Esquire People Operations Leader

Job Description

Job Description

Location: 58 East Oak Street, Gold Coast, Chicago, IL Employment type: Full-time Classification: Salaried, exempt Reports to: COO

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 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 first hire and the engine of the people function — and a collaborative thought partner to the COO and the Director of Operations on every people decision. This role owns recruiting, onboarding, and employment compliance, upholds Esquire's standards, and facilitates and oversees the two-week new-hire training to spec — it does not author the curriculum, it makes sure training is delivered on schedule and on standard. It is the guardian of the four pillars in the people systems themselves: hiring for hospitality and a growth mindset.

What You’ll Do

• Own the full recruiting funnel: postings, ATS, screening, scheduling, and the referral-bonus program.
• Facilitate and oversee the two-week new-hire training to the established spec — trainers, schedule, logistics, and completion; own delivery and standard, not curriculum design.
• Ensure compliance with wage/hour and tip-pool rules, pay-transparency postings (HB 3129), Chicago Paid Leave & Paid Sick Leave, One Day Rest in Seven (ODRISA) meal-and-rest scheduling, BIPA written consent for any biometric time clocks, required postings, I-9, and recordkeeping.
• Manage onboarding, payroll setup, and uniforms so new hires are floor-ready on time
• Manage benefit administration for new hires, qualifying life events, and open enrollment
• Oversee and execute employee relations including workplace investigations to ensure full legal compliance, prompt conflict resolution and mitigate organizational risk
• Uphold Esquire's standards, policies, and culture; steward recognition and the team experience across two compensation models.
• Serve as a collaborative thought partner to the COO and the Director of Operations on hiring, people decisions, and team development.

What You Bring

• 5+ years HR / people-operations leadership in hospitality or high-volume service.
• Hands-on recruiting and ATS experience; high-volume restaurant experience strongly preferred.
• Working knowledge of Chicago, Illinois, and federal labor compliance and payroll onboarding.
• Organized, warm, and credible with both hourly teams and senior leadership.

Certifications & Requirements

• PHR/SPHR/SHRM-CP certification preferred or willingness to obtain certification
• No food or alcohol certification is required to perform this role. As owner of the certification program, this role tracks and retains BASSET, Food Handler, CFPM,FSSMC and Allergen Awareness records for inspection by IDPH, CDPH, and the Illinois Liquor Control Commission.

Compensation — Pay Scale

$91,000–$108,000 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 & 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.

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.