Chief of Staff

About the Role This is a high-leverage generalist role at an early-stage AI-native insurtech startup that is reimagining how insurance policies are quoted, bound, and serviced — using autonomous AI agents operating across the full policy lifecycle. You'll sit directly beside the CEO as the closest extension of his leadership, touching everything from fundraising and operations to GTM strategy, analytics, and product thinking. The shape of this role changes week to week by design — that's the point. This position is on-site in San Francisco, 6 days per week including Saturday. No visa sponsorship is available; candidates must be legally authorized to work in the US. What You'll Do

• Support fundraising end-to-end: investor research, deck iterations, data room management, and follow-up coordination
• Own operational projects from start to finish — vendor evaluation, hiring pipeline buildout, and process design
• Analyze data to surface insights and inform decisions across lead conversion, unit economics, and carrier performance
• Support GTM strategy, lead generation, partnership outreach, and carrier relationship management
• Draft investor updates, internal documentation, and external communications independently
• Build out early-stage projects yourself first, then systematize, automate, or hand off to future hires
• Jump into whatever is most urgent that week — priorities shift fast and that's by design

• 1–3 years of experience in consulting, investment banking, startups, or similarly high-intensity environments (strong new grads considered)
• Strong analytical ability: comfortable in spreadsheets, able to build financial models, and find signal in data without direction
• Excellent written communication: can draft investor emails, internal briefs, and external partner notes without oversight
• High agency and bias toward action — ships before it's perfect, moves without waiting to be unblocked
• High integrity above all else — this is a right-hand role where trust is the foundation
• Based in San Francisco or genuinely willing to relocate; in-person 6 days/week including Saturday is non-negotiable
• Legally authorized to work in the US without visa sponsorship
• Proficiency with Google Workspace, Excel/financial modeling, and CRM/analytics tools
• Comfortable with cross-functional collaboration across GTM, operations, analytics, and executive leadership

• Prior experience at a startup, fintech, or insurtech company
• Exposure to insurance, financial services, or AI-native products
• Experience managing multi-stakeholder projects or external partnerships
• Experience hiring and scaling sales or GTM teams
• Background from top-tier consulting firms or elite academic institutions

• Salary: $130,000 – $180,000 USD annually
• Early-stage equity opportunity in a high-growth insurtech company

• On-site: San Francisco, CA — 6 days per week including Saturday
• No visa sponsorship available; must be authorized to work in the US