Executive Assistant

Executive Assistant to the CEO Full‑time · Remote from Colombia · Pentice / Cloud9 Windy City

About Pentice

Pentice is the operating system behind 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 and unlock new top‑line revenue for building owners. We are building toward an autonomous operating system for luxury high‑rises and expanding city by city across the U.S.

How We Work

We are a small, AI‑native team. You work alongside AI tools every day; they are co‑pilots, not buzzwords. The team is distributed (Chicago + Latin America), moves fast, and cuts politics. We don’t hire to fill seats. We hire people who can pull levers that move numbers. Outcomes beat effort.

We run on C.L.O.U.D.9:

• Customer Obsession
• Leadership Through Ownership
• Operational Excellence
• Urgency With Intelligence
• Do the Right Thing
• The 9x Mindset

Three of these are warnings:

• Leadership Through Ownership: You will be handed a number and very little scaffolding. Nobody sequences your week for you.
• Urgency With Intelligence: We ship, measure, then fix. A good decision today beats a perfect one in three weeks.
• Do the Right Thing: You will get chances to report numbers that flatter you. We check. One softening of a bad result is one too many.

The Role

We are hiring an Executive Assistant to the CEO, Marcus Halawi. Your job is to give Marcus his time back across Cloud9 and Pentice:

• No email is lost.
• No deadline is missed.
• No money or legal item waits.
• Every decision reaches him ready to approve in one read.

You start at “recommend and confirm” on everything. By day 90, you earn “act, then inform” on named routine categories. Money, legal, bank and signature items always go to Marcus first.

This role is for someone who would rather be the person nothing slips past than the person with the fanciest title.

What You’ll Own (Outcomes)

• No lost email: Every email you own gets a same‑day reply, without reminders.
• No surprises on money/legal/bank: Each one reaches Marcus the same day you see it, with your written recommendation.
• Decisions arrive ready: Every item you bring is a QTA (Question To Answer): the problem, three options, and your one recommendation.
• No missed dates: Licenses, leases, insurance, renewals, filings and personal deadlines are confirmed 60+ days ahead across U.S. companies, Colombia, and Marcus personally.
• Work closes on time: At least 90% of your tasks close by their due date, and your open list stays short.

What You Will Do

• Run Marcus’s calendar inside clear rules, including prep packets (agenda + one‑page brief) for external meetings one week ahead.
• Own assigned inboxes and labels in Gmail: read every message and document in full before you reply, forward, draft, or recommend a signature.
• Maintain one master calendar of every dated obligation for each company and for Marcus personally.
• Plan travel end‑to‑end: research, book, confirm, and handle changes; manage personal bills, vehicles, registrations, insurance, visas, and household logistics.
• Track payments that still go out by hand, file proof the same day, and escalate anything that does not clear. You do not approve or send money.
• Check any request passed to you with the original requester before you act.
• Keep the “Automate” list moving: write each recurring task clearly enough that a tool, agent, or process could take it over, and help hand it off when the date comes.
• Report your own misses and near‑misses before anyone else finds them.

Two rules that never bend:

• You do not contact guests, vendors or any outside party about a money or legal matter without Marcus’s written OK. An open recommendation is not an OK.

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

What We’re Looking For

Minimum bar (all required):

• Same‑day replies: you answer email the day it arrives, without being reminded.
• You read everything before you act on it. Our work sample checks this.
• You bring options, not questions: every escalation comes as a QTA with three options and your recommendation.
• Professional written English for U.S. owners and vendors, plus fluency in Gmail, ClickUp, and AI chat tools from day one. You already use AI daily and can explain how you check its output.
• Same‑day escalation of anything touching money, legal matters, or a bank.

Nice to have:

• 3+ years running the administrative or personal‑support side of a founder or executive, with real ownership.
• A system you built yourself to track many small dated obligations without lapses.
• Comfort with banks, insurers, utilities, licensing offices, and government portals in the U.S. and Colombia.
• Professional Spanish.
• Automations you have built (ClickUp, Gmail filters, scripts, agents).

Compensation & Details

• Engagement: Full‑time, remote from Colombia. Contrato a término indefinido under Colombian labor law, or contractor agreement, whichever fits you best.
• Base: COP 6,500,000 to 9,500,000 per month, depending on experience, English level, ownership history, and work sample quality.
• Quarterly scorecard bonus: Target 10% of your quarterly base, tied equally to five metrics (same‑day replies, QTA adherence, same‑day escalation, on‑time tasks, zero lapsed renewals). A metric pays when it hits target in at least 10 of 13 Friday reviews. Breaking either “never bend” rule sets the bonus to zero for that quarter.
• Raises: After you pass day 90 and move to “act, then inform,” then every 12 months based on results and ownership level.
• Holidays: U.S. federal holidays (11 per year), plus paid vacation.
• Hours: Monday to Friday, 8:00 AM to 5:00 PM Bogotá time, with full overlap with Chicago. No after‑hours or weekend coverage.

Hiring Process

All steps are in English and mirror the actual work:

• Written screen: Two written questions with your application, then a 30‑minute call (half in