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Head of Guest Experience
Full-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 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:
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, running it at partial capacity between 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:
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 whole 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.
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. You wire the tracking and you live on the dashboard.
The systems. SLAs, escalation trees, QA scorecard. Built from scratch, documented, run by the team.
The team. You hire to your bar, you coach on a cadence, and you 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. You build with LLMs, KB, automated responses, triage, alerts, and you 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.
The CEO has not answered a guest ticket in six months.
What You'll Need
Read this part carefully. This role has been open before and we paused it on purpose. We are done hiring the wrong shape.
What's Real About Cloud9 Right Now
Cloud9 is an AI-native luxury short-term rental operator in Chicago. We manage 60+ units across 13 Class-A residential buildings. We're expanding to 7+ U.S. cities. We exist to reinvent hospitality with AI-driven execution.
Our core values:
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.
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.
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, running it at partial capacity between 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
- Eventually, the team
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 whole 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.
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. You wire the tracking and you live on the dashboard.
The systems. SLAs, escalation trees, QA scorecard. Built from scratch, documented, run by the team.
The team. You hire to your bar, you coach on a cadence, and you 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. You build with LLMs, KB, automated responses, triage, alerts, and you 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.
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. SLA, escalation, QA, something. 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.
Read this part carefully. This role has been open before and we paused it on purpose. We are done hiring the wrong shape.
- 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.
What's Real About Cloud9 Right Now
- Guest experience is unbuilt. You are not inheriting a machine, you are building one from a mess.
- This seat has burned two finalists on the same wrong profile. We know exactly what we don't want now, and the bar is high.
- The CEO has been the hidden owner of CS. Your job is to take that from him permanently. That means early days are heavy and hands-on.
- We move at speed and cut mediocre work fast.
- Distributed team. LatAm-primary for this seat, with the field/turnover side run out of Chicago.
- Before any final interview, there is a paid case study. We test the work before we test the room.
Cloud9 is an AI-native luxury short-term rental operator in Chicago. We manage 60+ units across 13 Class-A residential buildings. We're expanding to 7+ U.S. cities. We exist to reinvent hospitality with AI-driven execution.
Our core values:
- Meritocracy — Performance is public. Measurable. Rewarded.
- Execution — Doers win. Deliver fast. Adjust faster.
- Radical Feedback — Real-time corrections. No politics.
- Championship Team — Only A-players stay.
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.