Top Workplaces 2026: Chicagoland employers are moving to embrace AI, but employees remain cautious

The artificial intelligence boom is reshaping the workplace, as employers rush beyond casual experimentation with generative tools to full-scale implementation.

In the Chicago area, companies ranging from tech upstarts to real estate firms and car washes are determining how business gets done with the help of AI, aiming to capture productivity gains and set themselves up for a more profitable future.

“It changes how creative you can be with things,” explains Chris Brown, president of Chicago-based Relativity, a technology company providing legal data intelligence through its AI-enabled software. “I would expect that there isn’t a workflow or an employee that isn’t talking to AI.”

One reason, Brown says, is that the technology is simply better than it once was. Frequently cited pitfalls of AI, including accuracy issues, have significantly improved over earlier iterations of platforms such as Anthropic’s Claude or OpenAI.

“Now, there’s just forward progress,” adds Brown. “I believe every company will adopt significant AI technology.”

Some local companies, including those on the Chicago Tribune’s 2026 Top Workplaces list, are using AI to handle emails, summarize spreadsheets, enhance marketing or address common customer queries, while others are leveraging more complex AI capabilities to advance research, data analysis and software development in-house.

“AI allows us to be smarter, sharper and faster with clients,” explains Bret Greenstein, chief AI officer at Chicago-based West Monroe, a business and technology consulting firm that ranks 16th among midsize employers on the Tribune’s Top Workplaces list. “If you’re good at anything, you’ll be able to have a bigger impact, because you’ll get to do it at scale.”

The technology is rapidly transforming the way people work, in part by eliminating some of the busy work and tedium of manual workflows, freeing up time for employees to focus on more complex issues.

But it has also put many employees, who fear automation will make their jobs obsolete, on edge. Companies say navigating those concerns and helping workers embrace the technology will be key to sustaining AI’s momentum.

‘It’s all about being curious’

At 1st Ayd Corp. in Elgin, CEO Tommy Schreiner estimates that between 10% and 20% of employees actively use AI in their daily work.

So far, AI has given the company, which distributes maintenance, safety and janitorial supplies and ranks 10th among small companies on the Tribune’s Top Workplaces list, a prime opportunity to boost its sales and marketing. Before AI, chasing down leads or coordinating multiple photo shoots to showcase 1st Ayd products to business prospects could have easily ratcheted up costs.

Today, the company can use AI to generate high-quality, photorealistic images mimicking those same products in action in various customer environments with a simple prompt, in minutes.

“What could have been a 30-minute conversation in 2019 is now a three-second (task),” says Schreiner, who also credits AI agents and tools for managing the more “boring” sides of business, such as managing inventory spreadsheets. “With search bots, you can create a prompt: ‘Act as a marketing executive’ and it will learn your preferences. After two months, it’s almost like you’ve hired somebody.”

Schreiner hopes a higher number of employees will embrace AI as they become more comfortable with the technology and the benefits play out over time.

“A lot of (sales) reps say ‘I don’t trust this AI stuff,’” he explains. “That’s a fair concern when you read the news. But there’s going to be good and bad with it. Be cautious, but learn these tools. AI is happening, and it is the wave of the future.”

Schriener says steering the legacy of his family’s 50-year-old business at a time when companies are hurtling toward AI transformation comes with its fair share of stress.

“We’re all new to this,” he says. “There may be folks ahead of me, but it’s all about being curious.”

Workplace tension

Even as business leaders champion the advantages of AI, many employees struggle to navigate the practical realities of embracing the technology on the ground.

Over the summer, Pew Research found that 71% of U.S. adults believe AI will lead to fewer jobs over the next 20 years, with the majority of adults adding that AI is advancing too quickly for society to keep up.

Research shows some of these job security concerns may be valid.

In April, a report from Challenger, Gray & Christmas cited AI as a top-driver of layoffs, with companies attributing the technology for roughly 26% of job cuts.

Energage, a human resources and technology company that surveys Chicago-area employers and formulates the Tribune’s Top Workplaces list, reports that the combination of unprecedented pressures and looming uncertainty is dividing workplaces — and stifling progress on more widespread AI adoption.

The group recently surveyed more than 88,000 employees at 600 companies to analyze AI adoption rates, and discovered a significant leadership-employee disconnect.

“Leaders have a more rosier view about the upside of AI,” says Kinsey Smith, a manager of People Science at Energage. “(The idea) to repopulate work with AI agents is much harder to grapple with at the employee level.”

Energage found that while half of employees regularly use AI to support their work, only half “feel optimistic” about its impact.

