Head of Claims

Outdoorsy•Austin, TX

1d•Onsite

About The Position

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

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).
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.
Direct experience building, deploying, or architecting proprietary claims software and automation solutions.
Ability to define the data architecture needed to create recursive leverage with our underwriting and product teams.
Data-driven decision-maker who can translate complex claims data into actionable business strategies.
Ability to work out of our dynamic Austin, TX office.

Responsibilities

Direct and inspire a 30+ person claims team, fostering a culture of accountability, continuous learning, and customer empathy.
Lead the claims infrastructure, workflows, and team structure to keep pace with the rapid growth of Roamly, Outdoorsy and Ride.Auto.
Oversee relationships with independent adjusters, legal counsel, and repair networks to optimize cost and quality.
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.
Establish and monitor key performance indicators (KPIs), including FNOL metrics, cycle times, reserve accuracy, subrogation recovery, and litigation management.
Ensure all claims practices strictly adhere to state regulations, fair claims handling acts, and internal underwriting guidelines.
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.
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.