Cocktail Server

About The Pearl Club

The Pearl Club is located at the apex of the Milwaukee, Halsted, and Grand Avenue “six-corners” in Chicago and blends the old-world elegance of the London cocktail scene with the modern sophistication of Chicago & NYC lounges. ( The Pearl Club ) We’re committed to delivering high-caliber, stylish service in an elevated, refined environment.

Position Summary

We’re looking for polished, guest-centric Servers to join our team at The Pearl Club. You’ll be working in a high-energy yet elegant setting, helping to deliver an exceptional experience to our clientele through discerning service, cocktail knowledge, and seamless teamwork.

Responsibilities

• Welcome, seat, and serve guests with warmth, professionalism, and a refined attitude in line with The Pearl Club’s luxury-forward atmosphere.
• Provide knowledgeable guidance through the cocktail menu and food offerings; confidently suggest pairings and highlight signature drinks.
• Collaborate closely with bartenders, hosts, and service staff to ensure coordinated, elevated guest experiences.
• Maintain clean, organized sections; uphold health & safety guidelines and the venue’s aesthetic standards.
• Manage payment transactions accurately and in a timely fashion.
• Anticipate guest needs and consistently strive to exceed expectations with upselling and service touches appropriate for a high-end lounge.

Qualifications

• Minimum 1–2 years of serving experience in an upscale cocktail lounge, fine dining restaurant, or sophisticated bar environment.
• Strong knowledge of classic and contemporary cocktails, spirits, and wine is highly preferred.
• Impeccable personal presentation, excellent communication skills, and a guest-first mentality.
• Ability to thrive in an evening and weekend schedule; flexible availability is a must.
• Team-oriented, proactive, and well-suited to a refined hospitality culture.

What We Offer

• Competitive hourly wage plus tip income.
• A beautiful, elevated workplace where style and service meet.
• Opportunities for learning and development — especially in cocktails, spirits, and guest experience.
• A respectful, professional team atmosphere that values guest delight and craftsmanship.