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 are expanding to 7+ U.S. cities. We exist to reinvent hospitality with AI‑driven execution. C.L.O.U.D.9 – Culture Operating System C ustomer Obsession – If they’re not raving, we missed it. L eadership Through Ownership – No passengers, only drivers. O perational Excellence – How we do one thing is how we do everything. U rgency With Intelligence – Act now, iterate later. D o the Right Thing – Character over convenience. 9 The 9x Mindset – 10% better is safe; 9x better is unforgettable. What This is Cloud9 runs 60+ luxury units across 13 buildings, scaling past 100. Guests expect five‑star service. Right now, guest experience has no owner but the CEO, and response is slow with missed calls falling through. The same problems are re‑solved every week because there is no SLA, QA, or dashboard. We are looking for someone to own this and never hand it back. What You'll Own 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; wire the tracking and live on the dashboard. The systems – SLAs, escalation trees, QA scorecard; built from scratch, documented, run by the team. The team – hire to your bar, coach on a cadence, and let people go when they don’t hold the line. The margin – refund and comp dollars are a number you protect; speed and quality can’t be bought by giving away margin. The AI stack – build with LLMs, knowledge base, automated responses, triage, alerts; own what ships. What Success Looks Like 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. What You'll Need A guest‑ops or service system you personally built from zero: SLA, escalation, QA – bring the artifact and the number it moved. The build matters more than the résumé. A metric you defined, wired the tracking for, and ran a function against. Show us the dashboard. Real AI in your daily flow. LLMs building your knowledge base and automating your 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. Who This Is Not For Hospitality‑corporate lifers who ran someone else’s playbook and never built one. If your track record is “operated within an existing system,” this is not it. People who manage by vibes. If you can’t name a metric you defined and moved, keep scrolling. “My team delivered” people. We need what you built and owned, not credit you shared on an org chart. Anyone who treats AI as beneath the role or someone else’s job. This is an AI‑native seat. People who need a finished SOP to move. There is no SOP. You are writing it. Anyone who thinks front‑line guest reality is beneath a “Head of.” It isn’t, and you’ll be in 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. #J-18808-Ljbffr Cloud9