Personal Assistant to CEO

Executive Assistant / Life Manager (Founder's Office)

Location: Washington, DC (Hybrid / Flexible Local Presence Required)
Position: Executive Assistant | Life Manager | Personal & Operations Support
Type: Full-Time | 1099 Contractor (with potential for long-term engagement)
Compensation: $50,000 – $60,000 annually (DOE) + performance-based growth potential

About the Employer

Tayvon Jackson is a high-profile author, financial advisor, and former Division 1 basketball standout based in the DMV area. As the founder of New Perspective Financial Solutions and a contributor to Forbes and CBS’s Great Day Washington, Tayvon manages a diverse portfolio including multiple companies, a basketball team, and various real estate properties.

We are seeking a high-energy, "high-drive" Life Manager to act as the central hub for Tayvon and his fiancée’s personal and professional lives. This is a role for an operator who thrives in a fast-paced environment and is ready to own the day-to-day execution of a multifaceted lifestyle.

About the Role

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.

Key Responsibilities

Personal & Household Management

• 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

Financial & Administrative Organization

• 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

✈️ Travel & Lifestyle Coordination

• 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

Executive Support & Communication

• 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

Scheduling & Calendar Management

• Maintain structured calendars for executive and partner
• Coordinate meetings, personal commitments, and business obligations
• Anticipate scheduling conflicts and proactively resolve them

Relationship & Personal Coordination

• 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

Requirements

⚙️ What We’re Looking For

• 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

️ Tools & Systems (Preferred but Not Required)

• 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

Benefits

Compensation & Contract

• $50,000 – $60,000 annually (based on experience)
• 1099 Independent Contractor arrangement
• 30-day probation period
• Opportunity for long-term growth based on performance

Why This Role Is Exciting

This is not a traditional assistant role.

You will be the operational backbone of a high-growth entrepreneur’s personal and business life, managing everything from household logistics to financial organization and travel coordination.

If you thrive in ownership, fast execution, and high-impact support roles, this position offers autonomy, trust, and real responsibility.