ABOUT CLOUD9
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.
WHAT THIS IS
Right now the CEO is in the middle of every performance conversation. He sets the goals, chases the follow-through, decides who's behind. The team runs on his work ethic, not on a system. We need someone to own the system so he can step out of the middle.
You'll own the team's weekly performance machine: a real scorecard for every seat, a weekly cadence that actually moves numbers, and accountability that runs on data instead of feel. ~12 people today, scaling.
This is a performance operator role, not an HR role. You are not here to run engagement surveys, hang values posters, or keep a tidy calendar of meetings that change nothing. You're here to make the team hit its own targets.
You work with AI as your multiplier. AI drafts scorecards, builds the dashboards, summarizes the performance data, flags who's slipping. You own the judgment, the hard conversation, and the number.
WHAT YOU'LL OWN
The number. Team goal-attainment: the share of the team hitting their own quarterly scorecard targets. That's your line.
Every seat's scorecard. A real 4-R scorecard for each role: clear goals, clear outcomes, tied to results, not activity.
The weekly cadence. 1:1s, team tacticals, the review rhythm. It runs every week. No dead weeks. No canceled reviews.
Accountability. Data-backed, not vibes. You run the hard conversation when someone is behind, and you run it to an outcome.
The Management OS. You build it from zero, then hand the cadence to the leads so they run their own. The goal is to make yourself, and the CEO, unnecessary to the day-to-day.
WHAT SUCCESS LOOKS LIKE
Day 30. Every seat has a drafted scorecard. The weekly cadence is mapped. Baseline team goal-attainment measured.
Day 90. 100% scorecard coverage live. Cadence running at 95%+ integrity. First underperformer case run to an outcome. The goal-attainment target is set.
Month 12. [Team goal-attainment at target. Retention above 90%.] The leads run their own cadence without you in the room. The CEO is out of the decision-middle.
WHAT YOU'LL NEED
- A scorecard or KPI/OKR system you personally built. Bring it. We want to see a fuzzy role turned into an owned number.
- A weekly performance cadence you ran that moved a team metric. Not meetings you attended, a rhythm you owned that changed a result.
- At least one real underperformer you performance-managed to an outcome, up or out. You did the conversation. You saw it through.
- Accountability that runs on data and dashboards, not feel.
- Heavy AI tool use. Claude or equivalent in your daily flow to draft scorecards, build dashboards, and surface at-risk signals.
- The ability to get adoption from people who don't report to you. You won't have hire/fire authority here. Influence is the lever.
- Fluent English, written and spoken.
WHO THIS IS NOT FOR
- HR administrators who run surveys and events but never moved a performance number.
- People who need positional authority to hold a line.
- Anyone who avoids the hard conversation, or who protects an underperformer to keep the peace.
- People who run on relationships and "feel" instead of data.
- People who think AI is beneath them, or who hide that they use it.
- People who want to insert themselves as the new bottleneck instead of removing one.
WHAT'S REAL ABOUT CLOUD9 RIGHT NOW
- There is no Management OS yet. You're not inheriting a system, you're building one from zero.
- The CEO is currently the bottleneck, on purpose and by accident. Your job is to take that off him, which means he has to actually let go, and you have to earn that.
- You have no hire/fire authority. People decisions stay with the CEO and the leads. You lead by system design and influence.
- The team is ~12 and scaling fast. The OS has to survive growth.
- You work alongside Claude. AI is the production multiplier, not a buzzword.
- Distributed team. Some in Chicago. Some in Latam.
- Decisions move at speed. Cadence that slips gets noticed fast.
WHY CLOUD9
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.