[Hiring] Chief of Staff @Sigmasight

Role Description

We’re looking for a Chief of Staff who can operate as an extension of the CEO — someone equally comfortable in the weeds of litigation analysis, financial modeling, and investor decks as they are driving cross-functional execution. You’ll serve as a strategic and operational right hand to the CEO of a fast-scaling AI startup that’s redefining how insurers and defense counsel respond to plaintiff AI tools in civil litigation. This role combines the analytical rigor of a litigator, the structure of an operator, and the communication finesse of a strategist.

What You’ll Do

• Strategic & Executive Support
  • Own preparation of executive briefs, board decks, investor updates, and external communications — transforming raw input from the CEO into polished, high-impact materials.
  • Create and maintain financial models, forecasts, and scenario plans in collaboration with the CEO and finance advisors.
  • Develop and deliver presentation decks (PowerPoint, Google Slides) for investor meetings, client demos, and internal strategic reviews.
  • Translate complex legal/technical topics into clear, compelling narratives for multiple audiences (insurers, defense firms, investors).
• Litigation Subject-Matter Contribution / Legal Ops Exposure
  • Leverage your litigation background to contribute meaningfully to product content — e.g., AI-generated Offer Packages, negotiation frameworks, and defensibility arguments.
  • Gain firsthand experience reviewing, editing, and validating LLM-generated case analyses to build a deep understanding of our workflows, quality standards, product dynamics and how Legal Ops functions.
  • Engage directly with clients (insurance carriers, defense counsel) early on to understand their expectations, feedback loops, and pain points.
• Operational Execution
  • Drive cross-functional alignment between Product, Data, and Client Success — ensuring the CEO’s priorities translate into execution.
  • Track key milestones across fundraising, client pilots, and product sprints; maintain accountability and momentum.
  • Manage and refine company-wide processes (OKRs, leadership cadence, communication rhythms).
• All-Purpose Leadership Extension
  • Step into the CEO’s shoes when needed — running meetings, making tactical decisions, or representing the company externally.
  • Handle special projects spanning finance, operations, legal, and partnerships.
  • Identify and fill execution gaps across the business — from investor research to client onboarding materials.
• Organizational Infrastructure & Administrative Leadership
  • Build and oversee the foundational operations of the company — including recruiting, onboarding, insurance, and vendor administration.
  • Systematize and streamline the processes founders typically manage early on, creating structure that scales.
  • Coordinate with external partners (legal, accounting, insurance, HR) to ensure the company remains compliant and operationally sound.
  • Act as a leverage point for the CEO, taking ownership of essential administrative and people operations so leadership can stay focused on growth and product.

Qualifications

• JD or equivalent litigation experience strongly preferred.
• 5–10 years total professional experience (law + startup/ops/consulting).
• Exceptional analytical, writing, and presentation skills.
• Experience working directly with C-suite executives or founders.
• Proficiency in creating presentations, spreadsheets and briefs.
• Prior experience in AI, data-driven, or high-growth LegalTech startups a major plus.

Why This Role Matters

This is not a traditional Chief of Staff role — it’s a founder-adjacent position for someone who wants to help lead and scale an AI company tackling one of the most consequential shifts in litigation and insurance in decades. You’ll be the CEO’s closest strategic ally, shaping how technology reshapes legal negotiation and claims resolution.