Sr Executive Assistant Contractor

We are seeking a Senior Executive Assistant who operates with precision, judgment, and complete ownership. This role is designed for individuals who anticipate needs, think ahead, and bring structure to complex, fast-moving environments.

You will manage priorities, protect time, and ensure the executive operates with focus, clarity, and consistency. This is not a task-based role; it is a performance role.

ROLE SUMMARY

This remote Senior Executive Assistant contractor role supports senior leaders through executive calendar management, communication oversight, operational coordination, strategic planning support, and high-level administrative execution. Ideal candidates have experience supporting executives in fast-paced, high-growth environments and can operate independently with sound judgment and discretion.

THE IMPACT

Your effectiveness is measured by the environment you create:

• Executive Effectiveness: Priorities are clear, time is optimized, and decisions are made efficiently

• Professional Presence: Communication is polished, and stakeholders are consistently aligned

• Operational Discipline: Work is structured, proactive, and executed without gaps

• Sustained Capacity: The executive maintains focus and bandwidth on what matters most

CORE RESPONSIBILITIES

• Prioritization & Planning: Align executive time to the highest-value outcomes weekly. Eliminate low-value commitments.

• Communication Management: Maintain inbox at decision-ready state. Draft and respond with executive voice and accuracy.

• Operations & Execution: Ensure all priorities move forward without prompting. No missed deadlines or follow-ups.

• Capacity Enablement: identify and remove friction before it impacts execution

WHAT A TYPICAL WEEK MAY INCLUDE

Managing complex executive calendars, coordinating meetings and travel, maintaining inbox and communication flow, tracking priorities across multiple initiatives, preparing executive-ready documents, and proactively resolving operational bottlenecks before they impact execution.

TOOLS & TECHNOLOGY

• Use AI and modern tools to increase speed, improve organization, and elevate output.

LOGISTICS

• Remote (U.S. only; excluding CA, CO, MT, NJ, NY, PA)

• 1099 Contractor | Starting at $30/hour depending on experience

• Monthly pay based on contracted hours; hours not guaranteed

WHO YOU ARE

• 5+ years supporting senior executives

• Demonstrated ownership, sound judgment, and discretion

• Clear, professional communication and strong presence

• Ability to operate independently in fast-moving environments

• High level of technical adaptability

• Expertise in building and maintaining workflows in ClickUp, Asana, or Notion. Proven ability to leverage AI (e.g., ChatGPT, Claude, Otter.ai) for transcription, drafting, and process automation

• Evidence of managing a complex executive calendar with competing priorities

• Experience supporting revenue-generating or high-growth leaders

• Examples of systems built or improved (not just maintained)

• Demonstrated use of AI/tools to increase output or efficiency

THIS ROLE IS NOT FOR YOU IF

• A task-taker role that waits for direction or constant oversight

• A traditional administrative role focused only on calendars and inboxes

• A reactive support position that escalates problems instead of solving them

• A role for someone uncomfortable with ownership, judgment, or fast-moving environments

WHAT SUCCESS IN THIS ROLE LOOKS LIKE

Executive priorities remain organized and moving forward, communication stays clear and decision-ready, calendars and operations run proactively with minimal friction, and leaders feel confident their time, focus, and highest-value work are consistently protected.