Underwriter Remote

Full Timemid

CAPosted Yesterday

Role Overview

Crossing Hurdles is hiring a mid-level Underwriter Remote. This is a full-time role in CA. Part of Crossing Hurdles's Lifecycle hiring, posted yesterday. Full responsibilities, required qualifications, and the apply link are listed in the description below.

Salary Context

Salary is not disclosed in this posting. Market median for Mid-level Lifecycle roles is $100k-$125k (based on 123 comparable listings). Many employers share specifics during the interview process or after an initial screen.

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Job Description

Underwriter - Remote Freelance AI Evaluation

Placed by Crossing Hurdles | On behalf of a US AI Frontier Lab

About the Role

Crossing Hurdles is partnering with a leading US-based AI frontier lab to source experienced insurance professionals for a remote freelance engagement. The company is building out a specialized team of domain experts to evaluate and improve AI systems used in insurance operations. This is a paid, flexible, long-term opportunity designed for working professionals who want to contribute to AI development without leaving their field.

What You Will Do

Review and assess AI-generated outputs related to claims handling, coverage decisions, and operational workflows

Identify errors, gaps, or misalignments in AI reasoning against real-world insurance standards

Provide expert written feedback to help train and refine AI models

Evaluate scenarios involving claims investigation, documentation, reserving, and resolution

Flag compliance or procedural issues based on your professional experience

Domain Focus

Property and casualty claims operations

Liability and subrogation processes

Claims documentation and reserving

Coverage interpretation and policy analysis

Regulatory compliance in claims handling

What We Are Looking For

5 or more years of experience in insurance claims or operations

Background in roles such as Claims Manager, Claims Analyst, Insurance Operations Analyst, Subrogation Specialist, or similar

CPCU, ARM, ACAS, or FCAS designation is a strong plus

Solid understanding of claims lifecycle, coverage analysis, and industry best practices

Strong written communication skills and ability to give structured, clear feedback

Comfortable working independently in a remote, asynchronous environment

Work Style and Expectations

This is a remote, self-managed engagement. You will complete evaluation tasks on your own schedule within agreed weekly hour targets. No meetings-heavy workflow. Onboarding is fast, typically within 24 hours of acceptance. The company values quality of feedback over volume, so attention to detail and professional rigor matter here.

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

You May Be a Good Fit If

You are an experienced claims professional looking to apply your expertise in a new way, want flexible remote work that fits around existing commitments, are curious about AI and how it is being developed for insurance use cases, and want to be paid competitively for your domain knowledge without taking on a full-time role change. To express interest, send your resume to Crossing Hurdles and we will be in touch to discuss next steps. No lengthy applications or interviews required.

About Crossing Hurdles

Crossing Hurdles

crossinghurdles.com

LifecycleOn-site

17 other open roles at Crossing Hurdles on TryApplyNow.

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Frequently Asked Questions

How do I apply for the Underwriter Remote position at Crossing Hurdles?

Use the Apply button above to submit your application directly to Crossing Hurdles. Most applications take less than 5 minutes if your resume and contact details are ready, and you'll be routed to the employer's official application system to finish.

Where is the Underwriter Remote position at Crossing Hurdles located?

This position is based in CA. Crossing Hurdles has not indicated remote or hybrid options for this role, so candidates should plan for on-site work.

What does a Underwriter Remote at Crossing Hurdles earn?

Crossing Hurdles has not disclosed a salary range in this posting. Many employers share specifics later in the interview process; you can also ask during a recruiter screen if compensation transparency is important to you.

When was the Underwriter Remote role at Crossing Hurdles posted?

This role was posted on June 26, 2026 (yesterday). It's still listed as actively hiring; we re-confirm openings against the source system multiple times per day and remove closed roles.