Event Information
2026 - Chicagoland Technology Event - AI Inside the Agency & Bowling - Oak Brook - July 22
Pinstripes, Oak Brook, IL
Wednesday, July 22, 2026
1:00 PM - 6:30 PM
iCalendar
Central Standard Time
AI Inside the Agency
3 IL CE hours - Approved
About the Session
AI Inside the Agency is a working session, not a tour and not a pep talk. Instead of walking the room through a catalog of AI tools, it puts the agencies in the room to work on their own real problems, then asks where a tool actually fits. Problem first, tool second. That order is where most AI adoption either succeeds or quietly dies.
The session opens by setting a shared floor in plain language: what AI actually is, the line between a chatbot you talk to and an agentic system that works in the background, a clear privacy boundary for client and policy information, and the documentation principle that every practical use depends on. From there, the bulk of the time is live work. Owners surface the daily bottlenecks that make them want to pull their hair out, map a real workflow end to end, and find the specific points where a tool relieves the pain. The throughline is simple: AI handles the predictable, people hold the relationship, and the relationship is what an independent agency actually sells.
What you will take away
Every attendee leaves with working material, not notes on a vendor pitch:
• A shared, honest read on where AI is today and what it is not.
• A clear privacy floor for handling agency and client information before any tool touches it.
• The documentation principle made concrete, with examples to copy.
• At least one of their own workflows mapped end to end, with the tool fit identified.
• A repeatable method, the Good Day walk-back, that works on any workflow after they leave.
Stick around after the CE session for bowling, food, drinks and good times. We will bowl until 6:30, and then encourage groups to go out to dinner and take in the local area.
Sponsorship opportunities are available, be a part of this unique session and find out more here.