Litigation Analyst / Technologist

Location Remote (Southern California preferred) Compensation Commensurate with experience; includes stock options About SigmaSight We are a VC-backed startup building negotiation intelligence for insurance carriers handling litigated claims. While 98% of these claims resolve through settlement, the process remains deeply unstructured. We believe insurers can do better—with evidence-based tools, jurisdiction-specific logic, and AI that extracts signal from case noise. Our platform combines structured prompts, litigation analytics, and a proprietary math engine to quantify settlement posture. We help litigation managers and defense counsel negotiate with rigor—not just instinct. The role We’re looking for a hybrid thinker: a litigation-savvy professional with analytical and technical skills who wants to help shape how negotiation is practiced at scale. This role sits at the intersection of legal subject matter expertise, structured data modeling, and applied prompt engineering. You’ll work cross-functionally with our CEO, CPO, engineers, and litigation advisors to define and deploy the intelligence that powers our platform. Expect a mix of research, prompt design, workflow testing, and data oversight—all aimed at delivering defensible, data-driven negotiation recommendations. Responsibilities Court Docket Data & Verdict Analytics Our platform relies on normalized court data and verdict records to benchmark risk and model case outcomes. You will: Become an expert in state court data systems, including docket structure, coverage gaps, and acquisition methods (scraping, APIs, parsing)Evaluate verdict datasets for completeness, consistency, and modeling valueOversee pipelines that ingest and standardize this data for platform useDefine new analytics (e.g., judge-level motion trends, venue-based timelines)Partner with engineers to productize and QA these analyticsDocument usage guidance to help clients apply the data meaningfully Negotiation Math Engine At the heart of our product is a structured model that quantifies negotiation leverage. You will: Map tort doctrines across jurisdictions (e.g., comparative fault, caps, lien rules)Develop logic for economic levers like expected value, BATNA, and offsetsDefine parameterized legal functions that engineers can implement at scaleCollaborate on rule-driven recommendations (e.g., liability-adjusted offers)Ensure all models are mathematically sound and legally defensibleContribute to evolving prototypes for AI-generated negotiation guidance Subject Matter Expert Prompt EngineeringOur platform extracts leverage from unstructured case files using structured LLM prompts. You will:Design and refine prompts that extract facts, issues, and argument patternsTest prompt sets on real case documents—e.g., depositions, medicals, police reportsCompare LLM output against expert expectations and iterate for accuracyWork with engineers to manage schema, tagging, and versioning across promptsHelp maintain retrieval and output quality in a RAG-based pipeline What You’ll Do Day-to-Day Review litigation documents to test prompts, evaluate data quality, and ground model assumptionsRun structured prompt sets on real case files and compare output to expert expectationsAnalyze docket and verdict data coverage across jurisdictions and diagnose quality gapsDefine requirements for new litigation analytics and economic modeling logicWork with engineers to structure tagging systems, legal functions, and API outputsIterate on core platform logic—whether prompt design, fault allocation, or jurisdictional rulesWrite clear business requirements and usage documentation for legal and technical audiencesParticipate in QA sessions to validate analytics, math engine calculations, and prompt reliabilityCollaborate daily with our CEO, CPO, engineers, and legal experts to guide feature development and troubleshoot edge cases Qualifications Experience & Education 3+ years in insurance defense, personal injury, and/or tort litigation (attorney, paralegal, claims analyst, or litigation manager)Strong analytical skills with fluency in structured data, logic, and iterationBA/BS required; JD, paralegal certification, or technical degree preferredFamiliarity with LLMs (e.g., ChatGPT, Claude) and prompt design a strong plus Skills & Traits Comfortable translating legal nuance into rules and logicClear communicator across legal, technical, and product teamsStrong pattern recognition and attention to detailSelf-starter who thrives in fast-moving, unstructured environmentsConfident challenging assumptions with evidence and analysis This role is ideal for someone who knows how litigation really works—and is excited to shape how negotiation should work. If you’re a structured thinker, a fast learner, and a builder at heart, we’d love to talk. Benefits Equity in a high-growth startup: Get in early and share in the success as we scale.Fully Remote Work: Work from anywhere in the US and enjoy a flexible work environment.Collaborative, ambitious team: Work with a group of highly motivated, talented individuals who are passionate about building something great.Career Growth: Join a fast-growing company with opportunities for advancement and personal development.Dynamic, exciting culture: Be a part of a company that thrives on creativity, innovation, and taking risks. If you’re an experienced engineering leader who thrives in a fast-paced startup environment and wants to help shape the future of an exciting company, we’d love to hear from you! How To Apply Please reach out to careers@sigmasight.ai with your resume to apply. Equal Opportunity Employer SigmaSight is an equal opportunity employer and values diversity in the workplace. We welcome applications from all qualified candidates, regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or age. Get started with SigmaSight Learn more about how SigmaSight can change the way you do business. Book a demo Read More