Proper is hiring an Offshore Chief of Staff to the CEO. This is a hybrid role that blends Executive Assistant precision with Chief of Staff strategic thinking, requiring you to act as the CEO’s strategic partner, trusted point of contact, and operational anchor across multiple companies.
What You'll Do
- Own and manage the CEO’s calendar end-to-end across multiple companies, including scheduling meetings, teams, and vendors.
- 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.
- 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.
- 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.
- Coordinate personal commitments, travel logistics, reservations, and household administrative needs as requested.
What We're Looking For
- 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.
Team & Environment
You will report directly to the Chief Executive Officer.
Benefits & Compensation
- 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.
Work Mode
This is a remote – offshore position.
