Lemonade Extends Its AI Push and Pressures the Insurance Pack

Big month for car insurance in the PYMNTS app provider rankings, with one big surprise at the top. The PYMNTS.com Insurance Apps page offers a monthly ranking of smartphone Insurance Apps, assessing them based on publicly available information and exclusive app usage data, helping users identify the top performers in the market. The ranking aims to provide precise insights into app performance, aiding stakeholders in making informed decisions.

The top spot for October in the insurance category comes from a newcomer: Jerry: The AllCar App. It posted a six point gain. Jerry markets itself as “America’s first AllCar app,” giving drivers a single mobile hub to compare car insurance quotes from dozens of carriers, buy or switch policies inside the app, monitor driving behavior, refinance auto loans, and track maintenance and repair costs, with features like PriceProtect, DriveShield and GarageGuard designed to cut premiums and make ownership less stressful. A spike in Jerry’s recent usage is consistent with the broader environment the company itself has documented, in which car insurance inflation has hit a four-decade high, with annual increases near 20 percent in October driving more consumers to shop aggressively for savings.

At the same time, Jerry has scaled to roughly 5 million U.S. customers and invested in visible consumer marketing, including October 2025 social campaigns positioning the app as a fast way to handle quotes, comparisons and switching in one place, while reviews highlight its ease of use and ability to surface better rates without spammy follow-up calls. Taken together, surging insurance costs, a clear “one-tap savings” value proposition and active October outreach give a plausible explanation for why Jerry would climb rapidly in PYMNTS’ insurance app rankings that month.

Also posting a six point gain was a more familiar name, Liberty Mutual. Liberty Mutual’s mobile app functions as a “one-stop insurance resource” that lets customers securely log in, view digital ID cards, pay bills, change payment schedules, update coverages, access policy documents, and file and manage auto and property claims, including uploading damage photos and calling 24/7 roadside assistance, all from a single interface. The app also ties into Liberty Mutual’s RightTrack telematics program, which runs in the background to capture driving behavior and reward safe drivers with premium discounts, giving policyholders a concrete reason to keep the app installed and active.

A sharp October usage gain would be consistent with the broader environment of elevated insurance premiums, as Liberty Mutual itself notes that inflation, higher repair costs and labor shortages are pushing auto and home insurance rates higher, prompting consumers to monitor bills, adjust coverage and seek discounts more aggressively via digital channels. Recent industry research also spotlighted Liberty Mutual among the top digital performers in P&C insurance, with strong mobile and security capabilities, which may have further nudged policyholders to rely on the app as their primary service touchpoint during that period.

Lemonade Insurance took the third spot with a three point gain. Lemonade’s app is the front door for its fully digital insurance business, letting consumers buy and manage renters, homeowners, car, pet and term life policies in one place and handle almost everything through an AI assistant. Customers are required to use the app (or web) to manage their policies and file claims, which are driven by Lemonade’s chatbots Maya and Jim, designed to guide users through quotes, policy changes and claims in a conversational flow that can approve simple claims in minutes. The same app surface also lets users swipe between multiple product lines and take advantage of bundling discounts across car, renters, homeowners and pet insurance, reinforcing the “all in one” positioning.

Lemonade has not reported an October app-usage spike specifically, but several developments around that period make a jump in PYMNTS’ rankings plausible. The company has been rolling out Lemonade Car to more states, reaching about 42% of the U.S. car insurance market by mid-2025, which directly increases the addressable base of app users. Management also highlighted strong Q2 2025 results, 35% revenue growth, rising in-force premiums and stepped-up customer acquisition spend in its August shareholder letter and early-October investor coverage, putting a brighter spotlight on the brand ahead of Q3 earnings and likely supporting higher download and engagement volumes into October. Combined with a backdrop of elevated insurance costs that push consumers toward digital tools for savings and faster service, those expansion and marketing dynamics offer a reasonable explanation for Lemonade’s three-point gain in the PYMNTS insurance app rankings.