Chief of Staff/Executive Assistant to Family Office Position Available In Chittenden, Vermont

Chief of Staff/Executive Assistant to Family Office Moore & Warner Farm Real Estate, LLC Williston, VT 05495 • Hybrid work 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