Discover
InsurTech Geek Podcast
174 Episodes
Reverse
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 unlockKey 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 thinkers15:12 — "I'm not into norming. I'm into storming." — Holly's leadership philosophy19:30 — Cancel cancellations: solving a 27,000-policy problem without technology23:57 — From 40% turnover to 4.5% — the people transformation at Montana State Fund27:04 — 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-26228452Montana 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/📌 Find InsurTech Geek:LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter/X: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Subscribe, rate, and comment. 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 workersHow INSHUR embeds insurance directly into platform onboarding — and what that data advantage means for underwritingThe usage-based wallet model: pay-per-ride, pay-per-delivery, pay-per-minuteHow COVID wiped out rideshare demand overnight — and became the pivot that launched INSHUR's delivery insuranceWhy INSHUR built Komodo Claims from scratch instead of outsourcing to TPAsWhat autonomous vehicles mean for frequency, severity, and the future of commercial auto insuranceKey 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 overnight23:49 — Building Komodo Claims: why INSHUR owns its claims infrastructure26:22 — 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’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Dominique Roudaut from Dai-ichi Life Holdings, inc. Dominique joins us to discuss how his global experience across AIG, Chubb, Hannover Re, and now Dai-Ichi has shaped his perspective on the future of insurance. Drawing on deep expertise in underwriting, strategy, and innovation, Dominique shares insights on how insurers are responding to climate-driven risk, leveraging emerging technologies, and collaborating across ecosystems to build more sustainable and resilient insurance solutions.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
As 2025 wraps up, James Benham & Rob Galbraith reunite in a special episode of the InsurTech Geek Podcast to reflect on a transformative year in the insurance technology space. With AI moving from theory to production, cloud-native systems becoming the new standard, and user adoption still presenting real challenges, this episode offers deep insights into what defined the past year—and what to expect in 2026. This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Andrew Bate from VelarisRe. Andrew shares his perspective on how insurance is evolving to better protect the modern hospitality industry. From emerging technologies to shifting guest expectations, Andrew offers insights on building trust, managing risk, and creating safer travel experiences.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Host James Benham is joined by David Bell from ALPS. David shares his expertise in driving innovation at the nation’s largest lawyers’ malpractice insurer. Discover how insurers in legal malpractice and P&C are rethinking risk, driving innovation, and shaping the next decade of change.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Host James Benham is joined by Steve Kappel from Safety National. Steve takes us inside the CIO’s lens on data, AI, and industry change. Discover why innovation from within matters, how global strategy conversations shape technology leadership, and why educating the industry on AI and data has never been more important.James Benham: https://www.linkedin.com/in/jbenhamSteve Kappel: https://www.linkedin.com/in/stevekappel/Safety National: http://www.safetynational.com/This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media!LinkedIn: https://www.linkedin.com/showcase/insuretechgeek/Twitter: https://twitter.com/InsurtechGeekInstagram: https://www.instagram.com/insurtechgeek/Follow James on Twitter: https://twitter.com/jamesmbenhamSubscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Matt Crum from Frank Winston Crum Insurance. Matt shares his expertise leading with purpose in insurance. Discover how leaders can tackle industry challenges, strengthen workplace culture, leverage technology like AI, and prepare for the future of work.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Stan Smith from Gradient AI. Stan shares his expertise in advancing workers’ comp through AI partnerships and predictive intelligence. Discover how Gradient’s partnership with Terra gives adjusters earlier insight into high-risk claims, reduces costs, and improves outcomes for injured workers.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Dean Fadel from Ohio Insurance Institute. Dean shares his expertise in connecting policy, people, and progress in the insurance industry. Discover why he believes insurance is in everything, everywhere, all the time, and how that perspective should influence innovation, public understanding, and the role of policy in shaping the industry's future.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Frank A. Schmid from Gen Re. Frank shares his expertise on the intuition behind generative AI. Discover how this emerging technology continues to reshape insurance decision-making, why narrative still matters, and what insurers can do to prepare for an AI-driven future.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Denise Olson from K2 Insurance Services, LLC. Denise shares her expertise on how analytics is rewriting underwriting. Discover how data is transforming risk evaluation, streamlining claims forecasting, and shaping the future role of the underwriter across diverse insurance programs. This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Brett Fulmer from Newport Beach Insurance Center LLC and Skyway Underwriters. Brett shares his expertise on how tech is powering the modern agent in licensing, launching and leveling up. Discover how digital tools are helping accelerate early success and reshaping what it takes to break into the insurance industry today. This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Chris Griffith from American Coastal and Skyway Underwriters. Chris shares his expertise on going from the help desk to the executives desk. Discover how strong execution, smart frameworks, and leadership drive innovation without compromising quality or compliance.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Host James Benham is joined by Jason Gross from TruStage. Jason shares his expertise on rethinking enrollment from the strategy seat. Discover how emerging technologies are reducing friction in the enrollment process, and how those improvements connect to larger goals like access, equity, and long-term customer value.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Preetha Sekharan from Unum. Preetha shares her expertise on why identifying the right pain points is key to AI success. Discover how to pinpoint the most impactful AI use cases, gain buy-in from stakeholders, and navigate the challenges of implementing AI in insurance.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Bobbie Collies from Coterie Insurance. Bobbie shares her expertise on intrapreneurship and disrupting insurance from within. Discover how to turn innovation into real change, leverage technology and data, and drive meaningful impact in the future of insurance.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham &Rob Galbraith are joined by Matthew Monson from The Monson Law Firm, LLC. Matthew shares his expertise and insights on the unethical practices threatening insurance claims. Discover the emerging legal trends, regulatory challenges, and technological advancements shaping the future of fair claims handling.This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ CompVisit 👉 https://terra.insure to learn moreFind us on social media! We're onLinkedIn, Twitter, and Instagram; or follow James onTwitter! Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
Hosts James Benham & Rob Galbraith are joined by Dr. Daniel Carlin from JobSiteCare. Dr. Carlin shares his expertise and insights on telemedicine, technology, and the future of care. Discover how his innovative concierge telemedicine model is transforming workers’ compensation, improving injury outcomes, and shaping the future of workplace safety with cutting-edge technology.
This Episode is sponsored by Terra, the Next Generation Claims and Policy Software for Workers’ Comp
Visit 👉 https://terra.insure to learn more
Find us on social media! We're on LinkedIn, Twitter, and Instagram; or follow James on Twitter!
Subscribe, rate, and comment. As always, Enjoy the Ride & Geek Out!
























Business user = Non Technically skilled user