Executive Assistant

Core Responsibilities

• Manage and structure calendars around strategic priorities and ensure leaders are fully prepared for all meetings.
• Defines and enforces calendar rules aligned to leader priorities. Actively declines or reshapes low-value meetings.
• Pre-reads and agendas prepared for 100% of meetings.
• Build systems and workflows that improve consistency while tracking deadlines and CRM records.
• Maintains a single source of truth for all projects. Weekly reporting cadence with status, risks, and next actions. Zero missed deadlines without proactive escalation.
• Oversee invoicing, billing, and expense tracking with high levels of accuracy. Monthly close checklist completed on time. Clean categorization of expenses with audit-ready records. Tracks budget vs actuals for key categories.
• Manage personal logistics with discretion, resolving friction points before they escalate. Personal logistics are planned 2–4 weeks ahead. Travel itineraries with contingencies. Proactive reminders for key personal commitments.

The Impact

• Focus & Time Freedom: Leaders regain meaningful time for strategic priorities.
• Operational Consistency: Systems and workflows run reliably with minimal breakdowns.
• Financial Clarity: Administrative and financial processes are organized and transparent.
• Life Integration: Business and personal operations run with structure and reduced friction.

TOOLS & TECHNOLOGY

Use AI-driven scheduling or documentation and project management tools (ClickUp, Asana, Notion, etc) to increase speed, improve organization, and elevate execution quality.

Logistics

• Remote (U.S. only; excluding CA, CO, MT, NJ, NY, PA)
• 1099 Contractor | Starting at $20/hour, depending on experience
• Monthly pay based on contracted hours; hours not guaranteed

WHO YOU ARE

• Proven track record with 3+ years of experience supporting high-level operations or executive leadership
• System-based thinker who takes ownership without needing detailed instruction
• Ability to operate effectively in ambiguous, fast-moving environments
• Maintains high standards for accuracy, execution, and professional communication
• Proactive executor who prefers accountability over reactive, checklist-based work

WHAT A TYPICAL WEEK MAY INCLUDE

• Managing executive calendars, coordinating meetings and travel, maintaining project workflows, preparing communications, organizing operational systems, tracking deadlines, and proactively resolving administrative friction before it impacts the business.

THIS ROLE IS NOT FOR YOU IF

• A task-based administrative assistant role limited to scheduling and inbox management without broader operational ownership
• A reactive position that waits for direction instead of anticipating needs and acting independently
• A role for someone who relies on constant instruction or detailed step-by-step guidance
• A maintenance-only role that manages tasks without improving systems, workflows, or outcomes

WHAT SUCCESS IN THIS ROLE LOOKS LIKE

• Leders experience consistent focus and time protection, with calendars structured around high-impact priorities.
• Workflows operate reliably with clear ownership and minimal breakdowns, while financial and administrative processes remain accurate and audit-ready.
• Business and personal operations run smoothly through proactive support and reduced friction.