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.