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Executive Assistant / Strategic Operations Lead (Chief of Staff Track)

May 1, 2026

Job Title: Executive Assistant / Strategic Operations Lead (Chief of Staff Track)Contract Type: Full-time, RemoteSalary Range: $2,000–$2,500/month (salary based on assessment)Working Hours: Monday to Friday, 9 AM - 5 PM ETLocation: LATAMAbout the RoleWe are seeking a proactive, empathetic, and aligned Strategic partner to support a leadership team driving two core businesses.This is not a traditional administrative role. You will function as a high-impact partner, protecting the leaders’ time and energy while driving operational rhythm. The role starts as an Executive Assistant with a clear, 12-month advancement path to mature into a Chief of Staff position at the business scale.Key Responsibilities<ul style="min-height:1.5em"><li>Calendar & Inbox Management: Own and safeguard executive calendars; optimize meetings for coaching sessions, strategic planning, and family commitments. Streamline communications, prioritizing urgent items and drafting responses with high discretion.</li><li>Strategic Operations & Project Ownership: Identify activities tied to revenue and growth. Take initiative on special projects (e.g., AI product development) from conception to completion independently.</li><li>Cross-Functional Coordination: Serve as the central communication hub and liaison between multiple business units, external partners, clients, and vendors.</li><li>Process Improvement & AI Enablement: Build systems and lightweight operating systems to streamline recurring processes. Be AI-forward by identifying opportunities to automate repetitive tasks and leveraging new tools.</li><li>Performance Management: Collaborate with leadership to define North Star KPIs; monitor progress, flag blockers, and ensure deliverables are completed with ownership and quality.</li><li>Logistics & Travel: Manage all travel arrangements, meeting coordination, and logistics for internal and external engagements.</li><li>Stakeholder & Family Alignment: Coordinate professional and family calendars to minimize conflicts, protecting personal energy and downtime.</li></ul>QualificationsExperience & Skills<ul style="min-height:1.5em"><li>3+ years of executive assistant, operations, or Chief of Staff-capable experience.</li><li>Fluent English (written and verbal) with exceptional interpersonal skills.</li><li>Proven Autonomy: Ability to work independently with minimal supervision and handle high-value, time-sensitive situations with composure.</li><li>Technical Proficiency: Tech-savvy with an aptitude for learning new tools and comfort with AI-enabled workflows and project management methodologies.</li><li>Strategic Judgment: Strong organizational skills and the ability to navigate ambiguity and "roll" with project timelines.</li></ul>Attitude & Fit<ul style="min-height:1.5em"><li>Ownership Mindset: High emotional intelligence, empathy, and the proactive ability to complete tasks without constant oversight.</li><li>Growth Orientation: Interest in scaling into a leadership role and supporting a visionary leader building multiple companies.</li><li>Values-Driven: Aligned with a mission to help clients grow; a collaborative, non-siloed thinker.</li></ul>Preferred Qualifications<ul style="min-height:1.5em"><li>Time zone alignment with Central or Latin America.</li><li>Experience supporting founders or small business leadership.</li><li>Familiarity with online coaching platforms, digital product launches, or professional services.</li><li>Background in operations for service-based businesses (e.g., construction/contracting).</li></ul>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...