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Lead Fine Dining Server Middleburg, VA, 20117, Goodstone

Lead Fine Dining Server

Full Time • Middleburg, VA, 20117, Goodstone

Goodstone is a luxury estate nestled in the heart of Virginia's horse and wine country, just minutes from historic Middleburg. Here, exceptional hospitality, personalized service, and unforgettable experiences come together. Our estate is home to The Goodstone Inn, offering elegant accommodations and curated guest experiences, and Grayson's at Goodstone, our estate-driven restaurant where the land inspires every menu through fresh ingredients harvested from Goodstone Farm. Whether guests are joining us for a weekend escape, a wedding celebration, an unforgettable dinner, or a relaxing retreat, every experience is made possible by passionate people who care deeply about hospitality. From Guest Services and Culinary to Food & Beverage, Events, Housekeeping, Grounds, and Administration, every member of our team plays an important role in bringing the Goodstone experience to life. If you're looking for more than a job—a place where you can grow, make an impact, and be part of something truly special—we'd love to welcome you to Goodstone.

Benefits:
  • Free uniforms
  • Health insurance
  • Opportunity for advancement
  • Training & development
  • Vision insurance
  • Wellness resources
  • Competitive salary
  • Dental insurance
  • Employee discounts
  • Flexible schedule

Lead Server

Grayson's

Bar • Restaurant • Estate
An elevated dining experience at the award-winning Goodstone Inn

Location: Middleburg, Virginia
Job Type: Full-Time
Compensation: Earn $800-$2,000+ per week (based on experience, schedule, and gratuities)
Join the team behind one of Virginia's newest and most exciting dining destinations. At Grayson's, exceptional hospitality begins with exceptional people. 

About Grayson's

At Grayson's, the land sets the menu.

Located on the award-winning Goodstone estate in the heart of Virginia's horse and wine country, Grayson's is an elevated dining experience rooted in authenticity, exceptional hospitality, and estate-grown ingredients.

Named after Grayson, the beloved llama who has become an icon of the Goodstone estate, our restaurant celebrates the beauty of the countryside and the connection between farm and table. Every morning, our culinary team harvests seasonal herbs, heirloom vegetables, and fresh ingredients from Goodstone Farm, allowing the changing seasons to inspire every menu we create.

At Grayson's, we're creating more than exceptional meals—we're creating unforgettable experiences. As the newest chapter in the Goodstone story, we're building a hospitality team that shares our passion for genuine service, thoughtful cuisine, and creating lasting memories for every guest.

If you're looking to be part of something special and grow your career with one of Virginia's premier luxury hospitality destinations, we'd love to meet you.

Why You'll Love Working at Grayson's

  •  Earn $800-$2,000+ per week, including gratuities. 
  •  Join an exciting new restaurant concept backed by the award-winning Goodstone Inn. 
  •  Work alongside talented chefs and hospitality professionals committed to excellence. 
  •  Be part of a true farm-to-table dining experience featuring estate-grown ingredients. 
  •  Opportunities for career growth and advancement into restaurant leadership. 
  •  Beautiful Middleburg location in Virginia's renowned horse and wine country. 
  •  Full-time benefits, employee discounts, and a supportive team culture. 

Your Opportunity

We're seeking experienced Lead Fine Dining Servers who are passionate about hospitality and understand what it takes to deliver an elevated dining experience.

This is more than a serving position. As a Lead Server, you'll help set the standard for service excellence, mentor newer team members, and play a key role in creating memorable guest experiences. We're looking for hospitality professionals who lead by example, thrive in a fast-paced environment, and take pride in exceeding expectations.


