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Job Closed

Executive Assistant

  • Source: LinkedIn
  • Trolley AI
  • Remote
  • East Toledo
  • Full-Time
  • Senior

Job Description

Job Details

Location: Remote (Must be based in North or South America and work within PST or EST)

Hours: Full-time, with flexibility for occasional evening and weekend support

PLEASE READ BEFORE APPLYING

We are only reviewing candidates who submit their application through this link: https://forms.clickup.com/9017085020/f/8cqbk2w-104517/7SLQABAR8AAA2TAH91 Applications submitted elsewhere will not be considered.

Who We’re Looking For

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.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.

Who You’ll Work With

About The CEO The executive you will support is ambitious, analytical, independent, and highly driven. She values efficiency, strategic thinking, and people who take initiative. She moves fast, gives direct feedback, and expects high standards. The right EA for this role thrives next to a strong-willed, high-energy executive, understands how to complement that leadership style, and brings sound judgment, discretion, and execution strength to the table. This role reports directly to the CEO and Managing Partner and works closely with the Senior Bookkeeper, investment team, legal partners, operations, marketing, and key external vendors and teams to manage both professional and personal responsibilities. We are a fast-moving, high-performance venture that values clarity, execution, and results. The expectation is that you come in ready to contribute at a high level, align quickly, and deliver without hesitation.

Who Thrives Here

This is a Founder Mode environment. Before you apply, make sure these resonate — they aren’t aspirational values, they’re baseline expectations.

Extreme Ownership. You connect your individual performance to company outcomes and feel the weight of a missed target, not just your manager. You don’t require reminders, you don’t over-promise, and you self-report when timelines shift before the deadline passes.

Autonomous Execution. You are motivated by completion and outcomes, not by the type of work or how interesting a project is. You finish what you start, even when the work becomes tedious or blocked. You show up with a plan.

Proactive Communication. You surface blockers early and renegotiate timelines before they are missed — not after. Going quiet when stuck is a trust-breaker in this environment. You flag constraints, ask for clarity, and keep stakeholders informed without being asked.

AI-First Mindset. You use AI tools as infrastructure — not optional extras. Claude, Perplexity, ChatGPT, and ClickUp Brain are part of your daily toolkit. Whether it’s drafting communications, research, workflow support, travel planning, or operational execution, AI-assisted work is the standard here. AI competency will be tested during the hiring process. This aligns with the recent discussion that hires should be more AI-native and evaluated with AI-specific testing.

Resilient Under Direct Feedback. The founder is direct. The pace is fast. Feedback is frequent and specific. You can receive critical feedback as useful information, course-correct quickly, and keep moving.

**Systems-Minded, N…

Skills

  • mode
  • resonate
  • claude-by-anthropic
  • perplexity
  • chatgpt
  • ClickUp
  • fullcalendar
  • ups
  • trolley-payouts
  • google-workspace
  • workspace
  • slack
  • 1password
  • testgorilla
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