President of Revenue and Growth The Paradigm ShiftThe mobility industry is undergoing its most radical transformation in a century: the shiftfrom Human-Operated to Software-Defined, Autonomous Mobility.As the world moves toward Level 4 and Level 5 Full Self-Driving (FSD), the conceptof risk changes entirely. Accidents will no longer be matters of human error, but ofsoftware edge cases and sensor fidelity. Therefore, the future of insurance is notdemographic profiling—it is algorithmic underwriting based on live vehicletelemetry.We are entering a new era. One that will prove to be the largest disruption in the historyof insurance and mobility. The insurance industry has been built on a single,fundamental premise: that human behavior is the primary variable of risk and this is howinsurance is priced and issued. But that premise is expiring. Austin is ground zero forthis revolution where growing fleets of Waymos and Robotaxis operateWith the maturity of Full Self-Driving (FSD) and Level 5 autonomy, the human is goingto be removed from the mobility equation. When the car becomes the operator, the carmust also become the customer. This requires an evolution for Roamly’s businessmodel. We are going to adjust from insuring human operators to insuring autonomousdecisions, where risk is priced on software quality, not driver history. Eg, we mustunderwrite for the code not the human.The Death of the “Operator”Risk is no longer about who is in the car, but what version of the software is runningand how the hardware and software systems are performing.In an autonomous future, the concept of a human “operator” will become a legal fiction.If the vehicle controls acceleration, braking, and steering 100% of the time, the humaninside is no longer the operator.About the Outdoorsy GroupThe Outdoorsy Group is the world’s leading outdoor travel and hospitality ecosystem.Our mission is to restore our relationship with the outdoors—and with one another—bymaking the life-changing experience of outdoor travel accessible to everyone.What started as Outdoorsy.com, the largest and most trusted peer-to-peer RV rentalmarketplace, has evolved into a multi-vertical powerhouse. Today, our group integratesmarketplace technology and a sophisticated AI Insurance business that is redefininginsurance in the mobility and rec lines markets.Roamly: Insurance Built for AdventureRoamly is the first AI based insurance platform specifically engineered to remove thebarriers to the sharing economy. For decades, traditional insurance policies preventedRV owners from renting their vehicles, leaving millions of assets idle. Roamly solvedthis by developing "rent-ready" insurance, allowing owners to unlock new revenuestreams while providing travelers with the peace of mind they need. Roamly has grownfast and now offers more than 22 products serving the mobility markets, recreationallines and marketplace economy. The company won the Celent 2025 Innovation Awardfor our AI Rater and will expand to international markets.As a Lloyd’s of London Coverholder, Roamly has grown beyond the Outdoorsyecosystem to become a dominant player in specialty insurance. It now provides AI-firstcoverage for RVs, carsharing fleets, boats and motorcycles, offering a seamless "quoteto-bind" experience that is lightyears ahead of legacy providers.We recently launched Myles, our Agentic AI Digital Employee. Myles representsthe next frontier of the Outdoorsy Group’s commitment to a seamless, "always-on"customer experience.As Roamly’s flagship Agentic AI, Myles is far more than an AI chatbot; he is anautonomous digital teammate who handles complex, multi-step workflows inherent inspecialty insurance. Whether it’s instantly qualifying leads, guiding a customer through anuanced "quote-to-bind" journey for a custom DIY van, or proactively managing policyupdates across various platforms, Myles operates with a level of context-awareness anddecision-making authority that mirrors a human expert. For our CCO, Myles serves asa primary proof point of how we use proprietary AI to eliminate friction in the sharingeconomy, allowing our human teams to focus on high-impact strategy while Mylesensures that every customer’s needs are met in real-time, 24/7.Roamly Labs: Our Innovation EngineAt the heart of our technical superiority is Roamly Labs. This is our dedicated AI-firstinnovation hub and sandbox where we architect the future of insurance, autonomousmobility and marketplace dynamics.Roamly Labs focuses on:• AI-Driven Actuarial Science: Developing proprietary tools like our AI ActuarialRater, which has won industry awards for reducing rate-deployment timelinesfrom months to days.• Autonomous Mobility: bridging the gap between hardware-led autonomousvehicle (AV) evolution and the commercial infrastructure required to run themprofitably.• Embedded Distribution: Engineering the APIs that allow partner marketplacesand dealerships to integrate insurance at the point of sale.• Identity & Risk Resolution: Leveraging massive data sets to create a"Customer 360" view, ensuring our ecosystem is safer and more personalized forevery user.• Agentic Systems – more Agents driving recursive leverage throughout thesystems, with continuous learnings and improvements.In this role, you won't just be marketing a marketplace or an insurance platform. Youwill be the architect of multiple initiatives that connect the emotional freedom of theOutdoorsy traveler with the invisible, cutting-edge security powered by Roamly’stechnology and our autonomous solutions to bring autonomous mobility intomarketplaces across multiple geos.Roamly is an AI first full-stack digital insurance platform built for the specialty lines andmobility markets. Roamly is at the heart of the ecosystem and operates as a whollyownedsubsidiary of Outdoorsy—the world’s leading online outdoor travel marketplace.At our beginning, we solved a problem no one else could: we eliminated the commercialuse exclusion clause that stopped RV owners