Advertise on podcast: The Virtual CISO Moment

In this episode of The Virtual CISO Moment, Greg Schaffer welcomes Travis Stein, a security engineer whose journey from IT help desk to leading enterprise security programs offers valuable lessons for cybersecurity professionals at every stage of their careers. Travis shares how burnout led him to pursue cybersecurity, why a strong IT foundation remains invaluable, and how networking on LinkedIn opened doors that traditional job searching could not. The conversation also explores leading security as a team of one, transitioning from technical expert to leader, and practical strategies for avoiding burnout while building a rewarding career. Whether you're looking to break into cybersecurity or grow into a leadership role, this episode is packed with practical advice and real-world insights from someone who has successfully navigated both paths.

In this episode of The Virtual CISO Moment, Greg Schaffer welcomes cybersecurity veteran, consultant, author, podcaster, and private pilot Andrew Kalat for a wide-ranging discussion spanning more than three decades in information security. Andrew shares his journey from the early days of bulletin board systems and managed security services to leadership roles at organizations including Check Point, U.S. Bank, and SalesLoft, along with the lessons learned from both successes and failures along the way. The conversation takes an unexpected and fascinating turn into aviation, as Greg and Andrew explore the many parallels between flying and cybersecurity. Together, they discuss risk management, incident response, checklists, decision-making under pressure, and what the cybersecurity profession can learn from aviation's mature safety culture. They also examine the realities of security leadership, the challenges of sharing lessons learned from breaches, the importance of preparation before a crisis occurs, and the ongoing struggle to maintain balance and avoid burnout in a demanding profession. Whether you're a security practitioner, consultant, aspiring CISO, or simply interested in leadership and risk, this episode offers practical insights and thoughtful perspectives from a seasoned industry leader who has spent decades helping organizations navigate cybersecurity challenges.

In this episode of The Virtual CISO Moment, Greg Schaffer welcomes Bruno Lecoq, Co-Founder, CEO, and CISO of BEMO, for a wide-ranging conversation on Microsoft's evolving security ecosystem, CMMC compliance, and the realities of securing small and midsized businesses. Drawing on nearly two decades at Microsoft and years leading an award-winning cybersecurity firm, Bruno shares insights on the rapid pace of AI innovation, why SMBs must carefully vet their technology partners, and the hidden risks organizations face when pursuing compliance without truly embracing security. The discussion also explores CMMC requirements, Microsoft security capabilities, and the importance of building trust-based relationships with clients. Bruno also reflects on his remarkable journey from France to Microsoft, the future of AI governance, and how a lifelong passion for football (soccer) helps him stay balanced in an ever-changing industry. A thoughtful conversation packed with practical advice for cybersecurity leaders, MSPs, and business executives alike.

In S8E22, Greg Schaffer sits down with Alan Clinard, founder of Athena vCISO Services, to explore what it really means to be a trusted security advisor. Drawing from a career that spans the U.S. Army, operational risk consulting, banking, critical infrastructure, and virtual CISO services, Alan shares how understanding the business—not just the technology—is the key to effective cybersecurity leadership. The conversation dives into translating cyber risk into business language, the challenges of moving from technical expert to consultant, and why humility and relationship-building are often more important than technical knowledge when influencing organizations. Alan also discusses entrepreneurship, mentoring the next generation of security leaders, and helping clients become self-sufficient rather than dependent on outside advisors. Whether you're a security practitioner aspiring to leadership, a current vCISO, or a business executive trying to bridge the gap between security and business objectives, this episode offers practical insights on governance, risk management, consulting, and building security programs that truly support organizational success.

Cy Sturdivant returns to the Virtual CISO Moment to share lessons from more than two decades in cybersecurity, financial services, and consulting. The conversation explores the importance of professional relationships, security program maturity, AI adoption in banking, and why organizations that focus solely on compliance often struggle to improve their overall security posture. Cy also discusses the concept of TEA—Time, Energy, and Attention—and why protecting these limited resources is critical for long-term success in both cybersecurity and life. Along the way, he offers practical advice for professionals looking to grow their careers, adapt to constant change, and maintain balance in a demanding industry. If you're a cybersecurity leader, aspiring consultant, community banking professional, or simply looking for practical advice on balancing career success with personal fulfillment, this episode offers actionable insights, thoughtful perspective, and plenty of wisdom from someone who has spent decades helping organizations navigate risk and change.

In this episode of The Virtual CISO Moment, Greg Schaffer sits down with cybersecurity leader and Cyber Risk Navigator founder Becky MacDonald to discuss the evolution of cybersecurity leadership, the realities of virtual CISO work, and why effective security programs must be built around risk—not just compliance checklists. Drawing from decades of experience across healthcare, higher education, and nonprofit organizations, Becky shares practical insights into building mature cybersecurity programs with limited budgets, communicating risk to leadership, and avoiding common traps like tool sprawl and “checkbox security.” Greg and Becky also explore the growing virtual CISO space, including what separates strong vCISO leadership from superficial security consulting. The conversation covers the importance of business communication skills, balancing technical and strategic perspectives, and the challenges organizations face when trying to operationalize security in real-world environments. Becky also offers candid perspectives on entrepreneurship, cybersecurity burnout, and the realities of building a boutique advisory practice. Whether you are an aspiring vCISO, a cybersecurity practitioner, or a business leader trying to better understand risk and resilience, this episode delivers practical insights grounded in real-world experience.

