Executive Assistant (EA) Virtual

• 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.

At the core of this role is a fundamental expectation: PLAY TO WIN, NOT TO AVOID MISTAKES. THE OBJECTIVE IS EXECUTION, NOT EXCUSES.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

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.