Chief of Staff (AI & Operations)

Cloud9 is an AI-native luxury short-term rental operator. We turn long-term luxury rentals into exceptional short-term stays, delivering hotel-grade quality to guests while helping property managers unlock the top-line potential of their buildings. We run 60+ units across 13 Class-A residential buildings in Chicago, and we're expanding city by city across the U.S. We exist to reinvent hospitality with AI-driven execution.

How we work: a small, AI-native team that builds 4:1 leverage. You work alongside Claude every day; AI is a co-pilot, not a buzzword. The team is distributed, some in Chicago, some in Latam. We move fast, decide fast, and cut politics. We don't hire to fill seats. We hire to pull levers that move numbers. Outcomes beat effort beats intentions.

We run on C.L.O.U.D.9, our culture operating system:

• C · Customer Obsession. If they're not raving, we missed it.

• L · Leadership Through Ownership. No passengers, only drivers.

• O · Operational Excellence. How we do one thing is how we do everything.

• U · Urgency With Intelligence. Act now, iterate later.

• D · Do the Right Thing. Character over convenience.

• 9 · The 9x Mindset. 10% better is safe; 9x better is unforgettable.

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.

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.

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.

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.

• 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.

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.

• This is a 90-day end-or-extend role. If you don't hit the milestones, the relationship ends cleanly. There are no quiet extensions.

• The first 90 days are 9-to-5 plus 5-to-9. The 9-to-5 is execution. The 5-to-9 is learning so you can execute better the next day. After 90 days, the systems you build buy hours back. Before then, expect intensity.

• Some weekends and evenings on-call during the first 90 days.

• Cloud9 is profitable but mid-pivot from arbitrage to RevShare. Revenue volatility exists month-over-month.

• The team is small (target: 12 people total). You will be one of them.

• Remote-first. You will be remote from a remote team.

• This role does not have a finished scorecard yet. You will help write yours at Day 60.

• The CEO is a coach, not a friend, on a bad day.

• Make small decisions without looping in the CEO. "What would you like me to do?" is not the question. "Here are two options, I recommend A, here's why" is the question.

• Provide options for resolution before escalating an issue.

• Use every available resource — AI tools, peers, documentation, Maru, Pablo, Althea — before reaching out to the CEO.

• Slack response time during business hours: 2 minutes for the CEO, 30 minutes for the team.

• You are looking for a traditional Executive Assistant role.

• You need clear instructions to start moving.

• You can't disagree with someone in authority. This is the single most common reason candidates have failed in this role.

• You haven't actually built an AI workflow with triggers, branches, fallbacks, and a metric.

• You're uncomfortable in environments where the scorecard isn't finished and you have to help write it.

• You will write your own job description at Day 60. If that scares you, this is not the seat.

If you want to own a number, move fast, and build with AI instead of around it, this is the place. Small team, real leverage, high standards, and the people who build the systems get to run them as we scale city by city. If you want a comfortable seat where effort counts more than outcomes, we are not it.

Cloud9 does not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.