In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Jonathan Weaver to discuss the evolving role of governance, risk, and compliance in today’s cybersecurity landscape. Jonathan shares his journey from the University of Tennessee into cybersecurity consulting, the lessons he learned building ProInsight, and why trust and relationships are often the most valuable assets in security consulting. The conversation also explores practical risk management, the challenges organizations face in understanding cybersecurity beyond compliance checklists, and the importance of breaking down silos between business and security teams. Beyond cybersecurity, Jonathan opens up about his nonprofit initiative, Reindeer for Hope, which provides gifts and support to underprivileged children and families across Middle Tennessee. Listeners should tune in for an insightful mix of cybersecurity leadership, entrepreneurship, community impact, and personal perspective from someone who is passionate about helping both organizations and people become more resilient.

In this episode, Jackie Shoback—Co-Founder of 1414 Ventures and seasoned C-suite leader—joins Greg to explore how cybersecurity has evolved from a back-office IT function into a core business strategy. Drawing on decades of experience across enterprise and financial services, Jackie breaks down why digital identity and trust are now at the center of modern security, and how organizations must rethink data as both an asset and a risk. The conversation dives into the growing importance of identity-driven security, the shortcomings of current privacy practices, and the role of boards and executives in building a true culture of security—not just checking compliance boxes. With insights on emerging threats, AI, and the future of digital trust, this episode offers a strategic lens for leaders navigating today’s rapidly evolving cyber landscape.

At the 2026 Middle Tennessee ISACA conference I had the chance to sit down for short chats with a few information security pros: India James, who spoke on the importance of security and digital trust at the conference; Ken Smith, Director of Sales Engineering Enterprise for the Great Lakes at Arctic Wolf; and Jonathan Weaver, Partner at ProNsight's Risk and Compliance Consulting Practice.

Rich Bates shares a candid look at his 30+ year journey into cybersecurity, from early computing days to leading GRC programs and now building his own advisory practice focused on helping organizations tackle CMMC and compliance challenges. Along the way, he breaks down why these frameworks matter, the real risks businesses face if they ignore them, and how to approach security in a practical, business-focused way. Listeners will get valuable insights into navigating regulatory complexity, making smart risk decisions, and what it really takes to succeed as a cybersecurity leader or consultant. Whether you're a business owner facing CMMC requirements or a security professional looking to sharpen your approach, this episode offers real-world perspective without the fluff

What does it really take to evolve into a modern vCISO—and why does it matter more than ever? In this episode, Joseph Gunnells shares his journey from early technical roles to a strategic governance, risk, and compliance leader, revealing how real-world experience—not just certifications—shapes effective security leadership. He breaks down the biggest challenges organizations face when engaging a vCISO, why empathy and business alignment are critical, and how strong relationships can define both career success and cybersecurity outcomes. Whether you're an IT leader, aspiring vCISO, or business executive trying to make sense of security risk, this conversation offers practical insights you can immediately apply to better align security with business value—and avoid the common pitfalls many organizations still struggle with today.

From firefighter aspirations to securing the defense industrial base—this episode of The Virtual CISO Moment dives into a career path that didn’t follow the plan… and turned out better because of it. Robert Duchesne shares how a pivot from the Air Force into cybersecurity led him to supporting national security missions, leading enterprise security operations, and ultimately launching RD3 Technologies. Along the way, he breaks down the realities of building a cybersecurity business, the difference between government and corporate risk mindsets, and why passion—not paychecks—has to be the driving force in this field. We also get into what it really takes to succeed in cybersecurity today: constant learning, understanding the business, and becoming a trusted advisor—not just a technical expert. If you’re navigating your own path in cybersecurity or thinking about starting something of your own, this is an episode you won’t want to miss.

In this episode of The Virtual CISO Moment, Jason Makevich shares his journey from MSP roots to building Greenlight Cyber and PORT1, along with his mission to simplify cybersecurity for SMBs. He unpacks the problem of “duct tape on duct tape” security—where too many tools create complexity without real protection—and makes the case for a secure-by-design, zero trust approach. The conversation also covers how SMBs can shift from reactive to proactive security and why translating cyber risk into business terms is critical. Jason closes with his perspective on the evolving MSP landscape, warning against chasing trends like AI at the expense of foundational security, and emphasizing the importance of balance in a high-stress industry.

Most cybersecurity professionals don’t have a talent problem—they have a visibility problem. In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Angelle Ferrer to unpack why even highly qualified professionals are struggling to get noticed in today’s AI-driven job market. From ghosting and overloaded applicant systems to the hidden power of personal branding and storytelling, Angelle shares practical strategies to help you stand out, communicate your value, and actually get hired. If you’ve ever felt invisible despite your experience—or wondered why sending hundreds of resumes isn’t working—this conversation will change how you approach your career.

Cybersecurity isn’t just about technology—it’s about mindset, risk, and understanding where organizations are truly vulnerable. In this episode of The Virtual CISO Moment, host Greg Schaffer sits down with cyber threat intelligence professional Travis Whitesel to explore the evolving intersection of military intelligence, cybersecurity, and emerging risks in unexpected places like the sports industry. Travis shares how his journey from Army intelligence analyst to cyber warfare technician shaped his approach to cybersecurity—and how that perspective led him to launch Victory Cybersecurity Consulting to help underserved sectors strengthen their defenses within real-world budget constraints. From the growing risks around NIL deals for college athletes to the challenge small organizations face in prioritizing security investments, the conversation highlights practical ways to think about cyber risk without enterprise-level resources. The episode also dives into the realities of nation-state threats, why process often matters more than technology, and how cybersecurity professionals can avoid burnout in a high-pressure field. It’s a candid discussion about bridging strategy and tactics, communicating cyber risk in language executives understand, and finding balance while working in one of the most demanding industries today. Tune in to hear how one cyber professional is helping organizations—from universities to sports programs—build smarter security strategies in an increasingly complex threat landscape.