Risk Appetite Dinner - Chicago

How CISOs Are Redefining GRC

You're not short on frameworks. You're short on time, headcount, and honest answers about what's actually working. The compliance program keeps growing. The team doesn't. And somewhere between the board presentation and the next audit, the actual security work is getting squeezed out.

This dinner exists for that gap. Michael Rasmussen, the analyst who defined the GRC category and RegScale are bringing together a small, hand-selected group of CISOs in Chicago for an evening of unfiltered peer conversation around modernizing GRC.

Dinner Experience

The evening takes place in the private lounge at Adalina, one of Chicago's premier Italian restaurants. An intimate setting that matches the conversation—providing the space for honest dialogue without the formality of a conference or the rushed networking of a larger event.

Discussion Focus

This exclusive gathering addresses the real constraints facing modern security and compliance programs: how to do more with less, balance security rigor with business velocity, and figure out which modernization approaches actually deliver measurable results versus those still falling short. Through candid peer exchange, participants explore practical solutions to the gap between growing compliance demands and constrained resources.

What You'll Walk Away With

• A clearer read on where automation is delivering and where it's still falling short

• Perspective from peers navigating the same tradeoffs between security rigor and business velocity

• Michael Rasmussen's unfiltered take on where GRC is heading and what separates programs keeping pace from ones that aren't

• Insights from RegScale executives who've built compliance programs at the NSA and AWS

What to Expect

This invitation-only Chicago dinner brings together CISOs facing similar resource constraints and modernization challenges for candid dialogue on GRC evolution. Through peer conversation, Michael Rasmussen's strategic perspective on industry direction, and RegScale executives' real-world experience building compliance programs at scale, participants gain honest answers about what's working while building relationships with fellow leaders navigating the balance between security excellence and operational efficiency.