Meet the insurtech: Roamly

In an effort to feature more insurtechs, Digital Insurance has modified the format of our Meet the insurtech series. 

Aaron Ammar, co-founder and chief insurance officer of Roamly, shared insights into the company and the technology it's using. Responses have been lightly edited.

What's the origin story of the company?

Roamly was born out of a frustration that came to prominence when its founders were building Outdoorsy.com, the world's largest RV rental marketplace. Traditional RV insurance policies placed a restrictive "commercial-use exclusion" on owners that impeded them from safely and legally renting out vehicles. 

Today, Roamly has grown to be a leader in digital specialty and mobility insurance and has gained prominence as a Lloyd's Coverholder and as the recipient of the 2025 Celent Model Insurer Award. Roamly is a provider of specialty insurance solutions built for the world of mobility and the dynamics of modern marketplaces. 

Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while effectively managing risk. Roamly's technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles like RVs, boats, motorcycles and ATVs, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management.

Roamly Enterprise is a suite of software tools to streamline insurance operations, from product development to management. It optimizes technological development and maintenance costs and speed for large and small insurance companies. It enables any non-traditional insurance company to monetize their data and drive new revenue streams by offering insurance values in their existing customer journey, such as dealerships distributing insurance products. 

Most recently, the company launched Roamly Carshare, which was built to integrate seamlessly with marketplaces, fleet operators, mobility providers and transportation network companies. Roamly Carshare combines machine learning, telematics, and both generative and agentic AI to streamline underwriting, automate claims, and deliver precision risk solutions. The platform's API-first, no code architecture ensures insurance is embedded directly into booking, checkout, and fleet management workflows, allowing operators to operate faster and scale more profitably while delivering embedded insurance on all vehicle transactions.

When was it founded and/or when was the product launched?

Roamly was founded in 2019. 

Can you tell me about the founders/founding team?

The company was founded by Jeff Cavins, Jen Young and myself, inspired by our vision for innovations in the insurance category to solve real world problems and define the future of mobility. Jeff and Jen are founders of the company's parent company, the Outdoorsy Group, while I joined them to build out the insurance arm. 

Jeff has over 22 years of senior-level experience. As the co-founder and CEO of the Outdoorsy Group, he steers a global leader in outdoor travel and accommodations, encompassing Outdoorsy.com, a peer-to-peer RV rental platform, and Roamly.

Jen is a results-driven marketplace executive with over 25 years of international marketing experience and global outlook gained from living and working on three continents over her career. Jen believes in the importance of being relentlessly optimistic, and always learning. 

I'm the chief insurance officer of both Roamly and Outdoorsy. In addition, I'm a multi-time entrepreneur, and I was one of the founding partners of Y-Risk, an insurance company focused on the sharing economy, that was acquired by The Hartford. I was also the founder and CEO of Brightside, an AI insurance platform.

Any meaning behind the company name?

The name Roamly encapsulates the company's goal to give owners of RVs, boats, ATVs and motorcycles the freedom to roam. This benefit has been extended to auto fleet owners, also allowing them the liberty to generate revenue from their mobility assets.  

How many employees?

Roamly has over 100 employees.

Where is the company based?

The company is headquartered in Austin, Texas, with a second headquarters in Aventura, Florida.

What pain points is the technology trying to solve?

Roamly's technology addresses several key pain points in mobility, with specific expertise in fleet management and shared economy marketplaces. 

The primary pain point is the "commercial exclusion clause" found in many traditional insurance policies, which prohibits RV owners from renting out their vehicles. Roamly's policies are specifically designed to allow this, creating a new economic opportunity for owners.

Traditional insurers often treat recreational vehicles like standard cars, failing to account for their unique usage and maintenance needs. Roamly offers tailored coverage for specific lifestyles, including those of full-time RVers and DIY van builders.

Roamly provides a streamlined, digital-first experience for getting quotes, buying policies, and managing accounts, which contrasts with the often cumbersome process of traditional insurance companies.

The company has introduced Roamly Care, a feature that leverages location data to send live alerts about weather or other hazards, helping to prevent disasters before they happen, rather than just covering the damages afterward.

What funding rounds has the company had?

In June 2021, the Outdoorsy Group raised $120 million in equity and debt financing. The purpose of this funding was to drive the growth and expansion of Roamly. 

What's ahead?

Roamly is focused on continued growth and expansion. 

The company has plans to expand its product lines, increase partnerships, expand geographically and leverage AI and technology.