HeyJaredClimbing the Stack
How do you go from Director to CIO? Host Matt Peters, CEO of Fixify, sits down with IT executives who've made the climb to unpack the pivotal decisions, career-defining moments, and hard-won lessons that got them there.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Sep 1, 2026
- Audience
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- Earliest in this view
- Jul 7, 2026
Latest episodes
Every AI agent is an identity: a CISO's security sequence | Kaarthick Subramanian (opens the original)
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Kaarthick Subramanian says AI initiatives rarely fail on model quality. They fail on foundations, governance, and adoption. Now Chief Customer Officer and CISO at Atlas Systems, he treats every AI agent as an identity that needs access, monitoring, and a SOC. He walks Matt through turning technology risk into business risk, why a partner wants the customer to win, and how shedding fear of a job title frees you to build a craft. Across his career, the real work was always the business problem beh
Why machines should stay in service of humans as AI goes always-on | Tope Iluyomade (opens the original)
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Tope Iluyomade thinks the job of a CIO and CISO is to teach companies how to do dangerous things carefully. He came up through defense and aviation, where errors get measured in body count, then fintech, where velocity is prime but velocity is blind. That range is why he does not ask whether the glass is half full or half empty. He asks whether the glass has a handle, since policies exist to throttle how fast new technology enters a business so leaders can keep a grip on it. As former CIO and CI
From engineer to C-suite: why financial fluency and storytelling separate real executives | Matthew Sharp (opens the original)
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Matthew Sharp came up as a computer and electrical engineer, moved through independent testing and audit work, and then took a sales role he was convinced would be the devil's work. Four years selling specialized security services taught him the opposite. He often walked into meetings knowing more about a client's business than the CISO across the table did, down to how they segmented revenue on their financial statements. Now CISO at Xactly and co-author of The CISO Evolution, his argument in t
A CEO sorted every employee into three AI buckets. Where would your team land? | Fred Bret-Mounet (opens the original)
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Fred Bret-Mounet , VP of Security, Compliance and IT / CISO at Accela, started his security career in 2001 at @stake, one of the handful of firms that invented security consulting. He was excellent at building Fort Knox. When he moved to the receiving end of those consulting reports, he realized recommending Fort Knox at all cost was the worst advice he could give. The framework he uses instead is the California speed limit. The sign says 65 or 75, but drive 85 without brandishing a gun or threa
CIO vs. CISO: Resolving the ROI-versus-risk conflict when you hold both | Georgeo Pulikkathara (opens the original)
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When Georgeo X. Pulikkathara joined iMerit Technology as CISO, the role came with infrastructure responsibility attached. His solution was to take the CIO title too and fund security controls directly from that budget. It's a structure he'd spent years viewing as a conflict of interest (CIO manages toward ROI, CISO manages toward risk), and this episode is his case for when it works. He also lays out how he presents security budget to boards: tied to specific revenue deals, never to abstract ris
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