Guest Experience Specialist (AI-Enabled) - Native Speaker

About Pentice

Pentice is the operating system behind Cloud9 Windy City: 63 units across 13 Class-A residential buildings in Chicago, turning long-term luxury apartments into hotel-grade short stays and unlocking top-line revenue for the buildings' owners. We are building toward the autonomous operating system for luxury high-rises, and expanding city by city across the U.S.

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, most in Latin America. 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.

How we pay

Every role we post carries its compensation in figures, in the currency you would be paid in. Base is one part. The rest is a quarterly bonus tied to the one number your seat owns. If you move the number you are paid for it, and if the number does not move the bonus does not pay. You get both halves before you apply.

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.

Three of those decide who lasts here, so read them as warnings rather than slogans.

Leadership Through Ownership. You will be handed a number and very little scaffolding. Nobody will sequence your week for you. If you need a manager to tell you what matters this Tuesday, you will be unhappy here inside a month.

Urgency With Intelligence. We ship, measure, then fix. A good decision today beats a perfect one in three weeks. If you need complete information before you move, this pace will feel reckless to you.

Do the Right Thing. You will get chances to report a number that flatters you. We check. Someone who softens a bad result once does not get a second chance to.

What this is

A guest messages at 11pm: the door code isn't working, they're locked out, and they leave for a flight in six hours. What you do in the next ten minutes is the job.

You own the guest experience in real time across 60+ luxury units. When something breaks (a lockout, a parking charge, a late-night issue) you make it right, fast, and you make sure it actually got fixed, not just answered. Then you do the thing most support people never do: you figure out how to make sure it never happens again.

This is a front-line seat, not a manager seat. You work alongside AI as your multiplier: it drafts, summarizes, and surfaces the right answer. You own the judgment, the tone, and the close.

What you'll own

Real-time resolution. Live guest issues, end to end, under time pressure. You clarify, you sequence, you solve, you confirm.

Speed. First-response time and time-to-resolution are your numbers, including off-hours. A guest is never left hanging.

The five-star bar. You win the guest back even when they're wrong. Warm, calm, on-brand, every time.

The fix. When a problem keeps coming back, you kill it. One small fix that prevents fifty tickets beats fifty fast replies.

The close. Nothing is "resolved" until the guest confirms it is.

What success looks like

Day 30. Trained on the stack, the SOPs, and the escalation paths. Handling live guest issues solo on your shift. Your speed baseline is set.

Day 90. At or above the team on first-response and resolution speed, with guest CSAT holding. You've spotted at least one recurring problem and proposed or shipped a fix for it. Off-hours coverage you can be trusted with.

Month 12. [A driver the CEO never has to chase.] Consistently fast, five-star CSAT, low recurrence on what you touch, and a few friction points permanently gone because you built the check.

What you'll need

• Real customer-support or guest-services experience handling live issues end to end. Not back-office, not pure admin.
• A story where a customer was furious and you turned it around. Bring it.
• Calm and judgment under pressure. You don't freeze when the script runs out.
• Strong written English (our guests are served in English) and clear spoken English.
• Comfort with CRM / helpdesk / messaging tools and juggling many open threads at once.
• Heavy AI tool use. Claude or equivalent in your daily flow, and you'll tell us how you use it.
• Reliability for a fixed shift: 5 days on, 2 off, across an 8am-10pm CT window, based in Bogota.

Who this is not for

• Order-takers who wait to be told what to do.
• People who escalate and wait instead of owning the outcome.
• Anyone who marks things "done" without checking the guest is actually okay.
• People who go defensive when a guest is angry.
• People who think AI is beneath them, or who hide that they use it.
• Anyone who needs clean 9-to-5 hours with no evenings.

What's Real About Cloud9 Right Now

• The processes are half-built. You'll own things before you feel fully ready, and some weeks are messy.
• The guest is sometimes wrong, and you still have to win them.
• You'll work evenings on a rotation. Guest problems don't keep business hours.
• You work alongside Claude. AI is the real multiplier here, not a buzzword.
• Distributed team. Guest team is in Bogota; the company is in Chicago and across Latam.
• If you want a finished playbook handed to you, this is the wrong seat. If you want free rein to own guest relationships in week one, it's the right one.

Why Pentice

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.

How we hire

Apply, about five minutes. Watch a short, honest video about how we work and answer a written questionnaire — both count. A 30-minute call. A working session on a real problem, with AI use expected and visible. Two reference calls. Then an offer. Every candidate gets an answer either way.

Equal opportunity

Pentice and its operating entities do 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.