SERVER
GRAYSON’S AT GOODSTONE | BAR • RESTAURANT • ESTATE
DEPARTMENT Food & Beverage | LOCATION Middleburg, Virginia
REPORTS TO Restaurant Manager / Restaurant Floor Supervisor | EMPLOYMENT Full-Time or Part-Time
FLSA STATUS Non-Exempt | COMPENSATION Tip-Based + $20/Hour Minimum Earnings Guarantee
Join the Team Behind an Exceptional Dining Experience
Located on the historic Goodstone estate in Virginia’s Hunt Country, Grayson’s at Goodstone is an estate-driven dining destination where exceptional hospitality, seasonal cuisine, and genuine connections create memorable experiences. We are seeking experienced Servers who combine thoughtful service, food and beverage knowledge, and a genuine passion for hospitality.
POSITION SUMMARY
The Server delivers warm, polished, and personalized dining service from arrival through departure. This position guides guests through seasonal menus, makes informed food and beverage recommendations, coordinates accurate and well-paced service with the culinary and front-of-house teams, and anticipates guest needs while representing the Grayson’s and Goodstone brands.
WHAT YOU’LL DO
Guest Experience & Hospitality
- Welcome guests warmly and deliver attentive, personalized service throughout the dining experience.
- Explain menu items, seasonal ingredients, daily specials, and preparation methods; recommend food, wine, cocktails, and nonalcoholic beverages.
- Anticipate guest preferences, respond discreetly to requests, and communicate dietary restrictions and allergies to the culinary team.
- Address questions and concerns promptly and involve restaurant leadership when needed.
Food & Beverage Service
- Take and accurately enter orders, communicate special requests, and coordinate the timing of courses and beverages.
- Apply proper elevated dining service techniques, including table presentation, course pacing, and responsible beverage service.
- Monitor assigned tables, ensure order accuracy, and process payments using established procedures.
- Maintain knowledge of menu changes, ingredients, allergens, wine, spirits, and cocktails.
Dining Room Operations & Teamwork
- Prepare tables and service stations; complete opening, closing, and assigned side work.
- Maintain clean, organized, and guest-ready dining and service areas.
- Work closely with Hosts, Back Servers, Bartenders, culinary partners, and restaurant leadership to ensure seamless service.
- Assist with private dining, special events, and peak-volume service as scheduled.
- Follow food safety, sanitation, responsible alcohol service, guest privacy, and company standards.
WHAT WE’RE LOOKING FOR
Required Qualifications
- At least two years of recent restaurant serving experience.
- Ability to deliver polished guest service and manage multiple tables in a fast-paced setting.
- Working knowledge of food and beverage service, wine, cocktails, and appropriate service techniques.
- Excellent communication, organization, teamwork, and attention to detail
- .Professional appearance, sound judgment, reliability, and a guest-first approach.
- Availability for evenings, weekends, holidays, and special events as required.
- Ability to meet applicable Virginia requirements for alcoholic beverage service.
Preferred Qualifications
- Fine dining or upscale restaurant experience; luxury hotel, resort, winery, or private-club service experience is a plus.
- Experience with multi-course dining, wine presentation, and restaurant point-of-sale systems.
COMPENSATION
This is a tip-based position with hourly base pay and eligible gratuities. Grayson’s provides a guaranteed minimum of $20 per hour in eligible earnings through its Minimum Wage Guarantee (True-Up Wage Supplement) Policy. When qualifying earnings fall below the guarantee, the Company provides a wage supplement in accordance with that policy. Servers may earn more than the guaranteed minimum through gratuities. Applicable service-period base rates, tip distribution, eligibility, and true-up calculations are governed by separately provided Company policies and pay notices.
WORK SCHEDULE
Full-time and part-time schedules vary with business needs and may include breakfast, brunch, lunch, dinner, evenings, weekends, holidays, private events, and high-volume service periods. Regular and reliable attendance is essential.
WHY JOIN GRAYSON’S AT GOODSTONE?
- Tip-based earnings with a $20/hour minimum earnings guarantee under the applicable Company policy.
- Complimentary team meals and employee discounts at Goodstone and Grayson’s.
- Medical, dental, vision, life, and disability benefits for eligible employees.401(k) with company match and paid time off subject to eligibility requirements.
- Employee referral opportunities, training, and career advancement in a luxury estate setting.
PHYSICAL REQUIREMENTS
Stand and walk for extended periods; bend, reach, stoop, balance, and navigate stairs regularly.Safely lift and carry trays, food, beverages, and supplies weighing up to 30 pounds.Work in active indoor and outdoor restaurant or estate event spaces as needed.Perform essential functions with or without reasonable accommodation.
SUCCESS IN THIS ROLE
Successful Servers anticipate needs, demonstrate confident food and beverage knowledge, maintain composure during busy service, communicate proactively, take ownership of their tables, and represent Grayson’s with warmth, polish, and genuine hospitality.
ADDITIONAL INFORMATION
This description summarizes the general nature of the work and is not an exhaustive list of duties or qualifications. Responsibilities and schedules may change based on operational needs. Reasonable accommodations may be made for qualified individuals with disabilities.
EQUAL OPPORTUNITY EMPLOYER
Goodstone is an Equal Opportunity Employer committed to an inclusive workplace. Employment decisions are made without regard to race, color, religion, sex, pregnancy, national origin, age, disability, genetic information, veteran status, sexual orientation, gender identity, or any other status protected by law. Goodstone maintains a drug-free workplace; employment-related screening may be required in accordance with Company policy and applicable law.
Goodstone Inn & Restaurant is a privately owned, luxury property located just minutes from the heart of Middleburg, Virginia. Set on a stunning countryside estate, Goodstone offers elevated dining, unique accommodations, and curated guest experiences that go far beyond traditional hospitality.
At Goodstone, we are known for delivering thoughtful, high-touch service where every detail matters. Our guests expect an exceptional experience—and our team delivers it.
We’re a group of passionate, hands-on professionals who take pride in our work. This is not a “clock in, clock out” environment. It’s a place for people who care about hospitality, enjoy working as part of a team, and want to be part of something that feels special every single day.
As part of the Goodstone team, you’ll be empowered to take ownership of your role, think creatively, and contribute to an environment where excellence is the standard—not the goal.
Why Join Goodstone?
Be part of a tight-knit, high-performing team that genuinely supports each other
Work in a unique, luxury setting where no two days feel the same
Gain hands-on experience across departments and grow your hospitality career
Have a direct impact on the guest experience—your work truly matters here
Join a culture built on accountability, professionalism, and pride in service
If you’re someone who:
Brings Energy, Attention to Detail, and a Passion for Hospitality, You Will Fit Right In!