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 seeking an Executive Assistant to the CEO to take full ownership of the administrative and financial engine behind the company and the CEO personally. You will ensure everything the business owes is paid on time and recorded, no license, lease, insurance policy, or renewal lapses, and that the CEO's calendar, travel, and personal commitments run seamlessly without follow-up.

This seat is not "calendar and inbox" management. It requires a high level of trust and autonomy for someone genuinely excellent at administration — someone who keeps dozens of moving obligations across two countries in one system, closes each with proof, and escalates problems the same day they appear.

Run this well, and in 18 to 24 months, there is a clear path into finance operations or operations management. We want to promote the person who already knows where every obligation lives and how each process runs.

What You Will Do

Payments, Vendors,



and Reconciliation

- Own the payment calendar for both Colombia and the U.S.: rent, utilities, office and vendor invoices, statutory contributions, subscriptions, and financing obligations.

- Execute every payment on or before its due date from the approved calendar, and file each receipt the same day.

- Maintain vendor records, payment references, and portal access; resolve rejected, returned, or duplicated payments end to end.

- Keep property-management and payment platforms synchronized so reservations never show as unpaid; issue payment links, chase outstanding invoices, process refunds and charges.

- Dispute incorrect commission invoices, customs charges, and fees quickly.

Accounting and Payroll Support

- Serve as point of contact for external accounting firms in Colombia and the U.S.: send required documents on schedule without reminders.

- Prepare and process payroll runs for both countries, reconciling each run against agreed rates before payment.

- Classify company and personal expenses correctly by entity and deliver clean handoff each month.

Licenses, Leases, Insurance, and Compliance

- Maintain a single annual calendar of all date-driven obligations: license renewals, lease dates, insurance policies, filings, and permits.

- Manage city and municipal license renewals for properties, confirming requirements before renewing or paying.

- Keep property insurance policies current and matched to the active portfolio.

- Provide written status updates on any open compliance items on a fixed cadence, without being asked.

Executive and Personal Support

- Manage the CEO's personal administrative life: household and utility accounts, appointments, contractors, school and family logistics.

- Plan and book end-to-end travel — flights, hotels, ground transport, itineraries — for business and personal trips.

- Handle purchases and returns across online/local suppliers, and reconcile purchases to invoices.

- Manage ad-hoc requests requiring high reliability.

Tools and Systems You Will Use

You’ll work with banking/government payment portals in Colombia and the U.S., Guesty, Stripe, ClickUp, custom-built spreadsheets, and internal AI agents that monitor recurring obligations. Part of your role is running and improving these automated processes.

Your Scorecard

- Zero late/missed payments and renewals per quarter across both countries, with receipts filed same-day.

- 100% of license/lease/insurance renewals scheduled and confirmed 60+ days ahead of deadline.

- 100% of payment/compliance issues escalated to the Chief of Staff within 24 hours, with summaries and next steps.

- CEO’s calendar and personal obligations conflict-free, with every commitment logged within 24 hours.

What We’re Looking For





- 3+ years’ experience in executive support, accounts payable, treasury, or finance administration with real hands-on payment responsibility.

- Proven record managing high volumes of recurring obligations across multiple entities, countries, or currencies without lapses.

- Comfort with Colombian banking/utility/government payment platforms and willingness to learn U.S. equivalents.

- Professional Spanish and English (spoken/written). Daily communication in both languages.

- Strong spreadsheet skills: you build and maintain trackers independently.

- Exceptional discretion. This role handles confidential business and personal information; confidentiality agreement required.

- The habit of stating "not done yet" the day a task is not done.

This Role Is for You If:

- You have owned recurring payments/renewals for multiple entities or countries.

- Checklists, trackers, and reconciliations are your bread and butter — you build them without being asked.

- You’re comfortable pushing back on senior leaders to protect the system.

This Role Is Not for You If:

- You see "assistant" as primarily email and travel booking.

- Government portals, banks, and utilities stress you out.

- You avoid raising problems and hope they resolve themselves.

Nice to Have

- Experience in real estate, hospitality, or short-term rental operations.

- Familiarity with U.S. payroll, municipal licensing, or property insurance administration.

- Experience with Guesty, Stripe, ClickUp, or Amazon Business.

- Clear interest in working with AI tools daily.

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 schedule: three days a week in Bogotá office (Monday, Wednesday, Thursday), two from home. Versátil hours.

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

- Small, senior team that automates and documents to avoid repetition.

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.

📌 Executive Assistant (Bogotá)
🏢 Importante empresa
📍 Bogotá