Claims Specialist - AI Trainer

Opportunity Overview

Handshake is seeking experienced Claims Specialists to support AI research through flexible, hourly contract work. This is not a traditional full-time claims role. You’ll use your real-world experience investigating, evaluating, and resolving claims to evaluate AI-generated content and provide feedback that helps AI better understand claims processes, policy language, and customer communication.

This is an ongoing, project-based opportunity that can be done alongside your primary employment.

This project is designed for professionals who are already working (or have recently worked) in roles such as:

• Claims Specialist or Claims Representative

• Claims Adjuster (property, casualty, auto, health, disability, or workers’ compensation)

• Claims Examiner or Claims Analyst

• Senior customer service professional with a strong claims focus

This is not a traditional full-time role. You’ll apply once and, if qualified, be considered for part-time, project-based work as new projects become available.

This project involves using your professional experience as a Claims Specialist to design job-related questions and review AI-generated responses for accuracy and relevance to real-world claims handling and customer interactions.

No prior AI or technical experience is required.

We’re looking for established professionals with:

• 4+ years of professional experience in claims handling or closely related roles

• Hands-on experience investigating claims, interpreting policy coverage, and communicating decisions to claimants or stakeholders

• Strong written communication skills and attention to detail

• Comfortable working independently and following written guidelines

• Professional judgment, reliability, and a high standard of discretion and confidentiality, especially with sensitive or proprietary information.

• Status:
  Independent contractor (not a full-time employee role)

• Location:
  
  Fully remote; work from anywhere with a reliable internet connection and access to a desktop or laptop computer

• Schedule:
  
  Flexible and asynchronous, with no minimum hour requirement. Many contributors work approximately 5–20 hours per week when assigned to an active project

• Duration:
  The Handshake AI program runs year-round, with projects opening periodically across different areas of expertise. Placement depends on current project needs, with opportunities to be considered for future projects as they become available

F-1 students who are eligible for CPT or OPT may be eligible for projects on Handshake AI. Work with your Designated School Official to determine your eligibility. If your school requires a CPT course, Handshake AI may not meet your school’s requirements. STEM OPT is not supported. For more information on what types of work authorizations are supported on Handshake AI.