auto-insurance
(21)
ComparaOnline sells the second opinion
The Latin American insurance marketplace built a business around getting shoppers to compare. Its harder job is turning a better-informed customer into an insured one.
Way.com wants the bills that come after the car
Parking got Way.com into drivers’ phones. Now it wants to handle the wash, the tow and the repair shop - a bigger business with a very physical test of trust.
The 120-Year-Old Insurance Broker That Bet the Future on a Very Human Algorithm
Munn Insurance dragged a Newfoundland family brokerage from cod-liver-oil commerce into cloud software and online quotes. Its sharper idea was knowing where automation should stop.
CAA-Québec Turned a Tow-Truck Membership Into Quebec’s Trust Department
Nearly 1.4 million members buy more than roadside rescue. They buy one familiar number for the messy moments of driving, travelling, insuring a home and keeping daily life moving.
CAA Knows Where Cars Will Fail Next - Inside the Membership Machine Built for Bad Days
The century-old auto club has become an insurer, travel desk, rewards network and predictive logistics operator. Its cleverest product may be the one members never see: a live map that moves rescuers before the breakdown call arrives.
The $40,000 Bet That Turned Bilingual Insurance Into a 280-Office Machine
Ivan and Ania Herrera bought a name with no customers in the middle of a financial crisis. Their useful insight was less glamorous than disruption: speak the customer’s language, compare more carriers and turn the neighborhood agent into a repeatable franchise.
Buckle Raised $106 Million to Insure Uber Drivers. It Survived by Becoming Insurance's Plumbing.
The Atlanta startup wanted to be the USAA of the gig economy. When the rideshare math refused to cooperate, it traded a consumer dream for a quieter, colder business - renting out its insurance license to other people's ideas.
The Insurance Company That Started With a Bet on Farmers
A hunch about farmers in 1927 grew into a top-ten American insurer. Here is how American Family Insurance built a mutual empire on the promise to inspire, protect, and restore dreams.
No Gecko, No Jingle: The Second-Chance Car Insurer Run From a Chicago Suburb
Founded in 1959 and still run by the Parrillo family, Safeway Insurance built a business worth hundreds of millions on the drivers big-name carriers pass over - sold through local agents, priced to be affordable, and advertised almost not at all.
Arbella Insurance Group
Arbella has built a billion-dollar regional insurer by staying close to home - backing more than 450 independent agents, learning New England's risks block by block, and treating community work as part of the operating model.
GEICO
The company that skipped the insurance agent, hired a British-accented lizard, and turned '15 minutes' into one of the most repeated sentences in American advertising.
Farm Bureau Insurance of Tennessee
A company created because insurers would not cover Tennessee farm structures now protects more than two million homes, vehicles and small businesses. Its advantage is deliberately local: membership, agents and claims teams embedded across one state.
Erie Insurance Group
Erie grew from a business plan scribbled on a dime-store tablet into a Fortune 500 insurer. Its enduring advantage is surprisingly analog: a narrow map, local agents and the belief that service is part of the policy.
Mercury Insurance
Mercury built a nearly $6 billion insurance business by pairing disciplined underwriting with thousands of independent agents. Now it is adding apps, telematics and online service without abandoning the human network that still produces most of its premiums.
Progressive Insurance
Progressive became an insurance giant by doing something that sounds commercially reckless: making prices easier to compare. Behind Flo and the blue lettering sits a disciplined machine for pricing risk, distributing through both screens and independent agents, and turning insurance from a mystery into a shopping decision.
Allstate
Allstate began as insurance by mail from a Sears catalog. Ninety-five years later, it is rebuilding the Good Hands around apps, driving data and a distribution network designed to meet customers wherever they shop.
The Hanover Insurance Group
The 174-year-old insurer has made a modern wager on an old-fashioned middleman: the independent agent. Behind that choice sits a broad coverage portfolio, specialized risk expertise and a business built to price the unexpected.
Clupp
Clupp is a Mexico City insurtech offering pay-per-kilometer insurance for cars, motorcycles, bicycles, scooters, and gadgets. Its app prices policies on how much and how well you drive, rewarding low-mileage and low-risk customers with lower premiums. Founded in 2021 and backed by Y Combinator (W22), Clupp partners with established carriers and reinsurers to cover claims, and has expanded into B2B SaaS tools for brokers and insurance products tied to startup financing.
Just
Just (Just Insure) is a Los Angeles-based insurtech offering pay-per-mile auto insurance. Instead of pricing premiums on demographics like age, sex or ZIP code, Just uses smartphone telematics to charge drivers for the miles they actually drive and reprices rates monthly based on how, when and where they drive. The model is aimed at low-mileage and safe drivers, with the company claiming savings of up to 50% versus traditional carriers. Founded in 2019 by Robert Smithson, Just launched in Arizona and has expanded into Nevada.
Caribou Financial, Inc.
Caribou is a Denver-based auto fintech that helps drivers cut the cost of owning their car. Through a digital platform, it connects car owners with a network of credit unions and community banks to refinance their auto loans, typically saving customers over $100 a month, and pairs that with an auto insurance marketplace and vehicle protection products. Founded in 2016 as MotoRefi and rebranded to Caribou in 2021, the company reached unicorn status with a $1.1 billion valuation after a $115 million Series C round led by Goldman Sachs in 2022.
Robert Smithson
Robert Smithson is the founder and CEO of Just (just.insure), a Los Angeles pay-per-mile auto insurer that prices drivers on how they actually drive instead of credit scores and zip codes. A Cambridge philosophy graduate and former fund manager, he previously built Genius Sports (sold for $280M in 2018) and the Python platform PythonAnywhere before turning telematics and AI loose on the $300-billion car-insurance market - aiming squarely at making coverage fairer for lower-income drivers.