Executive Assistant

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, Not Task-Minded. You think in workflows, not just to-do lists. You understand how your work fits into the broader operating system and you help maintain and improve it.

Executive Presence and Emotional Intelligence. This role has direct visibility to LPs, partners, founders, clients, and high-profile external contacts. Polished, structured communication is expected. You manage up and across without being coached through every interaction.

Judgment in Access and Communication. You know when to act as a gatekeeper and when to act as a facilitator. You handle sensitive information carefully, use sound judgment, and communicate with polish and discretion.

Growth-Motivated and Mission-Connected. You find meaning in the work and consistently deliver. If you don't see the personal growth and long-term benefit in operating at this level, this role is not for you.

What You'll Own

• 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

What We Need From You

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.

How You Do the Job & Why

At the core of this role is a simple expectation: play to win, not to avoid mistakes.

Phase 1: Core Deliverables & Mindset (0–9 months)

You will be exceptional in this role if you:

• 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

Phase 2: Mastery & Expansion (9–12 months)

You will grow into:

• 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

What This Role Is Not

This is not a role for someone who:

• Defaults to waiting for direction before acting
• Needs frequent check-ins or validation to stay on track
• Has only surface-level AI experience
• Expects a structured onboarding or training program
• Struggles with direct, fast-paced communication
• Treats remote work as an invitation to be informal or inaccessible

What to Expect: Our Application Process

We respect your time and aim for clarity, so here's how it works:

• Apply through ClickUp
• Complete a short assignment via TestGorilla
• Interview with Recruitment & Ops Coordinator
• Second interview or role assessment
• Final interview with Founder & CEO

Steps may vary slightly depending on the role — we'll guide you through it.

Submit your application here: https://forms.clickup.com/9017085020/f/8cqbk2w-104517/7SLQABAR8AAA2TAH91 Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed.

About Us

Who We Are

Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth.

AI Mindset & Continuous Innovation

We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. At Trolley, AI is part of everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement.

We Operate Under Founder Mode

Trolley operates on a Founder Mode mindset — focused on ownership, strategic thinking, and fast execution. We seek proactive, entrepreneurial thinkers who use AI to optimize work. Founder Mode emphasizes high-trust, collaborative teams where contribution outweighs control.

Benefits at Trolley

At Trolley, we believe in building a company that works for you — not the other way around. That means freedom, tools, and culture that support both your creativity and your execution. We offer:

• 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

Be Part of the Future of Work

Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.