Dellwood’s New Blueprint: Building Insurance for the Future

Two highly experienced executives joined host Mark Geoghegan on the latest episode of The Voice of Insurance podcast, produced in association with AdvantageGo.

Dellwood Insurance Group is aiming to redefine underwriting discipline at a time of rapid change in the property and casualty space, when many firms are balancing the competing desires for growth and pricing discipline.

According to Kean Driscoll, President and Chief Underwriting Officer, “The market opportunity is profound, but we want to do it in a really judicious and measured way.” For Dellwood, that means a deliberate approach to managing concentration risk, particularly in the wake of climate-driven events such as California’s wildfires.

Concentration risk

Driscoll pointed to urban conflagration and location-specific perils as central challenges. “There’s going to be continued pressure and emphasis on managing risk and pricing in a changing landscape,” he said.

Dellwood’s CEO Michael Price added that Dellwood’s clean-slate model makes it easier to manage accumulation: “We’ve got no insurance legacy and no tech legacy,” he said. “Our reinsurers can look right through our underwriting systems and see exactly what aggregations are on our books.”

The team is focused on maintaining this level of transparency as they scale. As Driscoll put it, “They’re a critical part of our capital structure, and we’ve been really pleased with the partnerships we’ve been able to develop in just a short period of time.”

AI as a tool, not a substitute

Dellwood is starting to embed artificial intelligence (AI) and structured data across its operations. From the outset, the firm has emphasised control of the user experience.

“We own the code. We’ve built it ourselves,” Price said. “Cycle times for quoting small property business are now under 30 minutes,” said Price. “That used to take days.”

Driscoll sees this not as a threat to underwriting talent, but a way to empower it. “We view technology as an enabler of relationships, not disintermediation,” he said. “It allows our underwriters to actually underwrite,” he said.

The benefits are already showing in productivity and hit rates. “The more efficiently we can manage queues, the higher our buying ratios,” Driscoll added. “And it gives underwriters more time to think critically and identify where they want to deploy risk capital.”

AI is also being applied to ingestion and triage, with data being scrubbed, modelled and prioritised as soon as it arrives, Price explained.

“That work happens instantaneously. Now underwriters can attack the best business more effectively,” he said.

Plans for the future

Dellwood is currently focused on the US market, with a big emphasis on small and medium-sized businesses. “We’re trying to build a great franchise,” said Price. “The value proposition is most pronounced in tailoring coverage for smaller businesses, enabled by great technology.”

Contract binding is a core pillar, supported by in-house brokerage teams and select MGA partnerships. “We’re very interested in the MGA space, but only if there’s a unique underwriting or distribution advantage,” Driscoll said.

Although the focus is currently domestic to the American market, there are longer-term ambitions to expand access to capital.

“We think of ourselves as another form of distribution,” said Price. “We’d like to access the London market to bring more thoughtful capacity on a syndicated basis.”

Both leaders stressed the point that Dellwood is being built to last. “We’re here for the long run,” said Driscoll. “We want to build something terrific that services the needs of our capital partners, customers, and distribution partners.”

Culture is another foundational priority for the two leaders. “Check your ego at the door. Two eyes are better than one. Collaboration is key,” said Price.

With 60 hires and licensing in all 50 states already secured, Dellwood is now focused on execution, Price emphasised. “We’re pouring the foundation,” he said. “The framing is up. Now it’s time to start the finish carpentry—and that’s the fun stuff.”