Trent Gillespie
May 27, 2026
The best part of my job is talking with business leaders everywhere. From every size and type of company. Logistics. Construction. Engineering. Mental Health. Credit Unions. Real Estate. Industry Associations. Entertainment. Golf course management. Portable storage and sanitation. The list goes on.
Although very different in industry, they all have one thing in common. They are good people running good companies, doing everything they know how to do, with no idea how much is sitting right in front of them.
That's not a criticism. It's an observation that keeps me up at night. Not with worry. But excitement. Intrigue, even.
Because here's what I know that most of them don't yet.
The tools that used to belong to the giants -- the ones that required enterprise budgets and IT departments and years of implementation -- are sitting on their desks right now. Affordable. Accessible. Ready.
And most of them are treating it like a curiosity instead of the opportunity of a generation.
I mapped one company recently. Looked at everything they should be doing to perform at their absolute best. Every process, every capability, every customer experience they could be delivering with what exists today.
374 total processes. The template for their perfect business, AI-enabled, and human-centric.
Today? They're running only about 75 processes manually. That means 299 processes they haven't even considered, let alone automated.
And I sat with that number for a while before deciding how to share it. Because a number like that can land two ways. It can feel like a verdict: look at everything you're not doing. You aren’t good enough. You can’t compete. You might as well give up.
Or it can feel like what it actually is. A picture of everything that's still possible. Every customer not yet reached. Every problem not yet solved. Every product not yet built. Every relationship not yet formed.
Those 299 missing processes aren't failures. They're the future of that business, sitting there waiting to be claimed.
That's the thing the AI conversation keeps getting wrong. It talks about replacement. About efficiency. About doing the same processes they have today with fewer people.
That's just wrong. It's limiting, zero-sum thinking. That we can't use AI to create growth and opportunity. That we can only imagine the future that we serve today.
And somewhere in that conversation, the companies that need this most start to feel like it isn't for them. Like it belongs to someone bigger, better resourced, further along.
It doesn't.
AI isn't for losers. It never was. It's for exactly the companies that have been told they can't compete.
The small company that knows every customer by name. The membership organization that's served the same community for thirty years. The regional firm that makes something genuinely good and has never quite had the resources to tell enough people about it. Those are exactly the companies AI was built for. For the first time in a long time, they have access to the same capabilities as the largest players in their industry.
Because they can do it faster, and cheaper, than those big competitors. They can eat their lunch.
That's not a small thing. That's a fundamental shift in who gets to compete.
One of those 299 missing processes -- one of the most valuable for almost any business -- is customer retention.
Most businesses find out a customer is leaving when they stop showing up. A membership lapses. A subscription cancels. A regular just quietly disappears. By then the relationship is already gone.
For any business built on recurring revenue, this is where margin lives. A 5% improvement in retention can increase profits by 25% or more. Keeping a customer costs a fraction of finding a new one.
The problem was never that businesses didn't care. It's that watching every customer relationship simultaneously, at the right level of attention, was never humanly possible.
Until now.
An AI agent working your retention looks like this:
Tracks login frequency, purchase recency, and engagement drops across every customer
Scores churn risk daily and surfaces the accounts that need attention
Sends a personalized check-in or offer triggered by behavior, not a calendar
Follows up automatically if there's no response within a defined window
Logs what worked, refines the playbook, and improves with every interaction
That's not a Fortune 500 capability anymore. It's available to any business willing to build it.
Most small businesses aren't doing this systematically. Not because they don't care. Because they never had the capacity.
Now they do.
The opportunity is real. The tools exist. The blueprint is within reach.
The hard part -- the only hard part -- is believing it. Believing the blueprint for your best possible company is within reach right now, not reserved for someone with a bigger budget or a fancier zip code. Most leaders I talk to already sense what's possible. They feel the gap. What they're missing isn't information.
It’s confidence.
Confidence in where to start. In how to cut through the noise, find the right path, and build the momentum to move.
That's the real barrier.
So over the past three years I've built and shared everything you need to overcome it.
The AI SPRINT methodology -- a project plan for how to actually move
The Future Customer framework -- a way to set your AI vision before you build toward it
My leadership and staff keynotes -- to align and motivate your group
A ChatGPT course -- online training your team can start this week
An AI Strategy Assessment -- a tool to show you exactly where you stand
Clarity -- a roadmap process to show you where to go next
The path is there. The only question left is whether you're ready to walk it.
Hit reply and tell me what's in the way.
Trent Gillespie is CEO of Stellis AI and a keynote speaker helping business leaders understand and operationalize AI in their companies. He spent almost nine years leading global innovation efforts at Amazon before leaving to help other companies build the capabilities they need to compete. Book Trent to speak to your group or book a call to discuss using AI within your business.
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