Most MSPs think cold email stopped working.
The reality?
Most outbound campaigns fail before anyone even reads the message.
In this episode, Brian Kelly breaks down why deliverability has become the real bottleneck in MSP marketing, and why most providers are still approaching outbound the wrong way.
Brian shares how he applied a technical, engineering mindset to sales and built systems focused on one core principle:
“The best way to avoid being treated like spam is to stop acting like spam.”
We cover:
→ Why most MSP emails never reach the inbox
→ The real impact of AI on outbound marketing
→ The role of context, timing, and relevance in outbound
→ How MSPs are doing the right things in the wrong order
If your outbound strategy feels inconsistent, overcomplicated, or ineffective, this episode will challenge a lot of assumptions.
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Learn more about Brian Kelly's services at Automated MSP - an MSP-native AI-powered outbound prospecting platform that helps managed service providers generate qualified leads, recruit talent, build strategic partnerships, and identify opportunities via cold email automation.
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"
Brian Kelly
Brian Kelly is the founder of Automated MSP, an MSP-native AI-powered outbound prospecting platform designed to help managed service providers generate qualified leads, recruit talent, build partnerships, and uncover M&A opportunities through high-deliverability cold email automation.
A veteran of the managed services industry since 2003, Brian started on the help desk right out of network engineering school and progressed to Tier 3 engineering, leading complex server migrations. Over the past decade, he became deeply focused on backend automation tools like ConnectWise Automate, embracing what he calls being “professionally lazy” by building systems so he never had to repeat the same task twice.
Brian leveraged his engineering mindset to solve outbound marketing challenges. By treating cold email deliverability as a technical system governed by rules, data, and constraints, he created Automate MSP to help MSPs grow without sounding like spam.