Job Description
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Chief of Staff to the CEO | AI-Native Startup | Seed Stage | San Mateo
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Become the founder's right hand at one of the most exciting AI startups you've never heard of.
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Ghost is partnering with a stealth, venture-backed AI startup that's rebuilding one of the largest—and least digitised—industries in the world.
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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.
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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.
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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.
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Why join?
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This isn't a traditional Chief of Staff role.
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It's the highest-leverage generalist position in the company.
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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.
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If your long-term ambition is to become a founder, GM, COO or senior operator, few roles will accelerate your career faster.
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Why you'll love it:
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- 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
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What you'll own
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You'll become the CEO's force multiplier, helping drive execution across every part of the business.
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Responsibilities include:
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- 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
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We're looking for someone who has:
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- 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
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Previous experience as a founder, founding team member or early-stage Chief of Staff is highly valued.
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Location
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San Mateo, California (full-time, in person)
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Compensation
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- Competitive salary
- Meaningful seed-stage equity
- Flexible cash/equity mix
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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. 👻