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Chief of Staff (AI & Operations) at Cloud9 | AINative.careers

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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 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.

DECISION-MAKING BAR

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.

WHAT DISQUALIFIES YOU

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.

WHY JOIN US?

Cloud9 is more than a company; it's a community of dreamers, doers, and problem-solvers who share a common goal: delivering excellence in every interaction. If you're passionate about innovation, value teamwork, and want to grow in a fast-paced environment, Cloud9 is the place for you. Together, we're not just building better stays—we're building a better way forward for the hospitality industry.

Our Core Values

Meritocracy – Performance is public, measurable, and rewarded.
Execution – Doers win. Deliver fast, adjust faster.
Radical Feedback – Real-time corrections, no politics.
Championship Team – Only A-players stay. Mediocrity is cut.

Cloud9 does not discriminate based upon 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.