Lead Fine Dining Server

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.

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.

Responsibilities

• 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.

Requirements

• 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

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
• Free uniforms
• Wellness resources

Pay

Earn $800-$2,000+ per week (based on experience, schedule, and gratuities).

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.