Weekday, Inc. Logo

Weekday, Inc.

Insurance Specialist

Reposted One Month 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

Entry level
Insurance • Financial Services
Verifies life and health insurance applications through outbound calls, documents information for underwriting, explains application procedures, completes paperwork, updates quality assurance records, transfers calls, and meets departmental KPIs. The role requires strong customer service, accurate data entry, multitasking, organization, computer proficiency, and preferably bilingual English-Spanish communication. This is a part-time remote position.
Top Skills: MS OfficeQuality Assurance Database
Yesterday
Remote
United States
Senior level
Senior level
Fintech
Own and optimize paid acquisition for auto insurance, beginning with hands-on Google Ads management and expanding into paid social and emerging channels. Responsibilities include SEM campaign strategy, state and DMA targeting, bidding, keyword and ad optimization, quote-funnel analysis, competitive auction management, performance reporting, and insurance advertising compliance. The role requires deep U.S. auto insurance paid media experience, budget ownership, lead-generation economics expertise, and independent optimization judgment.
Top Skills: Bing AdsGoogle AdsMeta AdsMicrosoft AdvertisingPerformance MaxSmart BiddingTiktok Ads
Yesterday
Remote
United States
20-20 Hourly
Junior
20-20 Hourly
Junior
Healthtech • Software • Financial Services
Resolves outstanding orthodontic insurance accounts by researching unpaid claims, contacting carriers, submitting and resubmitting claims, reconciling payments, and adjusting patient accounts. The role also supports patients with insurance questions, documents claim activity, navigates practice management systems and insurance portals, and independently manages high-volume accounts while meeting accuracy and productivity standards.
Top Skills: Cloud 9DolphinOrtho2OrthotracTops

What you need to know about the NYC Tech Scene

As the undisputed financial capital of the world, New York City is an epicenter of startup funding activity. The city has a thriving fintech scene and is a major player in verticals ranging from AI to biotech, cybersecurity and digital media. It also has universities like NYU, Columbia and Cornell Tech attracting students and researchers from across the globe, providing the ecosystem with a constant influx of world-class talent. And its East Coast location and three international airports make it a perfect spot for European companies establishing a foothold in the United States.

Key Facts About NYC Tech

  • Number of Tech Workers: 549,200; 6% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: Capgemini, Bloomberg, IBM, Spotify
  • Key Industries: Artificial intelligence, Fintech
  • Funding Landscape: $25.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Greycroft, Thrive Capital, Union Square Ventures, FirstMark Capital, Tiger Global Management, Tribeca Venture Partners, Insight Partners, Two Sigma Ventures
  • Research Centers and Universities: Columbia University, New York University, Fordham University, CUNY, AI Now Institute, Flatiron Institute, C.N. Yang Institute for Theoretical Physics, NASA Space Radiation Laboratory

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account