[Hiring] Executive Assistant @Trolley

Role Description

We're not looking for a traditional executive assistant. We're looking for an operator — someone who thinks in systems, moves before being asked, and uses AI the way a craftsperson uses their best tools: fluently, creatively, and every single day. You'll support our CEO, Moj Mahdara, directly — managing a high-velocity schedule, coordinating travel and logistics, owning communication across professional and personal priorities, and making sure nothing falls through the cracks. You'll be the person who makes chaos feel like calm. Not by doing more — but by building smarter.

• Manage high-profile relationships
• Optimize workflows
• Oversee high-stakes travel and logistics
• Eliminate distractions for the CEO

This is not your first time supporting a CEO or founder. You thrive alongside executives with big energy, shifting priorities, and high expectations. You know how to move fast, think clearly, and execute without constant direction. If you're proactive by nature, AI-fluent by practice, calm under pressure, and the kind of person who solves problems before anyone notices they existed — this role was written for you.

Qualifications

• AI-native fluency — demonstrated, not described
• Zero-onboarding readiness
• Proactive, independent execution
• Operator-level systems thinking
• Professional presence, always
• Calm under pressure
• Tech fluency across the stack

Requirements

• Full calendar management for the CEO across professional and personal commitments
• Business and personal travel coordination, including complex itineraries, luxury bookings, upgrades, and last-minute changes
• Email and communication triage: surfacing what matters, filtering what doesn't
• Project tracking and task management across multiple tools and workstreams
• Research, vendor coordination, and special projects as needed
• Investor, partner, and high-profile relationship coordination, including CRM, LP tracking, follow-ups, gifting, and professional outreach
• Podcast and content schedule coordination
• Customer service resolution, online purchasing, sourcing, and negotiation support
• Personal logistics, household coordination, wellness logistics, and occasional family travel or event support

Benefits

• Work from anywhere
• Flexible schedule and time off — no micromanaging
• Direct collaboration with the Founder
• Access to top-tier AI tools (Claude, 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