Vannin Chief of Staff has been retained by a significant multi-entity Family Office to identify a Chief of Staff.

Our client is a Boston-based Family Office led by two highly accomplished principals with a distinguished, multi-sector track record. One Principal brings extensive leadership experience, including successfully scaling a premier national EdTech company over 17 years, and holding CEO positions across K-12 education and mission-driven organizations. Collectively, their deep engagement spans civic history, philanthropy, and entrepreneurship, encompassing board service on major civic and philanthropic institutions (including prominent historical societies and presidential centers), experience in the investment sector, and the co-founding of an AI venture focused on historical archiving.

This crucial role is designed for a detail-oriented operator who moves fluidly from high-level project coordination to ground-level execution, brings genuine commitment to the education and civic mission, and thrives in a high-trust, low-ego environment built for the long term.

Job Description

The Chief of Staff functions as the operational and connective layer across the principals’ full portfolio. This role reports directly to both principals and is entrusted with the complete scope of execution, from coordinating civic initiatives and board relationships to managing property logistics and vendor oversight, demanding both strong initiative and complete ownership over all tasks.

The scope is deliberately broad, reflecting the principals' deep engagement across Family Office management, philanthropy, civic leadership, board service, and an early-stage company. The successful candidate will absorb complexity across all these areas, anticipating needs and executing responsibilities with a collaborative, results-oriented approach. This is neither an administrative support role nor a purely strategic position; the ideal candidate moves seamlessly across the full spectrum of execution and strategy.

The executive must be exceptionally organized, maintain composure under ambiguity, and possess the confidence and judgment necessary to provide thoughtful pushback. The highest level of discretion is required, particularly concerning confidential financial matters and anonymous philanthropic giving. While not a prerequisite, candidates with a genuine affinity for education, history, or civic life will find the mission of this work especially compelling.

This is a hybrid, full-time role with built-in flexibility, based primarily in Boston, MA.

Responsibilities

• Project and Civic Initiative Coordination:

  • Drive end-to-end execution of civic, philanthropic, and public history projects, including a statewide initiative that includes media, sponsor, and government stakeholder coordination

  • Implement a structure that allows the nonprofit financial aid counseling work to continue to scale, including tracking and follow-up systems, and project management for upcoming key initiatives

  • Support board and committee engagement across civic and philanthropic organizations, including preparation and follow-up

  • Provide operational support to the startup co-founded by the principal, as needed

• Family Office and Property Operations:

  • Oversee property logistics, vendor coordination, and maintenance across multiple residences, including lease review, insurance, and renovation oversight

  • Serve as the primary financial liaison, coordinating with tax, wealth management, and accounting partners to streamline bill pay and anomaly flagging, ensuring principal focus is reserved for mission-critical decisions.

  • Support the setup and ongoing operations of the principals’ new office space, including facilities logistics and tenant coordination

• Communications and External Relations:

  • Direct external relations, acting as the trusted proxy with reporters and PR partners, and strategically increasing ownership of media relationships to bring them in-house over time

  • Draft correspondence, prepare presentations, and produce polished materials for meetings, speaking engagements, and philanthropic projects

Recommended 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; polished and comfortable engaging with government officials, nonprofit leaders, media contacts, and high-profile stakeholders

• Proficient in Microsoft Office and Google Suite with the ability to produce polished decks, spreadsheets, and reports

• Based in or willing to relocate to Boston, MA; available for occasional travel to secondary domestic properties as needed

Preferred Skills & Attributes

• Mission alignment with a demonstrated affinity for education, public history, or civic engagement

• Direct experience within a Family Office, nonprofit, or high-growth, mission-driven environment; exposure to complex wealth management or trust structures is advantageous

• Confident, direct, and thoughtful communicator who is comfortable providing necessary pushback and maintaining professional boundaries

• Highly organized and disciplined operator with proven ability to maintain composure and clarity while managing complex, ambiguous situations

• Unimpeachable discretion, particularly concerning confidential and anonymous philanthropic giving and sensitive family matters

• Background in technology, EdTech, or commercial operations is highly valued given the entrepreneurial pace and scope of the principals’ portfolio

Compensation Range: $180,000–$220,000 USD annual salary, commensurate with experience

What are the Benefits of Joining Our Client’s Team?

This is an exceptional, high-trust opportunity that the client characterizes as "potentially the best job in the world" for the right individual. In exchange for full engagement and ownership across a diverse portfolio, the role provides:

• Competitive, full-time compensation and benefits, coupled with genuine flexibility in scheduling and hours

• Comprehensive, premier-level medical and benefits coverage

• A long-term commitment to professional partnership, evidenced by the retention of the principals' closest collaborators for a decade or more

• A front-row perspective on impactful civic, philanthropic, and entrepreneurial work spanning education, history, and community development

• The rare combination of full autonomy, high trust, and the trajectory to grow into a true Chief of Staff/Proxy role

What to Expect from Our Selection Process

The process includes:

1. Vannin Chief of Staff Predictive Index Behavioral Assessment
2. Vannin Chief of Staff Screening: 15 min phone interview & 30 min video interview
3. Client Interview 1: 30-min in-person with each of the Principals
4. Client Interview 2: Case study project and presentation
5. Client Interview 3: 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 here as you complete your application. 

Our client is committed to creating and maintaining a diverse and inclusive workplace where our employees can thrive and be themselves! We welcome all persons into our community. We embrace the diversity of gender, gender identity or expression, race, color, religious creed, national origin, ancestry, age, physical and mental disabilities, medical condition, genetic characteristic, sexual orientation, marital status, family care or medical leave status, military or veteran status, or perceived membership in any of these groups.