Executive Assistant

Trolley

17h • Remote

About The Position

We are looking for an operator — someone who thinks in systems, moves before being asked, and uses AI 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. This isn't a passive support role. This is about owning responsibilities, amplifying efficiency, and ensuring the executive's world runs seamlessly, both professionally and personally. You'll manage high-profile relationships, optimize workflows, oversee high-stakes travel and logistics, and eliminate distractions so the CEO can focus on big-picture strategy and execution. 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.

Requirements

• AI-native fluency — demonstrated, not described. You actively use AI tools in your day-to-day work. You have custom instructions configured, you've built workflows or automations, and you can show your setup on request. Using ChatGPT to proofread emails doesn't meet the bar.
• Zero-onboarding readiness. There is no long training period. You are expected to orient yourself quickly, ask smart questions, and contribute from Day 1.
• Proactive, independent execution. You don't wait to be asked. You notice what needs to happen, you handle it, and you report back. The CEO should rarely need to follow up on something she's handed off to you.
• Operator-level systems thinking. You don't just complete tasks — you build the infrastructure so those tasks run more smoothly next time. You spot inefficiencies, create structure, and continuously improve the way things work.
• Professional presence, always. This role is fully remote and you will be in direct contact with the CEO, clients, and stakeholders regularly. How you communicate, how you show up on video, and how you represent the company reflects directly on the CEO and Trolley.
• Calm under pressure. Priorities shift fast. The CEO moves fast. You absorb urgency without becoming reactive, and you stay focused when things change unexpectedly.
• Tech fluency across the stack. You're comfortable in Google Workspace, Slack, ClickUp, 1Password, and Claude. New tools don't intimidate you — you figure them out and move on.
• 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.
• 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.

Nice To Haves

• Operate in close alignment with the CEO's vision and decision-making framework
• Remove from the CEO's plate the responsibilities that do not require her direct input
• Manage high-value relationships with consistency, polish, and discretion
• Anticipate problems before they happen and think through them strategically
• Over-communicate execution status and maintain clear tracking across priorities
• Provide strong execution visibility, including end-of-day recap updates when required
• Use access to information intelligently and maintain sound judgment around sensitive details
• Stay composed under stress and handle shifting priorities without losing momentum
• Use AI tools daily to accelerate research, communication, and decision support
• Maintain high accuracy and avoid sloppy execution, incomplete reports, or dropped details
• Building and maintaining high-value relationship and talent pipelines where needed
• Delegating, automating, and systematizing repeatable work
• Standardizing workflows and exporting best practices across the organization
• Owning a core business function or operating domain
• Acting as a proxy for the executive in selected relationship-driven interactions
• Solving inefficiencies others overlook

Responsibilities

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed