Personal/Executive Assistant to CEO (High-Level / Proactive Role)

Overview

This is not a traditional assistant role.

We are seeking a high-level Personal Assistant/Executive Assistant to serve as the right-hand to the CEO. This individual must be proactive, detail-oriented, and able to think ahead without direction.

The right candidate anticipates needs, takes ownership, and ensures both personal and professional priorities run seamlessly.

What Success Looks Like

• Problems are solved before they reach the CEO
• The CEO is always prepared and never rushed
• Details are handled without follow-up
• The assistant operates independently and brings solutions

Key Responsibilities

• Own and manage the CEO calendar (business + personal integration)
• Anticipate conflicts and resolve proactively
• Prepare the CEO for meetings, travel, and events
• Coordinate travel, logistics, and event planning
• Manage vendors and follow up without reminders
• Oversee household and personal operations
• Act as a gatekeeper and protect the CEO's time

Required Experience (NON-NEGOTIABLE)

• 5+ years supporting a CEO, founder, or senior executive
• Experience managing complex schedules independently
• Proven examples of anticipating needs without direction
• Experience in fast-paced or high-demand environments

Important – Read Before Applying

This role is NOT for someone who:

• Needs step-by-step direction
• Waits to be told what to do
• Has only administrative or organizing experience

Application Requirement (MANDATORY)

Include responses to:

• Tell me about a time you anticipated a need before being asked.
• How do you ensure nothing is missed when managing multiple priorities?

Applications without responses will not be considered.

Job Type: Full-time

Pay: $70,000.00 - $90,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Paid time off
• Professional development assistance
• Tuition reimbursement
• Vision insurance

Ability to Commute:

• Upper Marlboro, MD 20772 (Required)

Work Location: In person