About SigmaSight
SigmaSight is the insurer-side answer to EvenUp Law—the unicorn reshaping settlements plaintiff-side. We’re building an AI-powered operating system for insurer negotiation, transforming how carriers evaluate, value, and resolve claims.
Our flagship product, AI-powered Offer Packages, helps claim handlers and defense counsel move from buried to prepared with a mouse-click. Early pilots with national carriers are already delivering 10x–50x ROI, proving the power of data-driven advocacy in a $200B market.
The Role
SigmaSight is hiring a Head of Legal Operations to lead client delivery and quality across our growing insurer partnerships.
You’ll own the full lifecycle of Offer Package delivery—reviewing AI-generated analyses, refining negotiation points, and engaging directly with claim professionals and defense counsel to ensure every package meets the highest standard of accuracy and persuasiveness.
This is a foundational leadership role. You’ll set the bar for quality, design the processes and playbooks that scale our LegalOps team, and serve as the trusted voice of SigmaSight in conversations with insurers and defense firms.
If you’re an experienced litigation attorney ready to combine legal expertise, negotiation skill, and technology curiosity, this is your opportunity to help define the future of insurance defense.
What You’ll Do
Lead the delivery and review of AI-generated Offer Packages for accuracy, tone, and strategic quality.
Partner directly with claim professionals and defense attorneys to align Offer Packages with case strategy and negotiation goals.
Represent SigmaSight in client discussions—confidently holding your own with defense counsel while earning their trust.
Develop QA standards, review checklists, and training systems to scale delivery quality.
Collaborate with Product and Engineering teams to improve automation accuracy through real-world feedback.
Build and manage a high-performing LegalOps team as the function grows.
Partner with the CEO and leadership team to shape our client delivery model and operational strategy.
Who You Are
Licensed attorney with 3+ years in insurance defense or injury tort litigation (auto, GL, or premises)
Litigation manager or claims professional with 5+ years handling P&C liability claims and litigation.
Confident communicator—able to interact with insurer leadership and defense counsel diplomatically and persuasively.
Comfortable leveraging AI and structured tools to enhance analysis and writing.
Excellent writer with strong analytical judgment and attention to detail.
Process-minded operator who thrives in a fast-moving startup environment.
Collaborative, pragmatic, and motivated by building something new that creates measurable industry impact.
Why Join Us
Be the founding LegalOps leader shaping how insurers use AI in settlement negotiations.
Work directly with insurers and defense counsel on real cases—no hypothetical projects.
Combine your litigation expertise with technology that multiplies your impact.
Build and lead the LegalOps team as we scale nationwide.
Competitive compensation, meaningful equity, and a mission-driven culture.
Compensation & Benefits
Stage-competitive base salary, commensurate with experience.
Equity participation in a high-growth LegalTech startup.
Primarily remote, with periodic in-person collaboration.
Ready to redefine the future of insurance defense?
Apply now or reach out directly to learn how you can help us build the next generation of insurer-side negotiation.
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