Remotery

Insurance Specialist

atWeekday (YC W21)RemoteUS flagUnited StatesPart-timeInsuranceSeniorLead$60 – $80/hour

Posted Jul 30

This is a fully remote position, open to applicants in United States.

πŸ“‹ Description

β€’ Collaborate with research and engineering teams to enhance AI comprehension of insurance concepts, encompassing underwriting, claims processing, risk assessment, and policy evaluation.

β€’ Create realistic, domain-specific insurance assignments and devise accurate, well-reasoned reference solutions grounded in industry best practices.

β€’ Assess AI-generated outputs using structured scoring rubrics, delivering comprehensive written feedback on precision, reasoning, and professional judgment.

β€’ Develop, refine, and sustain evaluation guidelines and scoring criteria customized for insurance-related tasks.

β€’ Work alongside fellow subject-matter experts to ensure consistency, accuracy, and quality across AI training and evaluation datasets.


⛳️ Requirements

β€’ Over 8 years of professional experience in the insurance sector, covering areas such as underwriting, claims, actuarial science, or enterprise risk management within a prominent insurance organization.

β€’ Proven hands-on experience in evaluating LLM or AI-generated outputs using structured rubrics or formal scoring frameworks. Candidates should clearly outline this experience in their application.

β€’ Demonstrated career advancement reflecting increasing responsibility and subject-matter expertise (for instance, Underwriter β†’ Senior Underwriter β†’ Underwriting Manager or similar leadership trajectory).

β€’ Ability to reliably commit to 35 or more hours per week during standard weekdays.

β€’ Exceptional verbal and written communication skills, along with strong analytical thinking, problem-solving capabilities, and collaborative skills.

β€’ Experience in designing evaluation rubrics, quality assurance frameworks, or assessment methodologies.

β€’ Familiarity with AI training, model evaluation, human-feedback processes, or data annotation projects.

β€’ Expertise across multiple insurance disciplines, including commercial or personal lines, property and casualty, life and health, reinsurance, actuarial modeling, or enterprise risk management.


🏝️ Benefits

β€’ Competitive salary and performance-based bonuses.

β€’ Comprehensive health, dental, and vision insurance.

β€’ Flexible work hours and remote work options.

β€’ Opportunities for professional development and continued education.

β€’ Collaborative and inclusive work environment.

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