Jobs at Cloud9 (Now Hiring) — 2 open

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.

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 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.