Weekday (YC W21)
Weekday (YC W21)
11 – 50 Employees
ConsultingHR TechSaaS
Weekday (YC W21) is an India-focused recruitment platform in the HR technology and SaaS space. It combines AI-driven tools with a broad candidate database to help companies identify and engage talent through proactive outreach. The platform supports communication across email, WhatsApp, and phone, while also giving candidates a straightforward way to discover and apply for roles.

Remote Insurance Expert for AI Training and Evaluation

Weekday is seeking an India-based insurance professional to create underwriting and claims scenarios for AI training. The role evaluates AI decisions for accuracy, reasoning, policy interpretation, and completeness.

Description

  • Create detailed underwriting scenarios covering applications, risk profiles, eligibility, and pricing decisions
  • Develop claims cases involving coverage decisions, policy language, exclusions, and fraud indicators
  • Examine AI-generated underwriting and claims decisions in detail
  • Assess AI responses for accuracy, sound reasoning, and completeness
  • Spot misunderstood policy language, overlooked exclusions, flawed risk judgments, and convincing but incorrect conclusions
  • Document evaluation outcomes with clear, well-supported explanations
  • Submit rigorous, high-quality work for team review

Requirements

  • At least three years of practical experience in underwriting, risk assessment, or claims
  • Background in life, health, general, or specialty insurance
  • Strong practical understanding of risk assessment and pricing
  • Working knowledge of claims decision-making
  • Ability to interpret policy language, including conditions, exclusions, and endorsements
  • High level of written precision
  • Ability to detect errors that appear credible
  • Dependable delivery against deadlines
  • Interest in the ways AI may transform insurance work
  • Motivation to contribute to AI development
  • Availability for project-based, task-based contract work

Benefits

  • Work remotely with flexibility around an existing full-time position
  • Choose flexible, task-based hours without set working days
  • Gain direct insight into how advanced AI models are trained and assessed for insurance applications
  • Help enhance AI model performance
  • Collaborate with a team backed by Y Combinator
  • Access additional tasks and larger projects through consistently strong performance

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