At Clearcover, A Principled Digital-First Approach Helps Customers Make Sense of Car Insurance

Built In Chicago gets under the hood to find out how a digital-first experience and AI-powered tools help this car insurance provider outpace traditional competitors.

Written by Robert Schaulis
Published on Dec. 09, 2022
At Clearcover, A Principled Digital-First Approach Helps Customers Make Sense of Car Insurance
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Standing in line at the Department of Motor Vehicles. Getting a cavity filled. Picking up drycleaning. 

We could all use time back in the day to take care of errands we don’t necessarily want to run, in addition to those we do. In an effort to save precious minutes, businesses are digitizing formally in-person processes, offering services via apps to make getting through the weekday as easy as clicking a button or two. 

Take, for example, car insurance company Clearcover. Using Clear ClaimsTM, an AI-powered claims processing tool accessible through the Clearcover app, Clearcover customers can go from filing a claim on their phone to receiving a payout in less than 10 minutes on eligible claims. 

“Our record is seven minutes,” Jerry Claghorn, Clearcover’s director of Clear AI® products said. “We paid a claim seven minutes after it was received.”

In turn, it’s easier for agents and their partners to do their jobs well –– and for customers to move on with their days.


Servicing Customers Through Technology

“Technology is the fundamental tool we wield to evolve and improve every aspect of our business,” Clearcover noted in a statement outlining the company’s leadership principles. “Clearcover-ers consistently examine our strategies and operations through the lens of how technology can create more customer value.”


Clearcover employees meet in an office setting


Turning Insurance on Its Head

“In my previous insurance experience I never would have thought about submitting a claim online and getting paid without interacting with my agent or someone from the insurance company,” Brent Walker, Clearcover chief technology officer, said.It really turns that whole understanding of insurance and how insurance companies operate on its head.” 

Walker joined Clearcover in May of 2020 as vice president of engineering. A veteran technologist with a leadership pedigree that includes senior engineering positions at Orbitz and a series of Chicago tech startups, Walker was drawn to Clearcover’s potential for growth and its disruptive use of technology in the insurance space. 

Clearcover’s digital-first, app-centric approach to car insurance was entirely unlike the large and stolid brick-and-mortar insurers that Walker associated with the industry. 

“It’s certainly disruptive,” Chat Shah, senior director, product management, said. “If you think about the retail insurance industry, everything’s about how it can move everyone to digital. Larger companies that started off brick-and-mortar are slowly shifting into a digital online presence. They call it the digital transformation. But Clearcover had a head start since we began developing our technology years ago with digital customers in mind. That’s the experience we provide to our customers.”

As the head of Clearcover’s servicing and claims product team, Shah is focused on supporting a mobile app experience that allows customers to manage payments, make changes to their policies and file claims. Additionally, Shah’s team is tasked with facilitating the communication lifecycle between customers and Clearcover. 



“Our mission is to help provide our customers confidence that they are making the smart insurance choice,” Shah said. “Any way that we can make it as easy and convenient through digital means we’re hitting on that mission.”

For Shah and the rest of the Clearcover team, a digital-first approach is an opportunity to provide the company’s customers with greater transparency and convenience, low prices and great value. 

“Ultimately, it’s about being able to actually do all of the things that every insurance company dreams of doing with AI and machine learning,” Claghorn said. “We are able to do things that are literally impossible if you have paper claims, which a lot of carriers still do.”


Digital Natives

Because Clearcover’s products and services have been built from the ground up with a focus on digital experience, the company’s technologists are able to make changes nimbly and be unburdened by legacy systems and analog processes. “To a product manager, the chance to be able to build something from the ground up is always a really big draw,” Shah said. “To be part of something that’s new and disruptive in the market was really attractive to me when I joined Clearcover.”


An over-the-shoulder view of the Clearcover offices


Embracing Technology, Being Principled

The idea of “embracing technology” is one of 10 leadership principles that Clearcover introduced in November of last year on the company’s fifth anniversary. From the interview process to professional development efforts, up and down the ranks of the company, Clearcover’s leadership principles inform the way Clearcover-ers think, behave and interact with each other. 

“‘Embrace technology’ really hits home because of the digital nature of what we do and because of where I sit within the company,” Walker said. “But each of our leadership principles are important. And they’re prevalent in the workplace. We talk about them all the time.”

“Know the customer, work for the customer” is one of the most critical of these leadership principles for Shah. It’s central to her process when hiring product team members — as are principles like “execute with urgency and focus,” “raise the bar” and “operate like an owner.”

“When we try to hire product managers, I look at whether a candidate is customer focused,” Shah said. “We all get excited by our technology and embracing technology, but I do believe, at Clearcover, it needs to be grounded on customers’ problems. I always focus on whether a product manager is able to talk about a feature or technology in terms of how it solves for a customer’s problem.” 

For Claghorn, “dive deep” is a principle that resonates resoundingly with his team. As data scientists, sifting through noise, gathering salient data points and gaining actionable insights from data sets is the heart of what Claghorn’s team does, and it’s instrumental to the ways in which Clearcover is able to employ ClearAI® and machine learning to better service customers. 

Claghorn credits Clearcover’s willingness to embrace data and to trust data scientists as a big reason the company is able to deftly employ AI and machine learning tools. 

“My team has an informal goal to be one of the best places for data scientists to work anywhere,” Claghorn said. “We want to make an impact. Everybody wants to have an AI proficiency, but very few companies are willing to actually put their AI team in position to succeed. Clearcover has done that from day one.”


Clearcover employees working on a storyboard


Taking Trustworthiness to Heart

Like Claghorn, Shah notes the particular importance of trust at Clearcover, citing the company’s “earn trust” leadership principle. It connotes a commitment to operate with empathy and integrity from each and every Clearcover-er.

“People here are very humble,” Shah said. “People are inclusive. There’s a sense of authenticity to how people interact with each other and how they present themselves. That’s the way that we can earn trust with each other.”

It’s an environment in which Clearcover-ers can succeed, support their colleagues and build the best product possible — all in service of a digital-first insurance experience that provides transparency, convenience and value to the company’s customers. 

“Everything is team based here,” Walker said. “You can have a home. You can have that trust. Our leaders are open to feedback. We have an open environment. I don’t know that I’ve been at any company — let alone a startup — that has this amount of transparency. And ultimately, our teams provide those capabilities that allow us to separate ourselves from other insurance companies and to optimize the digital side and make sure our customers are protected and confident in what they bought and that it’s there when they need it.”


Responses have been edited for length and clarity. Images provided by Clearcover.

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