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  1. Home
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  3. accounting & finance
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  5. Head of Claims
Outdoorsy logo

Head of Claims

Not Disclosed•Full-TimeOn-site

location_onTravis County Constable Precinct Five, 700, Lavaca Street, Austin, Travis County, Texas, 78701, United States

Apply Now

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. Our portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network, a collection of campgrounds and glamping retreats in iconic landscapes; and Roamly, our proprietary insurtech platform.

Together, our businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another.

About Roamly

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 to lead the shift from traditional claims handling to an Agentic AI-first function. You 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.

This isn't a traditional corporate insurance gig. You will lead, scale, and modernize our claims organization in Austin, overseeing a talented team of approximately 30 professionals handling specialized RV, peer-to-peer (P2P) rental, and automotive claims. You will architect the future of mobility and AI-first insurance, balancing strict financial discipline with the unique customer-success needs of a peer-to-peer marketplace.

Why Join Us

You will enjoy the stability and backing of a profitable marketplace and insurance entity, mixed with the high-growth, high-energy environment of a top-tier tech company. We value autonomy, innovation, and a shared passion for the open road and mobility. As a company in its early stages, you will have the opportunity to help build our foundation for success.

Equal Opportunity

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Work location

Work model: On-site

location_on

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Frequently asked questions about Head of Claims at Outdoorsy

What does a Head of Claims at Outdoorsy do?expand_more
In this Head of Claims at Outdoorsy role, you will lead and inspire a 30+ person claims team to foster accountability and customer empathy; direct the shift to an agentic ai-first claims function and modernize the organization; build claims infrastructure, workflows, and team structure to support rapid business growth; and oversee relationships with independent adjusters, legal counsel, and repair networks.
What are the requirements for this Head of Claims role?expand_more
To qualify for the Head of Claims at Outdoorsy position, applicants should have: 8+ years of progressive insurance claims experience; 3–5 years in a significant leadership role overseeing mid-to-large teams (30+ headcount); Strong background in Personal/Commercial Auto or Specialized Property lines; Direct experience building, deploying, or architecting proprietary claims software and automation solutions; and Ability to work out of Austin, TX office.
Where is the Head of Claims role at Outdoorsy located?expand_more
Head of Claims at Outdoorsy is based in Travis County Constable Precinct Five, 700, Lavaca Street, Austin, Travis County, Texas, 78701, United States. This is a on-site role.
Is this Head of Claims job remote, hybrid, or on-site?expand_more
Outdoorsy has listed this Head of Claims role as on-site.
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Travis County Constable Precinct Five, 700, Lavaca Street, Austin, Travis County, Texas, 78701, United States

Austin, Texas

Key Responsibilities

  • check_circleLead and inspire a 30+ person claims team to foster accountability and customer empathy
  • check_circleDirect the shift to an Agentic AI-first claims function and modernize the organization
  • check_circleBuild claims infrastructure, workflows, and team structure to support rapid business growth
  • check_circleOversee relationships with independent adjusters, legal counsel, and repair networks
  • check_circleOwn the strategic vision to automate high-leverage workflows like FNOL categorization and digital filing
  • check_circleEstablish and monitor KPIs including cycle times, reserve accuracy, and subrogation recovery
  • check_circleEnsure all claims practices strictly adhere to state regulations and internal underwriting guidelines
  • check_circleAct as a strategic bridge between Claims, Underwriting, and Product to refine risk selection and pricing
  • check_circleBalance financial discipline with customer success needs for a peer-to-peer marketplace

Requirements

  • verified8+ years of progressive insurance claims experience
  • verified3–5 years in a significant leadership role overseeing mid-to-large teams (30+ headcount)
  • verifiedStrong background in Personal/Commercial Auto or Specialized Property lines
  • verifiedDirect experience building, deploying, or architecting proprietary claims software and automation solutions
  • verifiedAbility to work out of Austin, TX office

Nice to Have

Experience with peer-to-peer (P2P), rental fleet, or marketplace insurance.

Benefits & Perks

check_circle100% company-paid medical premiums for employeescheck_circle401(k) with company matchcheck_circleFlexible PTOcheck_circleEquity compensation opportunitycheck_circleRV rental discounts
Outdoorsy cover image
Outdoorsy logo
Company

Outdoorsy

Industry

Internet Marketplace Platforms

Headquarters

Austin, Texas

Outdoorsy operates as an internet marketplace platform based in Austin, Texas, connecting travelers with recreational vehicle owners for unique accommodation experiences. The company focuses on RV travel and owned destinations, aiming to provide sustainable access to outdoor adventures while generating entrepreneurial opportunities for vehicle owners. By leveraging technology, Outdoorsy enhances the utility of underutilized mobility assets, fostering a deeper connection between guests and nature since its inception in 2015. The platform has facilitated over 10 million nights of outdoor stays for its users. While the service maintains a global footprint spanning 14 countries, North America remains the primary strategic focus for operations. Outdoorsy functions as a core component of the Outdoorsy Group, a global mobility entity that supports the future of travel through a diverse ecosystem. This broader organization includes specialized insurance solutions through Roamly and fleet management systems via Wheelbase, alongside ride.auto, creating a comprehensive suite of marketplace solutions for the mobility sector.
View company profilearrow_forwardlanguageWebsitelinkLinkedIn
Quick Overview

Experience

8+ yrs (Lead)

Job Type

Full-Time

Skills Required

InsurtechAgentic AiAi-FirstFnolDigital Claim FilingData Architecture
Not Disclosedarrow_forward
How much experience is required for this Head of Claims role?expand_more
Head of Claims at Outdoorsy typically requires 8+ years of relevant experience at the lead level.
What skills do you need for the Head of Claims role at Outdoorsy?expand_more
Key skills for Head of Claims at Outdoorsy include Insurtech; Agentic Ai; Ai-First; Fnol; Digital Claim Filing; Data Architecture; Loss Cost Control; and Kpi.
What category does the Head of Claims role belong to?expand_more
Head of Claims at Outdoorsy is part of the accounting & finance job category on Recrutus.

About Outdoorsy

Outdoorsy operates as an internet marketplace platform based in Austin, Texas, connecting travelers with recreational vehicle owners for unique accommodation experiences. The company focuses on RV travel and owned destinations, aiming to provide sustainable access to outdoor adventures while generating entrepreneurial opportunities for vehicle owners. By leveraging technology, Outdoorsy enhances the utility of underutilized mobility assets, fostering a deeper connection between guests and nature since its inception in 2015.

The platform has facilitated over 10 million nights of outdoor stays for its users. While the service maintains a global footprint spanning 14 countries, North America remains the primary strategic focus for operations. Outdoorsy functions as a core component of the Outdoorsy Group, a global mobility entity that supports the future of travel through a diverse ecosystem. This broader organization includes specialized insurance solutions through Roamly and fleet management systems via Wheelbase, alongside ride.auto, creating a comprehensive suite of marketplace solutions for the mobility sector.

Browse more roles: All Outdoorsy jobs, accounting & finance jobs on Recrutus.

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About usFAQContactPrivacy policyUS privacy noticeAccessibility

Recrutus helps candidates discover roles that match their skills and helps teams reach qualified applicants faster. Browse by metro, discipline, or work style — from internships to senior leadership.

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Loss Cost Control
Kpi
Subrogation Recovery
Litigation Management