Episode 11 · March 27, 2025
SaaS vs. MSP Sales: What Works and What Doesn’t
With Brian Gillette and Tanner Cookson
Why might SaaS sales reps struggle in MSP sales? On the surface, selling software and selling managed services may seem similar - but the reality is, they require very different approaches.
In this episode of The MSP Sales Podcast, we sit down with Tanner Cookson from Alternative Payments to break down the fundamental differences between SaaS sales and MSP sales. We discuss why many SaaS-trained reps struggle in MSP roles, and what MSP owners need to know before making their next sales hire. From the importance of relationship-driven selling to the challenges of longer sales cycles, we explore what it really takes to succeed in MSP sales.
If you’re an MSP looking to build the right sales team, don’t miss this conversation! We’ll help you understand what skills to prioritize, how to onboard sales reps effectively, and why a strong sales process is just as important as hiring the right person.
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.
Tanner Cookson
My personal mission is to help others along with myself in unlocking their highest potential, through mindset and action, and aid in shaping the next generation of world-class leadership.
I love to help B2B service providers save on ACH/Credit Card processing fees, and increase revenue through end-client invoice financing and payment flexibility.