Rework and Rebuild: How to Play the Long Game for Customer Success

Software companies love to talk about disruption, but real transformation rarely happens overnight. In my decades in the industry, I’ve seen that lasting value comes from the slow, deliberate work of solving actual business problems. That has been our focus this year at ControlUp; the results speak for themselves. A lot has changed in just one year, and I wanted to take the opportunity to look back and reflect on what we did right and what lessons we’re taking into our next phase.

Determined to be Different

Take our contract terms, for instance. No customer wants to constantly start over, seeking someone they can trust, trying to explain their needs, and hoping for a cohesive solution. That’d be exhausting, and yet it’s what many people have to settle for. We’re determined to be different. We’ve seen our average contract terms extend from 16 to 25 months. That’s not just a data point—it’s validation that we’re building something customers want to stick with.

This came from listening to and truly understanding how customers think and what they want. Here’s what’s interesting about the tech buying process today: 70% of purchase decisions are made before a customer ever speaks to sales. We heard that message, so we’ve completely restructured how we work. We’ve reorganized our customer success teams, bolstered our support organization, and rethought our renewal process. And internal reorganization is just the beginning.

Why Talk About Problems When You Can Prevent Them?

Our customers, especially those with 10,000+ employees, aren’t just looking for another vendor—they’re looking for a partner to help define success in the digital employee experience (DEX) space. That’s exactly the kind of challenge that gets me energized. While our competitors are content to report problems, we’re focused on preventing them.

Let me give you a concrete example. One of our customers, a major organization, recently faced the challenge of remediating 40,000 devices. Without our platform, it would have taken weeks. With ControlUp Secure DX, they handled it in hours. That’s a massive difference that saved them untold headaches, let alone conserving personnel hours and operational functionality.

Our first customer council and MSP advisory board meetings this year were eye-opening. When customers told us they needed help with browser-based experiences, we didn’t just nod and smile—we acted. Soon, we’ll be launching a solution tailored to tackle these challenges head-on. It’s the result of listening closely and acting decisively, and we can’t wait to show you what’s next.

A Willingness to Change

If you’re going to listen and really put in the time to build relationships, you also have to be committed to following through and implementing positive changes. Creating long-term relationships and long-term value isn’t about being the same the whole time. We can provide a consistent standard of service while evolving those services through our learnings. We’ve already made big changes, and we’ll keep making them to deliver the best possible experience and outcomes.

We’ve simplified our pricing and packaging and rebuilt processes to make working with us easier, whether you’re a partner or a customer. Our community platform has become a powerful tool for knowledge transfer and script sharing—exactly the kind of practical value our technical users need.

This willingness to change is paying off. We’re not just building an ARR machine—we’re creating a platform that can handle any application, any delivery method, and any user experience challenge. When a global customer sees an issue brewing in one time zone, they can now get ahead of it before it impacts another region. That’s not just monitoring—that’s actually solving problems.

That said, we’re not celebrating a finish line; we will keep evolving. Looking ahead, we’re focused on scaling these capabilities for enterprise demands while maintaining the responsiveness our customers count on. Bad things happen in complex IT environments—that’s just reality. But the faster you can find and fix issues, the less they impact the business. That’s the kind of practical value that builds twenty-year relationships, and that’s exactly what we’re here to deliver.