Every CISO is getting the same question from the CFO and CIO right now: should we go all-in on AI? 

Roland Cloutier sits down with Poonacha Kongetira, CEO of Classie AI and former Google and NVIDIA infrastructure leader, to break down token economics for security leaders who need to speak fluently in the CFO and CIO conversation, without becoming pricing analysts.

They cover how input, output, cached, and reasoning tokens actually work, why output tokens cost more than input, and why context - the thing that improves an answer's quality - is also the thing that quietly drives up cost and risk. 

They dig into when a workflow belongs in deterministic automation versus a model, how agentic workflows can spiral into expensive reasoning loops if nobody's watching the meter, and what real FinOps for AI looks like now that "tokenmaxxing" has stopped being a strategy.

The conversation lands on something every security leader can use this week: the three numbers to ask your team for before you sit down with the CFO and CIO.

#ShiftToAI #Cybersecurity #CISO #Tokenomics #AgenticSecurity

Most CISOs think their legacy is the program they built. They're wrong.

In this episode of Shift to AI presented by Cycode, host Roland Cloutier sits down with Stephen Ward - former CISO, board member, and cybersecurity investor - to unpack what it takes to lead security through the AI generation, and what most leaders are getting wrong about their own legacy.

Stephen has sat in every seat at the table: as an operational CISO rebuilding programs under pressure, as a board member seeing security from the other side of the table, and now as an investor watching the market decide what gets built next. He and Roland dig into what boards actually expect from security leaders that most CISOs still aren't delivering, why storytelling and executive presence now matter as much as technical depth, and why the best leaders are the ones building successors who can replace them - not protecting their own seat.

This isn't a conversation about tools or technology. It's about the leadership system every security executive needs to be building right now, before the next shift arrives.

If you're a security leader thinking about your own legacy - or how to build the next generation of leaders under you - this one's for you.

Machines used to be the predictable part of security. Not anymore. In this episode of Shift to AI, host Roland Cloutier sits down with Alex Levy, Chief Security Officer at BNSF Railway, to unpack why static playbooks can't keep pace with AI-driven change - and why frameworks, not fixed playbooks, are what security leaders need instead.

Alex brings a rare vantage point: defending one of the critical infrastructure systems the U.S. economy runs on, where the stakes go far beyond a single company. He and Roland dig into why vulnerability management is buckling under AI-driven speed, and what it actually takes to secure a software supply chain that now includes models, agents, and prompts as first-class risks.

If you're rethinking how your organization defends critical infrastructure in the age of agentic AI, this one's for you.

*This episode was recorded live at Black Hat USA 2026, so expect some background noise from the event

The decade-long promise of "shift left" never delivered. Developers didn't become security engineers - and now the developer is often an agent.

In this episode of Shift to AI, host Roland Cloutier sits down with Bret Arsenault, CVP, CISO Emeritus and Global Chief Security Advisor at Microsoft, to unpack what happens when the perimeter moves from the app and the endpoint to the software factory itself: prompts, pipelines, MCP servers, and non-human identities.

Together they ask a question every security leader is now facing: what does AppSec actually mean when the entity writing, reviewing, and committing code isn't human? And what does it take to secure a software development lifecycle that never sleeps?

A candid, practitioner-level conversation on the future of application security, software supply chain risk, and agentic development - from two of the industry's most experienced security voices.

🎧 Listen now, and subscribe to Shift to AI for unfiltered conversations with the world's leading CISOs on the shift to agentic security.