KBKAST

KB is on the ground at SAP Sapphire 2026 in Orlando, where AI has moved beyond experimentation and into the center of enterprise decision making. In this KB On The Go episode, Maura Hameroff (CMO, Cloud ERP Private and RISE with SAP) makes the case that modernizing your core is a business transformation decision rather than a technical upgrade, and that companies still running on legacy systems carry more operational and security risk than most realize.

Then Ted Way, PhD (VP & Chief Product Officer, Business AI Product Engineering, SAP) walks through what responsible enterprise AI actually takes: a governance layer, real business process knowledge, and data you can trust. As he puts it, AI first without security first is just a faster way to a data breach. A grounded look at what it takes to move from AI pilots to AI at scale without cutting corners that come back to bite you.

In this episode, Anna Wheeler, CEO of SSAW LLC, joins KB as she explains why so many cyber teams are stuck in event-driven strategy while calling it the real thing, why the doers can’t climb out of it because their KPIs won’t let them, and why visionary CEOs keep getting ousted when the board can’t see what they see. Along the way: the CEOs quietly burning more AI tokens than anyone else in their company, vendors winning unicorn exits on marketing rather than technology, adversaries stealing encrypted data as a long game, and what happens when boards start making decisions on synthetic confidence.

Her closing advice for leaders: get very comfortable with being uncomfortable, and go looking for the sources you’d normally avoid.

About Anna:
Anna Wheeler is a cybersecurity strategist and former Army Blackhawk crew chief who has spent the last two decades helping government and industry modernize how they secure missions, data, and critical infrastructure. She has led federal modernization and cyber campaigns across DHS and the wider national security community, shaping multi‑billion‑dollar technology portfolios and advancing cloud, Zero Trust, and AI‑driven approaches to resilience. As CEO of SSAW LLC and a trusted advisor to C‑suites, boards, and policymakers, Anna is known for turning buzzword-heavy innovation into pragmatic, mission‑aligned change. She serves on multiple advisory boards, mentors rising cyber leaders, and speaks frequently on moving from “FOMO to focus” in cybersecurity innovation.

Keywords: AI strategy, CISO, board of directors, CEO, cybersecurity leadership, event-driven strategy, strategic thinking, synthetic confidence, AI bias, go-to-market, vendor marketing, Symantec, SBOM, harvest now decrypt later, cybersecurity podcast

Recorded at Cisco Live 2026 in Las Vegas, where 20,000 operators, engineers and executives gathered at Mandalay Bay to shape the future of networking, AI and cybersecurity. KB sits down with two Cisco leaders confronting the problems AI is creating and the infrastructure built to outlast them. Tom Gillis, SVP and GM of Cisco’s Infrastructure and Security Group, explains why the gap between a vulnerability being disclosed and exploited has collapsed from months to hours, and how Live Protect shields critical flaws between patches with no reboot and no downtime. Then Ramana Kompella, Head of Cisco Research and Cisco Fellow, makes the case for quantum networking over ever bigger quantum computers, unpacks the new Universal Quantum Switch, and explains why “harvest now, decrypt later” makes quantum safe infrastructure a today decision, not a 2029 one.

Key topics: AI accelerated exploitation, vulnerability shielding and Live Protect, continuous infrastructure updates and digital twins, quantum networking, the Universal Quantum Switch, post quantum cryptography and CNSA 2.0, and the harvest now decrypt later threat.

John leads customer success, presales, and professional services across APAC at Workato and serves as Field CTO for the region. With more than twenty-five years of experience, including roles at Oracle and TIBCO and as co-founder of Rubicon Red, he focuses on helping enterprises unlock real, lasting value from AI and integration.

In this episode of KBKast, John joins KB to unpack why 42% of AI initiatives were abandoned in 2025, up from 17% the year before, and why the answer isn’t the technology. It’s trust.

John explains why AI is a bigger deal than cloud ever was: what used to be storage and processing is now decision and action inside core enterprise systems. He takes aim at “governance theater,” the steering committees and policy documents that create a feeling of control while nobody can actually see what an agent is doing. And he lands the warning every security leader needs to hear: you got away with over-provisioning access for humans, because humans never went looking. Agents will.

Also covered: the tokenomics panic, 700% month-on-month cost blowouts, why AI shouldn’t re-map a purchase order every single time, who owns the agent when things go wrong, and why a central control plane is the only way to govern agents at scale.

Keywords: AI agents, agentic AI, AI governance, governance theater, enterprise AI, AI security, control plane, observability, MCP, tokenomics, AI cost management, AI strategy, CISO, agent permissions, Workato, shadow AI, AI ROI, autonomous agents

KB grabs the mic backstage at SPHERE 2026 by Atmos for two conversations that sit on either end of the same problem: how leaders should be thinking about risk in an unstable world, and what it actually looks like when a sector has been living that instability for years.

First up, KB sits down with Chris Krebs, former Director of the U.S. Cybersecurity and Infrastructure Security Agency (CISA). They get into the CISA cuts making headlines, why old assumptions baked into risk registers no longer hold, and the five cracks Chris sees forming in the foundation of modern risk management. He also breaks down why boards need to push vendors harder on third-party risk, and why cyber has become the opening move in every modern conflict.

Then Tom Huth, Specialist in Energy Market Cyber Incident Coordination at AEMO, and Ryan McLaren, co-founder and COO of Retrospect Labs, bring it back to ground level. They unpack why the energy sector’s tight-knit supply chain has made it a genuine leader in cyber resilience, the difference between a tabletop exercise and a full functional simulation, and the trust problem nobody’s fully solved: how do you verify who’s really on the other end of the phone when your systems go down? A grounded look at what it takes to build real muscle memory before the bad day arrives.