[Hiring] Disability Claims & Underwriting Specialist @Weekday AI

Role Description

We are partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring Disability Claims & Underwriting Specialists to:

• Design realistic disability adjudication and risk-selection scenarios.
• Evaluate model outputs against established industry standards.
• Help shape how the next generation of AI reasons about disability definitions, medical and vocational evidence, and benefit entitlement.

We welcome group and individual disability claims examiners, disability underwriters, vocational rehabilitation professionals, return-to-work and absence-management specialists, and appeals reviewers from carriers, TPAs and employer-side programs.

What You'll Do

• Design realistic scenarios involving short- and long-term disability claims, elimination periods, own-occupation and any-occupation definitions, residual and partial disability, offsets, recurrent disability and claim duration management.
• Create work products such as claim determinations, benefit calculations, medical and vocational evidence summaries, transferable-skills analyses, return-to-work plans and appeal decisions.
• Write "golden" reference responses at experienced disability-professional quality.
• Grade AI-generated responses against structured rubrics for definitional accuracy, evidentiary support, benefit-calculation correctness and procedural fairness.
• Identify misapplied disability definitions, unsupported functional conclusions, missed offsets, incorrect benefit math, and failures to document the administrative record.
• Provide written feedback the research team uses to improve model behavior.
• Participate in onboarding office hours and calibration sessions.

Qualifications

• 2+ years of professional experience in disability claims adjudication, disability underwriting, vocational rehabilitation, or leave and absence management.
• Experience with at least one program type, such as group short-term disability, group long-term disability, individual disability income, statutory disability, or life waiver of premium.
• Understanding of how contract definitions, elimination periods, offsets, pre-existing-condition provisions and maximum benefit periods determine entitlement and duration.
• Ability to weigh medical, occupational and financial evidence and articulate a defensible determination with a documented rationale.
• Excellent written analysis, balanced judgment and high attention to detail.
• Ability to distinguish claim adjudication from treating-provider clinical decisions and from formal legal advice.

Bonus Qualifications

• CRC, CDMS, CCM, CPDM, RN, or comparable clinical or vocational credential.
• Experience with ERISA administrative records, appeals or litigation support.
• Individual disability income underwriting, including occupation class and financial underwriting.
• Social Security, workers compensation or other-income offset coordination experience.
• Experience with FMLA, state leave programs or ADA accommodation interaction.

Role Highlights

• Minimum 20 hours per week (ideally 40+).
• Role starts immediately, applications reviewed on a rolling basis.

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.