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Executive Assistant Job Opening In WorkFromHome – Now Hiring Trolley AI


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Executive Assistant (EA) Virtual | Full-Time | PST or EST Time Zones
Who Were Looking For
We're looking for an elite-level Executive Assistant who is ten steps ahead, thrives in high-stakes environments, and executes flawlessly .

This isn't a passive support role.

This is about owning responsibilities, amplifying efficiency, and ensuring the executive's world runs seamlessly, both professionally and personally.

You'll manage high-profile relationships, optimize workflows, oversee high-stakes travel and negotiations, and eliminate distractions so the CEO can focus on big-picture strategy and execution .

This role is not for the hesitant or reactive; it's for someone who is decisive, proactive, and deeply aligned with the executive's vision .

This is not your first time supporting a CEO and founder; you thrive alongside executives with big energy, matching their pace and intensity .

If you excel under pressure, can execute at an elite level , and thrive on making things happen instead of making excuses , this is for you.
Who You'll Work With
About the CEO
The executive you will support is a Type 8 - The Challenger , known for being ambitious, independent, and driven to lead.

They are highly analytical, deeply thoughtful, and approach challenges with confidence and intensity.

They value efficiency, strategic thinking, and people who take initiative.

The right EA for this role thrives next to a strong-willed, high-energy executive, understands their unique leadership style, and knows how to complement their strengths while bringing their own expertise to the table.

This role reports directly to the CEO and Managing Partner and works closely with the Senior Bookkeeper, investment team, legal partners, operations, marketing, and key external vendors and teams to manage both professional and personal responsibilities.

We are a fast-moving, high-performance venture that values clarity, execution, and results .

Our team is dynamic, ambitious, and deeply committed to excellence .

The expectation is that you come in ready to contribute at a high level, align quickly, and deliver without hesitation.
How You Do The Job & Why
EXHIBIT A: Operating Framework, Expectations, and Deliverables
At the core of this role is a fundamental expectation : PLAY TO WIN, NOT TO AVOID MISTAKES.

THE OBJECTIVE IS EXECUTION, NOT EXCUSES.
Phase 1: Core Deliverables & Mindset (0-9 months)
You will be exceptional in this role if:

  • You operate with full alignment to my vision and decision-making framework.

    When you speak, you speak for me and with my authority.

    If you are wrong, I will correct you.

  • You extend my influence by managing high-value relationships, ensuring seamless execution across CRM, LP management, investor relations, and strategic initiatives.

  • You remove from my plate all responsibilities that do not require my direct input.

  • You anticipate and think through problems as the executive does, aligning your thought process with strategic expectations.

    You are an avid reader and researcher, always seeking knowledge to enhance problem-solving and decision-making.

  • You add expertise, reinforcing and deepening my strategies, not simply mirroring them.

  • You do not make sloppy errors, this includes inaccurate data, incomplete reports, and failure to track critical updates.

  • You over-communicate execution status; every single priority is documented, with recap updates delivered daily at 10 PM PST.

    You are self-regulated, composed under stress, and skilled at de-escalation, ensuring smooth execution even in high-pressure situations.

  • You own your role within the organization, deciding when to be a gatekeeper vs.

    a facilitator, balancing authority and efficiency accordingly.

    You have strong personal boundaries, are curious, and are not afraid to try new things.

Phase 2: Mastery & Expansion (9-12 months)
  • Develop and manage high-value talent pipelines you identify, recruit, and maintain an ecosystem of strategic relationships.

  • Create leverage, you delegate, automate, and systematize to move lower-priority tasks off your plate.

  • Systemize everything you standardize workflows and export best practices across the organization.

  • Master a core domain you fully own and execute within a key business function.

  • Act as a proxy for the executive you operate on behalf of leadership in select areas, particularly in relationship-driven interactions.

  • Take ownership of inefficiencies you identify and solve operational gaps that others overlook.

  • Use strategic influence, recognizing that small, high-impact gestures create long-term business opportunities.

Final Operating Principles
  • Play the long game.

    Every move must be strategic, not reactive.

  • Zoom out.

    View the business as a system, not just a collection of tasks.

  • Leverage information.

    You will have more access to critical data than anyone else use it intelligently and efficiently.

    You have a strong sense of self, are highly self-aware, and know how to manage relationships with humor and diplomacy.

  • Stay ahead of the executive.

    If leadership has to follow up on something basic, you are already behind.

  • Do this for yourself.

    If you don't see the personal growth and long-term benefit in executing at this level, this role is not for you.

Key Responsibilities
1.

Elite Travel, Luxury Bookings & Negotiation
  • Book first-class travel experiences, ensuring VIP-level treatment.

  • Negotiate and secure upgrades, flights, hotels, dining, and exclusive perks.

  • Manage complex international itineraries, handling last-minute changes with ease.

  • Leverage concierge relationships to unlock high-end services.

2.

Executive Calendar & Prioritization
  • Own and optimize the executives schedule, ensuring every commitment is aligned with priorities.

  • Anticipate scheduling conflicts before they happen and solve them proactively.

  • Manage investor, advisor, and high-profile relationships, ensuring seamless coordination.

3.

Customer Service & Online Shopping Expertise
  • Negotiate the best deals & refunds from luxury fashion to tech purchases.

