Jesse Miller

In this interview, Jesse Miller, founder of PowerPSA Consulting and the PowerGRYD vCISO system, shares insights into scaling vCISO programs profitably, building operational models for success, and the importance of aligning security strategies with business outcomes. Through his expertise, Jesse highlights the challenges, opportunities, and evolution of the vCISO landscape, offering actionable advice for MSPs aiming to differentiate and thrive in the competitive cybersecurity market.

Security isn’t about perfection—it’s about balancing risk tolerance, budget, and business goals. You need to prioritize “good enough” security measures that deliver maximum impact without overburdening clients financially or operationally.

Why Watch

1. Why should MSPs consider offering vCISO services, and what prompted the shift toward this model in the cybersecurity landscape?
2. How can you adapt your messaging to make vCISO services resonate with clients by connecting security to business goals and desired outcomes?
3. What are the common triggers for clients seeking vCISO services, and how can these triggers guide MSPs in positioning their offerings?
4. What operational changes are necessary for MSPs to successfully transition to offering vCISO services, and how can you align sales and operations teams for success?
5. What trends and opportunities will shape the future of vCISO services, including the rise of attack surface management and the increasing importance of incident response planning?

About Jesse Miller

Jesse Miller is a distinguished and forward-thinking information security leader, strategist, and operational powerhouse. He brings extensive technology operations, information security, and regulatory compliance experience in helping managed service providers break through and elevate their business to another level. He is recognized as an information security executive, subject matter expert, and seasoned leader. Jesse is the founder of PowerPSA Consulting and the PowerGRYD vCISO system, specializing in helping Managed Service Providers (MSPs) scale their virtual Chief Information Security Officer (vCISO) programs profitably. His vCISO journey started in 2014 when he was appointed as the CISO to build a managed security service program for his MSP, and it was during this time that he launched his first vCISO program. This initiative unlocked new sales for the organization by helping clients understand the critical “why” behind cybersecurity. Since then, Jesse has been building vCISO programs and continues to help MSPs drive cybersecurity success today.

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.