Job Title: Virtual Executive Assistant to the CEO
Location: Offshore (Remote) – Must work EST hours (ideally located in EST time zone)
Reports to: Chief Executive Officer
Experience Required: 8+ years in a high-demand Executive Assistant or similar role
About Proper
Proper is leading a new era in property management through technology, innovation, and growth. With an expanding portfolio and multiple companies under the CEO’s leadership, this is an exciting time to join our team. We are looking for a highly skilled, proactive, and reliable Virtual Executive Assistant to support our CEO in a dynamic and fast-paced environment.
Position Overview
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.
Key Responsibilities
- 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.
Requirements
Qualifications
- 8+ 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.
- 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.
Benefits
Hourly Rate: $12-$18/hour based on experience
Why Join Proper?
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.
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What We Do
Proper is transforming the multifamily property management industry through a nationwide rollup model—leveraging AI, process innovation, and a strong focus on employee and resident experience.
We streamline building and back-office operations, drive higher NOI for property owners, and elevate the end-to-end experience for building owners, employees and residents alike. With multiple completed transactions and more in the pipeline, Proper acquires management companies with assets of all sizes, geographic locations, and asset classes.
Join us in shaping the future of property management.
