Inside the CISO Mind: Trust, Culture, AI, and the Sales Moves That Backfire
March 17, 2026
In this episode of the Cult Products Podcast from Yaya, host Phill Keaney-Bolland speaks with Ryan Lindley, Co-Founder and CEO of Aegis Cyber and former CISO. They discuss what CISOs experience every day, from role ambiguity and internal tension to compliance fatigue and becoming the “Department of AI.” Ryan shares what earns trust with security leaders, how to build security culture through influence, and what vendors do that instantly gets them blocked.
Every security product either lightens a CISO’s load or quietly adds to it. Ryan Lindley has seen that reality from every angle, from early hacker curiosity to years inside startups and enterprises, and ultimately from the CISO seat itself, where tension, politics, and personal risk are part of the job. His perspective comes from living with the consequences of security decisions, not just designing or selling tools around them.
In this episode of the Cult Products Podcast from Yaya, host Phill Keaney-Bolland speaks with Ryan Lindley, Co-Founder and CEO of Aegis Cyber and former CISO. They talk through why the CISO position is still evolving, how reporting structures and culture shape outcomes, and why influence and people skills matter as much as technical depth. Ryan also shares what earns his trust as a buyer, what design partnerships look like when they truly work, and the kinds of sales behavior that shut doors fast. Underneath it all is a clear message for builders and sellers: listen carefully, respect the human realities within organizations, and build relationships meant to last.
What You’ll Learn:
In this episode of the Cult Products Podcast from Yaya, host Phill Keaney-Bolland speaks with Ryan Lindley, Co-Founder and CEO of Aegis Cyber and former CISO. They talk through why the CISO position is still evolving, how reporting structures and culture shape outcomes, and why influence and people skills matter as much as technical depth. Ryan also shares what earns his trust as a buyer, what design partnerships look like when they truly work, and the kinds of sales behavior that shut doors fast. Underneath it all is a clear message for builders and sellers: listen carefully, respect the human realities within organizations, and build relationships meant to last.
What You’ll Learn:
- Why the CISO role still carries ambiguity and how that impacts decision-making
- How CISOs reduce internal tension through culture, influence, and security champions
- What founders miss about “security friction” and engineer context-switching
- What a “control plane” for governance can unlock across GRC, risk, and compliance
- Why so much compliance evidence fails the “reality test,” and what better looks like
- How CISOs should approach AI adoption, governance, and downstream liability
- What good design partnerships look like when value flows both ways
- How to earn a CISO’s trust in sales and what gets vendors ignored or blocked
Episode Resources:
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