Executive Assistant - Twin Farms

Located in the serene hills of Barnard, Vermont, Twin Farms is a private, all-inclusive luxury resort exclusively for adults. Set on 300 acres of pristine countryside, the resort is renowned for its Forbes Five-Star hospitality, exceptional farm-to-table dining, and deeply personalized service. Twin Farms is not open to the public and offers an intimate, all-inclusive guest experience.

Since opening in 1993, Twin Farms has been defined by timeless standards of excellence and a genuine commitment to thoughtful, detail-driven hospitality. Our team members are at the heart of the guest experience, bringing integrity, care, and pride to everything they do.

Twin Farms is an equal opportunity employer and is committed to providing a workplace free from discrimination and harassment in accordance with all applicable laws

Twin Farms is seeking a highly organized, thoughtful, and proactive Executive Assistant to support the Managing Director.

This role goes beyond traditional administrative support. The Executive Assistant will serve as a trusted partner, helping manage priorities, communications, meetings, projects, and follow-through across the property. The position will also help translate leadership priorities into action, keep key stakeholders aligned, and ensure important matters move forward with discretion, urgency, and accountability.

The ideal candidate is polished, calm, and comfortable in a fast-paced luxury hospitality environment. This person must exercise sound judgment, maintain strict confidentiality, anticipate needs, and communicate with warmth and professionalism.

Key Responsibilities

• Manage the Managing Director’s calendar, meetings, travel, and daily priorities.
• Coordinate meetings, agendas, materials, logistics, and follow-up.
• Monitor correspondence and identify time-sensitive matters.
• Prepare reports, presentations, meeting notes, and executive communications.
• Track decisions, deadlines, commitments, and action items.
• Support communication between the Managing Director and department leaders.
• Follow up with leaders and stakeholders to maintain momentum and accountability.
• Coordinate travel, itineraries, reservations, and expenses.
• Assist with confidential employee, operational, financial, and strategic matters.
• Support special projects, property initiatives, events, and leadership priorities.
• Review documents and communications for accuracy, tone, and completeness.
• Anticipate conflicts, operational needs, and upcoming deadlines.
• Provide occasional support outside normal business hours when urgent matters arise.
• Perform other duties and special assignments as requested.

Leadership and Communication Expectations

• Represent the Managing Director and Twin Farms with professionalism, warmth, and discretion.
• Build trusted relationships across departments.
• Communicate clearly, respectfully, and promptly.
• Remain composed and resourceful as priorities shift.
• Exercise sound judgment when acting independently or escalating concerns.
• Protect the Managing Director’s time while remaining approachable and responsive.
• Encourage timely follow-through and accountability in a collaborative manner.
• Navigate complex or sensitive situations with maturity and discretion.
• Take full ownership of assigned responsibilities through completion.

• At least three years of executive, administrative, hospitality, or senior-level support experience.
• Exceptional organization, time management, and attention to detail.
• Strong written and verbal communication skills.
• Demonstrated ability to handle confidential information.
• Ability to manage competing priorities and work independently.
• Proficiency with Microsoft Outlook, Word, Excel, PowerPoint, Teams, and shared document systems.
• Experience coordinating executive calendars, meetings, travel, and projects.
• Strong judgment, adaptability, follow-through, and problem-solving skills.
• Ability to influence outcomes and build alignment without direct authority.
• Luxury hospitality, resort, private-service, or Chief of Staff-style experience is strongly preferred.

Working Conditions

• Primarily office-based with regular movement throughout the property.
• Flexibility may be required for occasional early mornings, evenings, weekends, events, or urgent needs.
• The role involves handling highly sensitive employee, guest, ownership, and business information.
• Reliable transportation and regular on-site attendance are required.

Measures of Success

• The Managing Director’s time and priorities are organized effectively.
• Meetings are well prepared and followed by clear action items.
• Communications are accurate, polished, and timely.
• Confidential information is handled appropriately.
• Leadership commitments and deadlines are tracked to completion.
• Department leaders receive clear and dependable communication.
• Strategic and operational priorities move forward with coordination and accountability.

At Twin Farms, we believe that when our team members are genuinely cared for, they are empowered to deliver extraordinary hospitality. Our benefits are thoughtfully designed to support well-being, provide stability, and encourage long-term professional growth.

Our benefits include:

• Complimentary life insurance
• 401(k) retirement plan with employer match
• Paid holidays and sick time
• Employee Assistance Program (EAP) with confidential support and resources
• Daily staff meal
• Training, professional development, and tuition assistance
• Employee referral bonuses
• Exclusive dining and lodging privileges

Because taking care of our people isn’t a perk, it’s a tradition.