Roamly has launched an AI-driven Carshare insurance platform aimed at tackling one of the toughest challenges in shared mobility: cost-effective, flexible coverage for rental and rideshare fleets.
Carshare marks the first commercial vehicle insurance product embedded into a fleet management SaaS platform, Wheelbase.
Roamly is an Austin-based insurtech focused on embedded insurance for the RV, carsharing, and shared mobility markets.
The company was spun out of peer-to-peer RV rental marketplace Outdoorsy in 2021 to solve a problem many fleet operators and RV owners faced: traditional insurers either excluded vehicles listed on rental platforms or charged steep premiums that made the economics of sharing unworkable.
Operators using Wheelbase can now take direct bookings on branded sites, manage vehicles across multiple locations, and capture a larger share of revenue while insurance coverage adapts automatically to fleet size, geography, and usage.
The product already covers 7,000 vehicles and is set to expand beyond 12,000 in 2025. Premiums tied to Carshare are projected to top $12mn by year-end, highlighting strong early demand.
Insurance has long been one of the most significant expenses for fleet owners, often forcing operators to buy rigid commercial auto packages.
Roamly’s approach removes that friction by embedding dynamic, multi-use coverage across personal, parked, and rideshare usage, including Uber and Lyft.
CEO Jeff Cavins said the launch is designed to lower barriers for operators by making insurance scalable and affordable.
Embedding coverage into fleet workflows means owners can focus on running their businesses rather than wrestling with outdated policies
CEO Jeff Cavins
The rollout follows two milestones for Roamly: becoming a Lloyd’s of London coverholder and winning a Celent Innovation Award for its AI-powered Actuarial Rater. As a coverholder, Roamly gains direct access to Lloyd’s balance sheet, enabling it to underwrite and distribute specialty products globally.
The move underscores how embedded models are challenging conventional commercial auto insurance.
Traditional carriers still rely on selling standard fleet packages that fail to reflect real-time usage. By integrating insurance directly into booking and management platforms, Roamly is positioning itself as a technology-led alternative.
For the wider market, the shift could force incumbents to rethink fleet products. With carsharing and shared mobility projected to expand rapidly, insurers that don’t modernize risk losing business to embedded offerings that meet operators at the point of transaction.
Roamly positions itself as both a consumer and commercial carrier. For RV owners, it offers personal policies that allow vehicles to be rented without restrictions—something standard insurers typically exclude.
On the funding side, Roamly has raised more than $40mn to date. Its most significant financing came in May 2022, when it secured a $40mn Series A led by Munich Re Ventures, with participation from Altos Ventures, Autotech Ventures, and existing backers.
Earlier, the company received strategic seed capital from investors tied to Outdoorsy’s growth. The capital has been used to scale operations, accelerate its embedded insurance technology, expand partnerships, and secure licensing, including its appointment as a Lloyd’s of London coverholder.
Roamly insures tens of thousands of vehicles across the U.S. and has begun expanding internationally through Lloyd’s specialty markets.
With the launch of its AI-powered actuarial platform and embedded Carshare product, Roamly is positioning itself as a challenger to traditional commercial auto insurers in the growing mobility and vehicle-sharing economy.
