Wine Sales Specialist Jobs

is seeking a friendly, dependable, and hospitality-driven Wine Specialist/Bartender to join our Front of House team.

While each position has its own area of expertise, all of our Front of House team members are cross trained in other departments (including cafe and retail) and share the same goal: creating a warm, welcoming, knowledgeable, and seamless experience for every guest. We’re looking for people who take pride in hospitality, work well in a fast-paced environment, and enjoy being part of a collaborative team.

What You'll Do
Guest Service & Hospitality

• Provide warm, knowledgeable, and attentive service to every guest.
• Welcome customers and create a friendly, neighborhood atmosphere for both regulars and first-time visitors.
• Take food and beverage orders accurately and efficiently.
• Answer questions, make thoughtful product and menu recommendations, and proactively respond to guest needs.
• Help create a clean, organized, and visually appealing guest environment.
• Work collaboratively with bartenders, baristas, market staff, kitchen staff, and managers to ensure smooth service.

Food, Beverage & Product Knowledge

• Maintain strong working knowledge of our prepared food, coffee, and bar menus.
• Develop familiarity with our wine offerings and demonstrate a willingness to continue learning about wine, beer, spirits, specialty foods, and other market products.
• Provide knowledgeable recommendations and help guests discover products that fit their preferences.

Cross-Training

• Cross-train on positions in other FOH departments retail/bar/coffee service and support the rest of team as needed
• Learn to prepare drinks in other departments (espresso to cocktails to correct pouring of wine/beer) according to our recipes and quality standards
• Assist the other teams with cleaning and restocking, and make food and wine recommendations to guests.

Wine Specialist/Bartender

• Prepare classic and seasonal cocktails according to established recipes and quality standards.
• Pour and serve beer, wine, and spirits accurately and consistently.
• Guide guests through our beverage menu, including cocktails, wine, beer, and non-alcoholic beverages.
• Maintain a clean, organized, and fully stocked bar.
• Monitor the quality and freshness of garnishes, juices, syrups, mixers, and other bar ingredients.
• Follow all local and state liquor laws, responsible alcohol service practices, and company policies.

What We're Looking For

• Minimum 2 years of bartending experience with a strong wine background.
• A positive attitude and genuine passion for hospitality.
• Strong communication skills and a team-oriented approach.
• The ability to remain calm, organized, and efficient in a fast-paced, high-volume environment.
• Strong attention to detail and the ability to multitask and prioritize.
• Dependability, accountability, and reliability.
• Food Safety and Illinois BASSET certification, or the ability to obtain certification before employment.
• The ability to stand for extended periods and perform physically active work throughout a shift.
• Physical requirements including lift and carry up to 50 lbs

Availability

• All Front of House positions are generally scheduled 3–5 shifts per week.
• At least two weekend days (Friday–Sunday)
• At least two weekday PM shifts (Monday–Thursday)
• Most holidays, including Thanksgiving, Christmas Eve, New Year's Eve, and New Year's Day, Valentine's Day, etc.

Compensation & Benefits

• We are use a point based system in pool house
• Market Team Associate: $17.05/hour + tips
• Barista: $15/hour + tips
• Wine Specialist/Bartender: $12.96/hour + tips

All positions include:

• 401(k)
• Employee discount
• Paid sick time
• Paid time off

Why Join Piccadilly Market?

At Piccadilly Market, we're committed to creating an exceptional neighborhood market and dining experience through hospitality, quality products, and genuine community connection.

Our Front of House team plays an essential role in bringing that experience to life. You'll work alongside a supportive, hardworking team that values professionalism, collaboration, hospitality, and continuous learning. You'll gain hands-on experience across specialty foods, coffee, wine, cocktails, beer, and restaurant and market operations while having opportunities to learn, contribute, and grow within the company.

If you’re passionate about hospitality and want to be part of a team that takes pride in creating a great experience for every guest, we’d love to meet you.

Pay: $20.00 - $35.00 per hour

Benefits:

• Employee discount
• Paid time off
• Paid training

Work Location: In person