Chief of Staff

Vannin Chief of Staff has been retained by a significant multi-entity Family Office based in Boston, MA, to identify a Chief of Staff.

Our client is led by two highly accomplished principals with deep roots in K–12 education, civic history, and philanthropic giving. The lead principal successfully scaled a premier national EdTech company over 17 years and now serves as its Chairman while leading across multiple mission-driven civic and philanthropic organizations. The other Principal is deeply ingrained in working with first-generation college students throughout Boston public high schools. Together, the principals are actively growing their philanthropic footprint, engaged in public history initiatives, and building an AI-assisted archiving venture.

This is a rare opportunity to step into a role that our client characterizes as "potentially the best job in the world" for the right individual.

The Chief of Staff serves as the operational and connective layer across the principals' full portfolio of priorities. This is neither an administrative support role nor a purely strategic one. The right person moves fluidly across the full spectrum, from coordinating high-visibility civic initiatives and board relationships to managing property logistics and vendor oversight, without ego and without waiting to be asked.

This is a full-time, exempt hybrid position based primarily in-person in Boston, MA, with occasional travel to secondary domestic properties.

Responsibilities

Project and Civic Initiative Leadership

• Drive end-to-end execution of complex civic, philanthropic, and public history projects, including a statewide initiative involving media, government, and sponsor coordination
• Support the growth and operations of a nonprofit financial aid counseling program serving first-generation college students
• Coordinate board and committee engagement across civic and philanthropic organizations, including preparation and follow-up
• Provide operational support to a co-founded AI venture focused on historical document archiving

Family Office and Property Operations

• Manage property logistics, vendor coordination, and maintenance across multiple residences, including lease review, insurance, and renovation oversight
• Serve as the primary operational liaison across tax, wealth management, and accounting partners, ensuring the principals' attention is reserved for decisions that genuinely require it
• Support the setup and ongoing operations of the principal's new Boston office space

Communications and External Relations

• Act as a trusted proxy with PR partners, reporters, and external stakeholders, with increasing ownership of media relationships over time
• Draft correspondence and produce polished materials for meetings, board engagements, speaking opportunities, and philanthropic projects

Minimum Qualifications

• Bachelor's degree required; background in education, history, public policy, or a related field is a strong plus
• 5 or more years of experience in a Chief of Staff, operations, project management, or comparable role supporting a senior executive or principal
• Proven ability to manage multiple projects and stakeholders simultaneously with strong organizational systems and follow-through
• Exceptional written and verbal communication skills; comfortable engaging with government officials, nonprofit leaders, media contacts, and high-profile external stakeholders
• Unimpeachable discretion, especially around confidential financial matters and anonymous philanthropic giving
• Based in or willing to relocate to Boston, MA

Preferred Qualifications

• Genuine interest in education, public history, or civic engagement
• Experience in a family office, nonprofit, or mission-driven organization; familiarity with wealth management or trust structures is a plus
• Background in technology, EdTech, or commercial operations
• Confident and direct communicator who can push back thoughtfully when needed
• Calm, grounded, and highly organized; able to hold complexity without becoming reactive

Compensation and Benefits

• Salary: $180,000–$220,000 USD, commensurate with experience
• Full-time compensation and benefits with genuine flexibility in hours and schedule
• Comprehensive, premier-level medical coverage
• Deep investment in a long-term working relationship
• Autonomy, trust, and the opportunity to grow into a true proxy role over time

What to Expect from Our Selection Process:

We are seeking a trusted partner who can move seamlessly between strategy and execution. Our process is designed to assess the whole candidate and find a mutual match. The process includes:

1. Vannin Chief of Staff Predictive Index Assessment*
2. Vannin Chief of Staff Screening: 15 min phone interview & 30 min video interview
3. 30-min in-person with each of the Principals
4. Take-home case study
5. Case study presentation
6. In-person session with Principals

*Note: Vannin Chief of Staff partners with The Predictive Index to align work styles with the role. All applicants complete this quick, two-question, five-minute assessment—no right or wrong answers—and receive a profile readout.

--> Please take the assessment as you complete your application.

Our client is committed to building a team that reflects the communities it serves. They welcome candidates of all backgrounds and believe that diverse perspectives strengthen their work. They embrace diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental abilities, and all other characteristics protected by law.