Insurance Specialist

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Weekday (YC W21)

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2021

💼 Consulting

👥 HR Tech

☁️ SaaS

Consulting • HR Tech • SaaS

Weekday is a modern recruitment platform that combines AI technologies with a vast database of potential candidates, aiming to streamline the hiring process for companies in India. They offer various services, including a proactive outreach approach that helps employers connect with top talent, as well as tools for candidates to easily apply for jobs. Weekday's emphasis on candidate engagement through multiple channels, including email, WhatsApp, and phone calls, sets it apart in the competitive landscape of recruitment agencies.

📋 Description

• Partner with research and engineering teams to improve AI understanding of insurance concepts, including underwriting, claims processing, risk assessment, and policy evaluation. • Design realistic, domain-specific insurance tasks and develop accurate, well-reasoned reference solutions based on industry best practices. • Evaluate AI-generated outputs against structured scoring rubrics, providing detailed written feedback on accuracy, reasoning, and professional judgment. • Develop, refine, and maintain evaluation guidelines and scoring criteria tailored to insurance-related tasks. • Collaborate with fellow subject-matter experts to ensure consistency, accuracy, and quality across AI training and evaluation datasets.

🎯 Requirements

• 8+ years of professional experience in the insurance industry, including areas such as underwriting, claims, actuarial science, or enterprise risk management within a leading insurance organization. • Demonstrated hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or formal scoring frameworks. Candidates should clearly describe this experience as part of their application. • Proven career progression demonstrating increasing responsibility and subject-matter expertise (for example, Underwriter → Senior Underwriter → Underwriting Manager or similar leadership progression). • Ability to commit reliably to 35 or more hours per week during standard weekdays. • Excellent verbal and written communication skills, analytical thinking, problem-solving ability, and collaboration skills. • Experience designing evaluation rubrics, quality assurance frameworks, or assessment methodologies. • Familiarity with AI training, model evaluation, human-feedback workflows, or data annotation projects. • Expertise in multiple insurance disciplines, including commercial or personal lines, property and casualty, life and health, reinsurance, actuarial modeling, or enterprise risk management.