About the Role
A small, dynamic family business is seeking a highly organized, motivated, and positive Chief of Staff / Executive Assistant to partner closely with the family principal in managing and coordinating a diverse portfolio of business enterprises, real estate holdings, philanthropic initiatives, and personal projects.
This is a unique opportunity to contribute meaningfully across a range of interesting and impactful endeavors. The role requires intellectual curiosity, strong organizational skills, discretion, and a no-task-too-small mindset. You’ll play a vital role in making sure things run smoothly, with opportunities for both personal and professional growth as part of a good-hearted, high-integrity team.
Experience in every job area is neither required nor expected; a willingness to learn is.
Ability to represent the family business owners with professionalism, integrity, and kindness is a must.
Expectation for 4 days in-office, 1 day remote. Some travel required (about 1x/month, 2 nights)
Key Responsibilities
Entity & Business Management
- Oversee monthly and quarterly reporting for multiple business entities
- Maintain records related to insurance, registrations, and compliance
- Track tax deadlines; coordinate with CPA and legal counsel
- Handle basic bookkeeping and bill payments or work to automate where possible
Property Management
- Maintain master files for diverse real estate holdings
- Liaise with contractors, on-site managers, and oversee property readiness
- Coordinate long-term improvement projects and manage insurance coverage
- Perform basic bookkeeping and bill payments in QuickBooks
Fleet Oversight
- Track registration, insurance, and maintenance for commercial and personal vehicles
Philanthropic Coordination
- Help coordinate corporate philanthropy including scheduling, communication, and press releases
- Respond to sponsorship & charitable inquiries on behalf of the principal
HR Administration
- Manage payroll and HR compliance for W-2 employees across entities
- Liaise with attorneys for employment agreements and renewals
- Coordinate benefit administration and onboarding for new hires
Executive & Personal Assistance
- Manage travel planning, bookings, and detailed itineraries
- Maintain calendar and assist with scheduling and task prioritization
- Support personal errands & projects as needed
Ideal Candidate Profile
- Proven experience in financial services, operations, legal, or executive/business owner support role
- Thrives in a fast-moving, high-expectation, high-performance work environment
- Highly organized and detail-oriented with excellent follow-through
- Strong written and verbal communication skills
- Comfortable working with QuickBooks and managing light bookkeeping
- Emotionally intelligent, tactful, and discreet
- A natural problem-solver with a collaborative, can-do attitude
Key Skills & Tools
- Task & project management
- Calendar & travel coordination
- QuickBooks or similar accounting tools
- Microsoft Office / Google Workspace
- High level of discretion and confidentiality
Why Join Us?
- Join a supportive, respectful, and ethics-first family business environment with generous benefits
- Work closely with a driven and thoughtful principal
- Gain exposure to a wide range of business and philanthropic domains
- Enjoy meaningful flexibility and opportunities for long-term professional development
Job Type: Full-time
Pay: $75,000.00 - $100,000.00 per year
Benefits:
- Dental insurance
- Health insurance
- Paid time off
- Retirement plan
- Vision insurance
Schedule:
- Monday to Friday
Work Location: Hybrid remote in Williston, VT 05495