Chief of Staff

We are looking for a Chief of Staff with 9-10+ years of experience to serve as a strategic right-hand to the CEO at a $300M+ run-rate AI-native insurance company that is rapidly expanding into multiple new businesses. You'll take ownership of the most critical cross-functional problems, drive new growth initiatives, and position yourself to eventually own a P&L.

What will you be doing?

• Owning and driving the most critical cross-functional projects across multiple business lines — identifying bottlenecks, solving ambiguous problems, and delivering outcomes
• Serving as a thought partner to the CEO on new growth opportunities, potentially quarterbacking and launching new businesses or verticals
• Designing and scaling operating rhythms across the company — business reviews, data/insights cadences, and board storytelling
• Working directly with business unit CEOs and leaders to spot patterns, remove blockers, and accelerate growth
• Traveling 10-30% of the time to other offices and key meetings alongside the CEO

Key Requirements

• 9-10+ years of experience with a combination of a strong foundation (MBB consulting, banking, or similar demanding environment) AND operating experience at a high-growth, venture-backed startup (Series B-D stage)
• Demonstrated fast progression and high ownership — not a career coordinator or project manager
• Self-directed operator who thrives with limited direction and can work across senior stakeholders with executive presence
• AI-native mindset — actively builds tools and automations using AI, not just prompting
• Must be based in or willing to relocate to San Francisco (5 days in-office)