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?

In this episode, we sit down with Daniel Thulfaut, Head of Product at saas.group, one of Europe's most active SaaS acquirers. With 24 companies in the portfolio and more than €100M in ARR, Daniel has a unique perspective on how product organizations are evolving in the age of AI.

We discuss why many product managers have spent the last decade acting as backlog managers rather than true product leaders, and why AI is now forcing a return to the fundamentals of product management: customer understanding, strategic thinking, prioritization, and decision-making.

We also explore why "good enough" products are becoming easier than ever to build, why that raises the bar for SaaS companies, and what legacy SaaS businesses must do to stay competitive against a new generation of AI-native startups.

Topics we cover include:

• Why the traditional product manager role is changing rapidly • The difference between backlog management and real product leadership • Why AI makes customer discovery more important, not less • Why legacy SaaS companies struggle to realize the promised 10x AI productivity gains • The rise of the "product engineer" and what it means for teams • How feature flags, experimentation, and faster feedback loops change product development • Why shipping more features is not the same as creating more value • What CEOs and CPOs should do right now to prepare their product organizations for the future • Why understanding customer problems remains the most valuable skill in product management

One of the most interesting takeaways from the conversation is that AI is not replacing product thinking. If anything, it's making it more valuable. When building becomes easier, deciding what to build becomes the real competitive advantage.

If you're a founder, CEO, CPO, product leader, or anyone trying to navigate the future of SaaS, this episode is packed with practical insights and plenty of food for thought.

In this episode we sit down with Artti Aurasmaa, CEO of Staria, to discuss how the CFO role is evolving from financial reporting to strategic leadership.

Artti has spent more than 25 years helping companies scale internationally and today leads Staria, a €60M+ business serving growth companies across 50 countries. In this conversation, he shares why the future CFO must become a business partner, data steward, and forecasting expert rather than simply the person closing the books.

We discuss why forecasting accuracy may be the most important KPI for a modern CFO, how AI is changing finance teams, why strong data foundations matter more than the latest AI tools, and what separates companies that scale successfully from those that struggle.

You will also hear Artti's perspective on international expansion, the increasing complexity of global business, and why the best CFOs are moving from the back office to the front row.

Topics covered:

• Why the CFO role is becoming increasingly strategic
• The shift from historical reporting to future forecasting
• Why forecasting accuracy is a critical KPI
• How AI is changing the finance function
• Building the data foundation before deploying AI
• The future structure of finance teams
• International expansion and global compliance
• Why CFOs need stronger technical and data capabilities
• The rise of the "rockstar CFO"
• What growth companies need to scale successfully

Whether you're a CFO, founder, CEO, finance leader, or SaaS operator, this episode offers a practical look at how the finance function is changing and what it takes to stay ahead.