Chief of Staff
San Mateo, California
FULL_TIME | USD 160000.00 - 210000.00 YEAR

About the Role

Partner with the CEO at a seed-stage, AI-native commercial insurance startup, taking ownership of high-priority work across operations, go-to-market, and company planning. This is a hands-on role for an experienced operator who can turn ambiguous challenges into measurable progress, with potential to grow into a general management, functional leadership, or COO position.

What You'll Do

  • Manage day-to-day operations, partner follow-ups, and pilot execution to keep priorities moving.

  • Drive initiative prioritization, KPI tracking, and clear communication across the team.

  • Lead go-to-market efforts, partnership diligence, and vendor onboarding from start to finish.

  • Build financial models, board materials, and analysis to support major business decisions.

  • Shape the Office of the CEO and assess whether a special projects team is needed.

What We're Looking For

  • At least 5 years of experience in strategy, operations, or BizOps, ideally combining top-tier consulting with hands-on work at a high-growth technology company.

  • Experience owning and scaling go-to-market, sales, or business development operations at an early-stage B2B startup.

  • A track record of independently leading ambiguous projects through execution and delivering measurable outcomes.

  • Strong analytical skills and experience with financial modeling, Google Sheets, SQL, and AI or LLM tools.

  • A bachelor's degree from a highly selective university; an MBA from a leading program is a plus.

  • Comfort working in fast-moving environments and a genuine interest in seed-stage equity upside.

Compensation & Benefits

Base salary: $160,000 to $210,000 annually. Visa sponsorship is not available.

Location

Listed as remote within the United States, with San Mateo, California as the primary location. The role description also specifies daily in-person work in the Bay Area.