We had a community session on The CISO's Journey: From Expert to Leader featuring David B. Cross (SVP & CISO at Oracle), Bikash Barai (CEO, FireCompass; Advisor, CISO Platform) & David Randleman (Field CISO, FireCompass)
In this discussion, we covered the journey from cybersecurity expert to strategic leader including stages of a CISO’s evolution, the balance between technical expertise and leadership, the unique value veterans bring to cybersecurity, and strategies to stay ahead of emerging attack techniques in an ever-changing threat landscape.
Key Highlights:
- Career Evolution: Insights into the journey to becoming a CISO at Oracle and defining career moments.
- Success Metrics: Industry trends shaping how CISOs measure success.
- Veterans’ Role: The impact of veterans’ skills and clearances in cybersecurity hiring.
- Mental Health & Pop Culture: Managing stress as a CISO and pop culture’s take on cybersecurity.
About Speaker
- David B. Cross (SVP & CISO at Oracle)
- Bikash Barai (CEO, FireCompass; Advisor, CISO Platform)
- David Randleman (Field CISO, FireCompass)
Executive Summary (Session Highlights):
- The Journey from Expert to Leader: A CISO’s Perspective
The session delved into the evolution of security professionals into leadership roles. David Cross, CISO at Oracle, emphasized that becoming a CISO is a journey requiring patience, adaptability, and preparation, much like training for a marathon. Key insights included the importance of seizing opportunities, even when the path isn’t clearly defined, and continually evolving one’s leadership capabilities.
- The Power of Mentorship in Leadership Development
The speakers underscored mentorship as a cornerstone for growth. David Cross introduced three types of mentors:
- Long-term mentors for career guidance.
- Tactical mentors for skill-specific improvements.
- Peer mentors for candid, constructive feedback.
Bikash Barai highlighted the value of collaboration over mere networking, urging CISOs to “pay it forward” and contribute to community growth.
- Stress Management and Achieving Work-Life Harmony
Stress management was a central theme, with both speakers sharing personal strategies. David Cross described running as his form of meditation, enabling mental clarity and resilience. Bikash Barai spoke about evolving from task management to a philosophy of happiness, integrating mindfulness, gratitude, and awareness into his routine.
- Prioritization: A Key Challenge for CISOs
The discussion highlighted the complexity of prioritizing risks and tasks in cybersecurity. Bikash Barai compared life’s minimalism with cybersecurity’s intricacies, emphasizing risk-based and exploitability-based prioritization. David Cross advocated for standardizing prioritization frameworks to reduce ambiguity, ensuring decisions are fact-based rather than political.
- AI and the Future of Cybersecurity
AI emerged as a pivotal theme for 2025. The panel explored two key AI considerations:
- AI for Security – Leveraging AI to enhance threat detection, automate security operations, and optimize response.
- Security for AI – Integrating robust security development lifecycles for AI systems to mitigate vulnerabilities.
Both speakers stressed the necessity for CISOs to maintain a technical foundation, as understanding AI and its risks is now critical for leadership credibility.
- Networking, Community, and Continuous Learning
The session emphasized building strong professional networks and leveraging communities for shared learning. The speakers encouraged CISOs to prioritize ongoing skill development, aligning with evolving technologies such as AI and quantum computing.
Conclusion: Preparing for the Next Phase of Leadership
The conversation concluded with actionable takeaways for CISOs:
- Invest in mentorship and continuous learning.
- Standardize prioritization processes to manage risks effectively.
- Build resilience through stress management strategies.
- Leverage AI both as a security tool and as a protected asset.
- Focus on collaboration, networking, and contributing to the larger cybersecurity community.
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