Trolley AI · 5 months ago
Executive Assistant
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 oversee travel and negotiations to ensure the CEO can focus on strategic execution.
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
Strong organizational skills to optimize workflows
Experience overseeing high-stakes travel and negotiations
Ability to eliminate distractions for the executive
Decisive and proactive mindset
Ability to thrive in high-stakes environments
Strong communication skills to over-communicate execution status
Self-regulated and composed under stress
Ability to manage personal and household responsibilities
Experience in customer service and online shopping expertise
Ability to negotiate and secure deals
Experience in business and investor operations
Strong personal boundaries and curiosity
Ability to anticipate scheduling conflicts and solve them proactively
Experience in managing strategic gifting and investor relations
Ability to handle prescriptions, medical records, and wellness coordination
Strong sense of self and self-awareness
Ability to manage relationships with humor and diplomacy
Experience in leveraging information intelligently and efficiently
Ability to take ownership of inefficiencies and solve operational gaps
Benefits
Work from anywhere
Flexible schedule and time off no micromanaging
Direct collaboration with the Founder
Access to top-tier AI tools (Perplexity, ChatGPT, ClickUp Brain and more)
Clear path for long term career growth
A supportive company culture grounded in ownership and prioritizing progress over perfection
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