Luxury Lead Server — Upscale Dining & Growth Path

M Street Entertainment Group; Chicago (IL); On-site; USD 23,000 - 29,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k) plan

Life insurance

Paid time off

Job summary

Esquire is a modern luxury steakhouse on Oak Street in Chicago's Gold Coast seeking a Lead Server. You will guide guests through the dining progression, deliver tableside service with polish, and drive the guest experience within a Captain-led model.

Onboarding begins mid-to-late October 2026; compensation starts at $17.05/hr plus a share of the tip pool, with medical, dental, and vision, life insurance and a 401(k).

Qualifications

• 2+ years serving in upscale or fine dining.
• Strong knowledge of food, wine, sake, and spirits.
• Polished, gracious, and quick on the floor under pressure.

Responsibilities

• Guide menu selections and dining progression for the table.
• Execute food, beverage, and wine service to a high-touch standard.
• Support wine, sake, and premium-beverage recommendations; upsell effectively.
• Deliver tableside presentations and special moments with polish.
• Maintain continuity and coordinate with the support team.

Skills

Upscale dining experience

Wine/beer/spirits knowledge

Polished floor presence

Education

Illinois BASSET (alcohol) — REQUIRED

Illinois Food Handler — REQUIRED

Job description

Esquire is a modern luxury steakhouse on Oak Street in Chicago's Gold Coast seeking a Lead Server. You will guide guests through the dining progression, deliver tableside service with polish, and drive the guest experience within a Captain-led model.

Onboarding begins mid-to-late October 2026; compensation starts at $17.05/hr plus a share of the tip pool, with medical, dental, and vision, life insurance and a 401(k).