[Hiring] Reinsurance & Program Business 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 Reinsurance and Program Business Specialists to:

• Design realistic scenarios involving treaty and facultative reinsurance, attachment and exhaustion, cessions, recoverables, bordereaux, delegated authority, program governance, fronting, captives, and risk participation.
• Create work products such as structure comparisons, submission analyses, contract summaries, program reviews, counterparty assessments, and risk-transfer recommendations.
• Write "golden" reference responses at experienced reinsurance and program-business quality.
• Grade AI-generated responses against structured rubrics for structural accuracy, contract logic, financial understanding, stakeholder roles, and market realism.
• Identify misunderstandings of layers, limits, retentions, commissions, claims control, collateral, counterparty exposure, and carrier-MGA responsibilities.
• 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 reinsurance, program business, delegated authority, fronting, captive insurance, or alternative risk transfer.
• Understanding of at least one of the following: treaty reinsurance, facultative reinsurance, MGA/MGU programs, Lloyd's arrangements, captives, or fronted programs.
• Ability to identify the economic and operational responsibilities of cedents, reinsurers, brokers, MGAs, fronting carriers, and insureds.
• Understanding of how contract structure changes risk transfer, earnings, collateral, claims handling, and reporting.
• Demonstrated excellent written reasoning, commercial judgment, and high attention to detail.
• Ability to distinguish reinsurance decisions from direct underwriting and ordinary claim adjudication.

Bonus Qualifications

• CPCU, ARe, ARM, ACAS, FCAS, or comparable designation.
• Both ceded and assumed reinsurance experience.
• Reinsurance broking, treaty wording, recoverables, or claims experience.
• Program audit, delegated-authority, or bordereaux-management experience.
• Captive, large-deductible, retrospective-rating, or risk-sharing experience.

Role Highlights

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