[Hiring] Life & Annuity 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 Life & Annuity Specialists to:

• Design realistic scenarios involving needs analysis, product selection, illustrations, medical and financial underwriting, table ratings, replacements and 1035 exchanges, policy loans, surrenders, lapse and reinstatement.
• Create work products such as coverage recommendations, illustration comparisons, underwriting assessments, suitability rationales, replacement analyses and policy-service determinations.
• Write "golden" reference responses at experienced life and annuity practitioner quality.
• Grade AI-generated responses against structured rubrics for product accuracy, suitability, mathematical correctness and disclosure adequacy.
• Identify unsupported illustration assumptions, unsuitable recommendations, confusion between product types or tax treatments, and failures to apply replacement or disclosure requirements.
• 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 life insurance or annuity advisory, underwriting, new business, policy administration, product, or suitability review.
• Experience with at least one product family, such as term, whole life, universal or indexed universal life, variable life, or fixed, indexed and variable annuities.
• Understanding of how policy mechanics (cost of insurance, crediting, caps and participation rates, surrender charges, riders and guarantees) drive long-term outcomes.
• Ability to explain tax treatment and suitability considerations clearly, and recognize when licensed or legal review is required.
• Excellent written communication, quantitative care and high attention to detail.
• Ability to distinguish product and suitability judgment from investment advice and formal tax or legal advice.

Bonus Qualifications

• CLU, ChFC, FLMI, CFP, or comparable designation.
• Active or previously held life and health producer license, or securities registration.
• Medical or financial life underwriting experience, including APS review, lab interpretation or reinsurance referral.
• Experience with buy-sell, key-person, estate-planning, premium-finance or executive-benefit cases.
• Experience with suitability, Reg BI, or state replacement and disclosure review.

Role Highlights

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