John O’Donnell picked an interesting time to change jobs.

The way the world works is radically changing, and just as the pandemic—apparently—wanes, he’s taking the helm of a large workers compensation provider.

The biggest challenge he faces clearly is to try and “understand what future of work looks like,” he told a reporter during an interview on Feb. 28, the day he had officially started his new job as president and chief executive officer of Pinnacol Assurance.

Pinnacol is Colorado’s largest workers compensation carrier with roughly 55,000 businesses insured, and an estimated 1 million Colorado workers covered.

O’Donnell succeeds Phil Kalin, who is retiring on March 31.

More and more “help wanted” postings on the internet offer “hybrid,” or “remote” as perceived benefit for job applicants. In the Eastern U.S., a Federal Reserve Bank of Richmond survey showed more than a fourth of employers expect to have more remote workers next year.

Figuring out how to insure the risks faced by a workforce that may be increasingly allowed to work from home, or work both on-site and at home in a hybrid role, is a daunting task, O’Donnell acknowledged.

“That’s something we have to figure out is, ‘How does the nature of that risk change?” he said.

The changes he makes could be more profound than merely figuring things out; they could transform a company that’s been doing pretty much the same thing since its founding more than 100 years ago.

And it’s likely that whatever moves he and the company make, they’ll be closely watched.

As a company that has a big hand in the lives of so many Colorado firms, anything Pinnacol does in that state is noteworthy there.

Most of their recent moves have been positively received for obvious reasons. Pinnacol for the sixth straight time last year distributed general dividend checks to its customers. Pinnacol has also decreased rates for seven consecutive years for a cumulative decrease of 40 percent. The Denver Post last year named it one of the state’s “top workplaces.” (Pinnacol Assurance was also featured in Carrier Management’s look at “Talent Magnets: Carriers That Employees Love to Work For,” in 2020.)

O’Donnell doesn’t have a deep workers’ comp background. But he seems to have ample leadership chops. He joins Pinnacol with 30 years of leadership experience. He was most recently an executive vice president at Allstate, serving as the president of Western Territory, and he was board chair of Allstate Canada, where he was responsible for 27 states and the Canadian company. O’Donnell also served in leadership positions at GMAC, the Walt Disney Co. and Goldman Sachs.

Challenges are also not new to him. He began his career as an attack helicopter pilot in the U.S. Marine Corps.

O’Donnell outlined the task for the insurer to deal with the sweeping workforce evolution as first understanding how the mix of businesses in Colorado is changing, and then how those changes impact risk profiles.

What they’ve seen at Pinnacol is an increasingly remote work environment that has grown beyond state boundaries.

“We have a lot of remote workers that are located outside of the state,” O’Donnell said.

Such is the case with many who do business with Pinnacol, which puts the company in the unique position of being a one-state, monoline business with customers who are asking for and requiring broader coverage.

O’Donnell sees that solution to that as fairly straightforward, but also challenging.

“We’re looking at different ways we can start to expand our business to meet the needs of customers, to even go beyond Colorado or go beyond workers compensation coverage,” O’Donnell said.

Other questions, especially in an area as complex and convoluted as workers’ comp, remained for him to answer—”How do you plan to tackle soaring drug costs?” “What do you consider to be some of the biggest risks for Colorado employers?” —but those are questions best tackled far past one’s first day on the job.

O’Donnell, when talking about his plans, COVID-19 and remote work, risks, and just about anything else, stayed focused on the challenge theme.

“I always believe that with change like this comes opportunity,” he said. “I’m looking forward to the challenge. Status quo is not going to cut it.”