Episode #174
March 12, 2026
Leading Transformation Through Systems, Strategy, and People
with Holly O’Dell from Montana State Fund
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Holly O’Dell is the President & CEO of Montana State Fund, the state’s largest workers’ compensation insurer, covering more than 60% of the market in a fully competitive environment. She brings a rare combination of credentials — a BSN from Oregon Health & Science University, a JD from Lewis & Clark College, and an MBA from the Wharton School — that she’s deployed across careers in public health nursing, workers’ comp litigation, corporate strategy, and executive leadership. Before joining Montana State Fund in 2022, Holly spent nearly 17 years at SAIF Corporation in Oregon, rising from trial attorney to Vice President of Strategy, Government Relations, Legal, and Procurement.
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Risk Tolerance: The Foundation No One Talks About
When Holly O’Dell arrived at Montana State Fund in 2022, she didn’t bring a technology roadmap or a digital transformation initiative. She brought a philosophy: you cannot build anything worth building until you’ve built a culture that’s genuinely comfortable with risk.
“I’m not into norming. I’m into storming,” Holly told us — a phrase that captures her instinct for finding organizations at inflection points and pushing them through change. For Holly, risk isn’t the enemy of good insurance practice. It’s the product. “Risk is an opportunity for gain or for a loss,” she said. “That’s what I think is beautiful about insurance.” Applying that insight internally — building the cultural permission to make mistakes, challenge the status quo, and question how things have always been done — was the prerequisite for everything else that followed.
This reframe has practical consequences. Holly described a moment where Montana State Fund was canceling 27,000 policyholders per year — more than their entire customer base — for failing to submit payroll reports. The instinct was to reach for a technology solution. Pay-as-you-go had been discussed. But research showed pay-as-you-go had a 9% adoption rate among exactly the small businesses that were getting canceled. The real solution was simpler: stop requiring midterm reporting and estimate payroll automatically instead. Cancellations dropped to a third of their previous levels. “Cancel cancellations,” as Holly put it. The willingness to question a long-standing process — to accept the risk that estimating might be less precise than auditing — is exactly the kind of cultural muscle she’s building at Montana State Fund.
People First, Technology Second
One of the most striking data points Holly shared was the transformation of Montana State Fund’s workforce since she joined. Claims turnover was at 40% when she arrived — a number she describes as a symptom of an organization that was tightly focused on compliance and quality assurance at the expense of human judgment and professional trust.
The fix didn’t require a new HR platform or a compensation overhaul. It required changing the permission structure. Holly’s team created rover roles so that employees returning from leave didn’t come back to a pile of work. They opened pathways for claims professionals to work on IT and underwriting projects. They gave people permission to say yes to their customers without routing every decision through a QA checklist. “We got out of the way of being kind to each other and putting people first,” Holly said. The result: turnover fell to 4.5% and has stayed there. Gallup Q12 scores climbed to the 90th percentile among financial firms with more than 100 employees.
That foundation — employees who feel trusted and connected to mission — has become the fuel for Montana State Fund’s technology ambitions. Holly described CEO listening sessions where employees express genuine FOMO about innovation projects. Nurses are volunteering to use AI for medical record analysis. IT teams are collaborating with claims on Guidewire integrations. “All we had to do is get out of our own way,” Holly said. The cultural groundwork she laid first is what made that appetite possible.
Strategic Clarity in the Age of Shiny Objects
Holly is direct about the risks of technology-first thinking in insurance. “Technology could be flipped sometimes — we’re at risk of having a solution in search of a problem,” she said. Her antidote is what she calls being strategic: making an integrated set of choices about where to play and how to win, then pursuing only the initiatives that serve that strategy — even at the expense of things that seem appealing.
Montana State Fund is using Guidewire for claims and recently completed a cloud migration that Holly described as on scope, on schedule, and on budget — a significant achievement by any measure. They’re exploring AI for medical record analysis, cybersecurity training, coding support, and analytics. They’ve partnered with Gradient and WiseDoc pilots through the ASKIF network of state workers’ comp funds. Holly’s honest assessment: “Nobody’s nailed it yet.” But the strategic intent is clear — narrow the use case, understand the problem deeply, and let the technology serve a defined need rather than generate one.
Perhaps most striking was Holly’s description of building a workers’ comp regulatory sandbox with the Montana legislature — possibly the first of its kind in the world — specifically to create a protected space for insurance innovation experiments. That’s not the action of an organization waiting for the industry to change. It’s an organization trying to lead the change from the inside out.
“Nonprofit is not a business model.”