Chief of Staff

ABOUT US Our mission to revolutionize the hospitality industry. We exist to reinvent hospitality with AI-driven execution. By transforming long-term luxury rentals into exceptional short-term experiences, we deliver unparalleled quality and service to our guests. At the same time, we empower property managers to unlock the full potential of their properties, maximizing their buildings top line. Our vision? To become the go-to solution for property managers across the U.S. We're expanding city by city, bringing our innovative approach and passion for excellence to new markets and communities. What makes Cloud9 truly unique isn’t just our commitment to service—it's our people. We believe in the power of teamwork to drive success. Whether you're a guest, a partner, or part of our team, you'll find collaboration, trust, and shared purpose at the heart of everything we do. We don’t hire to fill seats. We hire to pull levers that move numbers. Outcomes > effort > intentions. Our core values are speed, meritocracy, accountability, and execution. THE PAIN Cloud9 hit $8M in revenue last year at a 24% margin, fully bootstrapped, and reinvested every dollar of profit ($1.8M) back into the team. We doubled revenue while halving headcount. The next leg of growth is automation — building the AI-native operating system that takes Cloud9 from a hospitality company to an AI company that happens to be in hospitality. The CEO is the bottleneck. He spends 15+ hours a week on inbox, calendar, and triage that should be running on agents. This role's job is to remove him from that work in 90 days by architecting AI agents that do it, then take ownership of the operating system from there. This is not an Executive Assistant role. It is a Chief of Staff role with an AI architect's mandate. VALUES (NON-NEGOTIABLE) You will work in close proximity to the CEO every day. Values alignment is the single hardest filter for this role. - 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). Inbox (Inbox Zero discipline, response within 2 minutes during business hours, judgment on what reaches the CEO). ClickUp. Tana. Slack. Nothing falls through the cracks. You provide options for resolution before escalating. You use every available resource — peers, AI tools, documentation — before reaching out to the CEO. You will be an Owner. Ad hoc projects come directly from the CEO and end on your desk. You move idea → execution faster than anyone else on the team. You fill gaps. You take the calls when the team needs a decision and the CEO is unreachable. You write your own scorecard at Day 60 because by then you'll know the role better than anyone else. 30 / 60 / 90 MILESTONES Day 30: - Shadowed the CEO for ≥40 hours of inbox, calendar, and meeting work - Owns one recurring workflow end-to-end (your choice, approved by CEO) - Shipped your first AI-automated workflow to production - Submitted a written "what I observed" memo Day 60: - ≥4 production workflows shipped (1/week pace established from Day 30) - One Claude-native SOP authored by you, in use by the team - First piece of the CEO's calendar permanently delegated to you - Weekly 1:1 cadence — you run the agenda - Drafted your own Day 90 scorecard Day 90: - ≥8 production workflows shipped - ≥80% reduction in CEO time on the workflows you've automated, verified - Renewal-or-end decision delivered. No quiet extensions. TWO KPIS - Action: 1 production workflow shipped per week (52/year). Days 1-30 exempt for ramp. - Guardrail: ≥80% reduction in CEO time on the automated workflow, verified 4 weeks post-ship. Workflows that don't hit 80% reduction don't count toward the action KPI. You cannot game the action by shipping trash. You cannot perfect the guardrail by shipping nothing. The pair is the point. RESULTS BAR You succeed when: 1. The CEO is removed from operator-tier work — measurable in hours saved per week. 2. The operating system runs smoothly — calendar, inbox, ClickUp, Slack, all clean. No balls dropped. 3. Cloud9's AI architecture compounds — every workflow you ship becomes a reusable pattern for the next one. THE MESS (READ CAREFULLY BEFORE APPLYING) - This is a…