The Virtual CISO Moment
The Virtual CISO Moment dives into the stories of information security, information technology, and risk management pros; what drives them and what makes them successful while helping small and midsized business (SMB) security needs. No frills, no glamour, no transparent whiteboard text, no complex graphics, and no script - just honest discussion of SMB information security risk issues. Brought to you by vCISO Services, LLC, a leading provider of vCISO and information security risk management services. Visit https://vcisoservices.com to learn more. A Second Chance Publishing, LLC podcast.
Episodes
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 sea...
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 w...
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 mu...
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 conversatio...
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, Ener...
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, B...
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 conversa...
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 ass...
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 g...
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 empath...
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 w...
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...
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 pra...
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...
Cybersecurity leaders often struggle to translate technical risk into something the business actually understands. In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Jack Rumbaugh, an experienced CISO and virtual CISO with a background spanning telecommunications, healthcare, finance, and global enterprises.
Jack shares how security leaders can communicate cyber risk in the language executives understand—...
Jeremy Krienke, founder and CEO of Sidewalk Security Advisors, shares his journey from early threat intelligence work alongside federal partners to leading security programs in banking and fintech—and ultimately launching his own advisory firm.
In this episode, Jeremy and Greg explore what it really means to serve as a fractional CISO, how to uncover and align to a company’s true risk appetite, and why many organization...
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Chris Kimpland, CEO of Velocity Incident Response, a service-disabled veteran-owned firm specializing in digital forensics and incident response
A former U.S. Army combat engineer, Chris has led hundreds of ransomware negotiations and brings a candid, frontline perspective to what unfolds during an active breach. He shares why negotiation is often more busines...
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with cybersecurity architect Dr. Natalia Semenova for a deep dive into the evolving world of AI risk and security architecture
With a Ph.D. in applied mathematics and experience spanning Google, Microsoft, Mercedes-Benz, and Deloitte, Natalia shares how her mathematical mindset shapes her approach to threat modeling, agentic AI, and governance frameworks. The conve...
What does real security maturity actually look like—beyond checklists and audits?
In this episode of The Virtual CISO Moment, Greg Schaffer sits down with Mariia Erokhina, a global security leader who challenges the industry’s obsession with controls and compliance theater. Mariia shares why security must be embedded into business operations, how executives misunderstand risk ownership, and what aspiring CISOs must learn...
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