Subrogation Specialist | Remote

About the role

Crossing Hurdles is partnering with a US-based AI frontier lab to identify experienced insurance professionals for a remote, freelance AI evaluation role. This is not a traditional insurance position. Our client is building and refining AI systems designed to reason through complex insurance scenarios, and they need working practitioners to assess whether those systems get it right. If you have hands-on subrogation experience and strong analytical instincts, this is an opportunity to apply your expertise in a flexible, well-compensated consulting capacity alongside your current work or as a standalone engagement.

What You Will Do

• Review and evaluate AI-generated outputs related to subrogation workflows, recovery strategies, and claims decisions
• Identify errors in legal reasoning, carrier liability assessments, and third-party recovery analysis
• Provide written feedback on accuracy, logic gaps, and real-world applicability
• Flag outputs that reflect misunderstanding of state-specific subrogation laws or industry standards
• Complete structured evaluation tasks on a flexible, self-managed schedule

Domain Focus

• Subrogation recovery across auto, property, workers compensation, and liability lines
• Third-party liability determination and demand package review
• Statute of limitations compliance and jurisdictional considerations
• Negotiation strategy and settlement assessment
• Coordination with legal counsel and external vendors

What We Are Looking For

• 5 or more years of subrogation experience in a carrier, TPA, or law firm setting
• Demonstrated knowledge of recovery processes across multiple lines of business
• Familiarity with state subrogation statutes and intercompany arbitration forums such as Arbitration Forums Inc.
• Strong written communication and analytical reasoning skills
• CPCU, ARM, or similar designation is a plus but not required
• Candidates currently or recently working as Subrogation Specialist, Recovery Analyst, Claims Examiner, or Subrogation Team Lead are strongly encouraged to apply

Work Style and Expectations

• This role is fully remote and asynchronous.
• You set your own hours and work independently within weekly targets.
• Strong performers are considered for retainer arrangements and expanded scope over time.
• Onboarding happens within 24 hours of offer, with no lengthy application forms or interview panels - just a resume review and a brief onboarding call.

Compensation

• Compensation Rate: $100-125/hr (USD)
• Payment: Via Deel, fortnightly
• Commitment: 15-20+ hours/week (minimum 10+ hours/week)
• Type: Long-term engagement, retainer opportunities for strong performers

To Apply

To apply, send your resume to Crossing Hurdles. A member of our team will follow up directly.