Chief of Staff to the CEO (AI-Native Insurance)

A large, fast-scaling insurance company built around AI is looking for a strategic partner to its chief executive. The company is moving into several new lines of business, and the person hired will take on its toughest cross-functional problems with an eye toward eventually running a P&L.

Mandate

Lead the most important projects that cut across business lines, finding bottlenecks and resolving unclear problems until results land

Act as sounding board for the CEO on growth bets, possibly spinning up new ventures or lines of service

Build and scale the company’s operating cadence, including business reviews, data and insight routines and board communication

Work side by side with unit heads to spot recurring patterns, clear obstacles and speed up growth

Accompany the CEO on trips to regional offices and important meetings, roughly ten to thirty percent of the time

Experience that fits

Nine to ten or more years combining a demanding foundation (management consulting, finance or a similarly demanding field) with hands-on operating time at a venture-backed startup in the Series B to D range

A pattern of quick promotion and high ownership, rather than a coordinator or administrative career

Self-directed working style and the executive presence to engage senior stakeholders

Strong analytical and financial-modeling ability

An AI-native habit of building tools and automations, beyond simply prompting

Experience building something new inside a scaling startup is a strong signal

On-site in the San Francisco Bay Area, five days a week. Visa transfers considered.