The Strategy Layer Live

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In this episode of The Strategy Layer Live, Steve  sits down with Richard Bird—multi-time CISO, former Chief Customer Information Officer at Ping Identity, author, and current Chief Security Officer at Singulr—for a conversation that pushes beyond conventional cybersecurity narratives.

For the first time on the podcast, an AI digital twin takes an active speaking role, opening the episode with a blunt assessment of where cybersecurity thinking has already fallen behind. From there, the discussion moves into the strategic implications of AI across cybercrime, governance, leadership, and careers.

This episode explores how AI is reshaping the threat landscape faster than most organizations are prepared for, why governance failures are increasingly systemic rather than technical, and what leadership looks like when machines operate at scale and speed. The conversation also turns personal, with reflections on Richard’s book Famous With 12 People and the legacy he hopes to leave behind.

Key Topics Discussed

• AI Digital Twins in Leadership Conversations
  What it means when AI systems don’t just assist—but actively participate in strategic dialogue.
• AI and the Acceleration of Cybercrime
  How attackers are using AI as force multiplication while many organizations reduce human defenders.
• Shadow AI and Unfinished Security Work
  Why decades of unfinished IT and security projects created the conditions for today’s AI risk.
• Governance Failures Are Systemic, Not Technical
  How leadership blind spots—not tooling—are driving AI governance gaps.
• Identity, Access, and Ownership in an AI World
  Why diffuse responsibility leads to no accountability when AI systems act at scale.
• The Future of Consulting and Verified Intelligence
  How AI is reshaping advisory work and exposing performative expertise.
• Career Strategy and Influence
  Insights from Famous With 12 People on building impact through depth, clarity, and relevance.
• Legacy and Leadership
  Richard’s reflections on service, contribution, and what comes next beyond titles and roles.

Insightful Takeaways

• AI rewards preparedness, not optimism.
  Attackers are using AI to move faster and more efficiently; organizations that fail to adapt governance and defenses will see the results in loss curves.
• Shadow AI is a leadership problem before it’s a technology problem.
  Uncontrolled AI use is the predictable outcome of years of tolerated sprawl and unfinished security work.
• Cutting people while attackers scale with AI is a dangerous asymmetry.
  AI augments those who use it strategically—and penalizes those who remove human judgment from critical systems.
• Governance must evolve from policy to ownership.
  When everyone owns identity, risk, or AI outcomes, accountability disappears.
• Impact comes from depth, not scale.
  Leadership, influence, and career growth are built by being meaningful to a few—not visible to everyone.
• Legacy is defined by service, not status.
  The most durable contribution comes from helping others move forward—especially in moments of uncertainty and change.

🎧 Listen to the full episode of The Strategy Layer Live
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In this episode of The Strategy Layer Live, Steve sits down with Bill Kehoe, Chief Information Officer for Washington State, for a rare, wide-ranging conversation recorded in person. Bill reflects on a career spanning state, county, and local government — and the leadership lessons he learned along the way.

From transforming the DMV experience in the early 2000s, to championing digital equity and modernizing resident identity services, to leading with calm resolve in the face of cybersecurity threats, Bill shares what it means to serve with purpose in the digital age.

What We Cover in This Episode

• Bill’s early path into public service and what has kept him committed for decades
• The turning-point projects that shaped his leadership philosophy
• Lessons from running and coaching — discipline, strategy, and individual development
• The bold vision behind digital equity and the Resident Portal
• Modernization without fear: incremental change, customer experience, and agile delivery
• The Resident Portal Challenge and the future of procurement innovation
• Multi-vendor collaboration and why competition can create better outcomes
• The CIO–CISO partnership and shared responsibility for cybersecurity
• Leading through complexity with calm, clarity, and trust
• Bill’s reflections on legacy, public service, and the next generation of leaders
• How AI is reshaping responsibility, decision-making, and efficiency in government

Quote of the Show:

• “I’m the front lines for everything that happens — good or bad — and I consider myself accountable and responsible for everything that goes on in my agency and in technology in the state.” - Bill Kehoe

Links:

• https://watech.wa.gov/
• https://www.linkedin.com/in/william-kehoe-a37a0714b/ 

#PublicSectorLeadership #GovernmentTechnology #CybersecurityLeadership

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In this episode of The Strategy Layer Live, we sit down with one of the most respected and candid voices in cybersecurity today — Jimmy Sanders.

Jimmy is the CISO of Save Mart overseeing more than 200 stores across the West Coast, the former CISO of Netflix DVD, and the current President of ISSA International — giving him a rare, global vantage point on how the role of CISO is being redefined in real time.

But this conversation isn’t just about job titles. It’s about transformation.

Together, Steve and Jimmy dive into how the CISO role is shifting from technician to strategist, why governance frameworks often crumble under real-world politics, and what it takes to lead when budgets are flat, expectations are exponential, and trust is the only currency that matters.

What we cover in this episode:

• Why automation must come before AI — and how to prepare your team for agents
• The hidden costs of being “just the technician” instead of the strategic partner
• The politics of governance and why frameworks often fail without enforcement
• How to measure human-centered risk: burnout, fatigue, and decision friction
• Why trust and presence — not titles — determine whether you get heard at the board level
• The future of the CISO: from risk manager to Chief Trust Officer, or even CIO

Whether you’re leading your first security team or steering global strategy, this episode will challenge you to rethink what leadership looks like when the CISO’s true mandate is to create resilience, not just reduce risk.

