Founded in 2015, Outdoorsy Group pioneered access to the outdoors by building the world’s leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to create lifelong family memories, while hosts rely on its products and innovations to grow their businesses and unlock life-changing sources of income. Outdoorsy Group’s portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network, a growing collection of campgrounds and glamping retreats set in some of the country’s most iconic landscapes; and Roamly, its proprietary insurtech platform powering Outdoorsy.com and enabling insurance infrastructure for global marketplaces. Together, Outdoorsy Group’s businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another.
Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, 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 reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at www.roamly.com.
Requirements
The "Why": We are witnessing the most radical transformation in the automotive industry in a century: the shift from Human-Operated to Software-Defined, Autonomous Mobility. As human behavior expires as the primary variable of risk, Roamly is pivoting to insure autonomous decisions, pricing risk on software quality and sensor fidelity rather than driver history.
The Mission: To lead the largest disruption in the history of insurance by moving from demographic profiling to algorithmic underwriting, effectively "underwriting the code, not the human".
Reporting Structure: This role reports directly to the CEO and works closely with the leadership teams of Outdoorsy, Roamly, and Wheelbase.
Benefits
Outdoorsy is the most trusted RV rental and outdoor experiences marketplace on the planet. We have grown from a lofty white-board idea in 2015 to over $1B in total transactions. Outdoorsy’s mission is making memorable outdoor experiences accessible to everyone. We are creating jobs and helping individuals, couples, and families realize financially life-changing freedom. With offices worldwide in the US, Canada, Australia, Europe and the UK, we’re mobilizing the 56+ million idle RVs and campervans around the world to ensure everyone has the access, choice, and opportunity to safely spend more time outside.We're passionate about our customers, collaborative consumption, community, and entrepreneurship. We’ve been motivated by our values from day one: we always put the customer ahead of ourselves. We like winning. We make long-term progress in the world and repay our gratitude in every community interaction.Outdoorsy has been recognized on the Forbes list of America’s Best Startup Employers in both 2020 and 2021.
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