Life & Annuity Specialist for AI Model Training
Job Description
Key Skills Required
Master these to land this role
Want to know if you're a match for this job?
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
How would you rate this job post?
See what other professionals think about this role.
Similar Opportunities
More Openings at Weekday
Python Engineer for AI Codebase Reasoning Dataset
Weekday
United StatesGo Engineer for AI Codebase Reasoning Dataset
Weekday
United StatesC Engineer for AI Codebase Reasoning Dataset
Weekday
United StatesReinsurance and Program Business Specialist (AI Training)
Weekday
Australia
CanadaExplore Top Companies in this Space
Candidate.fyi
HR Tech / Recruitment / Enterprise Software
Jobgether
HR Tech & Remote Work Marketplaces / AI Sourcing Platforms & Job Aggregators / Global Talent Acquisition & Recruitment Solutions
TestGorilla
HR Tech / Recruitment / Talent Acquisition
WorkMotion
HR Tech & Global Employment Platforms
Weekday
View Company ProfileWeekday is an AI-powered recruitment platform designed to act as a fully automated outbound sourcing engine. Instead of posting a job on traditional boards and waiting for active job seekers to apply, Weekday empowers companies to proactively hunt top-tier tech talent. They maintain a massive database of over 250 million profiles (heavily focused on the US and India) complete with verified contact data. Their AI contextually screens candidates to find the perfect fit, and then the platform automatically runs personalized, multi-channel outreach campaigns to engage those passive engineers and bring them directly into your interview pipeline.
Safety First
- Never pay for a job application.
- Do not share sensitive bank info.
- Verify the client before starting work.


