Insurance Specialist - Fully Remote | Upto $100/hr

Obsidian; San Francisco (CA); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Obsidian has engaged Cincinnatus LLC to place a senior insurance and actuarial domain expert in an onsite/hybrid capacity with an AI lab in the San Francisco Bay Area. The role focuses on reviewing insurance knowledge work, authoring instruction specs, and building robust benchmarks to evaluate frontier AI models.

The candidate should bring deep actuarial or insurance credentials, 4+ years of domain experience, and proven ability to translate complex insurance reasoning into teachable criteria.

Qualifications

• Proven experience applying actuarial methods to real insurance problems.
• Ability to review insurance knowledge work tasks for quality and accuracy.
• Strong written communication to define instructions and benchmarks.

Responsibilities

• Vet quality of insurance knowledge work tasks and model outputs.
• Write instruction specs and golden solutions for insurance problems.
• Design benchmarks and evaluation sets for domain depth.
• Work with researchers to translate tacit insurance judgment into explicit criteria.

Skills

AI fluency

Insurance knowledge

Technical writing

Education

Actuarial credential or math degree

Job description

Join a leading AI lab's cutting-edge GenAI team to be at the core of the AI revolution, where your expertise fuels the development of the most advanced AI models.

1. Overview

We are hiring a senior insurance and actuarial domain expert to work directly with a leading AI lab's research and program management teams, improving how frontier AI models reason about real insurance work.

Your insurance expertise is the substance of this role. You will review the quality of insurance knowledge work tasks, write the instruction specs and golden solutions that define what "correct" looks like, and build the benchmarks that show whether the model is genuinely improving. We are looking for a practicing specialist rather than a generalist.

This is a full-time W-2 employment position with Cincinnatus LLC, with the opportunity to be placed at a leading AI lab as part of their extended workforce. You will be provisioned with client-issued accounts and equipment, and will work inside the client's own tools alongside their research teams.

Location: This is a hybrid role based in the Bay Area, California. You must live in the Bay Area and work on-site with the client's team multiple days each week, when required. This is not a remote role. If you do not currently live in the Bay Area, you must be willing to relocate there at your own cost before the engagement starts. Relocation assistance is not provided.

2. Key Responsibilities

• Data QA and reviews: Vet the quality of insurance knowledge work tasks and model outputs, spotting missing behaviors, thin reasoning, flawed actuarial assumptions, misapplied policy language, and answers that read well but would not survive professional scrutiny.

• Instruction specs and golden datasets: Write high-quality instruction specs, produce golden solutions to insurance and actuarial problems, and define new tasks that reflect how the work is actually done in practice.

• Benchmarks and domain depth: Design challenging insurance tasks and evaluation sets, and help build domain-specific skills and tools together with the research team.

• Calibration: Work with client researchers and specialists in adjacent fields to keep standards consistent, translating tacit insurance judgment into explicit, teachable criteria.

3. Core Qualifications

• Credentials: Either an actuarial credential (FSA, ASA, FCAS, or ACAS) or an active state insurance license in adjusting, underwriting, or broking, for example an all-lines adjuster license. Actuarial candidates are expected to hold a degree in actuarial science, mathematics, statistics, or a related quantitative field.

• Experience: 4+ years of substantive insurance experience at a carrier, reinsurer, broker, adjusting firm, or insurance regulator.

• Domain depth: Genuine specialization in at least one area, for example life and annuity, group life and disability, property and casualty, health, reinsurance, pricing and reserving, enterprise risk management, claims adjudication, or underwriting.

• Seniority: Clear progression to a senior level, for example Actuary, Senior Actuary, AVP, Director, Chief Actuary, Claims Manager, or Head of Underwriting, with real ownership of a book, a reserve, or a claims portfolio.

• AI fluency: Hands‑on working use of large language models in your professional work, and the judgment to tell a well‑reasoned answer from a plausible‑sounding wrong one.

• Availability: Able to commit reliably to 40 hours per week for an initial engagement of 6 months.

• Location: Living in the Bay Area, California, and able to work on-site with the client's team multiple days each week, when required. Candidates not currently based in the Bay Area must be willing to relocate there at their own cost. Relocation assistance is not provided.

• Excellent written communication, and the ability to give precise, well‑structured written feedback.

About Cincinnatus LLC

Cincinnatus LLC is an enterprise staffing company that partners with leading technology companies to source and employ highly skilled professionals for contingent and contract-based opportunities. Cincinnatus serves as the employer of record for these engagements, providing W-2 employment, payroll, benefits, and compliance, while placing employees directly within client teams to work on high-impact initiatives.

Roles hired through Cincinnatus are not project-based or freelance engagements. They are structured, role-based positions that typically involve part-time or full-time commitments, close collaboration with a client's internal teams, and integration into standard enterprise workflows.

Cincinnatus is a legal entity separate from Mercor. While opportunities may be discovered through Mercor's platform, employment, onboarding, payroll, and benefits for these roles are administered by Cincinnatus LLC.

Equal Employment Opportunity

Cincinnatus is proud to be an Equal Employment Opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or any other legally protected characteristic.

Cincinnatus is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout the job application process.