Matt Ingersole has spent enough time in enterprise technology to know that expertise can occasionally become a liability.
After more than a decade working with enterprise platforms, including running NetSuite and digital transformation practices, the Chief Digital and Information Officer at Leadership Circle had developed a pretty good sense of what technology could – and couldn’t – do.
Or so he thought. In a last-ditch attempt to avoid bolting on yet another technology tool to an already heaving stack, Ingersole used a long road trip to seek a second opinion from his AI chatbot.
“I was on a long drive to Ulladulla, talking to Claude about the problem – and it kept telling me our existing platform could already do this,” Ingersole tells The CEO Magazine.
“I argued with it for about three hours. It was right, and I wasn’t.”
Rethinking what’s possible
The problem Ingersole was trying to solve was hardly unusual. Leadership Circle®, a global leadership development company whose flagship Leadership Circle Profile® assessment is used by around half of the Fortune 100, was growing – and the complexity behind delivering its programs was growing with it.
Its teams run large enterprise projects around the world, sometimes involving more than 500 leaders. While the underlying data was in all the right places, the people managing those programs had to navigate a collection of systems and spreadsheets to get their jobs done.
“We’re fully remote in every region, so the system is the office,” Ingersole points out.
“Delivery Center has tightened how we work as much as it’s sped it up.”
Buying another project management tool might have provided a short-term fix, but it would have also fragmented data the company had spent years consolidating.
Instead, the conversation with Claude led Ingersole to discover that Leadership Circle could build exactly what it needed on top of its existing NetSuite platform.
“The capability had been in their product for years, but nobody had ever aimed it at a problem like ours before,” he explains.
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“When I showed NetSuite, they hadn’t seen a customer take it that far either – and they got really excited about it.”
The result is Delivery Center, a bespoke application built within NetSuite’s framework that brings projects, scheduling, assessments and contractor payments into one workspace.
Ingersole, recognized for his outstanding innovation in The Innovators 2026, brought it to life, but he’s quick to acknowledge it was never a one-man project.
“I built it with AI coding agents, working with Katherine Anderson, who represented the users, and a volunteer group testing every release,” he shares.
Turning complexity into capacity
Today, around 250 people across Leadership Circle work differently because of Delivery Center.
Previously, project managers could be carrying more than 15 projects across multiple systems and spreadsheets, spending much of their time reconciling information to simply make sense of it. Now they work from a live view that shows them exactly what requires their attention.
“For the first time, our project managers have one live view of everything, and they manage by exception,” Ingersole says.
“The system tells them what needs their attention, and they only touch that.
“A weekly client report used to take two hours of spreadsheet formulas – it’s one click and five minutes now.”
“The time we get back is going straight into customers.”
Contractor payments have been similarly transformed. Rather than requiring coaches to submit invoices, Leadership Circle generates payments based on work completed. The benefits go beyond time saved, though.
“Delivery Center has tightened how we work as much as it’s sped it up,” Ingersole confirms.
“We’ve rolled the same experience out to sales now, too. And the time we get back is going straight into customers.”
Building for what’s next
Delivery Center may look like another overnight AI success story, but Ingersole says its foundations were laid years ago.
Since joining Leadership Circle, he’s built the company’s technology function across global platforms, data, security and AI alongside pricing work that improved EBITDA. Part of that work involved consolidating systems, cleaning data and deliberately reducing the number of strategic platforms the company relied upon.
“A lot of the foundations that made Delivery Center possible were built years before we knew we would build it,” he says.
Making work human
For Katherine Anderson, Global Director of Execution and Delivery Excellence Operations, Delivery Center’s impact comes down to what people can do with the time it gives back.
“This is not a case study about operations. It is that efficiency and humanity are not competing priorities,” she says.
“Every hour we give back to a project manager, finance colleague or coach, is an hour returned to the work that actually matters: being present with the leaders we serve.
“We built better systems so our people could do more human work, not less of it.
“And, in the end, that is how we evolve the conscious practice of leadership: by practicing it on ourselves first.”
That groundwork has created opportunities well beyond Delivery Center. Leadership Circle has become ‘customer zero’ for Atlassian’s AI-powered Customer Service Management (CSM) and has also been selected for Oracle NetSuite’s AI beta program.
Its help centers, built on CSM, now resolve many inquiries without a person stepping in, which has eased the load on the support team. Meanwhile, the company is increasingly removing point technologies from its stack and replacing them with capabilities built around its core platforms.
Ingersole believes it’s evidence of a much broader shift.
“AI changes what a small team can realistically build.”
“A lot of companies already have the platforms, data and people they need to create things that would have required a large engineering team only a few years ago,” he says.
“AI changes what a small team can realistically build. But the foundations still matter enormously – AI won’t magically fix data that is fragmented, platforms that aren’t connected and security that isn’t right.”
Next, Leadership Circle is exploring how the same combination of platforms, data and AI could be applied more directly to leadership development and the customer experience.
Ingersole isn’t revealing much about those plans yet. Perhaps fittingly, however, he is considerably less certain than he once was about where the limits lie.
“The biggest lesson for me personally is to keep challenging what I think I know,” he acknowledges.
“Just a few years ago, I had a very different idea of what was possible. It’s a reminder to never assume that today’s limits will be tomorrow’s.”
