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Claims Specialist - Automotive Loss; Madison, WI

Remote / Online - Candidates ideally in
Madison, Dane County, Wisconsin, 53774, USA
Listing for: Start With Level, Inc.
Remote/Work from Home position
Listed on 2026-07-01
Job specializations:
  • Insurance
    Risk Manager/Analyst, Insurance Claims, Insurance Analyst
Salary/Wage Range or Industry Benchmark: 60000 - 85000 USD Yearly USD 60000.00 85000.00 YEAR
Job Description & How to Apply Below
Position: Claims Specialist - Automotive Total Loss (Madison, WI)

About us

We’re a fast-growing startup rethinking how back-office work gets done in financial services. Our first product helps automotive lenders resolve insurance claims more effectively, delivering better outcomes for both lenders and consumers through automation and AI. Small improvements can unlock significant value for our customers. Along the way, we’ve helped consumers avoid millions in debt.

We’re an early stage venture-backed startup and scaling quickly.

We’re scrappy, intentional, and focused on solving real problems for our customers. We bias toward shipping, learning fast, and building solutions that work in the real world.

Our headquarters is located in New York City, NY — this role would be remote but have the opportunity to collaborate in person with coworkers in our Madison satellite office.

We’re backed by leading investors including 81 Collection, Better Tomorrow Ventures and Capital One Ventures.

The Role

We re seeking an experienced Claims Specialist to join our growing team. You ll leverage our cutting-edge tools to review and resolve automotive total loss claims.

Key Responsibilities
  • Resolve automotive total loss settlements with insurance carriers, adjusters, and third-party administrators
  • Utilize our platform to analyze claim data, identify opportunities to improve claim recovery, and optimize settlement outcomes
  • Collaborate with our product and engineering team to refine our technology and processes based on real-world claim outcomes
  • Maintain detailed documentation of negotiations and settlement rationales
  • Build and maintain relationships with carrier representatives and industry partners
Required Qualifications
  • Adjuster/Appraiser Licenses
  • 3+ years of experience in automotive claims, with specific expertise in a mix of:
    • Total loss settlements
    • Subrogation (subro) processes
  • Strong understanding of ACV (Actual Cash Value) calculations and valuation methodologies
  • Excellent negotiation and communication skills
  • Comfort working with technology
  • Knowledge of state-specific insurance regulations and compliance requirements
Preferred Qualifications
  • Experience with claims management systems and automation tools
  • Background in insurtech or technology-forward operations
What Sets This Role Apart

You won t just be processing claims – you ll be shaping how we transform the industry. Your expertise will directly influence our product development, helping us build smarter negotiation tools and more effective settlement strategies. This is an opportunity to be at the forefront of insurance innovation while applying your deep industry knowledge.

Role Requirements
  • Travel
    :
    Up to 25% travel required which may include but not limited to office meetings and customer site visits
  • Schedule
    :
    This is a dynamic environment and may require flexibility beyond traditional 9-5 hours. You ll need to adapt to varying time zones and urgent claim deadlines
  • Hybrid Work
    :
    We strive to foster a flexible working environment that supports high-quality work. Team members are expected to collaborate intentionally to plan meaningful and effective in-office time.
  • Remote Work Setup
    :
    Reliable high-speed internet connection (minimum 50 Mbps) and quiet, professional workspace for calls with clients and carriers
  • Security
    :
    Ability to maintain secure handling of sensitive claim data meeting our security standards
  • Communication
    :
    Must be responsive during core business hours with ability to manage asynchronous communication across multiple channels
  • Self-Direction
    :
    Strong ability to work independently, prioritize competing demands, and thrive in an ambiguous environment where processes are still being defined
  • Background Check
    :
    Must pass a background check and demonstrate clean driving record for travel requirements
Compensation & benefits
  • Competitive salary and meaningful equity.
  • Health, dental, and vision insurance.
  • Unlimited PTO and flexible hours.
  • New equipment to support your best work.
  • Regular off-sites and team travel budget to get together in person
  • The opportunity to play a foundational role in shaping both the product and the company.
  • Professional development in both insurance and technology domains

HQ in NYC. Satellite office near Madison, WI. Distributed team.

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