Esquire Captain - Senior Service Professional

M Street Entertainment Group; Chicago (IL); On-site; USD 23,000 - 28,000; Full time

Benefits offered by this job

Health insurance

401(k) plan

Life insurance

AD&D

Paid time off

Chicago leave

Sick leave

Bereavement leave

Job summary

Esquire located in Chicago’s Gold Coast is hiring a Captain for the Front of House to own the guest experience across the section. You will lead luxury service, perform sommelier duties, and deliver culinary-theater moments at tableside.

The role requires proven leadership, high-touch hospitality, and strong wine knowledge to elevate every guest experience. Onboarding begins mid-to-late October 2026 with a shared tip-pool structure and extensive training.

Qualifications

• Demonstrated sommelier/wine command and luxury-product knowledge.
• Proven high-touch hospitality and tableside presentation.
• Strong leadership of a section and team on the floor.

Responsibilities

• Lead the overall guest experience across all tables in the assigned section.
• Perform high-touch guest interaction and relationship-building; act as the section's luxury ambassador.
• Perform core sommelier responsibilities — wine recommendations, pairing guidance, premium beverage sales.
• Execute tableside presentations and culinary-theater moments.
• Communicate pacing and coordination needs; orchestrate the unit (Lead Servers, Server Assistants, Food Runners).
• Support service recovery and special requests; maintain communication with Service Managers.

Skills

Sommelier knowledge

Hospitality leadership

Tableside service

Education

Illinois BASSET certification

Illinois Food Handler

Job description

Posting Details

• Posted on August 26, 2026

Locations

• Esquire
  Chicago, IL 60611, USA
  
• On-site
• Rate : $17.05 USD per hour
• Front of House
• Full-Time
• Requisition #: ESQUI001115

Description

Location: 58 East Oak Street, Gold Coast, Chicago, IL Employment type: Full-time Classification: Hourly, tipped Reports to:Service Manager / General 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 pinnacle of hourly service and the leader of the service unit. The Captain owns the overall guest experience across the section, performs core sommelier and Japanese A5 Sommelier guidance, and carries the culinary-theater moments that make a meal unforgettable. This is hospitality, consistency, and teamwork at their highest expression on the floor — the standard the whole unit is built around.

What You’ll Do

• Lead the overall guest experience across all tables in the assigned section.
• Perform high-touch guest interaction and relationship-building; act as the section's luxury ambassador.
• Perform core sommelier responsibilities — wine recommendations, pairing guidance, premium beverage sales — and serve as the Japanese A5 Sommelier.
• Execute tableside presentations and culinary-theater moments.
• Communicate pacing and coordination needs; orchestrate the unit (Lead Servers, Server Assistants, Food Runners).
• Support service recovery and special requests; maintain communication with Service Managers.

What You Bring

• Top of the hourly service ladder — promoted through the Captain program from Lead Server, or equivalent senior fine-dining service leadership.
• Demonstrated sommelier/wine command and A5 / luxury-product knowledge.
• Proven high-touch hospitality, tableside presentation, and section leadership.

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.

Benefits & Perks

• group medical, dental, and vision insurance (the Company pays part of the premium)
• 401(k) plan
• Company-paid life insurance
• AD&D
• confidential Employee Assistance Program
• Paid Time Off for eligible salaried positions
• Chicago Paid Leave
• Paid Sick and Safe Leave
• paid bereavement leave
• 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

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.

Licenses & Certifications

IL Food Handler ANSI BASSET Certification (IL) Equal Opportunity Employer