Chief of Staff to CEO

Chief of Staff to the CEO | AI-Native Startup | Seed Stage | San Mateo

Become the founder's right hand at one of the most exciting AI startups you've never heard of.

Ghost is partnering with a stealth, venture-backed AI startup that's rebuilding one of the largest—and least digitised—industries in the world.

Having recently raised $5M in Seed funding from top-tier investors, the company is using AI to automate complex commercial insurance workflows that have traditionally relied on manual expertise. It's a massive market where better technology doesn't just improve efficiency—it fundamentally changes how businesses understand, price and manage risk.

Led by experienced founders with deep expertise across AI, engineering and high-growth technology, the company is building for long-term impact with an ambitious vision to become the operating system for commercial insurance.

They're now looking for a Chief of Staff to become the CEO's closest operating partner and help build the company from the inside out.

Why join?

This isn't a traditional Chief of Staff role.

It's the highest-leverage generalist position in the company.

You'll work side-by-side with the CEO, owning the company's most important cross-functional initiatives across strategy, operations, finance, GTM and special projects.

If your long-term ambition is to become a founder, GM, COO or senior operator, few roles will accelerate your career faster.

Why you'll love it:

• Join a well-funded AI startup at the earliest stage of growth
• Work directly with experienced founders every day
• Own company-defining projects with real autonomy
• Clear pathway into executive leadership
• Meaningful early-stage equity
• Build in-person with a small, high-calibre team in San Mateo (Hybrid)
• Sustainable culture with Monday-Thursday in office and Fridays remote

What you'll own

You'll become the CEO's force multiplier, helping drive execution across every part of the business.

Responsibilities include:

• Driving company-wide priorities and strategic initiatives
• Owning business operations and cross-functional execution
• Building financial models, board materials and KPI reporting
• Leading GTM initiatives, partnerships and vendor management
• Improving internal systems and operational processes
• Helping build the future Office of the CEO as the company scales

We're looking for someone who has:

• 5-8 years in Strategy, Business Operations, Chief of Staff or startup leadership
• Experience combining consulting (ideally MBB) with operating experience in a high-growth technology company, or a proven track record building and scaling startups
• A history of taking ambiguous problems and driving them to measurable outcomes
• Exceptional analytical and communication skills
• An AI-native workflow, actively using AI to improve productivity and decision-making
• A builder's mindset with high ownership and low ego

Previous experience as a founder, founding team member or early-stage Chief of Staff is highly valued.

Location

San Mateo, California (full-time, in person)

Compensation

• Competitive salary
• Meaningful seed-stage equity
• Flexible cash/equity mix

If you're looking for a role where you'll learn more in two years than most do in five—and want a front-row seat to building a category-defining AI company—this is it. We'd love to hear from you. 👻