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Jobs · OTHR · Illinois

Head of Guest Experience

Cloud9 · Chicago, IL · 5 days ago
HybridOTHRFull-time

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 operate 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. Our core values are:

  • 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.

What this is

Cloud9 runs 60+ luxury units across 13 buildings, scaling past 100. Guests expect five-star experiences, but currently, guest experience is managed by the CEO, running it at partial capacity between forty other fires. Response is slow, missed calls fall through, and the same problems get re-solved every week. There is no SLA, no QA, and no dashboard.

We are looking for someone to own guest experience and never hand it back. You will build the guest-experience function from zero, including:

  • The standard: what five-star response looks like at Cloud9, defined and encoded, not left to whoever is on shift.
  • The numbers: median first response under 5 minutes, 100% of missed calls called back inside 15 minutes.
  • The systems: SLAs, escalation trees, QA scorecard.
  • The team: hire to your bar, coach on a cadence, and let people go when they don't hold the line.
  • The margin: protect refund and comp dollars, ensuring speed and quality don't come at the cost of margin.
  • The AI stack: build with LLMs, KB, automated responses, triage, and alerts, owning what ships.

What You'll Own

Day 30: Instrumentation live. The current mess is measured, not guessed at: response times, callback rate, escalations, refund dollars all have a baseline.

Day 90: SLAs defined and tracking live. Missed-call callback at 100%. Escalations to the CEO near zero. Guest experience is off the CEO's desk.

Day 180: QA scorecard running. Weekly coaching cadence live. First hire made to your bar.

Month 12: Full team in place. Response times held under SLA. Review-score floor hit. Refund dollars inside guardrail.

The CEO has not answered a guest ticket in six months.

What You'll Need

  • A guest-ops or service system you personally built from zero, with SLA, escalation, QA, and something.
  • A metric you defined, wired the tracking for, and ran a function against, showing a dashboard.
  • Real AI in your daily flow, with LLMs building your knowledge base and automating your responses, with prompts you can show.
  • Management reps: people you've hired, coached, and let go, and a bar you held them to.
  • Comfort building the SOP instead of waiting for one.
  • Ambiguity is the job. The spine to disagree with the CEO to his face, with a reason.
  • Fluent English, written and spoken.

Who This Is Not For

  • People who ran someone else's playbook and never built one.
  • People who manage by vibes.
  • Readers who treat AI as beneath the role or someone else's job.
  • People who think front-line guest reality is beneath a "Head of."

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