Holly O'Dell, President & CEO of Montana State Fund, joins host James Benham to discuss how systems thinking, people-first leadership, and strategic clarity are transforming workers' compensation — from inside a mission-driven organization that competes and wins in a fully open market.

Holly brings a rare combination of credentials to the role: a BSN from Oregon Health & Science University, a JD from Lewis & Clark College, and an MBA from the Wharton School.

Before joining Montana State Fund in 2022, she spent nearly 17 years at SAIF Corporation in Oregon, rising from trial attorney to VP of Strategy, Government Relations, Legal, and Procurement. Montana State Fund covers more than 60% of Montana's workers' comp market — in a fully competitive environment where they earn every dollar.In this episode:- Why risk tolerance is the real foundation of innovation — and how to build it before anything else- How Montana State Fund reduced 27,000 annual policy cancellations by two-thirds — without a single new technology- The people-first shift that brought claims turnover from 40% down to 4.5%- Building a culture where frontline employees have genuine FOMO about AI and innovation projects- What it means to be strategic in an industry full of shiny objects- The world's first workers' comp regulatory sandbox — and what it could unlock

Key Quotes:

"I'm not into norming. I'm into storming."

"Risk is an opportunity for gain or for a loss."

"Nonprofit is not a business model."

"Strategy is an integrated set of choices."

"This is an industry worth hanging out in."

Timestamps:07:53 — The 20-sided dice: why insurance attracts multi-disciplinary thinkers

15:12 — "I'm not into norming. I'm into storming." — Holly's leadership philosophy

19:30 — Cancel cancellations: solving a 27,000-policy problem without technology

23:57 — From 40% turnover to 4.5% — the people transformation at Montana State Fund

27:04 — The FOMO effect: building a culture where everyone wants in on AI35:51 — Firefighter training injuries reduced from 50% to zero — the predict-and-prevent model in action

🔗 Connect:Holly O'Dell: https://www.linkedin.com/in/holly-o-dell-26228452

Montana State Fund: https://www.montanastatefund.com/ | https://www.linkedin.com/company/montana-state-fund/👤

Host:James Benham: https://www.linkedin.com/in/jbenham

🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp.Visit 👉 https://terra.insure / https://www.linkedin.com/company/terrainsure/

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As always — Enjoy the Ride & Geek Out! 🤓

Dan Bratshpis, CEO and Co-founder of INSHUR, joins host Rob Galbraith to discuss how commercial auto insurance is being reimagined for the platform economy — and why traditional products are failing the drivers powering the gig economy.

Dan built INSHUR from a two-person MGA startup into a 200-person global company operating across the US and UK, with embedded insurance partnerships with platforms like Uber, Amazon, and DoorDash. His approach: build coverage that works with how people actually live and work, not how insurers traditionally categorize risk.

In this episode:

• Why traditional commercial auto products fall short for gig and platform workers
• How INSHUR embeds insurance directly into platform onboarding — and what that data advantage means for underwriting
• The usage-based wallet model: pay-per-ride, pay-per-delivery, pay-per-minute
• How COVID wiped out rideshare demand overnight — and became the pivot that launched INSHUR's delivery insurance
• Why INSHUR built Komodo Claims from scratch instead of outsourcing to TPAs
• What autonomous vehicles mean for frequency, severity, and the future of commercial auto insurance

Key Quotes:

• "What doesn't kill you makes you stronger."
• "Technology is an enabler to do things differently, do things better."
• "Claims is kind of at the heart of insurance."
• "These things don't get into accidents nearly as much as humans do." — on autonomous vehicles
• "Insurance is a really big part of protecting this new economy."

Timestamps:

• 09:05 — The wedding night pitch that launched Columbia Pacific Finance (placeholder — update with actual)
• 10:55 — From Wall Street to rideshare insurance (placeholder — update with actual)
• 19:13 — The COVID cliff: how INSHUR pivoted to delivery insurance overnight
• 23:49 — Building Komodo Claims: why INSHUR owns its claims infrastructure
• 26:22 — Autonomous vehicles and the frequency drop coming for commercial auto

🔗 Connect: Dan Bratshpis: https://www.linkedin.com/in/dan-bratshpis/ INSHUR: https://inshur.com/ | https://www.linkedin.com/company/inshur/

👥 Host: Rob Galbraith: https://www.linkedin.com/in/robgalbraith1/

🎙️ This episode is sponsored by Terra — the next-generation claims and policy software for Workers' Comp. Visit 👉 https://terra.insure

📲 Find InsurTech Geek: LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/ Twitter/X: https://twitter.com/InsurtechGeek Instagram: https://www.instagram.com/insurtechgeek/

Subscribe, rate, and comment. As always — Enjoy the Ride & Geek Out! 🤓

Hosts ⁠James Benham⁠ & ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Rob Galbraith are joined by Reghan Brandt, Chief Digital Operations Officer at K2 Insurance Services.Reghan joins us to discuss how digital strategy and operational transformation are changing the way underwriting teams, MGAs, and carriers work. With experience co-founding Columbia Pacific Finance and Loss Run Pro, Reghan shares a practical perspective on building scalable systems, driving technology adoption, and aligning people, process, and technology to create more efficient and human-centered insurance operations.
This Episode is sponsored by ⁠⁠⁠⁠Terra, the Next Generation Claims and Policy Software for Workers’ Comp

Visit 👉 https://terra.insure to learn more

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Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!