Chief of Staff (AI & Operations)

Cloud9

🌍 100% Remote Full-time

Job Description

Values (Non-Negotiable)

  • Sincere Candor. You can disagree with the CEO directly, in the room, without softening the message. If you can't, you can't do this job.
  • Unimpeachable Character. What you do when no one is watching matches what you do when everyone is. Trust without discretion is impossible.
  • Competitive Greatness. You bet on yourself. You want hard problems. You'd rather argue for variable comp tied to outcomes than for a higher base.

The Job — Year 1

You will be an Architect. Every recurring workflow on the CEO's calendar gets pulled apart, mapped, and rebuilt as an AI agent or a human‑in‑the‑loop SOP. Trigger, branches, fallbacks, metric. You ship one production workflow per week. You teach Claude and other LLMs to do pieces of the CEO's job until 80% of his current operator‑tier work is automated or owned by you.

You will be an Operator. Calendar (1 month locked, weekly re‑prioritized)...