Executive Assistant

Executive Assistant

New York, New York, United States

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.

Who We're 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 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.

What to Expect: Our Application Process

We respect your time and aim for clarity, so here's how it works: 1. Apply through ClickUp 2. Complete a short assignment via TestGorilla 3. Interview with Recruitment & Ops Coordinator 4. Second interview or role assessment 5. Final interview with Founder & CEO 6. Welcome to Trolley! Steps may vary slightly depending on the role well guide you through it!

About Us

Who We Are Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhousecombining strategy, design, production, and performance analysis to deliver world-class results.

AI Mindset & Continuous Innovation We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. At Trolley, AI is part of everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement.