Episode 19  ·  July 21, 2025

Episode 19 - Cold Outreach That Actually Works

With Brian Gillette and James Milsom

Most MSPs fail at cold outreach. Not because it doesn’t work, but because they treat it like mass marketing.

In Episode 19 of The MSP Sales Podcast, James Milsom of Hunter.io joins Brian Gillette for a deep dive into what actually works in cold email - and what MSPs keep getting wrong. Backed by data from over 11 million emails, James shares hard-earned insights on deliverability, subject lines, personalization, and how to build trust from the very first message.

Learn:

  • Why personalization isn’t optional anymore
  • What subject lines actually earn opens
  • How to avoid spam folders and show up with value

Whether you’re sending outreach yourself or guiding your team, this episode will help you stop guessing and start improving.

 

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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.

James Milsom

Head of Marketing @ Hunter.io, James has a decade of SaaS experience in revenue teams, sending cold outreach, managing SDRs, and hunting for that perfect cold email.