New: Path to Becoming a vCISO Hub

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Greg Schaffer

Founder of vCISO Services

The signature vCISO interview series features top security leaders, inspiring service providers with guidance on starting and scaling their vCISO practices. Packed with expertise and personal stories, these conversations help elevate your vCISO journey.

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In this interview, Greg Schaffer, founder of vCISO Services, explores the rising demand for virtual CISOs (vCISOs) and why small and mid-sized businesses are turning to them for stronger security. He covers how vCISOs support various industries, build lasting client relationships, and debunk common misconceptions. You’ll also gain insights into key challenges, overcoming resistance to change, and establishing yourself as a trusted security advisor. 

The best virtual CISOs don’t just tell clients what they want to hear—they tell them what they need to hear. That honesty and focus on true risk management is what sets us apart.

Why Watch

  1. Why do small and mid-sized businesses need a virtual CISO, and how has the demand for vCISO services evolved over time?
  2. How can you approach working with clients across various industries, and what is the importance of long-term relationships in building effective security programs?
  3. What are common misconceptions about hiring a virtual CISO, and what sets successful vCISOs apart from purely technical security providers?
  4. What challenges do virtual CISOs face, and how can they overcome resistance to change and establish themselves as trusted advisors?
  5. How can aspiring virtual CISOs or MSSPs succeed in this field, and what qualities and skills should they focus on to build a successful practice?

About Greg Schaffer

Greg is a seasoned information security executive proficient in Information security management, vendor risk, policy implementation, and business continuity. He is the founding principal of vCISO Services, LLC, an information security consulting firm providing small and midsized businesses with strategic information security expertise. He hosts The Virtual CISO Moment podcast, is the author of the bestselling book Information Security for Small and Midsized Businesses, and has spoken at numerous conferences over 20-plus years.

About the Path to Becoming a vCISO

The Path to Becoming a vCISO is a curated collection of insights from some of the most respected voices in the virtual CISO space. Through in-depth interviews, these industry leaders share their journeys, challenges, and hard-earned lessons on building and scaling successful vCISO practices. The hub offers practical tips, real-world strategies, and proven advice to help service providers scale effectively, differentiate their services, and deliver measurable value to clients.

At Cynomi, we’re committed to supporting the growth of the vCISO community. This hub is our way of spotlighting the people shaping the future of cybersecurity leadership—and providing valuable guidance for MSPs, MSSPs, and aspiring vCISOs looking to elevate their services.