Chief of Staff

Chief of Staff Position Overview

An accomplished entrepreneur, investor, author, and philanthropist is seeking a highly capable Chief of Staff to serve as a trusted partner across a broad range of business, personal, philanthropic, and family office initiatives. This role is designed for an exceptionally bright, intellectually curious, and highly organized professional who thrives in complex environments and enjoys bringing structure, accountability, and momentum to a wide variety of projects.

Acting as an extension of the Principal, the Chief of Staff will help organize, advance, coordinate, and improve dozens of concurrent initiatives while ensuring important priorities remain on track. The ideal candidate combines strong business acumen with exceptional organizational skills and a continuous improvement mindset. They are equally comfortable managing high-level strategic initiatives and rolling up their sleeves to execute day-to-day projects.

They are technology‑forward, naturally resourceful, highly discreet, and energized by solving problems, creating systems, and helping ambitious ideas become reality. The Principal is seeking a true force multiplier who can not only manage complexity and drive execution, but also contribute ideas, judgment, and strategic thinking that improve outcomes across a broad range of initiatives. This role will have visibility into highly confidential personal, financial, legal, and family matters and therefore requires the highest levels of professionalism, discretion, judgment, and trustworthiness.

• Serve as a central coordinator across the Principal’s business, investment, philanthropic, family office, and personal initiatives
• Develop and maintain a comprehensive system for tracking projects, priorities, deadlines, decisions, and action items
• Establish project management frameworks that improve accountability, communication, and execution across multiple stakeholders
• Drive projects forward by independently advancing key initiatives while coordinating with internal teams, advisors, consultants, and external partners
• Identify obstacles, propose solutions, and ensure critical initiatives continue progressing
• Prepare status reports, dashboards, and summaries to provide visibility into project progress and key decisions
• Partner with the Principal to evaluate opportunities, refine ideas, and translate strategic priorities into actionable implementation plans

• Partner with the Principal to develop and manage annual and quarterly goals, priorities, and objectives
• Build and maintain OKR and performance tracking systems across various initiatives and entities
• Establish meaningful metrics and reporting mechanisms to measure progress and outcomes
• Ensure accountability by tracking commitments, deadlines, and follow‑up items across multiple stakeholders

• Support initiatives involving business operations, investments, estate planning, tax matters, legal matters, philanthropy, and family office projects
• Coordinate information flow between the Principal and external advisors, including attorneys, accountants, investment professionals, consultants, and other trusted partners
• Organize complex information and ensure key documents, decisions, and project histories are properly maintained
• Serve as a knowledgeable resource across ongoing projects and initiatives, helping preserve institutional knowledge and continuity

• Conduct research, develop recommendations, and provide thoughtful insights to support informed decision‑making and strategic priorities
• Evaluate existing processes and identify opportunities for increased efficiency, automation, and effectiveness
• Leverage modern technology, including AI tools and emerging platforms, to improve workflows and organizational effectiveness
• Design and implement systems that reduce complexity and improve execution
• Continuously seek opportunities to optimize how information is captured, organized, and utilized

• Attend meetings…