Weekday, Inc. Logo

Weekday, Inc.

Insurance Specialist

Posted 14 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in United States
60-80 Hourly
Senior level
Remote
Hiring Remotely in United States
60-80 Hourly
Senior level
Provide insurance subject-matter expertise to improve generative AI models: design insurance tasks, create reference solutions, evaluate AI outputs with structured rubrics, refine scoring guidelines, and collaborate with research and engineering teams to produce high-quality training and evaluation data. Commitment of 35+ hours/week and proven senior insurance experience required.
The summary above was generated by AI

This role is for one of our clients

Compensation: $60-$80 per hour

Join a leading AI lab at the forefront of Generative AI and contribute to building the next generation of foundational AI models. We are seeking experienced Insurance Specialists with deep expertise in underwriting, claims, actuarial science, or risk management, along with hands-on experience evaluating AI model outputs against structured rubrics. In this role, you will help improve AI systems by bringing real-world insurance judgment and domain expertise into high-quality training and evaluation data.

This is a fully remote engagement requiring approximately 35+ hours per week during weekdays.


RequirementsKey Responsibilities
  • Partner with research and engineering teams to improve AI understanding of insurance concepts, including underwriting, claims processing, risk assessment, and policy evaluation.
  • Design realistic, domain-specific insurance tasks and develop accurate, well-reasoned reference solutions based on industry best practices.
  • Evaluate AI-generated outputs against structured scoring rubrics, providing detailed written feedback on accuracy, reasoning, and professional judgment.
  • Develop, refine, and maintain evaluation guidelines and scoring criteria tailored to insurance-related tasks.
  • Collaborate with fellow subject-matter experts to ensure consistency, accuracy, and quality across AI training and evaluation datasets.
Core Qualifications
  • 8+ years of professional experience in the insurance industry, including areas such as underwriting, claims, actuarial science, or enterprise risk management within a leading insurance organization.
  • Demonstrated hands-on experience evaluating LLM or AI-generated outputs using structured rubrics or formal scoring frameworks. Candidates should clearly describe this experience as part of their application.
  • Proven career progression demonstrating increasing responsibility and subject-matter expertise (for example, Underwriter → Senior Underwriter → Underwriting Manager or similar leadership progression).
  • Ability to commit reliably to 35 or more hours per week during standard weekdays.
  • Excellent verbal and written communication skills, analytical thinking, problem-solving ability, and collaboration skills.
Preferred Qualifications
  • Experience designing evaluation rubrics, quality assurance frameworks, or assessment methodologies.
  • Familiarity with AI training, model evaluation, human-feedback workflows, or data annotation projects.
  • Expertise in multiple insurance disciplines, including commercial or personal lines, property and casualty, life and health, reinsurance, actuarial modeling, or enterprise risk management.
Equal Opportunity

We are committed to providing equal employment opportunities to all qualified applicants. Employment decisions are made without regard to legally protected characteristics, and reasonable accommodations are available throughout the application and engagement process upon request.

Contract & Payment Terms
  • Independent contractor engagement.
  • Fully remote with flexible working hours.
  • Projects may be extended, shortened, or concluded based on business requirements and individual performance.
  • Weekly payments are processed through supported payment platforms.
  • Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.

Similar Jobs

Yesterday
Remote
USA
Junior
Junior
Healthtech • Professional Services
Review, prepare, submit, and follow up on insurance claims; process insurance correspondence and appeals; perform collections and patient contact; identify underpayments and refunds; maintain AR reconciliation and documentation while adhering to HIPAA.
Top Skills: Claim ScrubberClearinghouseMS OfficeMicrosoft Outlook
Yesterday
Remote
US
Mid level
Mid level
Artificial Intelligence • Insurance • Software • Automation
Serve as a client-facing insurance operations specialist who drives adoption and outcomes across agency accounts. Learn client workflows, diagnose adoption barriers, design interventions (retraining, workflow redesign, champion programs), deliver trainings, create enablement materials, triage technical issues, and partner with CSMs on onboarding, reviews, renewals, and expansion.
Top Skills: Ams360Applied EpicHawksoftNexsure
2 Days Ago
Remote
US
Junior
Junior
Healthtech
Investigate and resolve unpaid or denied medical claims by reviewing UB04s, EOBs and medical records; use proprietary software, EMR portals, phone and written correspondence to obtain claim resolution while meeting production and quality targets and complying with HIPAA.
Top Skills: CernerEmrEpicInsurance Carrier Web PortalsMeditechProprietary Software System

What you need to know about the Boston Tech Scene

Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.

Key Facts About Boston Tech

  • Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
  • Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
  • Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
  • Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account