Please note: Applications must be submitted in English to be considered.
Job Title: Chief of Staff (Offshore) – CEO Support
Company: Proper (and affiliated portfolio companies)
Location: Remote – Offshore (U.S. EST hours required)
Reports to: Chief Executive Officer
Engagement: Full-Time
About the Role
We are seeking a highly organized, capable, resourceful, and proactive Chief of Staff (Offshore) to directly support the CEO across his multiple companies — both personally and professionally. This is a unique hybrid role that blends the precision and reliability of an Executive Assistant with the strategic thinking, judgment, and relationship-building strengths of a true Chief of Staff.
You will become the CEO’s strategic partner, trusted point of contact, and operational anchor, ensuring time, priorities, and communication are managed with clarity and consistency. The ideal candidate is someone who thrives on solving problems, bringing order to complexity, and acting as the connective tissue across a fast-paced organization.
This role requires excellent English, a neutral/no detectable accent, strong emotional intelligence, and the ability to think several steps ahead.
Key Responsibilities
CEO Support & Time Management
- Own and manage the CEO’s calendar end-to-end across multiple companies, including scheduling meetings, teams, and vendors with many parties.
- Proactively identify, troubleshoot, and resolve scheduling conflicts with sound judgment and clear communication.
- Book and manage all travel and be available outside of business hours to resolve travel related issues.
- Anticipate needs, prioritize obligations, and ensure the CEO is prepared for all meetings and commitments.
- Serve as the gatekeeper for time, information, and inbound requests.
- Confidentially manage inbox, save contacts, and flag high priority emails to CEO.
Strategic Coordination & Communication
- Ensure alignment, follow-through, and clarity on priorities.
- Provide executive-level support for meetings, including agendas, preparation materials, and post-meeting actions.
- Draft professional communications, memos, and updates to the Board and other executives.
- Maintain confidentiality and handle sensitive information with discretion.
Operations & Cross-Company Support
- Support workflows across the CEO’s portfolio of businesses, helping to streamline processes and improve communication.
- Partner with leadership teams to ensure priorities are understood, tracked, and delivered on time.
- Assist with light project management, follow-ups, and operational tasks to keep initiatives moving.
- Serve as a primary point of contact for internal and external stakeholders when the CEO is unavailable.
Professional & Personal Support
- Coordinate personal commitments, travel logistics, reservations, and household administrative needs as requested.
- Keep the CEO’s world organized, structured, and free of administrative bottlenecks.
Requirements
Qualifications & Experience
- 15+ years of experience supporting a senior executive (Chief of Staff, Senior EA, Executive Operations, or similar).
- Excellent verbal and written English with little detectable accent.
- Proven ability to manage complex calendars across multiple businesses or stakeholders.
- Strong judgment, discretion, and emotional intelligence.
- Strategic thinker with the ability to anticipate issues and offer thoughtful solutions.
- Highly organized and detail-oriented, with exceptional follow-through.
- Comfortable working in a fast-paced, dynamic environment with shifting priorities.
- Ability to work independently, make decisions, and maintain a calm, solutions-oriented approach.
- Reliable internet connection and dedicated workspace suitable for confidential work.
- Availability during U.S. Eastern Standard Time business hours is required and availability before or after business hours as needed
Who You Are
- Someone who enjoys being the CEO’s “right hand,” creating structure and enabling high performance.
- A connector who builds strong relationships across teams and keeps information flowing.
- A calm, confident communicator who navigates complex situations with professionalism.
- A proactive, self-directed partner who identifies needs before they arise.
- Someone who goes above and beyond and understands that work hours are fluid — when something must get done, you get it done.
- Someone who takes pride in being dependable, thoughtful, and two steps ahead.
Benefits
What We Offer
- Competitive offshore compensation aligned with experience and skill level.
- An exciting, dynamic work environment supporting the CEO of multiple fast-growing companies.
- Significant responsibility and impact, acting as a key partner and connector across the organization.
- The opportunity to grow into a highly trusted, strategic role with visibility across leadership teams.
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.
