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Jack and Jill AI
San Francisco,CA

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Jack and Jill AI Logo
Jack and Jill AI
San Francisco,CA

Description

Chief of Staff

As Chief of Staff, you will be the operational backbone for a company redefining AI autonomy. Working directly with the founder, you will design systems that replace low-leverage work with agentic workflows, manage strategic BizOps, and lead the company's exit from stealth. You are an AI-native operator who defaults to automation over headcount.

Salary: $140k $190k + 0.5% 1.0% Equity

Location: San Francisco, USA

Why this role is remarkable:

  • Direct partnership with the founder at a $5.1M seed-stage startup backed by top-tier investors including Matt Schlicht, Draper, and Liquid2.
  • You will be at the cutting edge of the agentic revolution, building systems that allow AI agents to run entire business functions autonomously.
  • High-impact leadership role with 0.5% 1.0% equity, offering a significant stake in a company exiting stealth with high market momentum.

What you will do:

  • Audit internal operations to replace manual human tasks with automated, agentic workflows using tools like Claude Code and OpenClaw.
  • Translate the CEO's product vision into actionable strategy, managing fundraising materials, competitive intelligence, and partnership conversations.
  • Build GTM infrastructure and communication systems to amplify the company's vision and attract world-class talent and customers.

The ideal candidate:

  • 4-7+ years of experience in consulting, growth-stage startups, or operations with a track record at Seed to Series B venture-backed companies.
  • Deeply AI-native skills with hands-on experience building real applications via Claude Code and running personal OpenClaw instances.
  • High-agency system thinker who prioritizes building scalable infrastructure and automation over simply adding human headcount to solve problems.

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