Smith says building AI awareness isn’t the main issue; maintaining employee mindsets and trust is.

“The hype may be overblown, but I have not yet heard about anyone’s role shrinking,” explains Smith. “The question is whether the positives are going to outweigh the negatives. I think organizations need to be really thoughtful with AI.”

Aaron Goldman, chief marketing officer at Mediaocean, points out this process of change management isn’t new.

The company, which is headquartered in New York and has an office in Chicago, uses a range of AI tools to route more than $200 billion of advertising annually for clients around the world.

“There is a lot of fear, uncertainty, and doubt right now,” said Goldman, whose firm ranks 26th among midsize employers on the Tribune’s 2026 Top Workplaces list. “As AI is able to automate the business, it’s not that it replaces humans,” but rather forces companies and employees to adapt quickly. Right now, there is a lot of ‘fear of missing out,’ he adds. “A year from now, we’ll see AI become a regular part of the business.”

Like other companies striving to move past experimentation toward practical solutions, the company is invested in how AI can be used to drive real business outcomes.

Goldman said the company’s internal AI programs have clocked nearly 500 hours per year in efficiency savings. Newly installed automations have resolved roughly 93% of customer service tickets without an expert, and a companywide hackathon — an event encouraging employees to build hands-on AI skills — successfully generated six prototypes, which are now live in its software applications.

“We’ve been around for 60 years,” Goldman explains. “We’ve had to continually be agile and adapt to new technologies. It’s a constant effort to help people understand what’s here today and what we can do tomorrow. Our technology has gotten better and customers have gotten better results.”

Research from Appian for the Harvard Business Review indicates that while AI adoption is still maturing, with the majority of organizations reporting incremental productivity improvements, financial metrics such as revenue and ROI have remained largely flat.

Brown, of Relativity, insists that adopting AI is a necessary move to maintain healthy peer-to-peer and global competition.

“For corporations and enterprises, they are educated on a set of problems and expected to solve these problems,” for customers, explains Brown, whose company ranks 31st among large firms on the Tribune’s Top Workplaces list. “But the same technology also enables other people to do the same thing. While this technology is coming online, people are saying ‘I need to learn to use this better’ or their competitors will do it for them.”

Navigating employee skepticism

Communication and culture are key when it comes to implementing AI tools and helping employees get comfortable with them.

Brown says building a culture where employers feel comfortable experimenting with the technology can foster collective learning and help push AI adoption along.

“Just getting lectured about it is not going to interest them,” Brown adds. “Having a champion that can help influence modeling what the change could be has always mattered. Right now, it matters more. They can help manifest the future.”

Employees are skeptical of AI when it’s presented as a “solution in search of a problem. But Brown explains that the technology can do “many more things than answering a question.”

“It’s easy for a human to understand asking a question and getting an answer. It’s a lot harder to (convey) how to leverage the manpower of 25 people and use it to my advantage to generate 10% in productivity.”

Greenstein agrees a top-down approach isn’t likely to woo employees who are already skeptical about embracing AI. To help employees overcome their fears about the technology, West Monroe holds weekly enablement sessions to showcase how fellow colleagues are innovating with AI and to ask questions about how to apply the technology to their own work. People show up in droves, and firmwide productivity is up.

“The culture of a business is probably more important than it’s ever been,” Greenstein said. “I don’t think leaders were prepared for this moment — not every leader is set up for this. Some businesses are better able to innovate with AI than others. We train people; we learn from what they do. Because it’s entirely about how people adopt, learn and transform. But I think everybody can be ready.”

Greenstein believes the full potential of AI is only just beginning to be realized. Over time, he expects employees to grow in confidence and get on board.

“Once you see the capabilities, I think it eases fears about (job) replacement,” Greenstein adds. “I think the fear is mostly through the lack of comfort and investing the time to learn it. It’s intimidating as a technology, and it’s easy to personify it as science fiction.”

Energage’s Smith says preparing an organization for AI readiness often comes down to managers empowering employees to identify the right use cases — and ensuring that leaders embed transparency and authenticity throughout each phase of adoption.

Blanket deployments, issued without clear communication or direction, are unlikely to be successful. Smith also says employers should trust implementation feedback from employees who know the ins-and-outs of their roles better than anyone else.

“AI as a tool is going to provide value like anything else, but you can’t give the wrong people a hammer,” Smith says of leaders. “If you don’t know what problem to solve, I don’t see how AI can help.”

S. Sorrina Beecher is a freelance writer.