Chief of Staff

We are looking for a Chief of Staff with 5-6+ years of experience to serve as the CEO's operating partner and force multiplier at a seed-stage, AI-native commercial insurance startup. This is the highest-leverage generalist seat in the company — you'll own the ambiguous, cross-functional, mission-critical work that drives execution and keeps the company moving in one direction, with a clear path to growing into a GM, functional lead, or COO.

What will you be doing?

- Own day-to-day operations, partner follow-ups, and pilot execution to free up the CEO and CTO for strategic work

- Drive prioritization of initiatives, KPI tracking, and communication across the team

- Run and manage go-to-market efforts, partnership diligence, and vendor onboarding end-to-end

- Build the financial model, board materials, and analytical backbone behind major business decisions

- Define and potentially build out the "Office of the CEO" — hiring a team of special projects associates if justified

Key Requirements

- 5-6+ years of experience, ideally combining top-tier management consulting (MBB preferred) with hands-on operational experience in a fast-growth tech environment

- Demonstrated high agency — can take vague problems, define the path, and drive to outcomes with minimal direction

- Sharp analytical problem solver who can break down complex issues, prioritize, and execute systematically

- Must be based in the Bay Area and work in-person daily — this is a build-side-by-side role

- Startup or zero-to-one experience where they owned initiatives end-to-end (not just advised)