---
title: AI Leaders in Chicago
date: '2026-06-30T03:05:42.000Z'
author: Rich Tabor
summary: Celebrating the first graduating class of the AI Leaders program in Chicago, insights on AI in the workplace, and the importance of staying curious.
published: true
type: blog
url: /ai-leaders-in-chicago
canonical: https://richtabor.com/ai-leaders-in-chicago/
id: 8431
---

Last week I flew to Chicago to celebrate the first graduating class of the [AI Leaders program](https://automattic.com/2026/06/23/congrats-university-illinois-chicago-ai-leaders/), a collaboration between the University of Illinois Chicago and the [WordPress Foundation](https://wordpressfoundation.org).

I did a fireside chat with [Jesse Friedman](https://jesse.blog/), where we talked about AI at work, what AI enablement means at Automattic, and how we’re helping teams adopt more agentic workflows. But the best part of the evening was spending time in a room full of people excited about AI, building real things with it, and using [WordPress](https://wordpress.org/) to publish their [work](https://aileaderswp.blog/).

Afterward, we stuck around and talked shop. People came up and asked about careers, engineering, data, and how to stay valuable as AI changes the way we work. The advice I gave them is the same advice I follow myself: stay curious and build.

I left inspired and optimistic about the future, and even more so about the people I get to shape it with.

Here’s to the next one!

![](https://i0.wp.com/rich.blog/wp-content/uploads/2026/06/20260623-223.jpg?resize=6000%2C4000&quality=89&ssl=1)

![](https://i0.wp.com/rich.blog/wp-content/uploads/2026/06/20260623-286.jpg?resize=6000%2C4000&quality=89&ssl=1)

![](https://i0.wp.com/rich.blog/wp-content/uploads/2026/06/20260623-371.jpg?resize=6000%2C4000&quality=89&ssl=1)