RevOps Champions Podcast

RevOps Champions Newsletter #53

Written by Kristin Dennewill | October 16, 2026 at 4:06 PM

It's rarely the big decisions that stop a growing business. It's the small change nobody noticed.

Someone on the marketing team changed a dropdown value in their CRM.

 

One value. On a drop down list with multiple options. The kind of edit that takes ten seconds and feels like housekeeping.

 

Within days, their lists stopped working. Their marketing automation stopped enrolling people. No error message. No alert. Campaigns just stopped reaching anyone.

 

The team spent days trying to figure out what broke.

 

When they dug into the logs, the answer was sitting in a single line:

 

"...was not one of the allowed options."

 

The value they'd changed in one system no longer matched what the other system expected. Every record that touched it got rejected. There wasn’t any notification or alert.

 

No one was to blame. Someone doing their job cleaned up a dropdown. That's it.

 

A similar story in a different industry…

 

A distribution company ran a data migration between their ERP and their CRM. 1,400 records went in.

 

1,152 came back with errors.

 

That would have been enough on its own. Then stranger problems showed up. Contacts started disappearing from the CRM. Sales reports left out transactions. Dates landed where invoice numbers should be.

 

The ERP was overwriting the CRM in the background. The team found out the way most teams do: the reports stopped making sense, and someone started asking questions.

 

Neither of these started with bad software or shoddy integrations. Both started with something small changing, and nobody being able to see what it touched.



On a recent episode of RevOps Champions, Brendon talked with Matt Kunz, CEO of Fastest Labs. Matt has spent nearly three decades leading franchise systems and has plenty of wisdom.

 

Matt shared a story from his time at Five Star Painting when they had two years in a row of 40%+ same-store sales growth. They were adding more than 35 new units a year. Estimates moving through the system jumped 120%. User accounts grew 60%.

 

Then, every afternoon around two o'clock, the software slowed to a crawl.

 

The software was fine. However, the business had outgrown the server capacity underneath it. It took a while, and a call to AWS, to figure that out.

 

In Matt's words: "This is a stupid problem, but it's still a problem."

 

We all have our own version of that story. And it's exactly what the two examples above have in common. Small. Unglamorous. Invisible until it brings things to a grinding halt.

 

Matt's advice for any leader growing faster than their systems is to step back for a few hours and ask one question:

 

What would take us out right now?

 

If you don't run a franchise, stay with me here. Franchising is one of the best classrooms for learning how to scale. A franchise system has to work for hundreds of owners who didn't build it, in markets the founder has never seen. If something holds up in a franchise system, it will hold up in a company with multiple locations, divisions, or acquisitions. Matt's 2 o'clock problem wasn't a franchise problem. It was a growth problem. Franchising just made it show up faster.



Here's what I think most leaders miss.

 

We treat revenue systems infrastructure like a project. Scope it, build it, launch it, check the box.

 

But nothing in business, or revenue, is a static environment. For example, an integration connects two systems that never stop changing. New fields. Renamed values. Software updates nobody asked for. A new location, a new product line, a new acquisition.

 

Matt quoted one of his mentors about this: "If you don't like change, you'll like irrelevance even less."

 

AI is speeding all of it up. More tools, more connections, more change, faster. The question isn't whether an integration will eventually break. It's whether you'll know when it does, and why.

 

That question kept coming up in our client work. So we built something for it.

 

You likely already have the two systems that matter most: your CRM and your ERP. The gap is the space between them. Our new integration tool, “Pairing”, connects HubSpot with your ERP, Salesforce, NetSuite, or whatever else you run, more easily and for less than what was possible even a year ago. And when something stops syncing, it tells you which records, why, and how to fix it, in plain language. It even flags upstream changes, like that renamed dropdown, before anything breaks.

 

It's the tool that would have been a game changer for both of those teams.

 

We know how frustrating it is to chase a problem you can't see. If you have an integration you're not sure you can trust, or one you're about to build, take a look at how Pairing works here. And if you'd rather talk it through, I'd love to hear about it.

 

Cheers to finding the 2 o'clock problems before they find you,

 

Kristin

Kristin Dennewill
—
Co-Founder & CEO
kristin.dennewill@denamico.com
Schedule time with me!