Server

Cooper's Hawk Winery; Annapolis (MD); On-site; USD 21,000 - 34,000; Full time

Benefits offered by this job

Dining discount 50%

Wine discount 40%

Event discount 20%

Monthly wine tastings

Medical/dental/vision

401k match

PTO & flexible schedules

Early wage access

Wellness programs

Wine & culinary education

Career growth plan

Referral bonuses

Job summary

Cooper’s Hawk Winery is seeking friendly servers who will guide guests through dining experiences, wine selections, and the Wine Club benefits. You will engage with guests, take and deliver orders, and ensure a polished table side interaction in a fast-paced environment.

Candidates should be comfortable with POS systems, handling payments, and maintaining a welcoming atmosphere. Training includes hospitality standards and team-based service to create memorable visits.

Qualifications

• Experience delivering friendly, accurate service in a fast-paced dining setting.
• Ability to explain menu and wine club benefits clearly.
• Comfort with handling POS systems and payments.
• Must be able to read, write, and understand English.

Responsibilities

• Greet guests and take orders with accuracy and warmth.
• Serve food and drinks with speed and care.
• Follow alcohol service guidelines and safety rules.
• Coordinate with kitchen and bar to ensure smooth service.
• Promote Cooper’s Hawk Wine Club and its benefits.

Skills

Customer service

Communication

Multitasking

Teamwork

Job description

At Cooper’s Hawk, our Servers are more than just order takers. They are curators of unforgettable experiences. Grounded in high standards and brought to life through Uncompromising Hospitality, they create moments that connect, delight, and inspire. Through warm, team-based service and thoughtful conversation, they guide guests through our food, wine, and Wine Club with confidence and care. Every visit becomes more than a meal, it becomes a memory.

Compensation: $3.63/hour plus tips

What You Will Get

• 50 percent Dining and Carryout Discount; 40 percent Retail Wine Discount; 20 percent Discount on Retail and Private Events
• Monthly Wine Tastings for Two
• Medical, Dental, Vision, and Telehealth
• 401k with Company Match
• Paid Time Off and Flexible Schedules
• Early Pay Access
• Wellness and Mental Health Support
• Wine and Culinary Education
• Career Growth Flight Plan
• Team Member Rewards, Milestone Recognition, and Referral Bonuses

How You Will Succeed

Show Up Ready: Come prepared, stay sharp, and start strong.

• Arrive on time, and in proper uniform standards
• Know the menu, wine list, and steps of service
• Use the POS system and handle payments with accuracy
• Understand the benefits of Cooper’s Hawk Wine Club and its offerings
• Follow departmental checklists and standard operating procedures to ensure work areas are prepared for opening, mid-shift, or closing.

Own What You See

Own What You See: Take responsibility, jump in, and do what needs to be done.

• Jump in where needed to help the team
• Serve food and drinks with speed and care
• Follow legal guidelines for alcohol service
• Take initiative to solve problems and support the guest experience

Stay in Sync

Stay in Sync: Communicate often, move with your team, and keep service flowing.

• Anticipate the needs of guests and fellow team members
• Communicate clearly with the Kitchen, Hosts, Runners, Bartenders, and Managers
• Help the team stay coordinated and focused

Make It Personal

Make It Personal: Be genuine, listen well, and tailor the experience.

• Welcome every guest with warmth, use guests names, celebrate milestones.
• Answer questions and make recommendations that feel genuine
• Use your Wine Club knowledge to educate the guest on its perks, and invite them to join our community of members.
• See the person, not just the task

Add a Touch

Add a Touch: Go beyond the expected to create memorable moments.

• Find small ways to delight the guests
• Share the story of our Wine Club and invite guests to join
• Introduce wine tastings and help guests enhance their experience
• Let your personality shine & leave your signature on every interaction

What You Will Bring

• At least 21 years of age and six months of server experience
• Experience in full service or upscale casual dining preferred
• Comfort speaking about food, wine, and our Wine Club program
• A passion for hospitality and working as part of a team
• Ability to multitask and stay calm in a fast-paced setting
• Ability to lift 40 pounds and work on your feet up to 10 hours
• Must be able to read, write, and understand English
• Flexible availability, including weekends and some holidays

Cooper’s Hawk reviews several factors when establishing compensation. Salaries and hourly wages appearing in a job posting may be published by third parties and may not reflect the salaries or hourly wages offered by Cooper’s Hawk.

Cooper’s Hawk is an equal opportunity employer. All qualified applicants are considered for employment without regard to the person’s race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Cooper’s Hawk makes reasonable accommodations during all aspects of the employment process, including during the interview process.

The information provided above indicates the general nature and level of work required of the position and is not a comprehensive list of all responsibilities or qualifications. The Benefits list is only a highlight of some of the benefits offered to team members; eligibility for certain benefits apply.

About Us

Cooper's Hawk features a Napa-style tasting room with wine-inspired retail for entertaining and a full-service restaurant, bar and private event space, offering a modern-yet-casual dining experience. Each scratch-kitchen menu item is designed to pair with our wines. Speaking of wine...the Cooper's Hawk Wine Club is perhaps the largest in the world, offering not only top-notch award-winning wines but also exclusive Wine Club membership benefits, including curated dining and travel experiences. Since 2005, we've brought the Napa Valley experience to our guests and Wine Club members, and now, with Piccolo Buco by Cooper’s Hawk, we’re bringing the vibrant flavors of Rome to them as well. Together, we’re creating a lifestyle brand like no other.