Exclusive in person event

Executive leadership dinner

The AI Productivity Gap: Why More Adoption Isn't Producing More Output

October 22, 2026, 6:30 PM
New York, United States

An exclusive in-person dinner for CEOs and founders leading growing companies on moving from AI adoption to AI accountability: what's worth measuring, what's a distraction, and how to answer the question your board is already asking.

AI adoption is high and climbing, but proof of output is missing. Most leaders rolled AI tools out across their teams without a reliable way to know whether it's actually producing more output, more capacity, or better margin. This is a chance to meet fellow CEOs and founders to discuss how to close that gap first, and make faster calls on hiring, pricing, and where the next AI dollar goes.

Hosted byHubstaff logo

Hubstaff is a workforce productivity platform that helps teams track time, measure output, and understand how work actually gets done, so leaders can make faster, better-informed calls on hiring, capacity, and spend.

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What you'll experience

An evening in New York for CEOs and founders in peer discussion on what AI is actually producing for their business.

Conversations

An off the record discussion with peers who have made the same AI investment and are asking the same hard question: is it actually producing more output?

Perspectives

Hear how other CEOs and founders are measuring (or struggling to measure) what AI delivers across their teams, and what they're doing about the gap.

Playbooks

Pressure test how leading organizations tie AI usage to output, capacity, and margin, and how that evidence shapes hiring, pricing, and the next AI dollar.

From AI Adoption to AI Accountability

A small group of growth-stage CEOs and founders digging into what it really takes to prove the AI investment is working, and what to do with the answer.

Why AI adoption is high but proof of output is missing, and what closes that loop
What's actually worth measuring when it comes to AI-driven productivity, and what's a distraction
How leading organizations connect AI usage to output, capacity, and margin
How to answer the question your board is already asking about the next AI dollar

Who is this event for

Growth-Stage CEOs and Founders

Senior leaders who own decisions about AI investment, workforce productivity, and where technology spend goes next.

Leaders Based in New York

A curated group of CEOs and founders in and around New York facing the same pressure to prove what AI is delivering for the business.

A Curated CEO Peer Group

The guest list is hand curated around your stage, so you sit with CEOs and founders of similar company size, not a room of vendors.

140K+

Businesses rely on Hubstaff to see how work actually gets done

21M+

Hours of real work tracked and turned into productivity insight

500K+

Active users giving leaders real output data, not guesswork

4M+

Tasks completed with visibility from first hour to final report

Sources: Hubstaff

About this dinner

An exclusive in-person dinner in New York for CEOs and founders building growing businesses. Small group, candid conversation, no pitch.