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.

Executive Assistant to the CEO

The Role

We are looking for an Executive Assistant to the CEO to hold everything Cloud9 and Marcus owe that is not yet automated — and to hand each piece to a system, on a date.

Most of this seat is the CEO's administrative life: that everything is paid, the car is insured, the registrations are current, the flights are booked, the appointments happen, and none of it ever needs a follow-up. The rest is the company's dated obligations that no automation has reached yet — licenses, leases, insurance, renewals, and the occasional payment that still goes out by hand.

One thing about how we work that you should know going in. Every manual task in this seat goes on a list called Automate, with a target date. Until that date you do it by hand, to a standard, without dropping it. When the date comes, you help hand it to a tool, an agent or a process.

That list never empties, and it is not meant to. We are growing, so new obligations arrive faster than old ones get automated — a new property, a new license, a new country, a new supplier. What changes over time is which things are on your desk, not how full it is. The routine bill-checking you do by hand in month one may be a script by month eight, and the space that frees up gets filled by something that needs a person.

So this is a long-term seat and the work is genuinely yours. What we ask is that you do not hoard it: write down how you do things, hand over what can be handed over, and let the boring repetitive parts go so you can take on the parts that actually need judgment.

Run this well and there is a clear path into operations for whoever wants it — the person who knows where every obligation lives is the obvious person to run them at a larger scale.

What You Will Do

The CEO's administrative life — the largest part of the seat

• Everything is paid, on time, without being asked: household and utility accounts, subscriptions, personal services and suppliers.

• Vehicles, registrations and insurance current — nothing expires quietly.

• Travel end to end for business and personal trips: flights, hotels, ground transport, itineraries. Booked and confirmed, not researched and handed over.

• Appointments, contractors, family logistics, school arrangements.

• Purchases and returns across online and local suppliers, reconciled against what was ordered.

• Ad-hoc requests that need to be reliably closed rather than discussed.

The company's dated obligations that are not yet automated

• One calendar of every date-driven obligation: license renewals, lease dates and notice windows, insurance policies, permits and filings, across Colombia and the U.S. entity.

• Confirm and schedule each one at least 60 days before its deadline. A blank date is not "fine" — it is an open item.

• The payments that still go out by hand: chase them, file the proof the same day, and escalate anything that does not clear.

• Keep the external bookkeeper and both accounting firms supplied with what they need, on schedule, without being chased.

The Automate list

• Maintain one list of every manual task in this seat, each with a target date to be automated and a note on who is building it.

• Write each recurring task down clearly enough that someone — or something — else could run it. This is a deliverable, not documentation hygiene.

• Work with the Chief of Staff and the CEO on the handoffs, then stay the human who catches what the automation gets wrong.

• Add to the list as fast as things come off it. New properties, new licenses, new suppliers — the point of the list is that nothing manual stays invisible.

• Report honestly on what is not moving. A task that has sat on the list for six months without a date is a problem to raise, not to absorb.

Tools and Systems You Will Use

Banking and government portals in Colombia and the U.S., ClickUp, Google Workspace, Guesty, QuickBooks Online, custom spreadsheets, and the internal AI agents that monitor recurring obligations. You will use AI daily and you will be expected to say how you checked its output.

Your Scorecard

• Nothing lapses: zero missed renewals, filings, insurance dates or payments in a quarter, across both entities and the CEO's personal obligations.

• 100% of renewals confirmed and scheduled 60+ days before deadline.

• Every miss, slip or near-miss reported by you before anyone else finds it.

• The Automate list moves: items handed off on or before their target dates.

• The CEO stops being asked about administrative things.

What We're Looking For

• 2+ years running the administrative or personal-support side of a business owner, founder or executive — with real ownership, not as one of a team of assistants.

• A record of holding a large number of small dated obligations without lapses, and a system you built yourself to do it.

• Comfort with portals and institutions: banks, utilities, government desks, county licensing offices, insurers. You have been told no by a website and found the way through.

• Professional Spanish and English, written and spoken, used daily.

• Exceptional discretion. This seat sees the CEO's household, his family's arrangements and the company's private matters. A confidentiality agreement is required.

• The habit of saying "not done yet" the day something is not done.

• Willingness to write down how you work and hand pieces of it over. You should be able to point at something you simplified, documented or stopped doing by hand.

This Role Is For You If

• You are the person who remembers the thing nobody else remembered — and you have a system rather than a good memory.

• You would rather write down how you do something and hand it over than be the only one who can do it.

• You like a job where the specific tasks evolve, even though the ownership stays yours.

• You are comfortable being close to someone's private life and entirely uninterested in talking about it.

This Role Is Not For You If

• You want an identical set of duties every month for the next five years.

• The personal-support half sounds like it is beneath the title. It is the largest part of this seat.

• You measure your value by how much only you can do.

• Government portals, insurers and utilities stress you out.

• You avoid raising problems and hope they resolve themselves.

Nice to Have

• Experience supporting an executive across two countries.

• Familiarity with U.S. municipal licensing, property insurance or vehicle registration.

• Guesty, Stripe, ClickUp, QuickBooks, Amazon Business.

• Having built an automation yourself — a Zap, a script, an agent, a form that replaced an email thread. At any level.

What We Offer

• Competitive compensation for the Colombian market, based on seniority and track record.

• Contrato a término indefinido, with full statutory benefits: EPS health, pension, ARL, cesantías and interest, prima de servicios, and paid vacation.

• Hybrid in Bogotá: three days a week in the office (Monday, Wednesday, Thursday), two from home. Flexible hours.

• Direct daily exposure to the CEO and the Chief of Staff, with real ownership from day one.

• A small, senior team that documents and automates rather than repeating itself — so the boring parts of your job get lighter over time and the interesting parts get bigger.

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.

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.