Measuring the ROI of AI

About the Event

AI is now embedded across modern organizations from copilots and internal tools to workflow automation and internal systems. Leaders are investing heavily in AI licenses, platforms, and experimentation, yet many still struggle to understand what value they’re actually getting in return.

This evening brings together a small group of CEOs, founders, and COOs for an off-the-record conversation focused on measuring the real ROI of AI where it’s delivering tangible impact, where it’s falling short, and how leaders are rethinking metrics, ownership, and accountability inside their organizations.

GILD events are designed experiences. This event follows The Curated Circuit, GILD’s signature format built to maximize meaningful connection and insight in a small, high-trust room. The structure is intentionally designed to encourage honest exchange, create new relationships, and keep energy high through rotating micro-roundtable discussions and focused prompts. Every element exists to protect room quality, pace, and trust.

Guests will enjoy elevated appetizers and drinks throughout the evening.

What to Expect

• A short, intentional networking mixer
• A focused 20–30 minute expert lightning talk
• Structured table discussions to apply insights to your own company
• Time to continue the conversation and build meaningful peer relationships

No panels. No pitches. No product demos.

What We’ll Discuss

• How leaders evaluate AI investments 
• Which AI spend actually drives automation and internal productivity
• How CEOs decide what work AI should replace, augment, or accelerate
• What metrics executives use to measure real AI ROI beyond usage stats
• Where AI initiatives break down—and what’s working inside real companies

Why Attend

You’ll leave with a clearer framework for evaluating AI investments, practical ideas you can apply immediately, and new relationships with senior leaders navigating similar challenges around productivity, scale, and performance.

Who This Is For

This dinner is curated for senior company leaders, including:

• CEOs
• Founders
• COOs
• Presidents and owners responsible for operational performance

Attendance is limited to keep the room focused, candid, and high-signal.

Privacy & Format

Chatham House Rules apply.
Discussion stays private. This is what unlocks candor.