Episode 30 · December 22, 2025
Episode 30 - Building the Modern MSP: AI, Cloud &
With Brian Gillette and Jim Spignardo
In Episode 30 of The MSP Sales Podcast, Brian Gillette sits down with Jim Spignardo, Director of Cloud Strategy & AI Enablement at ProArch, for a practical conversation about what it actually takes to build a modern MSP today.
With over 25 years in IT across networking, cloud, cybersecurity, and consulting, Jim brings a grounded perspective on how MSPs must evolve beyond tools and tech stacks. Together, they explore how cloud maturity, AI enablement, and user experience now intersect - and how ignoring any of them creates friction for clients and internal teams.
They discuss;
➡️ Why “modern MSP” is more about experience than tech
➡️ How AI is reshaping service delivery
➡️ The role of cloud strategy in long-term MSP relevance
➡️ Why UX matters just as much for internal teams as end users
➡️ Common mistakes MSPs make when adopting AI
If you’re an MSP owner, technical leader, or consultant trying to modernize your services, this conversation will help you think more clearly about where to focus.
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.
Jim Spignardo
Jim Spignardo is the Director of Cloud Strategy & AI Enablement at ProArch, a global IT services and consulting firm. With over 25 years in IT, Jim’s journey spans network engineering, cloud management, cybersecurity, and strategic consulting. What drives him is helping organizations cut through the noise and deliver real, measurable business outcomes.