Life & Annuity Specialist
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Weekday AI
US
Summary
Design realistic insurance scenarios and evaluate AI-generated model outputs against industry standards for accuracy and suitability. Provide written feedback to the research team to improve model reasoning regarding mortality risk and long-horizon guarantees.
Job Description
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.
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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Founded
2022
Company size
11-50 employees
Industry
Technology, Information and Internet
Org type
Privately Held
Finding a great startup job should not feel like a second job.
Weekday AI brings the most exciting roles from premium YC and VC-backed startups into one place. Our team hand-picks every listing, so you skip the agency spam and the dead links and go straight to companies building things that matter.
Why people use Weekday AI?
Curated roles from premium YC and VC-backed startups
Fresh jobs every week, picked by humans
AI that helps you apply in minutes
Free to join
Your next role should come from a company you are proud to work at. We help you find it.
Browse live roles at jobs.weekday.works
Founded
2022
Company size
11-50 employees
Industry
Technology, Information and Internet
Org type
Privately Held