Trolley AI · 5 months ago
Executive Assistant (EA) Virtual
United States
Full-time
Remote
Senior LevelTrolley AI is a fast-growing creative operations company delivering high-impact digital and marketing solutions. They are seeking an elite-level Executive Assistant who will manage high-profile relationships, optimize workflows, and ensure seamless execution of both professional and personal responsibilities for the CEO.
Computer Software
Responsibilities
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
Qualification
Required
Must be based in North or South America and work within PST or EST time zones
Full-time availability with flexibility for occasional evening and weekend support
Experience supporting a CEO and founder
Ability to manage high-profile relationships
Proactive and decisive mindset
Strong personal boundaries
Ability to operate with full alignment to the executive's vision and decision-making framework
Exceptional communication skills, including over-communicating execution status
Ability to manage complex international itineraries and handle last-minute changes
Expertise in customer service and online shopping
Strong negotiation skills for travel and luxury bookings
Experience in managing strategic gifting and investor relations
Ability to oversee personal scheduling and household logistics
Self-regulated and composed under stress
Strong sense of self and self-awareness
Ability to identify and solve operational gaps
Experience in CRM and LP tracking
Ability to create leverage by delegating, automating, and systematizing tasks
Ability to act as a proxy for the executive in relationship-driven interactions
Strong analytical and strategic thinking skills
Ability to manage wellness coordination and medical records
Company
Trolley AI
Trolley AI is the control room for founder-led execution—uniting creative vision and operational rigor in one integrated platform.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase