Roamly

About Roamly

Roamly pioneers specialty insurance solutions for the evolving mobility and travel economy. As an AI-first innovator and Lloyd's Coverholder, we empower consumers, fleet owners, and marketplaces. We offer robust platforms, deep carrier partnerships, and an expanding ecosystem. Our technology uses AI, advanced automation, and embedded distribution. This powers tailored coverages for RVs, carsharing, and emerging mobility models. We cover everything from underwriting and claims to compliance and real-time risk management. We are a wholly-owned subsidiary of Outdoorsy Holdings, Inc., an RV rental marketplace. We launched an AI-powered carshare insurance platform in August 2025. It covers 7,000 vehicles across the U.S. and is projected to reach 12,000 units this year. In early 2022, we produced over $7M in written premium. We launched Roamly FSD, real-time insurance for autonomous fleets, in April 2026. This includes integration with Tesla vehicles via an API.

Why Join Us

• Build the foundation of a growing insurtech company from its early stages.
• Earn uncapped commissions and a competitive OTE range of $110,000 - $150,000.
• Receive equity compensation, aligning your success with the company's growth.
• Benefit from RV rental discounts and a culture that values work-life balance and adventure.

Benefits & Perks

• Competitive compensation with uncapped commissions
• Opportunity to earn equity compensation
• Full health and welfare benefits package
• 401(k) match
• Flexible Paid Time Off
• RV rental discounts