How Analytics Is Rewriting Underwriting

Denise Olson from K2 Insurance Services

Denise Olson from K2 Insurance Services 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.

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In Episode 162 of the InsurTech Geek Podcast, James Benham and Rob Galbraith sit down with Denise Olson, Chief Underwriting Officer at K2 Insurance Services. With a remarkable career spanning actuarial science, underwriting leadership, and tech transformation, Denise offers a compelling look into how analytics and AI are redefining insurance underwriting. From her early days at CNA to a long tenure at Zurich and now her role at K2, Denise is an exemplar of adaptive leadership in the fast-evolving insurtech landscape.

The Power of Program Business

At the heart of Denise’s career journey is a deep-rooted passion for program business. For over 20 years, she has gravitated toward this model for its specialization and problem-solving richness. According to Denise, program underwriting “lets you really understand unique risks,” breaking away from the bland predictability of standard lines.

At K2, an MGA aggregator with 35 business units, she now helps a diverse portfolio of niche operations grow through strategic capacity partnerships, tech enablement, and centralized actuarial and exposure support. The Midwestern Insurance Associates case – growing from $20 million to $120 million in workers’ comp premium – is a prime example of K2’s effectiveness.

Analytics in Claims and Underwriting

A standout portion of the episode focuses on how predictive analytics is revolutionizing catastrophe claim handling. With massive data from quake, wind, and wildfire exposures, Denise explains how models assess claim severity at the first notice of loss. This allows insurers to decide whether to send adjusters or simply issue payment, helping speed up resolutions while maintaining the critical human touch.

“We can now predict claim severity right from the first notice of loss,” Denise states, emphasizing the importance of quick, empathetic contact during major events.

The Human Side of Change Management

Transforming underwriting with tech isn’t just about the tools—it’s about people. Denise provides a masterclass in change management, underscoring the importance of empathy, listening, and testing.

“You’ve spent months with the solution; they’re seeing it for the first time. Take the time to walk them through it,” she advises. Her approach to introducing underwriting tools? Map them to specific user pain points, respect tech-averse personas, and build pilot groups to foster co-ownership.

The Next Wave: Claims + Underwriting Collaboration

Looking ahead, Denise champions one transformative idea: tighter integration between claims and underwriting. She dreams of a real-time loop where claims data directly informs new underwriting decisions, unlocking opportunities to price and cover risks previously denied.

“If we’re denying 20% of claims for a certain risk—should we write that risk better instead?” she asks. Her call is clear: move beyond a file-by-file mindset to a portfolio-level strategy that leverages data for smarter, broader coverage.

Denise Olson’s episode is a must-listen for anyone in the insurance industry navigating the shift from legacy processes to data-informed decisions. It’s a forward-thinking conversation grounded in practical wisdom—one that showcases how people, processes, and platforms come together to drive meaningful change.

Past Episode Recommendation:

Episode 2: Predictive Analytics with Skip Brechtel
A perfect complement to this episode, exploring foundational analytics use cases in insurance.