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Weekday, Inc.

Life & Annuity Specialist

Posted 28 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in Canada
Junior
Remote
Hiring Remotely in Canada
Junior
Design and evaluate life insurance and annuity advisory, underwriting, policy-service, suitability, and replacement scenarios for AI training. Create expert reference responses, assess model outputs for product accuracy, mathematical correctness, suitability, tax treatment, and disclosure compliance, and provide feedback to improve model performance. Participate in onboarding and calibration sessions.
The summary above was generated by AI

This role is for one of our clients

Compensation: $80 per hour

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.

We welcome life and annuity producers, advisors, life underwriters, new-business and policy-service professionals, product specialists, and suitability or replacement reviewers from carriers, brokerage general agencies, IMOs, and independent practices.


Requirements

What You'll Do

  • 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

You're a Good Fit If You

  • Have 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

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

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

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