Chief of Staff

About the Role

Join a well-backed, AI-native consumer insurtech startup as Chief of Staff — a high-leverage generalist seat sitting directly next to the CEO. This is not a coordination role. You will be the closest operational extension of the CEO, touching fundraising, operations, GTM, analytics, partnerships, product strategy, and whatever the highest-priority problem is that week.

The company is an AI-powered consumer insurance broker operating at real scale — partnering with 40 of the largest US carriers, expanding nationally across all 50 states, and launching new product lines. Backed by seed-stage funding with top-tier angel investors, this is a rare opportunity to see the full architecture of building a company in real time.

What You'll Do

• Serve as the right hand to the CEO across every functional area of the business
• Own discrete high-priority projects end-to-end — solve them, systematize them, automate or hand them off
• Support and drive fundraising processes including investor communications and financial modeling
• Build and maintain operational infrastructure across GTM, hiring, and partnerships
• Conduct analytical deep-dives and synthesize insights to inform strategic decisions
• Draft high-quality written communications for investors, partners, and internal stakeholders
• Jump between contexts fluidly — one day might span recruiting, marketing optimization, carrier onboarding, and financial modeling

What We're Looking For

• 1–3 years of experience in consulting, investment banking, startups, or a similarly high-intensity environment (exceptional new grads considered)
• Strong analytical skills including spreadsheet proficiency, financial modeling, and data interpretation
• Excellent written communication — crisp, clear, and professional across investor emails, internal docs, and partner notes
• High agency and a bias toward action — you ship before it's perfect and move without waiting to be unblocked
• High integrity — this is a trust-based, right-hand role; integrity is foundational
• Based in San Francisco or genuinely committed to relocating (role is in-person 6 days/week including Saturdays)
• Comfort operating in ambiguity with a blank-canvas mindset and genuine ownership mentality

Nice to Have

• Background in fintech, insurtech, or a similarly regulated consumer-facing industry
• Experience at a top-tier strategy consulting firm or investment bank (e.g. McKinsey, JPMorgan)
• Prior exposure to early-stage startup environments

Compensation & Benefits

• Salary: $130,000 – $180,000 USD annually
• Equity participation in a fast-growing seed-stage company
• Visa sponsorship is not available for this role

Location

San Francisco, CA — on-site, 6 days per week (including Saturdays). Candidates must be local or committed to relocating.