In this episode of Cyber Security Matters, hosts Harry Baldwin and Matt Rose are joined by Alfredo Hickman, Chief Information Security Officer at Kai.
Alfredo discusses his journey from a 1990s fascination with early internet technology, through infantry service in the US Marine Corps, national security roles, and nearly eight years building the security organisation at Obsidian Security, to his current role at Kai. The conversation explores why AI is fundamentally reshaping the balance between attackers and defenders, what needs to happen before organisations can hand more autonomy to AI in security operations, and whether the industry is heading toward a genuinely new security operating model rather than another generation of point solutions.
Alfredo also shares his thinking on what separates the best cybersecurity professionals, the mentors who shaped his career, and the achievement he is most proud of.
Key Topics Covered
- Alfredo’s path into cybersecurity through 1990s internet and hardware culture
- Serving as a Marine Corps infantry sergeant in counterterrorism after 9/11
- The mentors who shaped his career, including his mother and Dmitri Alperovitch
- Rising from individual contributor to CISO in one continuous run at Obsidian Security
- Why he joined Kai to help build autonomous defence for security teams
- What separates the best cybersecurity professionals from the rest
- How AI is changing the role and required skill set of security professionals
- Kai’s mission to give defenders an asymmetric advantage through autonomous defence
- The structural imbalance between AI-augmented attackers and resource-constrained defenders
- What’s needed – governance, guardrails, and a “trust fabric” – before AI can safely take autonomous security actions
- Emerging AI governance standards, including ISO/IEC 42001 and Cloud Security Alliance guidance
- Whether the future of security is a new operating model or another generation of point solutions
- His five-year prediction that at least 60% of manual security work will be automated
- The career achievement he describes as his proudest moment
- His advice for people entering cybersecurity: get comfortable being uncomfortable
About Alfredo Hickman
Alfredo Hickman is Chief Information Security Officer at Kai, an agentic AI cybersecurity platform built to help defenders execute security work at machine speed. Founded by Galina Antova (co-founder of Claroty) and Dr Damiano Bolzoni (co-founder of SecurityMatters), Kai emerged from stealth with $125 million in funding to build autonomous defence capabilities for enterprise security teams.
Before joining Kai, Alfredo spent close to eight years at Obsidian Security, rising from an individual contributor to Chief Information Security Officer and building the company’s security organisation from its earliest days. Earlier in his career, he led security product engineering at Rackspace Managed Security, and held roles at the Center for Strategic and International Studies and the US Department of Defence. Alfredo’s path into technology began in the early-to-mid 1990s, teaching himself to code and reverse-engineer software. That early interest was interrupted, and ultimately redirected, by his decision to enlist in the US Marine Corps as an infantry sergeant following the September 11th attacks, where he was later exposed to cyber operations in a national security and counterterrorism context.
His work today sits at the intersection of cybersecurity leadership and AI governance, with a focus on helping organisations safely realise the benefits of autonomous, AI-driven defence.
This episode is brought to you by neuco.
