Executive Assistant

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

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

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

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.

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.

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.

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.

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.