Esquire Lead Bartender

Job Description

Job Description

Location: 58 East Oak Street, Gold Coast, Chicago, IL Employment type: Full-time Classification: Hourly, tipped Reports to:  Bar Manager / Beverage 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 after training begins.

The Role

The senior bartender and shift lead of the bar. The Lead Bar holds the bar and Trophy Room programs to standard, leads the bar team through service, and is the bar's first line of consistency and quality.

What You’ll Do

• Lead the bar team through service; set up, run, and close the bars to standard.
• Hold the cocktail and Trophy Room programs to recipe and presentation standard.
• Coach bartenders and bar support; manage well organization and par.
• Partner with the Bar Manager and Beverage Manager on the program, inventory, and training.

What You Bring

• 3+ years bartending in upscale or craft-cocktail settings, including lead or senior shifts.
• Deep spirits and cocktail knowledge; rare-spirits exposure preferred.
• Calm command of a busy bar and a developing team.

Certifications & Requirements

• 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.)

Compensation — Pay Scale

$19 to $20 per hour base (lead premium over the $17/05 Chicago minimum wage, no tip credit) plus a share of the tip pool. Good-faith figure; the final offer is confirmed in writing.

Benefits & Perks

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.

How to Apply

Interested? Send your résumé — and references where applicable — to View email address on us.fitly.work 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.

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.