Visit www.strategylayer.com for more episodes like this. 

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What does it really take to lead as a modern CISO?

In this episode of The Strategy Layer, Steve sits down with Andy Ellis — former CSO of Akamai, CISO Hall of Fame inductee, and author of How to CISO 1.1 — for a wide-ranging, no-fluff conversation on the future of cybersecurity leadership.

Andy brings clarity, candor, and decades of experience to the table as we explore:

• The core leadership principles behind How to CISO 1.1
• The Zero Trust paradox — and how it’s creating more confusion than clarity
• Why the next-gen CISO might not be who you expect
• How to lead with presence — in the boardroom, and in the moments that matter most

Whether you’re new to the role or a seasoned executive, this episode is packed with insights to elevate your mindset, sharpen your strategy, and lead with intention.

Listen now and rethink what it means to be a CISO today — and tomorrow.

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In Episode 2 of The Strategy Layer Live, we dig into one of the most urgent — and least acknowledged — leadership challenges in cybersecurity today.

The CISO role isn’t dying. But it is being slowly redefined, compressed, and undermined by structural misalignment, rising board expectations, and misused metrics. What one security executive called the “co-morbid poisoning” of the role has become a shared, often unspoken reality for many cybersecurity leaders — especially those navigating the tension between visibility and actual control.

In this episode, host Steve Tout, Founder & CEO of Identient, sits down with Steve Zalewski, former CISO of Levi Strauss & Co., trusted advisor, and respected voice in the cybersecurity leadership community. Together, they unpack how the CISO role is being reshaped — not by failure, but by a system that was never built to support sustainable, high-impact security leadership in the first place.

📌 What we cover in this episode:

• The origins of the term co-morbid poisoning and why it resonates now more than ever
• How modern CISOs are over-indexed on responsibility and under-indexed on authority
• The role of frameworks, dashboards, and performance theater in eroding trust
• What aspiring and seasoned CISOs alike need to understand about governance drift
• How Strategic Performance Intelligence (SPI) can anchor the next evolution of security leadership
• Reflections on RSA Conference and how many “leadership” panels are missing the real conversation

This conversation directly inspired a chapter in Steve Tout’s upcoming book,
 The CISO On The Razor’s Edge: Leading Cybersecurity When the System Is Designed to Break — launching June 2 on Amazon.

🎯 Whether you’re a CISO, CIO, or cybersecurity executive navigating the shifting expectations of your role — or you're simply trying to lead with more clarity in an increasingly fragmented environment — this episode will give you language, perspective, and energy for what’s next.

📘 Pre-order the book or download a free chapter: https://tout.media
🧠 Join the SPI 360 Executive Circle: https://www.identient.ai/slack
🌐 Learn more: https://identient.ai

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In the premiere episode of The Identient Podcast, Steve Tout sits down with Mark Settle, a seven-time CIO and author of Truth from the Trenches, to explore the dual-edged power of metrics in IT leadership. Mark shares how metrics, when mismanaged, become "loaded weapons" that create unintended consequences—but when designed thoughtfully, they drive alignment, continuous improvement, and strategic impact. They delve into fostering security culture, balancing operational excellence with strategic initiatives, and avoiding the pitfalls of typecasting. Tune in for actionable insights that redefine how CIOs and CISOs approach Identity and Access Management and IT leadership.

Key Takeaways

• CIOs must design metrics that align with business goals
• Behavioral metrics can lead to unanticipated consequences
• A culture of continuous improvement is essential for IT success
• Security culture starts within the IT organization
• Aggregate metrics can obscure individual contributions
• CIOs need to balance operational efficiency with strategic initiatives
• Understanding customer perspectives is crucial for effective IT management
• Expectations for IT performance are continually rising
• Metrics should evolve with changing business conditions
• Building relationships across departments enhances IT effectiveness
• Street credibility increases with hands-on involvement
• Echo chambers can help assess team alignment
• Cultural alignment is crucial for cybersecurity initiatives
• CIOs play a vital role in cybersecurity budgeting
• Risk profiles dictate cybersecurity priorities
• A Chief Identity Officer may not be necessary
• Self-assessment is key for tech leaders' success
• Technical skills may atrophy in leadership roles
• Accountability is essential for team morale
• Learning from failures can drive personal growth

Episode Chapters

1. Introduction to the Conversation
2. The Role of Metrics in IT Management
3. Dynamic Metrics and Behavioral Change
4. Creating a Culture of Continuous Improvement
5. The Importance of Security Culture
6. Balancing Business Value and Employee Satisfaction
7. Political Skills for CIOs
8. Building Relationships and Understanding Needs
9. Navigating the Echo Chamber: Internal vs External Perspectives
10. Managing Identity and Access Management (IAM) at Okta
11. Cultural Alignment and Support in Cybersecurity
12. The Role of CIOs in Cybersecurity Budgeting
13. The Case for a Chief Identity Officer
14. Self-Assessment for Tech Leaders: Avoiding Typecasting
15. Learning from Failures: The Importance of Accountability

For show notes and more episodes, visit www.identient.ai/podcast