Chief of Staff (AI)

TL;DR

Chief of Staff (AI): Driving strategic initiatives and scaling business operations for an AI-native commercial insurance platform with an accent on operational efficiency and cross-functional leadership. Focus on solving critical bottlenecks, managing board relations, and executing board-level strategies.

Location: On-site in San Francisco, CA

Salary: $180,000 – $300,000

Company

An AI-native commercial insurance company using proprietary IoT data and predictive models to reimagine the insurance value chain.

What you will do

• Drive clarity around critical decisions and ensure follow-through until outcomes are achieved.
• Own high-priority projects and cross-functional initiatives without a predefined home.
• Scale company operating rhythms, including business reviews, off-sites, and planning.
• Proactively identify and solve operational bottlenecks across the organization.
• Manage board and investor preparation and shape external company storytelling.

Requirements

• 5+ years of experience in high-ownership roles such as consulting, finance, product, or business operations.
• Must be based in San Francisco, CA for on-site work.
• Strategic and analytical thinker with strong written and verbal communication skills.
• Bias-to-action with an AI-native mindset and ability to operate in ambiguous environments.
• High judgment and maturity when handling sensitive, high-stakes information.
• Executive presence and the ability to influence experienced leaders.

Nice to have

• Previous founding experience.

Culture & Benefits

• Competitive salary and equity for all full-time employees.
• 100% employer-paid medical, dental, and vision insurance.
• 401k plan with up to 4% company match.
• Unlimited PTO.
• Wellness reimbursement and work-from-home stipend.