Profile · Insurtech · Leadership
Kevin Reilley
The operator turning the insurance repair claim into something digital, transparent, and - for once - bearable.
The operator turning the insurance repair claim into something digital, transparent, and - for once - bearable.
Kevin Reilley runs Westhill, an Atlanta insurtech built on a simple, stubborn idea: the property insurance claim should not feel like a punishment.
When a pipe bursts or a storm peels back a roof, the homeowner enters a process that has barely changed in decades - phone tag with an adjuster, an unfamiliar contractor, no clear sense of who is coming or when. As Chief Executive Officer of Westhill, Reilley is trying to collapse all of that into one digital platform that connects the three parties who have historically talked past each other: the insurance carrier, the policyholder, and the contractor doing the work.
Westhill calls itself the first end-to-end digital managed repair solution. In plain terms, it digitizes the paperwork, adds real-time project tracking, and routes work to a vetted contractor network - so a claim reads more like tracking a delivery than filing a grievance. Reilley's job is to make that promise real at scale, and to convince large, cautious insurers that transparency is a feature worth paying for.
"Westhill has developed a platform that effortlessly connects the policyholder, service provider, and claims professional," Reilley said on joining. The word he keeps returning to is transparency - not speed for its own sake, but visibility: knowing who is coming, when, and what it costs.
Bars are illustrative of relative tenure and seniority, not exact figures.
"I am excited to join at this pivotal time - helping unlock immense potential for clients and the broader industry."
Westhill's story does not begin in a lab or a pitch deck. It begins in 2017, in a coffee shop in Atlanta, where co-founder Larry Parker sketched a big idea on a napkin after living through the frustration of his own insurance claim when water damaged his home. The claim was slow. The communication was worse. The question that followed was obvious: why does this have to be so painful?
Reilley did not sketch that napkin - he was brought in later to turn the idea into a company that could stand up to the scale and skepticism of the insurance industry. That is the pattern of his career. He is an operator, the person who arrives when a promising concept needs go-to-market discipline, commercial relationships, and someone who has done it before.
He knows this corner of the market intimately. At Pictometry, part of the executive team that merged into EagleView, he worked on aerial property imagery. At HOVER, he spent eight years helping scale a platform that turns phone photos into precise home measurements for insurers and contractors. Property, data, insurance - the same three ingredients, reassembled. Westhill is the version where the repair itself finally gets connected.
Reilley frames Westhill not as a contractor app or a carrier tool, but as the connective tissue between all three - a single place where a claim actually moves forward.
His 2025 advisory role points at the through-line of his whole career: use data to turn a murky, disputed decision into a clear one.
Read top to bottom, the résumé looks like a series of different companies. Read sideways, it is one long argument. Legal information services, intellectual-property data, aerial imagery, home measurements, and now repairs - each is a case of taking something opaque and slow and making it legible.
Reilley earned his Bachelor of Arts from Hamilton College, a small liberal-arts school in upstate New York. He is not a founder-of-everything archetype; he is the executive who compounds. Companies bring him in because he has already built the trusted relationships with carriers and contractor firms that these platforms live or die on.
That reputation is why an auto-liability analytics startup like QuantivRisk wanted him on its board in 2025, even though its focus - determining fault in car accidents - is a different corner of insurance than roofs and water damage. The domain shifts; the skill does not.
The end state Reilley is chasing is quiet and unglamorous: a property claim that a homeowner barely has to think about. File it, watch the vetted contractor get matched, track the job in real time, see the cost, done. For carriers, the pitch is cost savings and fewer angry phone calls. For contractors, steady, transparent work. For the homeowner, the rarest thing in insurance - the sense that someone has it handled.
Getting there means winning the trust of large, slow-moving insurers and building a contractor network that is both wide and reliable. Reilley's advantage is that he has spent thirty years learning exactly how those relationships work, and where they break. Westhill is the bet that all of that experience adds up to a repair process people no longer dread.
Digitized workflows and a vetted network aim to cut the cost and friction of every claim.
Real-time tracking replaces the phone-tag guessing game about who is coming and when.
An industry-leading contractor network matched to jobs, with clear project management.
Carrier, policyholder, and contractor operating in the same place, in real time.
A technology executive and the Chief Executive Officer of Westhill, an Atlanta-based insurtech building a fully digital managed repair platform for property claims.
He was appointed CEO of Westhill on October 29, 2020.
He spent about eight years at HOVER as CEO and Executive Vice President, and previously held leadership roles at Pictometry (EagleView), CPA Global, LegaLink, Vaultus, and LexisNexis.
A fully digital managed repair solution that connects insurance carriers, homeowners, and vetted contractors on one platform, digitizing the claims and restoration process.
He earned a Bachelor of Arts from Hamilton College.