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.

Key Responsibilities

Strategic Project Management & Execution

· 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

Goal Setting, Accountability & Performance Tracking

· 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

Business, Investment & Family Office Coordination

· 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

Research, Analysis & Continuous Improvement

· 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

Communications, Meetings & Follow-Up

· Attend meetings alongside the Principal as needed

· Capture key decisions, discussion points, action items, and follow-up requirements

· Prepare meeting summaries and coordinate follow-up activities

· Assist with speeches, presentations, marketing initiatives, thought leadership efforts, and public-facing communications

· Draft correspondence, talking points, briefing materials, and presentation content

Personal & Family Support

· Assist with a variety of personal projects and administrative initiatives designed to improve the Principal's effectiveness and quality of life

· Coordinate gifting programs, relationship management efforts, and special personal initiatives

· Support travel planning and optimization efforts

· Organize and digitize information, records, contacts, and personal knowledge management systems

· Assist with personal health, wellness, and lifestyle-related initiatives

· Provide limited oversight and coordination related to residences, household projects, and select construction initiatives

Knowledge Management & Organizational History

· Develop and maintain comprehensive project records and historical documentation

· Create systems that capture the rationale, objectives, stakeholders, outcomes, and lessons learned from major initiatives

· Build and maintain project binders, knowledge repositories, and organizational archives

· Preserve institutional knowledge and ensure important information remains accessible and organized

Qualifications

Required

· Bachelor's degree required

· 5+ years of experience in a Chief of Staff, business operations, management consulting, project management, family office, entrepreneurial, or similarly complex coordination role

· Exceptional project management and organizational skills

· Strong business judgment and problem-solving abilities

· Demonstrated ability to manage multiple complex priorities simultaneously

· Excellent written and verbal communication skills

· High degree of professionalism, discretion, and emotional intelligence

· Proven ability to work independently with limited direction

· Advanced proficiency with technology, productivity tools, and project management platforms

· Strong attention to detail combined with the ability to maintain a strategic perspective

Preferred

· MBA, JD, or other advanced degree

· Experience supporting entrepreneurs, founders, executives, investors, or family office principals

· Familiarity with investment, legal, tax, estate planning, or governance-related matters

· Experience implementing AI-enabled workflows and productivity tools

· Exposure to philanthropy, nonprofit leadership, or foundation management

· Background in consulting, business operations, or strategic planning

Job Type: Full Time, Hybrid (expected on average 3 days per week in-person); office located in Boston, MA

Compensation: Annual compensation range of $300,000 - $350,000, based on experience and qualifications, with comprehensive benefits