Episode 22  ·  September 01, 2025

Episode 22 - How MSPs Build Sales Confidence

With Brian Gillette and Brian Doyle

Fear and uncertainty hold back more MSP sales opportunities than most owners realize. You land the meeting, deliver the proposal, or finally get that chance you’ve been waiting for — and then doubt creeps in. The truth is, confidence isn’t something you’re born with. It’s something you build.

In Episode 22 of The MSP Sales Podcast, Brian Gillette sits down with Brian Doyle to unpack how imposter syndrome shows up in MSP sales — and how to move past it. They reveal why mindset, preparation, and process are the antidotes to hesitation, and how MSPs can turn self-doubt into steady confidence.

You’ll discover:
 ✅ How reframing sales as helping changes everything
 ✅ Why process, preparation, and practice eliminate fear
 ✅ Practical ways MSPs can build lasting confidence

If sales still feels uncomfortable, this episode is your playbook for breaking free from imposter syndrome - and winning with confidence.

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.

Brian Doyle

Brian Doyle is the Co-founder and CEO of vCIOToolbox, a SaaS platform designed to help technology service providers build stronger client relationships and drive strategic growth. 

Through MSP Rebellion, his consulting firm, Brian also delivers Virtual Sales Management, vCIO-as-a-Service, and business consulting to help MSPs and IT providers improve sales performance and client engagement.