Welcome to Ctrl Alt Deliver: MSP Mastery Podcast.
I’m Jeni Clift, joined by my husband and business partner Nick Clift. Together, we spent nearly 30 years building, scaling, and eventually exiting our own MSP business.
Along the way, we learned something fundamental.
Recurring revenue only works when it’s managed properly.
In this episode, we’re joined by Adam Ross, Co-Founder of CloudOlive and a long-time leader in the MSP ecosystem, with senior roles spanning Autotask, Datto, and now the venture-backed startup world.
Adam has spent more than 15 years working alongside MSPs across Australia, Europe, and globally. Today, through CloudOlive, he has visibility into the billing, licensing, and recurring revenue structures of hundreds of MSPs — and what he sees is both simple and confronting.
What becomes clear in this conversation is that most margin problems don’t explode.
They leak.
We explore:
We also discuss retention discipline, operational maturity, and Nick’s pointed reminder:
“If you are not calling existing customers, you're not calling new customers. Somebody else is calling your customers.”
This episode is not about shiny tools.
It’s about operational clarity.
Margin integrity.
Leadership discipline.
If you are an MSP owner who assumes your recurring revenue is “under control,” this conversation may challenge that assumption — in a constructive way.
Connect with Adam Ross on LinkedIn: https://www.linkedin.com/in/madassor/
Learn more about CloudOlive:
https://www.cloudolive.com/
Listen to this episode and explore more Ctrl Alt Deliver conversations at:
https://www.mspmastery.blog/episodes
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