Hippo’s CEO Says InsurTech Grew Up and the Progressive Deal Proves It

Watch more: Monday Conversation With Hippo’s Rick McCathron

Ask most people about their homeowners insurance and you’ll get a shrug. It’s not exactly a dinner-table conversation starter. But behind that ho-hum product sits one of the most structurally complicated, climate-rattled and technologically disrupted markets in financial services. And right now, it’s at a genuine inflection point.

That’s the terrain Karen Webster navigated in a sharp Monday Conversation with Rick McCathron, the CEO of Hippo, a company that has been through its own very public reckoning with what it means to be an InsurTech in 2026. McCathron didn’t come to the conversation with spin. He came with evidence: a turnaround story, a new strategic partnership with Progressive Insurance and a pretty clear-eyed view of where the industry goes from here.

For decades, the insurance model remained largely unchanged. Policies were written through agents, underwriting cycles stretched across weeks, and customer relationships were mediated through paperwork and intermediaries.

As McCathron noted, the industry often focused inward. “Insurance companies didn’t even call customers ‘customers’ until recently,” he said, recalling an era when they were referred to as “insureds” or “policyholders.”

That inward focus now collides with a more complex operating environment. Climate-related losses have introduced volatility that makes pricing and risk selection more difficult. Insurers must price policies without knowing when claims will occur, a dynamic McCathron described pretty directly.

“Insurance is the only product I can think of that you don’t know what the cost is to manufacture until years down the road.”

Payments, Regulation and the Burden of Longevity

The pressures extend beyond underwriting. Payments remain fragmented, with checks still embedded in workflows, even as fraud risks grow. At the same time, insurers operate within a regulatory framework that limits how quickly they can modernize.

Those constraints are compounded by the industry’s age. Many insurers have operated for decades, if not more than a century. As McCathron observed, these companies have built scale and expertise over long periods, making rapid transformation difficult.

Webster framed the challenge in terms of scale and distribution, noting that reaching customers efficiently remains central to growth.  Technology alone does not solve for customer acquisition or retention.

Technology at the Front End

Where technology has begun to reshape the industry is at the front end of the customer relationship. Insurers can now assemble detailed customer profiles before an application is completed, drawing on third-party data and internal models.

That capability allows insurers to align risk appetite with customer characteristics in real time. McCathron described how distribution partners, like his new deal with Progressive, can route prospective customers to carriers based on underwriting criteria, geography and exposure.

AI supports this process but does not replace human judgment. Regulatory requirements still mandate licensed professionals for key decisions such as claims adjudication. AI, instead, reduces friction in routine tasks and surfaces data for human review.

“Those human agents that very much embrace technology are upleveling their work,” McCathron explained, shifting from routine processes to more complex decision-making.

What It Takes to Compete

Against that backdrop, competitiveness in insurance has become a function of discipline as much as innovation. Hippo’s own trajectory reflects that reality.

When McCathron assumed the CEO role from his seat on the Board, the company was attempting to address multiple priorities at once. “We were trying to do sort of all things to all people,” he told Webster, describing a period that required strategic recalibration.

The reset centered on underwriting discipline, geographic diversification and product focus, not to mention McCathron’s experience in the insurance industry for nearly three decades. Growth would no longer be pursued without a path to profitability. His approach mirrors a broader shift across InsurTech, where early expansion has given way to more measured strategies.

Distribution emerged as a central constraint. Digital-native insurers, McCathron acknowledged, underestimated the difficulty of scaling without established channels. “They miscalculated how difficult it is,” he said, pointing to the time required to build both products and customer pipelines.

From Disruption to Partnership

That realization informs Hippo’s partnership with Progressive, which places its homeowners’ products within a large-scale distribution network across multiple states.

The mechanics of the arrangement are straightforward. Progressive identifies and qualifies customers, while Hippo applies its underwriting and pricing models. The alignment depends on matching customer profiles with each insurer’s risk appetite, a process enabled by data and analytics.

McCathron characterized the outcome as additive. By combining distribution scale with underwriting precision, the partnership creates what he described as a “one plus one equals three scenario in which the customer ultimately benefits.”

The use of AI supports that alignment, particularly in screening and routing prospective customers. However, the structure remains grounded in regulatory compliance and human oversight.

The agreement also reflects a more selective growth strategy. Rather than broad expansion, Hippo is targeting specific geographies and customer segments that align with its underwriting model.

“You can’t run all your business in one particular area,” he said. “You need to diversify geographically. And we very much did that. We got right-sized in each of the areas in which we wrote business. And we refined the strategic direction of the company, which is to have discipline, make sure you’re geographically diversified, but then also make sure the products that you support, offer and take underwriting risk on are also geographically diversified.”

The New Shape of InsurTech

The partnership signals a broader evolution in InsurTech. Early narratives emphasized disruption, with digital-native firms positioned against incumbents. That framing has softened.

McCathron expressed a clear preference for collaboration over confrontation.

“What InsurTech…companies are very good at doing is helping the incumbents modernize their tech stacks,” he stated, while legacy insurers contribute data, scale and experience.

This synergy suggests that the next phase of the industry will be defined less by competition between platforms and more by integration across them.

As McCathron emphasized, the goal is not to capture the entire market but to participate in it more effectively.

“Where we can partner with others, and create better outcomes, it’s a true win-win.”