In this episode of the SaaSiest Podcast, we sit down with Didi Gurfinkel, Co-founder & CEO of DataRails, to talk about what it takes to make a radical strategic shift while your company is still growing fast.

DataRails was already a high-growth SaaS company when Didi and his team became convinced that AI was fundamentally changing their market. Instead of protecting what was already working, they made a bold call: the traditional FP&A software category was dying, and DataRails needed to evolve from a point solution into the foundation for the Office of the CFO.

We dig into what happened next, the strategic bet, the internal resistance, the impact on sales, and why Didi believes SaaS leaders need to start separating their “old ARR” from the “new ARR” that will drive their companies in the AI era.

We discuss:

• Why DataRails declared its own software category “dead”
• The difference between “old ARR” and “new ARR”
• Why successful SaaS companies may need to reinvent themselves before growth slows
• How DataRails moved from an FP&A product to a broader finance platform
• Why AI is making the application layer increasingly commoditized
• What becomes the moat when building software gets dramatically easier
• How to get 400 employees behind a major strategic repositioning
• Why sales teams can become one of the biggest sources of resistance to change
• How far ahead of the market a SaaS company should position itself
• Why small changes may not be enough in the AI transition

Didi also shares one of the strongest analogies we've heard for navigating the current AI shift: when the flood is coming, don't keep moving from balcony to balcony. Find the hill.

A great conversation for SaaS CEOs, founders and executives asking themselves a difficult question: Is the business that got us here also the business that will take us forward?