Episode #166
Sep 18, 2025
Leading with Purpose in Insurance: Culture, Tech, and the Future of Work
with Matt Crum from Frank Winston Crum Insurance
SPONSORED BY
Matt Crum from Frank Winston Crum Insurance 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.
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In a time where digital transformation and generative AI dominate headlines, few voices in insurance strike the balance between innovation and heritage like Matt Crum, President of Frank Winston Crum Insurance. In Episode 166 of the InsurTech Geek Podcast, Matt joins James Benham and Rob Galbraith to explore how a third-generation family business is thriving in one of the most regulated and rapidly evolving industries—by leading with purpose.
Building a Legacy from the Ground Up
Matt Crum didn’t plan to lead his family’s insurance business. A hockey player at heart, he considered a career in finance before embracing the opportunity presented by his father after the passing of his grandfather. What started as a summer job at Frank Crum evolved into a mission: to scale a family-run PEO and insurance company into a modern, tech-driven insurer.
“There are a million different paths in insurance, and that’s what makes it fascinating.” – Matt Crum
Frank Winston Crum Insurance has grown from insuring only PEO clients to becoming a nationwide carrier offering workers’ compensation, general liability, and soon, commercial package products.
Innovation with Intent: Embracing AI and Tech
Matt is candid about the challenges that come with balancing compliance and innovation, especially across 50 states with vastly different regulatory environments. But his company has taken a proactive approach to embracing AI.
“If you’re not evolving, you’re going to die.” – Matt Crum
The company uses AI to streamline underwriting, enhance training, and improve claims processes. A recent proof-of-concept impressed Matt by pulling third-party data to accelerate agent quote turnaround time—showing how even incremental innovations can make a major impact.
“AI is the most transformational technology since the internet.” – Matt Crum
Human-First, Tech-Enabled
Despite being an innovation advocate, Matt reinforces a foundational belief:
“We’re using technology to enhance the human experience, not replace it.”
Whether through AI-powered chatbots or internal training tools, Frank Winston Crum Insurance uses technology to remove friction, empower employees, and support customers—not eliminate the people who drive the experience.
This perspective resonates deeply in an industry built on trust, relationships, and service. Matt’s leadership shows how digital transformation can support, not disrupt, a people-first culture.
Leading a Family Business in a Consolidating Industry
In an era marked by consolidation, Matt’s decision to remain privately held allows his company to stay nimble and mission-driven.
“My dad, sister, and I are the shareholders—being privately held gives us freedom.” – Matt Crum
This structure lets them fend off acquisition pressures while maintaining strategic focus and agility. It also allows them to cultivate a company culture rooted in transparency, open communication, and collaborative innovation—values rarely prioritized in large corporate structures.
What’s Next?
Looking forward, Matt is most excited about the impact of AI on underwriting, claims, and customer engagement. He predicts rapid transformation in the next 18–24 months, particularly as the barrier to entry for using AI tools continues to shrink.
“The world is going to look very different in 18 to 24 months.” – Matt Crum
For insurance leaders navigating a volatile and tech-heavy landscape, Matt Crum’s story offers a blueprint: start with purpose, embrace innovation, and never lose sight of the people.