This month I'm chasing the same question across four stages, from Chicago to Columbus to a virtual room with 5,000 leaders.
I'm writing this from Chicago. Today I'm moderating a panel at The Future Of conference with Carly Price from ServiceNow, Anthony Wolf from Canadian Tire, and Roger Rohatgi from Chai. Three leaders, three different industries, three different scales. And in our prep calls over the past two weeks, every conversation landed on the same place.
Which parts of your business were built on assumptions that AI just broke?
Carly's design team at ServiceNow is encoding their entire design system into Claude Code as an explicit rules layer. They're generating clickable prototypes in hours that used to take weeks. That's the production layer collapsing. And she's asking a harder question underneath it: if experienced designers can now move at 10x speed, what happens to the foundational skill-building that made them experienced in the first place?
Anthony is driving AI transformation across a $12B company with 500 stores and 6,000 employees. His frame: 10% of transformation is the models, 20% is the data and technology, 70% is the people. He tells his organization this is a design challenge, not a technology challenge. The thing that's obsolete isn't Canadian Tire's product. It's the assumption that transformation is a technology project.
Roger, the former Head of Design at BP, is building full agentic workforces at Chai and argues that Jensen Huang's five-layer AI stack is missing a critical sixth layer: experience. He has production examples running today, and he's asking what happens to your brand when an AI agent is making the purchasing decision, not the human.
The rest of the conference is just as timely. Phil Gilbert from IBM in a fireside. Phil Duncan, Global Design Officer at P&G, in a fireside chat moderated by Bob Jennings from 3D Color. Pete Blackshaw from BrandRank.ai on why brands lost curiosity and AI found it. Leaders from Whirlpool, KraftHeinz, Colgate-Palmolive, Capital One, McKinsey, 3M, Booz Allen Hamilton, W.K. Kellogg, and Global Payments working through the same questions from different angles. Every conversation converging on the same uncomfortable realization.
In The Rooms This Month
ServiceNow. Canadian Tire. Chai. P&G. IBM. Whirlpool. KraftHeinz. Colgate-Palmolive. Capital One. McKinsey. 3M. Booz Allen Hamilton. W.K. Kellogg. Global Payments. 3D Color. Nationwide. Google. Path Robotics. Anduril Industries. Upstart. Intercom. Zapier. Logitech. Mars. Diageo. GSK. TD Bank. Microsoft. Deloitte. Bosch. AlignAI.
The Future Of. OhioX Tech Summit. AUTONOMOUS: OBSOLETE. 1871 Emerging Tech Innovation Summit.
The Month Ahead
This is where I'll be spending May, and what I'll be bringing back to you.
Thursday: OhioX Tech Summit, Columbus
Two days from now I'll be at the Ohio Union for the fifth annual OhioX Tech Summit. Nationwide's Chief AI & Digital Transformation Officer Chetan Kandhari is keynoting on the heels of the company's $1.5 billion AI transformation investment. Path Robotics and Anduril Industries are on a re-industrialization panel about what happens when AI meets the factory floor and the defense supply chain. Google, Upstart, and University Hospitals are talking about where AI is already deployed and what had to change to get from pilot to operating advantage.
One session I'm watching closely: "Building in the Age of AI: Pivot, Partner, or Perish?" with founders debating whether startups can outpace horizontal AI infrastructure or need deep vertical specialization to stay relevant. AlignAI's co-founder Rehgan Bleile is moderating a panel on converting enterprise pilots into purchase orders, the exact bottleneck most AI companies are stuck on right now.
The AI thread running through every session in Columbus: it's about whether your organization can absorb the change fast enough to matter.
May 21: AUTONOMOUS: OBSOLETE, Virtual
Board of Innovation is gathering 5,000+ senior leaders for a half-day virtual summit built around one premise: AI is breaking the assumptions your business model, workflows, and organization were built on.
The agenda reads like an audit of everything enterprise leaders assumed was permanent. Intercom's CTO Darragh Curran is talking about why most AI transformations are too polite to actually matter. Zapier's CEO Wade Foster is walking through what happened when his company faced a code red and had to redesign its entire value proposition. Logitech's Chief AI Officer Eric Porres is making the case that optimizing the old machine is the fastest path to irrelevance.
The closing session is a live obsolescence audit with leaders from Mars, GSK, and KPN stress-testing their own business models in front of thousands of people. Diageo, TD Bank, and Bunq are on a panel about what happens to judgment and operations when the machine is smarter than you.
The themes I'm watching:
Where value shifts when intelligence becomes nearly free
Pricing models that break when your service can be replicated at a fraction of the cost
Decision architecture: who decides and who does the work in an AI-first organization
Why transformation keeps failing at the organizational layer, not the technology layer
Free to attend. Register at autonomoussummit.ai. If you're planning to be there, reach out. Would love to compare notes on the sessions.
May 28: 1871 Emerging Tech Innovation Summit, Chicago
The following week, I'm back in Chicago at Hyde Park Labs for the 1871 Emerging Tech Innovation Summit. This one brings together founders, enterprise operators, platform builders, and investors who are deploying and funding emerging tech right now. Supported by Microsoft, Deloitte, Bosch, and United. The focus: what's real versus hype in 2026, what actually breaks between a demo and a global deployment, and what's getting funded in a production-first market.
If the AUTONOMOUS: OBSOLETE summit asks "what's becoming obsolete," the 1871 summit asks "what's replacing it, and who's writing the check."
What To Do This Week
I'm spending May in these rooms because the conversations are moving faster than any report or newsletter can capture. The density of insight in a single hallway conversation with someone who's actually building often beats months of research.
My encouragement for you is to find at least one room to walk into this month.
A conference. A webinar. A lunch or coffee with someone who's further into AI transformation than you are. The format matters less than the friction. You need someone who will challenge your assumptions. One conversation with an operator who's already shipped what you're still planning can compress months of internal debate into a single hour.
And if there are conferences, summits, or communities where these conversations are happening that I should know about, I'd be grateful if you reach out. I'm always looking for the next room worth walking into.
From The Portfolio
Board of Innovation is the AI Transformation Studio behind the AUTONOMOUS: OBSOLETE summit. They work with mid-market and Fortune 500 companies to redesign how they identify, validate, and capture value in an AI-first environment. If the themes above sound like the conversations happening inside your organization, that's because BOI is helping enterprises answer them in practice, not just on stage. boardofinnovation.com
AlignAI is the operating system for enterprise AI portfolio management. One visibility layer, one approval workflow, one place to see what's running, what's working, and what's stuck. Companies using AI governance push 12x more projects to production. AlignAI's co-founder Rehgan Bleile is moderating at OhioX this Thursday because the gap between pilot and purchase order is the same gap AlignAI was built to close. getalignai.com
The conversations are converging. The question is whether your organization is converging with them.
Reach out if you'll be in any of these rooms. I'd love to compare notes.
Jason Hauer Founder & CEO, HauerX Holdings jason@hauerX.com
