Description

Recurring revenue is the lifeblood of modern IT services—but scaling it without friction is where most MSPs struggle. In this episode, John Rice sits down with Jeff Klebine, Chief Strategy Officer at Milo Massimo, to unpack how MSPs and SaaS companies can streamline their quote-to-cash processes, eliminate billing chaos, and reduce ticket volume.

Jeff shares a consultant’s perspective on the subscription economy, the rise of usage-based pricing, and how “dirty data” creates costly technical debt. From pizza-slice transformations to the coming wave of AI-powered automation, this episode offers a roadmap for MSPs and IT leaders navigating rapid change.

If you’re an MSP looking to clean up operations, boost recurring revenue, and future-proof with AI, you won’t want to miss this conversation.

Episode Highlights

• [00:42] Jeff Klebine introduces Milo Massimo and their focus on quote-to-cash consulting

• [04:35] Why recurring revenue is the foundation of today’s subscription economy

• [08:15] The shift from seat-based pricing to usage-based models (AWS, Netflix, Adobe)

• [12:20] How “data debt” slows down MSPs and blocks AI adoption

• [16:55] Practical ways MSPs can cut billing errors and reduce support tickets

• [22:40] Jeff’s “pizza slice” approach to business transformation

• [28:10] The talent challenge—training, retaining, and promoting from within