HomeRental ResourcesPodcastsHow AI and Automation Are Transforming Equipment Rental Operations

How AI and Automation Are Transforming Equipment Rental Operations

25 Min
September 17, 2026
Episode #118
how ai and automation are transforming equipment rental operations

For years, the least glamorous part of running a rental business was everything that happened behind the counter. Operations. Process. The workflow that turns a phone call into a machine rolling out the gate. It was the work nobody bragged about, and it usually got the least attention of anything in the company.

That has changed fast. On episode 118 of The Rental Roundtable, I sat down with Dan Crowley, owner of Peer Executive Groups, for his fifth time on the show, officially holding a Rental Roundtable record. Dan runs peer groups for hundreds of independent rental owners, so while we see the trends on the data side, he is in the room hearing what operators are actually doing. This quarter his groups are focused on operations and processes, so we spent the episode on where AI is already changing that work.

It was a shorter, sharper conversation than usual. Here is what stuck with me.

It All Starts With the Customer

Dan is a student of business. When he talks about operational excellence, he can rattle off the 5S’s, ISO 9000, quality improvement, all the frameworks for workflowing the inefficiency out of a company. But when I asked him where an owner should actually begin, he did not start inside the shop or the mechanical bays. He started at the front door.

“From my perspective, it begins with the customer. It begins with the prospect and their ability to kind of navigate into your company and become a customer of yours.” Dan Crowley, Owner of Peer Executive Groups, (3:32)

That framing matters because it is easy to chase efficiency in the wrong place. You can shave minutes off a maintenance bay and still lose the customer at the quote. Operations improvement that starts with how a prospect finds you, checks availability, and becomes a paying renter is the version that actually shows up in gross profit.

From Seven Clicks to Zero

Most rentals still happen at the counter or over the phone. Someone calls, your staff looks up availability in the software, checks out the machine, and sends a quote. It works, but it is a lot of clicking. We took our own contract flow from ten clicks down to seven, and even that felt like a win. Dan made the point that the person doing all that clicking is rarely doing just one job.

“They’re actually doing probably three to four different jobs to get to that point where there is a piece of equipment outside ready to rent.” (7:46)

So here is the question we have been chasing at Quipli: why are there any clicks at all? Why should your counter staff enter seven fields when an AI agent could listen to the call, recognize the customer, know their terms are already set up, and fill out the whole contract for you? That is exactly what we have been building with Quinn, and we have launched it with early customers where that seven-click process is now zero. For an operator, that is real labor saved on every single rental, and it is people freed up to do the three or four other jobs that actually need a human.

What AI Still Cannot Do

None of this replaces the thing independents are best at. I told Dan where I think the line is, and he agreed. The relationship is never going away. The independent that answers the phone, knows your name and your birthday, and remembers the machine you always rent is not something an agent competes with. Neither is the physical side. Being in the field, diagnosing and fixing equipment, getting a machine delivered and running, that is where AI does not touch the work right now.

The more useful way to think about it is not replacement, it is filling the jobs rental companies were never able to staff in the first place. Good people have always been hard to find in this industry. If the software runs the button-clicking, your team spends more time in the field, on more customer visits, prospecting, and maintaining equipment better. The work moves to where humans are actually the advantage.

Operations Went From Afterthought to Main Event

Dan has been facilitating peer groups long enough to watch the industry’s priorities shift in real time. He described the four quarterly themes his groups rotate through, and admitted that operations and process improvement was always the one nobody got excited about. Not anymore. If you want the longer version of how Dan’s groups think about strategic planning alongside operations, his earlier appearance on episode 76 covers it in depth.

“This redheaded stepchild has always been process improvement and operations. And I can honestly say that it’s been flipped on its head.” (13:07)

In the last year, AI has become a regular, structured segment on his meeting agendas, right alongside safety and cyber theft. His groups run idea contests where members pitch their best idea and vote, and Dan told me that for the last three years running, whoever brought the best AI idea usually walked away with the win. The point for any owner reading this: the operators sharing ideas with each other are pulling ahead of the ones going it alone.

The Tool Is Only as Good as Your Curiosity

This was my favorite line of the conversation, and it is the one I would put on the wall. It is easy to treat AI like a switch you flip. Dan sees it differently, and after three years of watching members use it, he has a clear read on who actually gets results.

“At the end of the day it’s only as good as how curious you can be to make an improvement or make a change.” (14:27)

The members making real gains are not the ones with the fanciest tools. They are the ones curious enough to keep asking what else the tool could do. You can hand two owners the same software and the same AI assistant, and the one who keeps poking at it, refining prompts, and chasing the next small improvement will run circles around the one who ran it once and moved on.

Your Inbox Is About to Run Itself

Dan is not theorizing about this stuff from the sidelines. He is already living the version of the workday most of us are heading toward, starting with the single most universal time sink in business: email.

“I get a hundred emails a day. I don’t look at email. It gives me a summary every four hours and says, hey, you got 30 emails. These are the four that matter.” (17:43)

He does not open his inbox anymore. An agent triages it, surfaces the handful that matter, and flags a few more worth a look. He thinks everyone will be there within a year, and honestly, so do I. My agent replying to your agent is not a bit from a keynote, it is close. The same logic runs through dispatch and sales. Route planning for a rep with ten stops in a day is thirty minutes of planning an agent can just hand you, which is thirty more minutes with customers. That is the same problem Dillon Baird tackled in episode 113 on building a winning rental sales team, and it is baked into our own dispatch and scheduling tools now.

Data Should Tell You What’s Coming, Not Just What Happened

Dan’s bread and butter with his members is rate-of-change data, the twelve-month, three-month, and one-month trends that tell you how the business is actually moving. It is powerful, but by definition it is backward-looking. What has him excited is using AI to push that view forward. He told me about a member, going back about ten years, who found the leading indicators for his own market before anyone had the tools to make it easy. For more on the data side, the equipment rental business performance calculator is a good place to start benchmarking your own numbers.

“He had identified very specific economic indicators that the graphing of their rate of change was absolutely exactly what was happening to his business in Ohio.” (20:37)

That indicator, for the record, was the PMI, and for earth-moving rental it tracked his up years and down years with about a twelve-month lead. What used to take a data scientist and a clunky dashboard, you can now stand up in an afternoon. Pull weather data, seasonal data, permit and future-project data, drop it in next to your rental software numbers, and ask what is coming six months out. The top operators are already making decisions this way. It is the same theme we dug into in episode 107 on using data and AI, and the advantage is only growing.

Use the Data to Drive Change, Not Just to Watch It

Dan’s closing warning is the one every owner needs to hear before they go build a dozen dashboards. Data for data’s sake is worthless. If you set a goal for a metric, you have to actually check whether it is moving, and if it is not, make it an issue and ask why.

“Are you seeing progress in the utilization? Are you seeing progress in the shortening of cycle times?” (23:52)

His warning is that you get numb to numbers you stare at every day. The metric stops driving decisions and just becomes wallpaper. Use the data to drive change, not to admire it.

That is exactly why we built Quipli the way we did: to take the button-clicking off your team’s plate, surface the numbers that actually move gross profit, and give you back the hours to spend where you and your people are the advantage. If operations is your focus this quarter too, come see what the platform can do.

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About the Speakers

Dan Crowley

Dan Crowley

Dan Crowley is the owner of Peer Executive Groups, which runs peer advisory groups for business owners across industries including equipment rental. He facilitates groups for hundreds of independent rental owners, structuring their meetings around quarterly themes, rate-of-change benchmarking, and member idea contests. He also hosts the Peer Talk podcast. This is his fifth appearance on The Rental Roundtable, more than any other guest.

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