This was probably one of our most impactful and actionable interviews to date. Jesse Miller is, for my money, the absolute voice on vCISO. If you are trying to figure out where this industry is heading next, Jesse lays out the exact roadmap to stop playing the commodity "tech guy" game and start acting like a true strategic advisor.
- The Big Takeaways?
“The Death of the "Tech Guy" Value Proposition: Why the MSP of the future will either be a vCISO or won't exist at all, and how to stop selling tool stacks so you can start translating technology into business risk. - The "Monkey Paw" Entry Offer: How to use universal baseline needs—like incident response planning and tabletop games—as the ultimate foot-in-the-door strategy to land larger accounts and displace incumbent competitors.
- SaaSifying Your Strategy and Pricing: Why pricing security on a per-user basis means you are going to lose your shirt, and how to structure modular flat-rate monthly retainers from $3,500 to $15,000.
- Climbing the 5-Layer AI Risk Pyramid: How to cut through the chaotic market FOMO and leverage AI governance to create a three-to-five-year runway of high-margin, enterprise-level advisory work.
If you're trying to figure out where MSPs are headed next, this episode provides a roadmap.
Episode Hosts
Brian Gillette
Brian Gillette, the founder of Feel-Good MSP, stands out in the Channel with his unique, empathy-driven approach to sales and client relationships.
Formerly a VP of Sales for an MSP, his expertise now shines as a consultant, where he transforms traditional sales tactics with a focus on understanding and meeting client needs.
Renowned for his strategies in overcoming sales objections, Brian champions selling outcomes over technicalities, emphasizing value, trust, and the importance of peace of mind and productivity for clients. His dynamic, client-centered philosophy makes him an invaluable asset in the MSP landscape.
He is the host of The MSP Sales Podcast and author of the book, "How to Sell a Sh*tload of Managed Services: Without Selling Your Soul"
Jesse Miller
Jesse Miller is the founder of PowerPSA Consulting and creator of the PowerGRYD vCISO System. A longtime former MSP CISO, he is a leading expert and strategist who helps Managed Service Providers (MSPs) build, package, monetize, and scale profitable virtual Chief Information Security Officer (vCISO) services.
His system focuses on transforming security from a cost center into a high-margin revenue driver, often adding seven-figure ARR, through strategic cyber advisory, governance/risk/compliance (GRC), incident response planning, and operational models that align security with business outcomes. Jesse is also known for his practical insights on AI readiness, risk management, and the evolving role of MSPs as business advisors. He is based in St. Paul, Minnesota.