Reinsurance & Program Business Specialist

Weekday AIยท AI Training
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๐ŸŒ Remote๐Ÿ“ Remote๐Ÿ“ United StatesContract๐Ÿ’ฐ USD 80+

About this role

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 Reinsurance and Program Business Specialists to design realistic risk-transfer and delegated-authority scenarios, evaluate model outputs against established market standards, and help shape how the next generation of AI reasons about treaty structures, facultative placements, MGAs, fronting, and alternative risk arrangements.

We welcome professionals from reinsurers, cedents, reinsurance brokers, MGAs, MGUs, program administrators, fronting carriers, captive managers, and Lloyd's market participants.

What You'll Do

  • 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

You're a Good Fit If You

  • Have 2+ years of professional experience in reinsurance, program business, delegated authority, fronting, captive insurance, or alternative risk transfer
  • Understand at least one of the following: treaty reinsurance, facultative reinsurance, MGA/MGU programs, Lloyd's arrangements, captives, or fronted programs
  • Can identify the economic and operational responsibilities of cedents, reinsurers, brokers, MGAs, fronting carriers, and insureds
  • Understand how contract structure changes risk transfer, earnings, collateral, claims handling, and reporting
  • Demonstrate excellent written reasoning, commercial judgment, and high attention to detail
  • Can 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

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

Frequently Asked Questions

What is the salary for the Reinsurance & Program Business Specialist role at Weekday AI?
The listed salary for this Reinsurance & Program Business Specialist position at Weekday AI is USD 80+. This is a remote Contract role.
Is the Reinsurance & Program Business Specialist job at Weekday AI remote?
Yes, this Reinsurance & Program Business Specialist position at Weekday AI is remote, with team members based in Remote, United States. You can work from home or anywhere in the supported regions.
Is the Reinsurance & Program Business Specialist role at Weekday AI full-time or part-time?
This is listed as a Contract position. It is posted as a Reinsurance & Program Business Specialist role in the AI Training department at Weekday AI.
Which team or department does the Reinsurance & Program Business Specialist at Weekday AI belong to?
This Reinsurance & Program Business Specialist position is part of the AI Training department at Weekday AI. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Reinsurance & Program Business Specialist position at Weekday AI?
Click the "Apply Now" button on this page. You will be redirected to Weekday AI's official application portal hosted on workable where you can submit your application directly.
When was the Reinsurance & Program Business Specialist job at Weekday AI posted?
This Reinsurance & Program Business Specialist position at Weekday AI was posted on Sep 16, 2026. Apply as soon as possible โ€” early applications are often reviewed first.
Reinsurance & Program Business Specialist
Weekday AI ยท ๐Ÿ’ฐ USD 80+
Apply for this role โ†—

You'll be redirected to Weekday AI's official application page on workable.