Chicago AI Pilot Exchange: Startups, Operators & Real Use Cases

Chicago AI Pilot Exchange: Startups, Operators & Real Use Cases

Practical Focus: A curated B2B exchange connecting AI software builders with COOs, Heads of Operations, product leaders, and corporate decision-makers to evaluate real-world workflows and negotiate 30-to-60-day pilot opportunities.

Pilot Profile Working Cards: Skip repetitive elevator introductions. Every participant completes a structured card specifying their operational domain, immediate bottlenecks, solutions offered, and pilot evaluation criteria.

45-Second Solution Spotlights: Exactly 12 rapid-fire, tightly moderated introductions from participating AI companies highlighting target users, workflows impacted, and viable test cases (strictly no slide decks or fundraising pitches).

Curated Pilot Tables: Small-group breakout tables structured around operational themes: Customer Operations, Internal Workflow Automation, Revenue/Sales Ops, and Applied Analytics.

Opt-In Connection Routing: Request introductions to relevant peers at the end of the evening; contact information is routed by the organizer only when both parties provide explicit consent.

Strict Anti-Solicitation Policy: Aggressive direct selling, multi-level marketing (MLM), lead harvesting, unapproved mass email signups, and financial product prospecting are strictly prohibited.

Hospitality & F&B: Filtered drinking water and light refreshments are provided complimentary; full meals or bar beverages are not included with admission.

Agenda

• 5:40 PM – 6:00 PM: Doors open, check-in, nametag collection, and Pilot Profile completion.
• 6:00 PM – 6:15 PM: Welcome briefing, exchange ground rules, and room rotation orientation.
• 6:15 PM – 6:30 PM: 45-Second AI Solution Introductions (maximum 12 timed company spotlights).
• 6:30 PM – 7:05 PM: Pilot Exchange Round 1 (facilitated small-group use-case discussions).
• 7:05 PM – 7:15 PM: Reset & Table Change (10-minute transition and circulation buffer).
• 7:15 PM – 7:50 PM: Pilot Exchange Round 2 (new table groupings and problem-solution matching).
• 7:50 PM – 8:00 PM: Refreshment break and priority conversation review.
• 8:00 PM – 8:40 PM: Open Pilot Networking (focused 1-on-1 deep dives with complementary operators).
• 8:40 PM – 8:55 PM: Opt-In Connection Submissions (submit direct introduction requests via digital form).
• 8:55 PM – 9:00 PM: Closing remarks and post-event introduction timeline.