Episode 31 · January 05, 2026
Episode 31 - Reactive to Intentional: How MSP Leaders Actually Level Up
With Brian Gillette and Chris Day
In Episode 31 of The MSP Sales Podcast, Brian Gillette is joined by Chris Day (CEO at ScalePad) for a no-nonsense conversation about the shift every MSP leader must make to move from reactive survival mode to intentional leadership.
Too many MSPs remain dependent on the owner. Every decision, escalation, and bottleneck runs through one person. Chris breaks down why this happens, how it silently limits momentum, and what it actually takes to build an MSP that can operate and grow without constant founder involvement.
Together, Brian and Chris explore:
➡️ Why reactivity keeps MSPs stuck (even when revenue is growing)
➡️ How intentional leadership creates leverage
➡️ How to build systems instead of dependencies
➡️ How to step out of the day-to-day without losing control of the business
If you’re an MSP owner who feels indispensable to your business - or concerned that your growth still feels fragile - this episode will challenge how you think about what “leveling up” looks like.
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.
Chris Day
Chris Day is a prominent technology entrepreneur in the Managed Service Provider (MSP) sector, with over 20 years of experience starting in 2002. He founded IT Glue, an industry-leading documentation platform that was acquired by Kaseya, after building and exiting his own MSP which he sold to Canada's largest telco.
In 2015, Day co-founded ScalePad (initially Warranty Master), where he now serves as CEO, focusing on tools that enhance MSP efficiency, client outcomes, and strategic growth through innovations like AI-driven task management and lifecycle assessments.