For startup founders, cybersecurity often enters the conversation later than it should, usually after a deal stalls, a customer asks hard questions, or an incident forces the issue. But the most resilient companies don’t treat security as a reactive function. They learn early from the people who have already navigated growth, pressure, regulation, and public scrutiny.
This list brings together today’s CISOs alongside security leaders who have moved beyond the role, into executive leadership, investing, entrepreneurship, public policy, and education. Some are actively securing fast-growing platforms right now. Others no longer carry the CISO title but continue to shape how security is built, communicated, and governed at scale. For founders, that distinction matters less than impact. Each of these leaders offers lessons on how security can enable trust, accelerate growth, and protect a company long before it reaches enterprise maturity.
Jason Clinton — Deputy CISO, Anthropic (Current Security Executive)
Currently serving as Deputy CISO at Anthropic, Jason Clinton operates at the frontier of AI security, where safety, governance, and velocity collide. For startup founders, especially those building AI-native companies, his work demonstrates how security leadership must evolve alongside product innovation rather than trail behind it.
Rachel Tobac — CEO, SocialProof Security (Founder & Security Practitioner)
Rachel Tobac is not a traditional CISO, but founders should study her precisely because of that. As CEO of SocialProof Security and a nationally recognized ethical hacker, she exposes how human behavior (not technology alone) creates risk. Her work reminds founders that security culture starts long before a CISO is hired.
Ann Johnson — Corporate Vice President, Microsoft; Former Deputy CISO
Ann Johnson recently transitioned from Deputy CISO to Corporate Vice President at Microsoft, underscoring how modern security leaders increasingly operate at the highest business levels. Founders can learn from her ability to frame cybersecurity as a long-term trust and ecosystem challenge, not a short-term technical fix.
Troy Hunt — Founder & CEO, Have I Been Pwned (Security Builder & Educator)
Troy Hunt has never held a formal CISO title, yet millions, including governments and Fortune 500 companies, rely on what he built. As the founder of Have I Been Pwned, he shows founders how transparency, simplicity, and public trust can become security differentiators at a massive scale.
Yassir Abousselham — Chief Information Security Officer, Calendly (Active CISO)
As CISO of Calendly, Yassir Abousselham secures a product used daily by millions without disrupting usability. His background in product security and go-to-market alignment makes him a model for founders who want security to quietly enable growth, not slow it down.
Rinki Sethi — Chief Security & Strategy Officer, Upwind Security (CISO + Operator)
Rinki Sethi currently holds a CISO-equivalent role while also serving on boards and advising startups. Her career spans enterprise security, M&A, and product leadership, offering founders a rare view into how security decisions shape valuation, acquisitions, and long-term company strategy.
Nicole Perlroth — Founder, Silver Buckshot Ventures; Former NYT Cybersecurity Reporter
Nicole Perlroth is not a CISO, but founders ignore her at their peril. After more than a decade exposing global cyber failures at The New York Times, she now invests in and advises cybersecurity startups. She teaches founders how security incidents look from the outside, especially when regulators, media, and markets are watching.
Shane Barney — Chief Information Security Officer, Keeper Security (Active CISO)
Currently CISO at Keeper Security, Shane Barney previously led security for a major U.S. federal agency. His experience translates well to startups navigating compliance-heavy environments, proving that disciplined security doesn’t have to come at the cost of speed.
Lance Spitzner — Director, Workforce Cybersecurity Training, SANS Institute (Security Culture Leader)
Lance Spitzner has moved beyond the CISO path to focus on what many startups neglect: human risk. His decades of work on security culture show founders why early employee behavior often matters more than early tooling.
Tim McKnight — EVP & Chief Security Officer; Venture Partner (Former CISO Turned Executive & Investor)
Tim McKnight now operates as an executive security leader and venture partner, advising boards and startups alike. For founders, his career illustrates what mature security leadership looks like after the CISO role, deeply tied to governance, growth, and long-term business resilience.
Wendi Whitmore — Chief Security Intelligence Officer, Palo Alto Networks (Security at National Scale)
While not a traditional CISO, Wendi Whitmore’s role places her at the intersection of enterprise security, national policy, and board-level decision-making. Startup founders can learn how cyber risk escalates from technical incidents to existential business and reputational threats.
Why These Voices Matter
The CISO role is evolving, and so is the path that follows it. Many of the most influential security leaders today are no longer confined to a single organization or title; they’re advising boards, shaping policy, building companies, and funding the next generation of security innovation.
For startup founders, that evolution is instructive. It shows that security leadership is not just about defending systems, but about understanding markets, human behavior, regulation, and reputation. Learning from both current CISOs and those who’ve expanded beyond the role offers a broader, more realistic blueprint: one where security is embedded early, communicated clearly, and treated as a long-term business advantage, not a late-stage necessity.