Executive Assistant (EA) – Virtual | Full-Time | PST or EST Time Zones

Trolley; California (MO); Remote; USD 85,000 - 120,000; Full time

Job summary

Trolley is seeking a high-caliber Executive Assistant to provide elite-level support to the CEO. The successful candidate will manage critical tasks, optimize workflow, and handle high-profile relationships. Join a dynamic team committed to excellence, operating in a fast-paced, technology-driven environment within the PST or EST time zones.

Benefits

World-class training

Flexibility in working hours

Qualifications

• Must be an elite-level Executive Assistant experienced with supporting a CEO.
• Ability to adapt and thrive in high-stakes environments is essential.
• Strong relationship management skills required.

Responsibilities

• Manage high-profile relationships and optimize workflows.
• Oversee high-stakes travel and negotiations for the executive.
• Ensure seamless execution of both professional and personal responsibilities.

Skills

Proactive

Decisive

High-energy

Strategic thinking

Problem-solving

Communication

Job description

Executive Assistant (EA) – Virtual | Full-Time | PST or EST Time Zones

Executive Assistant (EA) – Virtual | Full-Time | PST or EST Time Zones

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Executive Assistant (EA) – Virtual | Full-Time | PST or EST Time ZonesWho we're looking for

We’re looking for anelite-level Executive Assistant—someone who isten steps ahead, thrives in high-stakes environments, and executes flawlessly. This isn’t a passive support role. This is aboutowning responsibilities, amplifying efficiency, and ensuring the executive’s world runs seamlessly—both professionally and personally.

You’llmanage high-profile relationships, optimize workflows, oversee high-stakes travel and negotiations, and eliminate distractionsso the CEO can focus onbig-picture strategy and execution.

This role isnot for the hesitant or reactive—it’s for someone who isdecisive, proactive, and deeply aligned with the executive’s vision. This is not your first time supporting a CEO and founder—youthrive alongside executives with big energy, matching their pace and intensity. If you excel under pressure, canexecute at an elite level, and thrive onmaking things happen instead of making excuses, this is for you.

Who You’ll Work WithAbout the CEO

The executive you will support is aType 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 theCEO and Managing Partnerand works closely with theSenior Bookkeeper, investment team, legal partners, operations, marketing, and key external vendors and teamsto manageboth professional and personalresponsibilities.

We are afast-moving, high-performance venturethat valuesclarity, execution, and results. Our team isdynamic, ambitious, and deeply committed to excellence. Theexpectation is that you come in ready to contribute at a high level, align quickly, and deliver without hesitation.

How You Do the Job & WhyEXHIBIT A: Operating Framework, Expectations, and Deliverables

At the core of this role is afundamental 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:

• Youoperate with full alignmentto 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.
• Youextend my influenceby managinghigh-value relationships, ensuring seamless execution acrossCRM, LP management, investor relations, and strategic initiatives.
• Youremove from my plateall responsibilities thatdo not require my direct input.
• Youanticipateandthink 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.
• Youadd expertise, reinforcing and deepening my strategies, not simply mirroring them.
• You donot make sloppy errors—this includesinaccurate data, incomplete reports, and failure to track critical updates.
• Youover-communicate execution status—every single priority is documented, withrecap 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.
• Youown your role within the organization—deciding when to be agatekeeper vs. a facilitator, balancingauthority 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 ofstrategic relationships.
• Create leverage—youdelegate, automate, and systematizeto move lower-priority tasks off your plate.
• Systemize everything—you standardize workflows and export best practices across the organization.
• Master a core domain—you fullyown and execute within a key business function.
• Act as a proxy for the executive—you operateon behalf of leadership in select areas, particularly inrelationship-driven interactions.
• Take ownership of inefficiencies—you identify and solve operational gaps thatothers overlook.
• Use strategic influence—recognizing thatsmall, high-impact gesturescreatelong-term business opportunities.
  

Final Operating Principles

• Play the long game.Every move must bestrategic, not reactive.
• Zoom out.View the business asa system, not just a collection of tasks.
• Leverage information.You will havemore 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 tofollow up on something basic, you are already behind.
• Do this for yourself.If you don’t see thepersonal growth and long-term benefit in executing at this level, this role isnotfor 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 relationshipsto unlock high-end services.
  

2. Executive Calendar & Prioritization

• Own and optimizethe executive’s schedule,ensuring every commitment is aligned with priorities.
• Anticipate scheduling conflictsbefore they happen andsolve them proactively.
• Manage investor, advisor, and high-profile relationships, ensuring seamless coordination.
  

3. Customer Service & Online Shopping Expertise

• Negotiate best deals & refunds—fromluxury 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 contactfor key partners.
• Own CRM, LP tracking, and follow-upsfor 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: 40hrs/week (Full-time, with flexibility for occasional evening and weekend support.)

Submit your application here

Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed.

About Us

Who We Are

Trolley is an online marketplace and platform that pairs best-in-class people with best-in-class companies. We are the future of work, create, and play, powered by our proprietary LiveWorkOS.

What We Do

Trolley builds world-class teams using best-in-class SaaS tools, AI, and project management systems. Our mission is to empower professionals with world-class training and the latest tools to work smarter, faster, and more efficiently.

Why Join Us?

• Work with the Best:We recruit globally to connect top talent with forward-thinking companies.
• Tech-Driven Efficiency:Leverage the latest AI and tools to amplify your impact.
• Human-Centric Approach:Our systems are designed to support and elevate people, not replace them.
• Training for Success:We provide world-class training to ensure you excel in every aspect of your role.

Be Part of the Future of Work

• Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Administrative

• Industries

  Technology, Information and Media

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