Personal Assistant to CEO

Trivium•Bethesda, MD

4d•$50,000 - $60,000•Hybrid

About The Position

We are seeking a highly organized, proactive, and resourceful Executive Assistant / Life Manager to support a fast-paced entrepreneur managing multiple businesses, real estate assets, and personal responsibilities. This is a high-trust, high-responsibility role designed for someone who thrives in managing complexity, bringing order to chaos, and creating efficiency across both personal and business operations. You will act as a central right hand, ensuring the executive’s life runs seamlessly so they can focus on business growth and strategic priorities.

Requirements

Proven experience as an Executive Assistant, Personal Assistant, or Life Manager
Highly organized with strong attention to detail
Ability to multitask across personal and business responsibilities
Comfortable working in a fast-paced, always-on environment
Strong communication skills (written and verbal)
Proactive mindset — anticipates needs before they are expressed
Ability to handle confidential and sensitive information with discretion
Must have reliable transportation and live near Washington, DC

Nice To Haves

Google Workspace (Calendar, Gmail, Sheets)
Microsoft Excel
Task management tools (Notion, Asana, Monday.com, etc.)
Experience with AI tools like ChatGPT is a plus
Basic financial tracking tools or budgeting systems

Responsibilities

Coordinate household operations including cleaning staff, meal prep services, and vendors
Ensure smooth daily home logistics for executive and partner
Manage errands, personal requests, and day-to-day coordination
Oversee pet-related scheduling and household needs
Organize and maintain overview of multiple properties and recurring bills
Track utilities, invoices, and payment schedules to ensure nothing is missed
Assist in basic financial tracking and expense organization
Maintain structured systems for personal and business obligations
Plan and manage domestic and international travel end-to-end
Provide itinerary breakdowns, cost summaries, and recommendations
Handle bookings for flights, hotels, dining, and experiences
Manage last-minute changes and travel disruptions
Monitor and filter high-volume personal and business emails
Identify priorities and provide daily/weekly email summaries
Draft responses and coordinate follow-ups when needed
Act as gatekeeper to protect executive time and focus
Maintain structured calendars for executive and partner
Coordinate meetings, personal commitments, and business obligations
Anticipate scheduling conflicts and proactively resolve them
Assist with personal gifting, reminders, and special events (birthdays, holidays)
Help coordinate personal experiences and relationship activities (dinners, surprises, etc.)
Support lifestyle organization to ensure efficiency and balance