Executive Assistant

Executive Assistant
Full-time · On-site in Bogotá, Colombia · Pentice / Cloud9 Windy City · Reports to the CEO

Mission

This role exists so nothing reaches Marcus Halawi, our CEO, late, unread, or without a recommendation.

The Seat, The Intensity & The Comp

• The Seat: You sit directly next to the CEO in Bogotá as his operational gatekeeper and execution engine. This is not a passive 9-to-5 job. You are an obsessed, punctual operator who clears task lists relentlessly and jumps on urgent evening or weekend items when the business requires it.

• Compensation: COP 6,500,000 to 9,500,000/month base (Contrato a término indefinido with a 2-month período de prueba) + up to 10% quarterly bonus tied directly to the 5 outcomes below.

• The 90-Day Trade (Path): You start at "recommend and confirm." By Day 90, you earn "act, then inform" autonomy across routine categories (travel/personal logistics, calendar defense, obligation renewals, and standard inbox routing) greater than 90% of the time, with fewer than 2 corrections per month. Hit the scorecard, and your scope and pay grow at Day 90 and every 12 months after.

Outcomes (Tracked Weekly)

1. Zero Inbox Lag: 95% or more of the email you own gets a same-day reply. Anything you can't answer is escalated by 5:00 PM Bogotá.

2. Decision Packaging: 100% of money, legal, and bank items reach Marcus the same day you see them, written as a QTA (Question To Answer: the problem, three options, and one recommendation).

3. Zero Lapsed Dates: Every license, lease, insurance policy, renewal, filing, and personal deadline is confirmed 60+ days ahead, across the U.S. companies, Colombia, and Marcus personally.

4. Relentless Closure: 90% or more of your tasks close on or before their due date.

5. Router Protection: At least 80% of issues in your lane are resolved or fully packaged without needing Marcus to gather info or chase people.

Responsibilities

• Own your assigned Gmail inboxes and read every message and document in full before acting. (Outcomes 1 & 5)

• Gather missing context from internal team members or documents before escalating, and package every money, legal, and bank item as a QTA. (Outcomes 2 & 5)

• Keep one master calendar of every dated obligation across U.S. and Colombian entities. (Outcome 3)

• Run Marcus's calendar with extreme precision and prepare external meetings one week ahead. (Outcome 4)

• Plan and book travel, and handle personal bills, vehicles, registrations, insurance, visas, and household logistics. (Outcomes 3, 4 & 5)

• Track manual payments and file proof the same day. You never approve, release, or send money. (Outcome 2)

• Turn recurring tasks into instructions an AI tool or agent can take over. (Outcome 4)

Two Rules That Never Bend

1. No contact with guests, vendors, or any outside party about a money or legal matter without Marcus's written OK.

2. Any money, legal, or bank item reaches Marcus the same day, as a QTA.

Requirements

• University degree with a demonstrated track record of high academic and professional achievement.

• Bilingual fluency: Professional written and spoken English and Spanish.

• Daily use of Gmail, ClickUp, and AI tools, and the ability to explain how you verify AI output.

• Core in-office hours Monday to Friday, 7:00 AM to 4:00 PM in Bogotá, Colombia, plus responsiveness for urgent after-hours and weekend items.

• Nice to have: 3+ years supporting a founder or executive; experience with U.S. and Colombian banks, insurers, and government portals; custom obligation-tracking systems or AI automations you built yourself.

How You Work

• You are fanatical about punctuality and inbox zero; an unchecked box bothers you personally.

• You hit deadlines without reminders and close loops before being asked.

• You read everything in full before you act.

• You report bad news, including your own misses, the same day.

• You keep sensitive information confidential.

• You take direct, unfiltered feedback and fix things fast.

About Pentice

Pentice runs Cloud9 Windy City: 63 luxury units across 13 Class-A residential buildings in Chicago. We turn underperforming long-term apartments into hotel-grade short stays for building owners, and we're expanding city by city across the U.S. We're a small, AI-native team spread across Chicago and Latin America. We run on C.L.O.U.D.9: Customer Obsession, Leadership Through Ownership, Operational Excellence, Urgency With Intelligence, Do the Right Thing, and The 9x Mindset.

How to Apply (All Steps in English)

Submit your CV and answers to the 4 application questions below. Our process moves fast:

1. A 30-minute call where we confirm alignment and pay.

2. A live 30-minute QTA case.

3. A 45-minute in-person conversation with Marcus in Bogotá.

4. At least two references, including someone whose inbox or calendar you ran.

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.