Insurance Executive Assistant Remote Jobs (NOW HIRING)

Executive Assistant (Remote)

We are seeking high-leverage operators who bring structure, clarity, and execution consistency to fast-moving, high-performing leaders. This role is designed for individuals who possess ownership, think in systems, and anticipate needs in complex environments.

You will reduce friction, improve operational flow, and enable leaders to focus on their highest-value work. This is not a task-based role; it is a performance role.

ROLE SUMMARY

This remote Executive Assistant contractor role supports business leaders through calendar management, operational coordination, communication management, scheduling, and administrative support.

Ideal candidates have experience supporting executives in fast-paced environments and can operate independently with strong organization, discretion, and follow-through.

THE IMPACT Your effectiveness is measured by the environment you create:

• 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.

CORE RESPONSIBILITIES

• Focus & Time Protection: 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

• Operational Execution: 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

• Financial & Admin Support: 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

• Personal & Life Support: 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

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.

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.

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

Leaders 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.