What happens when employees have a private, always-on place to ask their real benefits questions?

Something shifted during Open Enrollment 2025. The questions employees asked were fundamentally different from the year before, not just in volume, but in sophistication, timing, and what they were willing to disclose when they had a private place to ask. Cascade AI CEO Ana-Maria Constantin sits down to unpack what the data actually revealed, what it means for benefits strategy going into 2026, and why the organizations that move on this now will have a meaningful advantage in the next enrollment cycle.

WHAT YOU’LL LEARN

How to make the CFO case without talking about chatbots. If your AI business case has stalled because leadership sees it as “another HR tool,” this reframe will give you a different way into the conversation entirely.

The behavioral shift most benefits teams didn’t see coming. One year-over-year stat in particular caught our attention, and it changes the way you should think about your entire OE communication strategy.

What employees do at 10 p.m. when nobody’s watching. The after-hours data tells a story that no employee survey has ever captured, and it has real implications for how you staff, budget, and plan your next enrollment window.

The fiduciary workaround hiding in plain sight. There’s a structural constraint that has limited what employers can offer employees during enrollment for decades. Ana walks through how leading organizations are solving it right now without taking on advisory risk.