Virtual Executive Assistant to the CEO

Role Description

The Virtual Executive Assistant will serve as a critical right-hand to the CEO, managing schedules, coordinating travel, and supporting day-to-day priorities across multiple companies. This role requires exceptional organizational skills, the ability to handle ambiguity, and the flexibility to respond to urgent needs outside of standard hours when travel or other high-priority matters arise.

• Manage complex scheduling, including internal and external meetings, calls, and events across multiple time zones.
• Coordinate travel arrangements (domestic and international), including flights, accommodations, and ground transportation.
• Support event planning for leadership meetings, board sessions, and special projects.
• Anticipate the CEO’s needs and proactively resolve issues before they arise.
• Provide day-to-day administrative support, including email management, document preparation, and follow-ups.
• Maintain strict confidentiality while managing sensitive company and personal information.
• Serve as a point of contact between the CEO and internal/external stakeholders.
• Adapt seamlessly between multiple companies and business priorities, handling shifting demands with professionalism.
• Be available during evenings or weekends when urgent CEO support is required.
• Utilize technology and AI tools to improve efficiency and streamline workflows.

Qualifications

• 10+ years of experience as an Executive Assistant, supporting C-level executives in a fast-paced environment.
• Fluent in English, with excellent written and verbal communication skills and very neutral accent.
• Proven ability to manage complex schedules, travel, and events with precision.
• Highly proactive and detail-oriented, with strong organizational and problem-solving skills.
• Tech-savvy and comfortable adopting new systems, tools, and AI solutions to increase productivity.
• Strong discretion and judgment when handling sensitive information.
• Ability to work EST hours consistently, with flexibility for urgent needs outside of standard business hours.
• Comfort working across multiple companies and priorities, with the ability to navigate ambiguity and change.

Requirements

• Hourly Rate: $12-$18/hour based on experience ($2,400-$3,000/month)

Benefits

• This is an exciting time to be part of Proper.
• You’ll play a vital role in enabling our CEO to focus on strategic priorities, while gaining exposure to multiple fast-growing companies.
• We value reliability, initiative, and professionalism — and are looking for someone who thrives under pressure, embraces technology, and is motivated by impact.