always take precedence over security controls.

In the episode's second half, Alex addresses AI's role in security operations with refreshing pragmatism. Rather than chasing grandiose AI visions, he advocates for starting with narrow, well-defined tasks where agents can replace security toil—like automated CVSS scoring or vulnerability triage—building trust and expertise before tackling more ambitious projects. He warns against the current trend of AI tools that find more problems when security teams desperately need help fixing the mountain of issues they already know about.

Alex also challenges CISOs to stop over-owning problems like asset inventory management that rightfully belong to other executives, emphasizing the importance of cross-functional collaboration over building security-owned solutions that ultimately fail. Throughout the discussion, he champions a philosophy of empathy, customer-centricity, and accepting hard truths about security's actual place in business priorities—a mindset shift that paradoxically makes security leaders far more effective.

Key Topics Discussed:

1. Why "safety third" should be every CISO's operating philosophy
2. The problem with victim blaming in cybersecurity incidents
3. Building customer-centric security programs that enable rather than block
4. Lessons from scaling Facebook's security program with 70 pen tests per year
5. The origin story of HackerOne and crowdsourced security testing
6. How to avoid becoming the security team everyone resents
7. Practical AI implementation: Starting with toil elimination, not transformation
8. Why CISOs over-own asset management and other problems
9. The importance of process mapping before deploying AI agents
10. Aligning security teams closely with AI and software development