Esquire Captain - Senior Service Professional

Job Description

Job Description

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

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 after training begins.

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.

• 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.

• 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.

• Illinois BASSET (alcohol) — REQUIRED. Valid BASSET certification after 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.)

$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.

Interested? Send your résumé — and references where applicable — to View email address on ziprecruiter.com or apply through the platform where you found this role.

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

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.

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.