Last week, our CEO Ravit Gutman and Matt Leigh represented Extropy Advisors at the Esker All Access Conference in Chicago, a two day gathering that brought together Esker’s partner community on day one and its customers on day two. We left with pages of notes, but one word kept coming up more than any other: community.
Hearing Esker lay out its vision for where the partner ecosystem is headed gave the team useful context. But the real value, the part that actually stuck, was the conversations happening in the hallways and over dinner. Practitioners living in source-to-pay and order-to-cash every day, comparing notes on the same problems in slightly different words.
One theme surfaced again and again: cash application. Most finance teams still treat it as a necessary evil, something to get through rather than something to optimize. What became clear in Chicago is how much leverage most teams are sitting on without realizing it. Faster, more accurate cash application isn’t just an efficiency play, it can be genuinely competitive.
Day two brought a sharper realization. Technology partners in that room were being asked to measure outcomes, not just describe features, especially when the conversation turned to AI. Nobody wanted to hear what a model can technically do. They wanted to know what it actually did for a team like theirs: hours returned, exceptions cleared, people freed up for higher value work. The burden of proof has shifted onto the vendor, and honestly, that is exactly where it belongs.
There was a human moment worth mentioning too. Clients and vendor teams who had spent years connected only through support tickets and calls finally met face to face. It is a small thing on paper, but it changes the relationship in a way a demo never could.
None of this changed what we already believed going in: the hard part of transformation was never the technology. It is change. It is resistance. It is building a team that can thrive in a digital environment rather than just survive it. That belief is exactly why we started Transforming Out Loud, a space built for AP and AR leaders to talk honestly about the people side of change, how to measure whether a transformation actually worked, and what they would do differently next time. The industry has plenty of places to talk about tools. It has very few places to talk about this.
If you are leading AP or AR through a period of change, we would encourage you to get yourself to events like Esker All Access. Not for the swag. For the people in the room who understand your Tuesday. And if you want to keep that conversation going year round, Transforming Out Loud is where we are doing it. We would love to have you join us.
If you lead AP or AR through change and want the conversation to keep going after Esker All Access, Transforming Out Loud is where AP and AR leaders talk honestly about it year round.
