Careers at SigmaSight

Help Us Redefine Insurance Defense

SigmaSight is reshaping the $200B settlement market with AI-powered solutions that put negotiation science back in the hands of insurers. Plaintiffs are already using AI to inflate claims and control narratives—our mission is to level the playing field. We’re not building just another tool. We’re building the operating system for insurer negotiation: Analyzer for risk clarity, Synthesizer for AI-powered advocacy, and Negotiator for valuation discipline. Together, these solutions give defense teams what they need most: data, leverage, and confidence.

Current Openings

Analytics

Why Work With Us

Exceptional Market Access

Unmatched access to C-level buyers at leading carriers

A massive pipeline built on deep personal relationships

30+ customer feedback sessions and 4 industry surveys already shaping our roadmap

A growing reputation as the thought leader in AI powered claims negotiations

Technical Frontier

Tackling hard problems in modeling litigation outcomes (patent pending)

Structuring and learning from messy, high-volume datasets like verdicts and court dockets

Applying game theory and reinforcement learning to litigation negotiations

Operating simultaneously as a data company (aggregation, pipelines), AI
company (LLMs/ML), and SaaS platform connecting insurers and defense
counsel

Early-Stage Impact

At SigmaSight you’ll be more than a role—you’ll be part of a team shaping a new category. Every function, from engineering to sales to product and operations, has a direct hand in building the foundation of a VC-backed company at a pivotal moment.