Executive Assistant (EA) Virtual Full Time NEW

Trolley is a rapidly expanding creative operations firm specializing in delivering high-impact digital and marketing solutions for high-profile clients. Our mission is to craft compelling content that enhances brand visibility, drives engagement, and accelerates business growth. We operate as a fully integrated team, combining strategic planning, innovative design, production excellence, and performance analysis to achieve world-class results. Our culture is built on a Founder Mode mindset, emphasizing ownership, strategic thinking, rapid execution, and high-trust collaboration. We foster an environment where initiative, resourcefulness, and clear communication are valued, and where team members are encouraged to think entrepreneurially and leverage cutting-edge tools such as AI to optimize workflows.

About The Role

We are seeking an elite-level Executive Assistant (EA) to support our CEO and Managing Partner remotely, with a focus on high-level executive support within North or South America, aligning with PST or EST time zones. This full-time role offers flexibility, including occasional evening and weekend support, to ensure seamless operation of both professional and personal responsibilities. The ideal candidate is proactive, decisive, and capable of managing high-stakes relationships and complex workflows with precision. This role is not merely supportive but strategic, requiring ownership of responsibilities, anticipation of needs, and execution at an elite level. You will serve as a trusted partner to a driven, analytical, and ambitious executive, helping to amplify efficiency, streamline communication, and facilitate strategic initiatives across the organization.

Qualifications

• Proven experience supporting C-level executives, preferably CEOs or founders
• Exceptional organizational and time management skills
• Strong negotiation skills, especially in travel, luxury bookings, and vendor relations
• Excellent communication skills, both written and verbal
• High proficiency with CRM systems, calendar management tools, and project management software
• Ability to handle complex international travel arrangements and last-minute changes
• Demonstrated ability to manage high-profile relationships with discretion and professionalism
• Self-regulated, composed under pressure, and skilled in de-escalation techniques
• Strong research and problem-solving skills
• Experience in luxury lifestyle management, personal scheduling, and household logistics is a plus
• Tech-savvy with the ability to leverage AI and automation tools to enhance productivity
• Aligned with a growth mindset and eager to contribute at a high level within a fast-paced environment

Responsibilities

• Book and negotiate elite travel arrangements, including flights, hotels, dining, and exclusive perks, ensuring VIP-level treatment and seamless itineraries
• Manage and optimize the executive’s calendar, proactively resolving conflicts and aligning commitments with strategic priorities
• Handle all customer service issues related to luxury shopping, tech purchases, and vendor interactions, securing the best deals and rare items
• Maintain high-stakes relationships with investors, advisors, legal partners, and external vendors through CRM management and strategic follow-ups
• Coordinate personal and household logistics, including scheduling medical appointments, managing household vendors, and planning family events and vacations
• Act as a gatekeeper and trusted point of contact for key stakeholders, ensuring efficient communication and follow-through
• Oversee professional outreach, strategic gifting, and investor relations activities to strengthen relationships and foster long-term engagement
• Standardize workflows, automate repetitive tasks, and export best practices across the organization to improve operational efficiency
• Identify operational gaps and implement solutions to streamline processes and eliminate inefficiencies
• Support strategic initiatives by managing high-value relationships and providing research and analysis to inform decision-making

Benefits

• Competitive salary commensurate with experience
• Flexible remote work environment with a focus on work-life balance
• Opportunity to work closely with high-profile clients and industry leaders
• Professional development opportunities, including training in new tools and methodologies
• Inclusive and collaborative team culture that values innovation and initiative
• Health and wellness stipends or benefits (if applicable)
• Generous PTO and leave policies to support personal and family needs

Equal Opportunity

We are an equal opportunity employer committed to fostering an inclusive environment for all employees. We celebrate diversity and are dedicated to providing a work environment free from discrimination or harassment of any kind. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. We believe that diverse perspectives and backgrounds drive innovation and success, and we welcome applicants from all walks of life to apply.