Executive Assistant

About Pilot House Associates and the Position

Pilot House Associates, LLC (Pilot House) is a Boston-based, single-family office providing philanthropic, investment, and administrative services to the Hostetter family and the Barr Foundation, a private foundation established in 1998.

Since its inception, Pilot House has provided administrative, financial, and operational support to the Hostetter family and related entities. We are seeking an experienced, highly organized Executive Assistant who can manage sensitive information, competing priorities, and high-touch relationships with discretion and professionalism.

About the Role

This person will support the Family Office CEO, with additional administrative and project support for the Director of Residences, and family members as the role develops. This hire will help shape that growth, with real opportunity to build alongside the family office as it evolves.

The primary focus of the role is providing high-level EA support to the executive, including calendar management, meeting coordination, and compiling and delivering briefing materials ahead of key meetings. The remainder is fluid, split between broader administrative and project support and, over time, individualized support for members of the next generation. That balance will shift as the role develops.

Key Responsibilities
• Manage complex calendars, scheduling, and meeting coordination for the primary executive
• Compile and deliver briefing materials in advance of key meetings
• Coordinate meetings and board-related logistics for the Family Office CEO
• Book travel, manage Zoom links, and coordinate project-related meetings
• Handle invoice scanning, contact management, and forward-looking scheduling needs
• Act as a proactive project manager, identifying what needs to get done rather than waiting to be asked
• Provide light-touch, individualized administrative support to family members with different working styles and needs
• Serve as a point of contact with an outside concierge travel team
• Connect accountants, family members, and payment systems to keep bill pay moving smoothly
• Provide support for occasional after-hours requests as needed

Qualifications
• A minimum of 7+ years of experience working as an Executive Assistant ideally in a family office environment
• Local Boston-based candidates are strongly preferred and will be given priority review
• Confident, calm communicator who can problem-solve under pressure
• High discretion at all times, especially around personal and financial matters
• Comfortable managing up and holding boundaries with multiple stakeholders, each with different communication and working styles
• Strong self-starter instincts, someone who proposes solutions rather than waiting for direction
• Tech-savvy across Microsoft, Asana, and shared cloud drives, open to learning new systems, with a genuine curiosity about AI tools as a plus
• Polished, adaptable, and able to pivot quickly between very different personalities and priorities day to day
• Legally authorized to work in the United States
• Willing to undergo an in-depth background check and provide excellent professional references

Position Details
• Position Type: Full-time, exempt
• Reports To: Chief Executive Officer
• Location: Boston, Massachusetts
• Travel: Occasional travel may be required to support business, residence, or event-related needs.

Compensation and Benefits

The anticipated annual salary range for this position is $150,000.00 - $170,000.00. This range represents Pilot House's good-faith estimate of the compensation for the role at the time of posting. Final compensation will be determined based on a variety of factors, including relevant experience, education, skills, qualifications, internal equity, and the scope and responsibilities of the position.

Pilot House offers a generous and comprehensive benefits package, including health, dental, vision, life insurance, and retirement benefits. Additional information regarding the benefits package will be shared during the interview process.

Hybrid Work Schedule

Pilot House offers employees flexibility to work remotely for a portion of the workweek. For this position, the Executive Assistant is expected to work from the Boston office a minimum of three days per week.

During onboarding and orientation, as well as at other times when executive, residence, event, or organizational needs require, the Executive Assistant may be expected to work on-site more frequently.

How to Apply

Pilot House has retained a recruiting firm to support the search for this position. Interested candidates should submit a résumé and cover letter to:

Jenni Vaughan at View email address on click.appcast.io

Pilot House Associates, LLC is an equal opportunity employer committed to fostering a diverse, equitable, and inclusive workplace. We welcome applicants with varied backgrounds, experiences, identities, and perspectives. Employment decisions are based on qualifications, merit, and organizational need, without regard to race, color, religious creed, sex, sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, military or veteran status, or any other characteristic protected by applicable law.