  • Handle all customer service issues, escalating only when necessary.

  • Secure rare or high-demand items, using strategic sourcing and vendor relationships.

4.

Business & Investor Operations
  • Act as a gatekeeper and trusted point of contact for key partners.

  • Own CRM, LP tracking, and follow-ups for high-stakes relationships.

  • Manage strategic gifting, investor relations, and professional outreach.

5.

Personal & Household Management
  • Oversee all personal scheduling, household logistics, and vendor management.

  • Handle prescriptions, medical records, and wellness coordination.

  • Ensure seamless execution of family vacations, events, and experiences.

Job Details
Location: Remote (Must be based in North or South America and work within PST or EST time zones)
  • Hours: Full-time, with flexibility for occasional evening and weekend support.

Submit your application here:

Seniority level

  • Seniority level

    Not Applicable

Employment type

  • Employment type

    Full-time

Job function

  • Job function

    Administrative
  • Industries

    Technology, Information and Media

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Required Skill Profession

Marketing De Productos Y Gestión De Marca


  • Job Details

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Unlock Your Executive Assistant Potential: Insight & Career Growth Guide


Real-time Executive Assistant Jobs Trends (Graphical Representation)

Explore profound insights with Expertini's real-time, in-depth analysis, showcased through the graph here. Uncover the dynamic job market trends for Executive Assistant in WorkFromHome, Chile, highlighting market share and opportunities for professionals in Executive Assistant roles.

1446 Jobs in Chile
1446
1014 Jobs in Workfromhome
1014
Download Executive Assistant Jobs Trends in Workfromhome and Chile

Are You Looking for Executive Assistant Job?

Great news! is currently hiring and seeking a Executive Assistant to join their team. Feel free to download the job details.

Wait no longer! Are you also interested in exploring similar jobs? Search now: .

The Work Culture

An organization's rules and standards set how people should be treated in the office and how different situations should be handled. The work culture at Trolley AI adheres to the cultural norms as outlined by Expertini.

The fundamental ethical values are:

1. Independence

2. Loyalty

3. Impartiapty

4. Integrity

5. Accountabipty

6. Respect for human rights

7. Obeying Chile laws and regulations

What Is the Average Salary Range for Executive Assistant Positions?

The average salary range for a varies, but the pay scale is rated "Standard" in WorkFromHome. Salary levels may vary depending on your industry, experience, and skills. It's essential to research and negotiate effectively. We advise reading the full job specification before proceeding with the application to understand the salary package.

What Are the Key Qualifications for Executive Assistant?

Key qualifications for Executive Assistant typically include Marketing De Productos Y Gestión De Marca and a list of qualifications and expertise as mentioned in the job specification. The generic skills are mostly outlined by the . Be sure to check the specific job listing for detailed requirements and qualifications.

How Can I Improve My Chances of Getting Hired for Executive Assistant?

To improve your chances of getting hired for Executive Assistant, consider enhancing your skills. Check your CV/Résumé Score with our free Tool. We have an in-built Resume Scoring tool that gives you the matching score for each job based on your CV/Résumé once it is uploaded. This can help you align your CV/Résumé according to the job requirements and enhance your skills if needed.

Interview Tips for Executive Assistant Job Success

Trolley AI interview tips for Executive Assistant

Here are some tips to help you prepare for and ace your Executive Assistant job interview:

Before the Interview:

Research: Learn about the Trolley AI's mission, values, products, and the specific job requirements and get further information about

Other Openings

Practice: Prepare answers to common interview questions and rehearse using the STAR method (Situation, Task, Action, Result) to showcase your skills and experiences.

Dress Professionally: Choose attire appropriate for the company culture.

Prepare Questions: Show your interest by having thoughtful questions for the interviewer.

Plan Your Commute: Allow ample time to arrive on time and avoid feeling rushed.

During the Interview:

Be Punctual: Arrive on time to demonstrate professionalism and respect.

Make a Great First Impression: Greet the interviewer with a handshake, smile, and eye contact.

Confidence and Enthusiasm: Project a positive attitude and show your genuine interest in the opportunity.

Answer Thoughtfully: Listen carefully, take a moment to formulate clear and concise responses. Highlight relevant skills and experiences using the STAR method.

Ask Prepared Questions: Demonstrate curiosity and engagement with the role and company.

Follow Up: Send a thank-you email to the interviewer within 24 hours.

Additional Tips:

Be Yourself: Let your personality shine through while maintaining professionalism.

Be Honest: Don't exaggerate your skills or experience.

Be Positive: Focus on your strengths and accomplishments.

Body Language: Maintain good posture, avoid fidgeting, and make eye contact.

Turn Off Phone: Avoid distractions during the interview.

Final Thought:

To prepare for your Executive Assistant interview at Trolley AI, research the company, understand the job requirements, and practice common interview questions.

Highlight your leadership skills, achievements, and strategic thinking abilities. Be prepared to discuss your experience with HR, including your approach to meeting targets as a team player. Additionally, review the Trolley AI's products or services and be prepared to discuss how you can contribute to their success.

By following these tips, you can increase your chances of making a positive impression and landing the job!

How to Set Up Job Alerts for Executive Assistant Positions

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