Esquire Server

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

Location: 58 East Oak Street, Gold Coast, Chicago, IL Employment type: Full-time Classification: Hourly, tipped Reports to:Service Manager

Why Esquire

Esquire is a 265-seat luxury steakhouse in Chicago’s Gold Coast where Japanese precision meets French technique — anchored by an elite Wagyu and seafood program, a four-level Wine Tower, the OakShō omakase counter, and the invitation-only Maison 58. We hold an uncompromising standard and hire people who want to set it, not just meet it. Esquire is operated by M Street Collective, the group behind Nashville’s Virago, Moto, Kayne Prime, and Saint Añejo.

Onboarding and training is estimated to begin mid-to-late October 2026. Because our permanent location is wrapping up construction, the initial onboarding and training may be adjusted. We will provide the exact address and finalized dates at least two weeks before training begins.

The Role

The Lead Server is the face of Esquire's service philosophy and the primary steward of the guest experience. Working within Esquire's Captain-led service model, Lead Servers guide guests through every stage of the dining experience — from menu navigation and beverage recommendations to tableside presentations and special moments. More than a server, the Lead Server is an educator, storyteller, host, and salesperson, tailoring recommendations to each guest's preferences and occasion. This position is one of the highest levels of hourly service and a primary development path into the Captain program and future leadership.

What You’ll Do

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

What You Bring

• 2+ years serving in upscale or fine dining; aspiration toward the Captain program.
• Strong and growing command of food, wine, sake, and spirits; appetite to master the programs.
• Polished, gracious, and quick on the floor under pressure.

Certifications & Requirements

• Illinois BASSET (alcohol) — REQUIRED. Valid BASSET certification before any shift that involves selling, serving, or checking ID for alcohol, and no later than 30 days after hire (company policy; statute allows 120); renew every 3 years.
• Illinois Food Handler — REQUIRED. ANAB-accredited food-handler certificate within 30 days of hire; renew every 3 years. (Waived for holders of a current CFPM.)

Compensation — Pay Scale

$17.05/hr base (full Chicago minimum wage, eff. July 1, 2026, no tip credit) plus a share of the tip pool. Good-faith figure; the final offer is confirmed in writing.

Eligible team members receive group medical, dental, and vision insurance (the Company pays part of the premium), a 401(k) plan, Company-paid life insurance, AD&D, and a confidential Employee Assistance Program. Time off includes Paid Time Off for eligible salaried positions, Chicago Paid Leave and Paid Sick and Safe Leave, and paid bereavement leave, plus the protected leaves required by federal and Illinois law (FMLA, VESSA, military, jury, and voting). Tipped roles also share the tip pool (a good-faith estimate, not a guaranteed wage). Final plan details and eligibility are confirmed in the written offer.

Held to Esquire’s four pillars — quality, consistency, hospitality, and innovation — and the five universal competencies: professionalism, teamwork, growth mindset, excellence, and hospitality.

About Esquire

Esquire is a modern luxury steakhouse on Oak Street in Chicago’s Gold Coast — Japanese precision built on a French foundation, anchored by an elite Wagyu program and a seafood-and-sushi program that earns equal billing. Across a 265-seat dining room, a four-level ~5,000-bottle Wine Tower, the Trophy Room, the invitation-only 58 Club, and the OakShō omakase counter, it delivers omotenashi-inspired hospitality and culinary theater in a vintage-Hollywood setting.

About M Street Collective

M Street Collective is the hospitality group behind Esquire, with operations in Nashville and Chicago. Built on four pillars — quality, consistency, hospitality, and innovation — and a commitment to innovation, leadership development and world-class training, the Collective creates restaurants and experiences defined by an uncompromising standard and genuine, anticipatory care.

M Street Collective is an equal opportunity employer. We consider all qualified applicants without regard to race (including traits associated with race under the CROWN Act), color, religion, sex, pregnancy, sexual orientation, gender identity or expression, national origin, ancestry, age, marital or family-responsibilities status, disability, military or veteran status, citizenship or immigration status, arrest or conviction record (as limited by law), credit history, genetic information, or any other characteristic protected by federal, Illinois, or Chicago law. Consistent with the Illinois Job Opportunities for Qualified Applicants Act, we do not ask about criminal history on the application, and we do not ask about salary history. Reasonable accommodations are available for applicants with disabilities, for pregnancy and related conditions, and for religious observance — contact People Operations. This position is performed in Chicago, Illinois.

Qualifications

Experience

Required

2 years: Serving in upscale or fine dining; aspiration towards Captain program

Licenses & Certifications

Required

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.