Executive Assistant

About the Role

We are searching for highly effective operators who bring order, transparency, and reliable execution to quick-paced, top-performing leaders. This role emphasizes ownership, systems thinking, and proactive anticipation of needs in complex, dynamic settings. Rather than a task-focused position, it is a performance-driven role aimed at enhancing operational flow and enabling leaders to focus on their highest priorities.

Role Summary

This remote Executive Assistant contractor position supports business leaders by managing calendars, coordinating operations, handling communications, scheduling meetings, and providing broad administrative assistance. Ideal candidates have experience assisting executives in fast-moving environments and can work autonomously with strong organizational skills, discretion, and follow-through.

Key Impact Areas

• Focus & Time Freedom: Helping leaders reclaim valuable time for strategic tasks.
• Operational Consistency: Ensuring systems and workflows function dependably with minimal disruptions.
• Financial Clarity: Keeping administrative and financial tasks organized and transparent.
• Life Integration: Providing structured business and personal operations with minimal friction.

Core Responsibilities

• Protecting Focus and Time: Structuring and managing calendars in line with strategic priorities by enforcing calendar policies, reshaping or declining low-value meetings, and preparing detailed agendas and pre-reads for every meeting.
• Operational Execution: Designing and maintaining consistent systems and workflows, tracking deadlines and CRM data, maintaining a unified source of truth for all projects, producing weekly reports on status, risks, and next steps, and ensuring no deadlines are missed without prior escalation.
• Financial and Administrative Support: Managing invoicing, billing, and expense tracking with accuracy. Completing monthly close checklists punctually, maintaining well-organized and audit-ready expense records, and monitoring budgets against actual expenses.
• Personal and Life Support: Handling personal logistics discretely, resolving potential issues proactively, planning personal schedules 2–4 weeks ahead, organizing travel with backups, and sending timely alerts for critical personal commitments.

Typical Weekly Activities

Tasks include calendar management, coordinating meetings and travel, maintaining project workflows, preparing communications, organizing operational processes, tracking important deadlines, and anticipating and resolving administrative challenges before they affect business operations.

Tools & Technology

Utilize AI-powered scheduling and documentation tools, as well as project management platforms like ClickUp, Asana, and Notion to enhance efficiency, organization, and the quality of execution.

Logistics

• Remote work within the U.S., excluding California, Colorado, Montana, New Jersey, New York, and Pennsylvania.
• Contract position (1099) starting at $20 per hour, adjustable based on experience.
• Monthly payment correlates to contracted hours; hours are not guaranteed.

Candidate Profile

• At least 3 years experience supporting senior executives or complex operational leadership.
• Systems-oriented thinker who independently manages responsibilities without detailed instructions.
• Capable of thriving in ambiguous, fast-moving environments.
• Maintains high accuracy, execution standards, and professional communication.
• Proactive and accountable; prefers ownership over reactive checklist-driven work.

Who This Role Is Not For

• Individuals seeking purely task-based administrative assistant duties focused only on scheduling or inbox management.
• Professionals who rely on frequent direction instead of anticipating and acting independently.
• Those needing extensive step-by-step instructions to perform daily activities.
• Applicants preferring maintenance work without improving systems, workflows, or overall outcomes.

Success Indicators

Success is defined by leaders consistently experiencing enhanced focus and time protection with calendars reflecting high-impact priorities, stable workflows with clear ownership, accurate and audit-ready financial and administrative processes, and seamless business and personal operations through proactive and friction-reducing support.