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Fresh off $120m. funding round, Outdoorsy debuts roadmap for rapid expansion of insurtech business, Roamly

Following the company’s latest investment, Roamly is on the fast track to becoming a revolutionary RV insurance provider, with international expansion to Canada and additions to its claims business.

AUSTIN, TEXAS – Outdoorsy, the global online RV rental and outdoor travel marketplace, announced a key appointment for its insurtech business, Roamly, as well as international expansion plans and growth areas for its claims business. 

Roamly, which recently came out of beta in the U.S., provides innovative digital insurance products for recreational vehicle owners, eliminating the commercial exclusion clause that traditionally prevents online rental activity.  

Aaron Ammar, a former co-founder of Y-Risk, an underwriting company providing insurance solutions for companies in the on-demand and sharing economy, has been named Chief Insurance Officer of Roamly. As Chief Insurance Officer, Ammar will harness his expertise in the insurance space to lead and build out the Roamly team as the company ventures into previously uncharted territory in the insurtech scene. 

“There is a significant opportunity to bring new insurance offerings to the RV space, and we are just getting started. Roamly is taking a customer-first approach to bring immediate value to our clients with better pricing, digital tools for policy management, and ‘rent ready’ coverage that allows for marketplace rentals,” said Ammar. “The demand for relevant RV products is increasing rapidly, and we are excited to provide new and innovative solutions.” 

“The insurance industry had been making a clerical error regarding RV insurance for the past 30 years,” said Outdoorsy’s co-founder and CEO, Jeff Cavins. “With Aaron in the driver’s seat, we can all buckle up for our most anticipated journey yet – the continued build-out of Roamly and new RV insurance offerings. We know there’s a problem to be solved in the RV insurance industry because we continue to hear these frustrated pleas from our customers.” 

In addition to hiring Ammar, Roamly continues to expand its footprint and recently went international with the launch of a strategic relationship that will bring insurance solutions to RV owners in Canada. Through a commercial agreement with Aon, Roamly has launched an insurance offering that makes RVs rent-ready in Outdoorsy’s second-largest rental market outside the U.S. The ability to insure RVs as rent-ready in Canada will be vital in bringing more RV owners onto the Outdoorsy platform in a country that’s both rich in natural beauty and at the top of traveler bucket lists. 

Another positive ripple effect of Outdoorsy’s latest funding news is the migration from the Outdoorsy Claims Group to the Roamly Claims Group. Although it sports a new name, the group will continue to manage all claims from the Outdoorsy platform while also opening the door to handle claims for other marketplaces, including Riders Share, the first and largest peer-to-peer motorcycle rental community with over 3,000 motorcycles nationwide, 120,000 users and 30,000 5-Star reviews. The Roamly Claims Group will manage all claims stemming from vehicles insured by Roamly and listed on Outdoorsy and Riders Share. Looking to the future, as the Roamly Claims Group continues to grow, the department will have more capacity to handle claims for other online marketplaces. 

In June, Outdoorsy announced plans to use the recent $120M funding to drive its growth and expansion of Roamly, the company’s innovative insurtech business. The $120 million raise includes a $90 million private placement equity round led by Moore Strategic Ventures, ADAR1 Partners, Monashee Capital, SiriusPoint Ltd, (NYSE: SPNT), and Convivialite Ventures, the corporate venture group of Pernod Ricard, with participation from existing investors Altos Ventures, iAngels, and Greenspring Associates. Pacific Western Bank provided the $30 million debt facility.

Tatiana Rokou

Tatiana is the news coordinator for TravelDailyNews Media Network (, and Her role includes monitoring the hundreds of news sources of TravelDailyNews Media Network and skimming the most important according to our strategy.

She holds a Bachelor's degree in Communication & Mass Media from Panteion University of Political & Social Studies of Athens and she has been editor and editor-in-chief in various economic magazines and newspapers.