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The Place Companies Start: Ten Years of Answering “Where Do We Begin?”

Adam Dillman, Founder and CEO of UTurn Data Solutions, marks a decade in business and four straight Crain’s Fast 50 wins by explaining why the AI moment mirrors the cloud one UTurn was built for.

Author

Adam Dillman

Founder and CEO at UTurn Data Solutions

Highlights

• Get a founder’s honest reflection on ten years in business and four straight Crain’s Fast 50 wins
• Learn why the question that built UTurn a decade ago is back, now about AI
• Understand why history does not repeat but rhymes, and why that matters now
• See why the people who bet on an unproven company are the reason it lasted
• Discover why UTurn meets the AI moment as an established firm, not a scrappy startup

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July 7, 2026

UTurn Data Solutions just earned its fourth consecutive place on Crain’s Chicago Business Fast 50, in the company’s tenth year in business. In the final installment of UTurn’s three-part executive blog series, Founder and CEO Adam Dillman steps back from the milestones to name a pattern he keeps hearing: the question that built UTurn in the cloud era, “we know we need this, we just don’t know where to start,” is now the question every company is asking about AI. He argues the parallel is not a coincidence but a map, and that cloud is the enabling technology that powers AI. With a decade of data discipline, a deep AWS partnership, and hands-on AI adoption behind it, UTurn is positioned to be that first step again, this time as an established firm rather than a startup earning trust from zero. It is a founder’s case for why the next ten years look a lot like the last ten, only bigger.

There’s a moment each of the past four years, when Crain’s Chicago Business announces the Fast 50, that I let sink in before responding to congratulatory messages. Not out of false modesty, I’m genuinely proud of what this team has built, but because that pause is how I stay honest about where we’ve been, what it cost us to get here, and what’s still ahead.

This year, that moment carries extra weight. UTurn appears on the Fast 50 for the fourth consecutive year, in what is also our tenth full year in business. That combination, ten years of operation and four straight years of top-tier growth, is not the product of a couple of good years. It reflects a decade of disciplined execution by a team I am proud to lead, and it sets up what I believe is a defining opportunity ahead.

“We Know We Need This. We Just Don’t Know Where to Start.”

Ten years ago, that sentence defined the market we entered. Cloud computing was not a hard sell. Business and technology leaders already understood it mattered. The difficulty was execution: which workloads to move first, what a well-architected environment actually required, how to modernize without disrupting operations, and which partner could be trusted to lead the process.

That uncertainty was not a failure of ambition. It was the natural consequence of a technology shift outpacing most organizations’ internal expertise. It created demand for a specific kind of partner: not a vendor selling a single product, and not a large consultancy that hands clients off to junior staff, but a firm capable of understanding a business and converting intent into an executable plan. UTurn was built to be that firm, by a small group of people who took a real risk on an unproven company to do it.

We are hearing the same statement today, with the technology changed. “We know we need to integrate AI into our business, we just don’t know where to start.” This has been the central theme of client conversations over the past eighteen months, across nearly every industry we serve. The pattern is the same one that built our business a decade ago.

History Does Not Repeat, But It Often Rhymes – Mark Twain

The parallel is instructive, and it is central to our confidence in what comes next.

Ten years ago, companies recognized cloud as inevitable, but the path forward was unclear and carried real risk if executed poorly. Today, companies recognize AI as inevitable. Boards are asking about it. Competitors are testing it. Yet operationalizing AI safely, on a sound data foundation, in a way that produces measurable outcomes rather than isolated demonstrations, remains just as unclear. The margin for error may be smaller this time. The pace of change is faster, and the cost of failure (a flawed model in production, or ungoverned data feeding it) is higher.

This is the moment UTurn is built for. Not the point at which a playbook already exists, but the point before it, when the destination is clear but the path is not. That is when organizations need a partner with direct experience navigating uncertainty.

Why UTurn Is Positioned to Lead

We have guided companies through a major technology shift before. Cloud is the enabling technology that powers AI, and AWS continues to lead the way. Our AWS partnership has grown over the decade (case studies, specializations, certifications, and Strategic Collaboration Agreements), built through sustained investment rather than assembled to capture a trend. We understand what a real data foundation requires, because we have spent ten years building the governance, pipelines, and taxonomies that foundation demands. And we understand what operationalizing AI requires in practice, because we are embedding AI into our own operations.

That last point matters. Clients are not simply looking for AI expertise in theory. They need a partner who has worked through the practical process of adoption, who knows where AI delivers quickly, where it requires patience, how it integrates with your cloud investment, and where the risks concentrate. We bring that perspective from direct experience.

It is also the premise behind our Architect-in-Residence (AiR) program. AiR embeds a senior technical leader inside a client’s organization, with sufficient proximity to its systems, people, and constraints to move AI adoption from pilot to production. We built this model years before “forward deployed engineer” entered the industry vocabulary, because the underlying question has always been central to our work: how does a technology shift take hold inside a real organization, not just inside a proof of concept.

What Comes Next

We are positioned to be that starting point again, this time for an opportunity larger than the one that built this company.

Every organization uncertain about AI adoption needs an initial conversation, an initial assessment, an initial step forward. A decade ago, UTurn was built to be that step for cloud. Today, with ten years of data discipline, cloud expertise, direct AI implementation experience, and a deep AWS partnership, we are that step for AI. Unlike a decade ago, we enter this moment as an established firm, not a startup building credibility from scratch. We bring the accolades, certifications, client relationships, and track record to demonstrate that credibility immediately.

This means organizations that come to us today asking where to start receive a faster, more informed, experience-based answer. It also means we are positioned to spend the next decade doing what we do best: converting uncertainty into a plan, and a plan into measurable results.

Positioning Didn’t Build Itself…Acknowledgements

None of this happens without people, and I want to name them plainly rather than in general terms.

I think often about our earliest employees, the ones who joined a company with no track record, no brand recognition, and no guarantee it would still exist in a year, let alone win awards a decade later. They took a real risk on an idea, and everything we have built since rests on that decision. I do not take it for granted, and neither should anyone reading this.

I am equally grateful for the leaders across UTurn today, the people who run our practices, manage our client relationships, and set the standard for how this firm operates. Their judgment, day in and day out, is the actual reason we have grown responsibly rather than recklessly, and the reason clients trust us with decisions that matter to their businesses. A firm’s reputation is built by its leaders long before it shows up on any list, and ours have earned every bit of the one we have.

Our clients placed their trust in us before we had an established track record, and they continue to place that trust in us today for work of comparable significance. Our partners at AWS have invested in this relationship in ways that give us a platform few firms our size have access to. Our advisors and the broader Chicago business community have supported this growth at every stage.

To all of them: thank you. I can’t wait to see what we’ll achieve together over the next ten years.

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