Subrogation Specialist - Remote AI Evaluation Consultant
Placed by Crossing Hurdles | Immediate Start

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
Rate : $100-125/hr (USD)

Payment : Via Deel, fortnightly

Commitment : 15-20+ hours/week (minimum 10+ hours/week)

You May Be a Valuable Fit If
You are an experienced subrogation professional who wants to contribute to AI development in a meaningful way, without leaving your area of expertise. You think critically about how insurance logic is applied, you can articulate why a recovery decision is right or wrong, and you value flexible, well‑paid work that fits around your life. To apply, send your resume to Crossing Hurdles. A member of our team will follow up directly.

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📌 Subrogation Specialist | Remote (Manitoba)
🏢 Crossing Hurdles
📍 Manitoba