Jobs · OTHR

Life & Annuity Specialist

Weekday AI (YC W21) · United States · 1 mo ago
RemoteRemoteOTHR$80/hrContract

About the role

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 advisory, underwriting and policy-service scenarios, evaluate model outputs against established industry standards, and help shape how the next generation of AI reasons about mortality risk, long-horizon guarantees and suitability.

Responsibilities

  • 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

Requirements

  • 2+ years of professional experience in life insurance or annuity advisory, underwriting, new business, policy administration, product, or suitability review
  • Have worked with at least one product family, such as term, whole life, universal or indexed universal life, variable life, or fixed, indexed and variable annuities
  • Understand how policy mechanics (cost of insurance, crediting, caps and participation rates, surrender charges, riders and guarantees) drive long-term outcomes
  • Can explain tax treatment and suitability considerations clearly, and recognize when licensed or legal review is required
  • Demonstrate excellent written communication, quantitative care and high attention to detail
  • Can distinguish product and suitability judgment from investment advice and formal tax or legal advice

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

Pay

$80 per hour

Schedule

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

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