Director of Service

Esquire, Chicago's luxury steakhouse in the Gold Coast, is hiring a Director of Service.

Location: 58 East Oak Street, Gold Coast, Chicago, IL   Employment type: Full-time   Classification: Salaried, exempt   Reports to: Director of Operations   Start date: Week of January 4, 2027

Why Esquire

Esquire is a 265-seat luxury steakhouse in Chicago's Gold Coast where Japanese precision meets French technique. It is anchored by an elite Wagyu and seafood program, a four-level Wine Tower, the OakSh omakase counter, and the invitation-only Maison 58 Club. 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.

The Role

The Director of Service owns the guest-facing operation of the Esquire dining room: the Captain-led service brigade, bar, and host teams. The Director of Operations holds the whole-venue standard. The Director of Service makes consistency and hospitality real every night, stewards the four pillars on the floor, and owns the numbers behind them, including P&L, labor, retention, and the bench that keeps the room excellent as it grows.

What You'll Do

• Own nightly service execution across the dining room against documented steps-of-service and timing standards.
• Own FOH P&L performance (revenue, labor, and cost lines) and manage to the par grid and budget.
• Lead recruiting and selection for the FOH team in partnership with People Operations; the Director of Operations holds final hiring authority.
• Build succession: identify and develop the Captain and Lead Server bench so leadership depth outpaces growth.
• Own guest retention: VIP and repeat-guest development, recovery, and the relationships that fill the room.
• Lead, schedule, and develop the salaried FOH leadership (Maître d', Service Managers, and Beverage Director).
• Partner with the Executive Chef and Beverage Director on pacing, expo, and the full guest journey.

What You Bring

• 5+ years FOH leadership in upscale or fine dining; multi-room or high-volume experience preferred.
• P&L ownership and labor-management track record; fluency with the par grid and budget.
• Command of steps-of-service standards and a Captain-led service model.
• POS and reservation-system fluency (Toast, SevenRooms); calm, gracious presence under pressure.

Certifications and 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); renewed 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.)
• Certified Food Protection Manager (CFPM): RECOMMENDED, so the role can serve as an on-duty CFPM (at least one required on site during all food prep and service hours). 
• Chicago Food Service Sanitation Manager Certificate (FSSMC): REQUIRED. Local certificate issued by the City of Chicago Department of Public Health using National CFPM certification
• Allergen Awareness (manager): REQUIRED with CFPM. Illinois-approved, ANAB-accredited allergen training within 30 days; renew every 3 years; kept on site.
• Sommelier certification: preferred
• M Street Collective actively participates in the E-verify process

Compensation and Pay Scale 

$120,000 to $150,000 per year, paid as an annual salary (market-aligned). The final offer is confirmed in writing. This position is eligible for a performance bonus as a component of total compensation.

Benefits and 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, STD, and LTD; 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). 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 Maison 58 Club, and the OakSh 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 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 to request one. This position is performed in Chicago, Illinois.