Freelance - AI Enabled Executive Assistant - Remote

The People Group is a fractional talent and support business focused on connecting exceptional professionals with growing founders and leadership teams. We pride ourselves on quality, consistency, and long term partnerships. We believe that when our contractors are treated with respect, clarity, and fairness, that standard naturally carries through to the clients they support. Clear expectations, open communication, and mutual accountability are central to how we work. We are currently seeking a highly skilled and tech savvy Executive Assistant with strong AI and automation experience to join our talent pool on a freelance basis. In this role, you will support founders and senior leaders by managing operations, optimizing workflows, and leveraging AI tools to drive efficiency and productivity. This is a fully remote, fractional role supporting clients across multiple time zones, ideal for someone who is proactive, detail oriented, and comfortable working independently in a fast paced environment. Please note: We are currently talent pooling for future client opportunities. Placement and engagement availability will depend on your skill set, experience and the availability of suitable client opportunities. Joining our talent network does not guarantee immediate placement. Responsibilities Manage calendars, schedule meetings and appointments for clients Coordinate travel arrangements and accommodations Prepare and edit documents, reports, and presentations Handle phone calls, emails, and other correspondence Organize and maintain files, records, and databases Assist in the preparation of meeting agendas and take minutes Collaborate with other team members to ensure efficient workflow Arrange and coordinate events and conferences Perform ad-hoc administrative tasks as needed Respond to and manage client requests, including ad hoc tasks, with professionalism and attention to detail Requirements Experience using AI tools like ChatGPT, Claude, Gemini Prompt writing and optimization Ability to automate workflows (Zapier, Make, etc.) Experience using AI for: Research Summarization Email Drafting Task Management Experience working in a fractional, freelance, or contract based role Exceptional organizational and time-management skills Excellent communication and interpersonal abilities Proficient in MS Office and Google Suite Ability to multitask and prioritize tasks effectively Strong attention to detail and accuracy High degree of professionalism and confidentiality Ability to work independently and remotely Flexible schedule and availability Demonstrated experience supporting multiple executives or clients simultaneously Experience with project management tools Familiarity with video conferencing and online collaboration tools Knowledge of office management systems and procedures Experience working with HNW individuals preferable but not essential. Experience working with Family Offices preferable but not essential. Experience working with Business Leaders preferable but not essential. Flexible with occasionally meeting clients in person if requested. Knowledgeable about emerging AI software, tools, models, and methodologies that challenge the conventional approach to executive assistance Benefits You will be working as a contractor under the The People Group company name, therefore you are not a direct employee and only work as a contractor for our business. The benefit of this structure means, all of our clients sign contracts directly with The People Group and not you as the Contractor, therefore you are protected as a remote contractor as The People Group take cares of the client service side of the function. Show more Show less