What You'll Do

  •  Deliver exceptional, personalized service throughout every guest's dining experience. 
  •  Lead by example and maintain Grayson's luxury hospitality standards. 
  •  Welcome guests with warmth, professionalism, and genuine hospitality. 
  •  Develop extensive knowledge of our menus, wine list, cocktails, and seasonal offerings. 
  •  Confidently guide guests through menu selections and make thoughtful recommendations. 
  •  Collaborate with culinary and front-of-house teams to ensure seamless service. 
  •  Anticipate guest needs before they arise and resolve concerns with professionalism. 
  •  Assist in training and mentoring new servers while fostering a collaborative team environment. 
  •  Maintain impeccable dining room presentation and cleanliness. 
  •  Support restaurant leadership during service to ensure smooth operations. 
  •  Uphold all food safety, sanitation, and responsible alcohol service standards. 

What We're Looking For

  • Minimum of 2 years of fine dining serving experience required.
  •  Luxury hotel, resort, country club, or upscale restaurant experience strongly preferred. 
  •  Strong knowledge of food, wine, and beverage service. 
  •  Exceptional communication and interpersonal skills. 
  •  Professional appearance and polished demeanor. 
  •  Passion for hospitality and creating unforgettable guest experiences. 
  •  Ability to remain calm and organized during busy service periods. 
  •  Positive attitude with a willingness to mentor and support teammates. 
  •  Flexible schedule, including evenings, weekends, holidays, and special events. 

Career Growth

At Grayson's, we believe in developing our people and promoting from within whenever possible. Outstanding Lead Servers will have opportunities to grow into positions such as:

  •  Restaurant Floor Supervisor 
  •  Banquet Captain 
  •  Restaurant Manager 
  •  Food & Beverage Leadership 
  •  Guest Experience Leadership 
If you're looking for more than just your next serving job and want to build a long-term career in luxury hospitality, Grayson's offers the opportunity to grow with us.

Benefits

  •  Competitive earning potential 
  •  Employee Discounts at Goodstone Inn & Grayson's 
  •  Medical, Dental, Vision, Life, Short-Term and Long-Term Disability (eligible beginning Day 61) 
  •  401(k) with Company Match 
  •  Paid Vacation and Sick Time 
  •  Employee Referral Bonus Program 
  •  Career Development and Advancement Opportunities 

Work Schedule

This is a full-time position requiring flexibility to work breakfast, lunch, dinner, weekends, holidays, and special events. Lead Servers are expected to be available during peak business periods and consistently deliver exceptional guest experiences.

Physical Requirements

  •  Ability to stand and walk for extended periods. 
  •  Ability to lift and carry trays, food, beverages, and supplies up to 30 pounds. 
  •  Frequent bending, reaching, and carrying throughout service. 
  •  Ability to work in a fast-paced restaurant environment. 

Additional Information

This job description outlines the general responsibilities and qualifications for this position. Duties may change based on business needs and operational priorities.

Equal Opportunity Employer

Goodstone Inn & Restaurant is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive workplace where every team member is valued and respected. We are a drug-free workplace. Pre-employment and ongoing drug and alcohol screenings may be required.
Compensation: $800.00 - $2,000.00 per week

We are an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.





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Why Join Goodstone?

Hospitality with Purpose

At Goodstone, you're not just filling a role—you're helping create experiences that guests remember long after they leave.

We believe exceptional hospitality starts with exceptional people. That's why we've built a supportive, collaborative culture where team members step in to help one another, take ownership of their work, and are encouraged to grow professionally.

Whether you're welcoming guests at The Goodstone Inn, serving at Grayson's at Goodstone, preparing unforgettable meals, coordinating special events, or caring for our beautiful estate, you'll have the opportunity to make a meaningful impact every single day.

Team Culture / Environment
A hands-on, team-driven environment where people show up, support each other, and take ownership—no egos, just getting it done the right way.
Growth & Development
Real, hands-on experience across departments with opportunities to grow your skills and take on more as you prove yourself.
Health Benefits
Comprehensive medical, dental, and vision coverage to support you and your well-being.
401(k) + Financial
401(k) with company match to help you plan ahead.
Employee Discounts
Discounts on dining and stays.
Work Environment
Work on a beautiful countryside estate just minutes from Middleburg—no typical hotel setting here.
Goodstone
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