Weekday, Inc. Logo

Weekday, Inc.

Reinsurance & Program Business Specialist

Posted 28 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in Canada
Junior
Remote
Hiring Remotely in Canada
Junior
Design reinsurance and program-business scenarios, assess AI-generated responses, create market-quality reference materials, and provide detailed feedback on treaty structures, delegated authority, fronting, captives, risk transfer, contract logic, financial responsibilities, and market realism.
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 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.


Requirements

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.

Similar Jobs

36 Minutes Ago
Easy Apply
Remote
Canada
Easy Apply
Senior level
Senior level
Big Data • Fintech • Mobile • Payments • Financial Services
Own the vision and roadmap for Affirm’s consumer loyalty program, launching rewards, tiers, engagement loops, and redemption experiences. Lead program economics, experimentation, incrementality, LTV measurement, and reward optimization. Partner with Risk, Credit, Legal, Compliance, Finance, Marketing, engineering, and design to deliver compliant products and drive repeat usage, retention, share of wallet, and incremental GMV.
Top Skills: AmplitudeClaude CodeCursorSQL
2 Hours Ago
Easy Apply
Remote or Hybrid
CA
Easy Apply
Senior level
Senior level
Artificial Intelligence • Cloud • Computer Vision • Hardware • Internet of Things • Software
Architect and own marketing data infrastructure, Databricks pipelines, Gold Layer tables, semantic models, and AI-enabled data products. Lead complex cross-team initiatives, translate ambiguous business needs into scalable solutions, ensure data quality and reliability, and mentor engineers and analysts. Build, evaluate, and monitor production LLM and agent systems while automating marketing and go-to-market workflows with AI. Partner with BI, Data Science, Marketing, Sales, and R&D teams to support self-service analytics and trusted business KPIs.
Top Skills: Ai AgentsBigQueryClaude CodeCursorData WarehousesDatabricksDbtEltETLLakehouse ArchitecturesLlmsPythonSalesforceSemantic LayersSnowflakeSQLStreamlit
2 Hours Ago
Easy Apply
Remote
Canada
Easy Apply
Entry level
Entry level
Big Data • Fintech • Mobile • Payments • Financial Services
Leads Marketing and Consumer Privacy Engineering teams, developing engineers and establishing a shared operating model. Translates business and product priorities into engineering plans across logged-out web, experimentation, marketing integrations, attribution, measurement, consent, privacy experiences, and consumer data collection. Partners with Product, Marketing, Privacy, Legal, and Engineering stakeholders to deliver reliable, scalable, privacy-aware systems while balancing customer needs, quality, speed, and risk.
Top Skills: AnalyticsAttributionAustralian Privacy ActCcpa/CpraConsent ManagementCookiesGdprInstrumentationMarketing TechnologyMeasurement SystemsTaggingWeb Experimentation

What you need to know about the Calgary Tech Scene

Employees can spend up to one-third of their life at work, so choosing the right company is crucial, not just for the job itself but for the company culture as well. While startups often offer dynamic culture and growth opportunities, large corporations provide benefits like career development and networking, especially appealing to recent graduates. Fortunately, Calgary stands out as a hub for both, recognized as one of Startup Genome's Top 100 Emerging Ecosystems, while also playing host to a number of multinational enterprises. In Calgary, job seekers can find a wide range of opportunities.

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account