Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller) episode artwork

EPISODE · Jun 8, 2026 · 46 MIN

Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller)

from The MSP Sales Podcast · host Brian Gillette

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. -------------------------------------------------------------------------------------------- Learn more about Learn more about Jesse Miller, the Founder of Powergryd. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.com Brian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format! It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values. Get it now at Amazon.com https://a.co/d/hJKoFxg . . #MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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. -------------------------------------------------------------------------------------------- Learn more about Learn more about Jesse Miller, the Founder of Powergryd. Learn all about Feel-Good MSP and our end-to-end MSP sales training, growth and development program at: www.FeelGoodMSP.comBrian's book "How To Sell a Sh*tload of Managed Services (without selling your soul)", is now available in both hard-copy and audiobook format!It’s your roadmap to build repeatable growth, higher margins, and stronger client relationships without compromising values.Get it now at Amazon.com https://a.co/d/hJKoFxg. .#MSP #MSPSales #ManagedServices #ManagedServiceProvider #TechSales #MSPCommunity #ITServices #ManagedIT #CloudServices #ITConsulting #MSPSalesTraining #SalesProcess #BusinessStrategy #BusinessGrowth #MSPMarketing #SalesTraining #LeadGen

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Episode 45 - The MSP of the Future Will Be a vCISO (Guest: Jesse Miller)

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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...

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