Chief of Staff

I'm hiring for a Chief of Staff role at a Series A AI startup in San Mateo. The company has raised $41M, has a team of roughly 55 people across engineering, sales, and go-to-market, and has had zero engineering attrition since founding. They're now investing heavily in enterprise sales and scaling their go-to-market motion.

This is a high-ownership generalist role. You'll work directly with the VP of Product and Post-Sales, effectively operating as an extension of her so she can move at 10x speed. There's no playbook. You'll be figuring things out and building process as you go, and the scope of the role will grow as the company scales.

What you'll own

• Recruiting coordination end to end. You'll take first-round candidate calls, manage the interview pipeline, and build a repeatable hiring process across teams.
• Post-sales process building, including QBR frameworks, upsell tracking, G2 review programs, and customer success documentation.
• Executive calendar management. Protecting time, resolving conflicts, and prioritizing across internal and external commitments.
• KPI visibility across sales, product, and bugs, through internal dashboards and tracking systems you build and maintain.
• Board decks, all-hands presentations, and other high-stakes internal communications.
• Outbound prospecting experiments on LinkedIn and other channels, including content and testing what drives pipeline.

What we're looking for

• 1 to 4 years of experience in a fast-moving startup, operations, generalist, or customer-facing role.
• Strong interpersonal presence. You're comfortable holding conversations with candidates, customers, and prospects, and can do it confidently.
• High drive and hustle. You're energized by ambiguity, not paralyzed by it.
• Based in the San Francisco Bay Area or willing to relocate. No visa sponsorship available.
• Willing to work in-person at the San Mateo office five days a week, with occasional flexibility for remote days.

Nice to have

• Prior experience at a startup in an operations, chief of staff, or founder's associate capacity.
• Background in investment banking, consulting, or product management.
• Degree from a competitive academic program.
• Experience with outbound prospecting, LinkedIn content, or customer-facing sales workflows.

Compensation and benefits

$110,000 to $150,000 base, plus competitive equity. Company-covered medical insurance (individual). FSA available. 401k, employee-contributed. Lunch and dinner in office.

Who this isn't for

If you want a defined scope, a clear playbook, or a role that stays the same size over time, this probably isn't the right fit. This role is built for someone who wants ownership and is comfortable with the job changing shape as the company grows.