Virtual Assistant Jobs in Rutland, VT (NOW HIRING)

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 serves as a trusted administrative and operational partner, helping manage priorities, communications, meetings, projects, and follow-through across the property. The Executive Assistant will help keep leadership priorities moving 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 confidentiality, anticipate needs, and communicate with warmth and professionalism.

Key Responsibilities

• Manage the Managing Director's calendar, meetings, travel, correspondence, and daily priorities.
• Coordinate agendas, materials, logistics, notes, and follow-up.
• Prepare reports, presentations, and executive communications.
• Track deadlines, decisions, commitments, and action items.
• Support communication and coordination between the Managing Director and department leaders.
• Assist with confidential employee, operational, financial, and strategic matters.
• Support special projects, property initiatives, events, and leadership priorities.
• Assist with marketing coordination, including occasional on-property photography and support with public relations and social media needs.
• Review documents and communications for accuracy, tone, and completeness.
• Anticipate needs, resolve issues, and provide occasional support outside normal business hours when necessary.

• At least three years of executive, administrative, hospitality, or senior-level support experience.
• Exceptional organization, judgment, discretion, and attention to detail.
• Strong written and verbal communication skills.
• Ability to manage competing priorities and work independently.
• Proficiency with Microsoft Outlook, Word, Excel, PowerPoint, Teams, and shared document systems.
• Experience coordinating calendars, meetings, travel, and projects.
• Luxury hospitality, resort, private-service, or Chief of Staff-style experience is preferred.

Working Conditions

This is primarily an on-site, office-based role with regular movement throughout the property. Flexibility may be required for occasional early mornings, evenings, weekends, events, or urgent needs. Reliable transportation and regular on-site attendance are required.

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.