Head of Guest Experience

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.

We are 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 our culture on C.L.O.U.D.9:

• Customer Obsession. If they’re not raving, we missed it.
• Leadership Through Ownership. No passengers, only drivers.
• Operational Excellence. How we do one thing is how we do everything.
• Urgency With Intelligence. Act now, iterate later.
• Do the Right Thing. Character over convenience.
• The 9x Mindset. 10% better is safe; 9x better is unforgettable.

Cloud9 runs 60+ luxury units across 13 buildings, scaling past 100. Guests expect five‑star. Right now, guest experience has no owner but the CEO, working at partial capacity while juggling forty other fires. Response is slow. Missed calls fall through. The same problems get re‑solved every week. There is no SLA, no QA, no dashboard. We are not looking for someone to help with that.

We are looking for someone to own it and never hand it back. You will build the guest‑experience function from zero: the standard, the SLAs, the escalation logic, the QA scorecard, the coaching cadence, and eventually the team.

You will wire the tracking so the whole thing runs on numbers, not feelings. You will use AI as the engine – triage, first‑draft replies, SLA tracking, missed‑call alerts – so a small team delivers luxury‑grade response across the portfolio.

Day one there is no machine to inherit. There is a mess and a mandate.

If that excites you, keep reading. If it scares you, this is not your role.

• The standard – what five‑star response looks like at Cloud9, defined and encoded.
• The numbers – median first response under five minutes, 100% of missed calls called back within fifteen minutes. You wire the tracking and live on the dashboard.
• The systems – SLAs, escalation trees, QA scorecard, documented and run by the team.
• The team – you 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; speed and quality can’t be bought by giving away margin.
• The AI stack – you build with LLMs, KB, automated responses, triage, alerts, and own what ships.

• Day 30 – instrumentation live; current mess is measured: 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 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.

• A guest‑ops or service system you personally built from zero – SLA, escalation, QA, or similar. Bring the artifact and the number it moved; the build matters more than the résumé.
• A metric you defined, wired tracking for, and ran a function against; show us the dashboard.
• Real AI in your daily flow – LLMs building your knowledge base and automating responses with prompts you can show. Not “I’ve used ChatGPT.”
• 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.

• Hospitality‑corporate lifers who ran someone else’s playbook and never built one. If…