About the Outdoorsy Group

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.

About Roamly, Outdoorsy & Ride Marketplaces

Roamly is rewriting the rules of insurance for the modern, autonomous, and asset-sharing world. As the embedded insurance engine powering global marketplaces like Outdoorsy (the leading RV rental platform) and Ride.Auto (our expanding auto, EV and AV marketplace), we build innovative products for mobility assets. We don’t just process claims; we protect experiences, communities, and livelihoods.

About the Role 

We are seeking an experienced, visionary Head of Claims who will lead the shift from traditional claims handling to an Agentic AI-first function. The Head of Claims is AI-native and can successfully lead, scale, and modernize our claims organization in Austin. You will oversee a talented team of approximately 30 claims professionals handling specialized RV, peer-to-peer (P2P) rental, and automotive claims.

This isn't a traditional corporate insurance gig. You must be AI-first and will sit at the intersection of insurtech, marketplace operations, and customer experience, ensuring our claims process is as seamless, fast, and empathetic as the platforms we protect.

Requirements

Key Responsibilities & Deliverables

Strategic Leadership & Scaling

• Lead the Charge: Direct and inspire a 30+ person claims team, fostering a culture of accountability, continuous learning, and customer empathy.
• Build for Growth: Lead the claims infrastructure, workflows, and team structure to keep pace with the rapid growth of Roamly, Outdoorsy and Ride.Auto.
• Vendor & Partner Management: Oversee relationships with independent adjusters, legal counsel, and repair networks to optimize cost and quality.

Operational Excellence & Tech Innovation

• Insurtech Integration: Own the strategic vision and implementation to automate high-leverage workflows such as first notice of loss (FNOL) categorization, digital claim filing, and transferring data from external platforms to our core systems, with the support of product and engineering. Loss Cost Control: Establish and monitor key performance indicators (KPIs), including FNOL metrics, cycle times, reserve accuracy, subrogation recovery, and litigation management.
• Compliance & Governance: Ensure all claims practices strictly adhere to state regulations, fair claims handling acts, and internal underwriting guidelines.

Cross-Functional Collaboration

• The Feedback Loop: Act as the strategic bridge between Claims, Underwriting, and Product. Use claims data and insights to help refine risk selection, pricing, and product features for both RV and auto lines.
• Marketplace Harmony: Balance strict financial discipline with the unique customer-success needs of a peer-to-peer marketplace, ensuring both hosts/owners and guests/renters receive a world-class experience.

Who You Are (Candidate Profile)

• Experience: 8+ years of progressive insurance claims experience, with at least 3–5 years in a significant leadership role overseeing mid-to-large teams (30+ headcount).
• Domain Expertise: Strong background in Personal/Commercial Auto or Specialized Property lines. Experience with peer-to-peer (P2P), rental fleet, or marketplace insurance is a massive plus.
• Tech-Forward Mindset: Direct experience building, deploying, or architecting proprietary claims software and automation solutions. We are looking for a leader who can define the data architecture needed to create recursive leverage with our underwriting and product teams
• Analytical Rigor: Data-driven decision-maker who can translate complex claims data into actionable business strategies.
• Location: Ability to work out of our dynamic Austin, TX office.

Benefits

Why You’ll Love Working Here

• The Best of Both Worlds: The stability and backing of a profitable marketplace and insurance entity, mixed with the high-growth, high-energy environment of top-tier tech environments.
• Impact: You won't just be managing a department; you will be architecting the future of mobility, AI-first insurance.
• Culture: We value autonomy, innovation, and a shared passion for the open road and mobility. Competitive salary, equity and a generous benefits program included.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) [Match], and Flexible PTO.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.