Luxury Service Captain & A5 Sommelier Lead

M Street Entertainment Group

Chicago (IL)

On-site

USD 23,000 - 28,000

Full time

14 days+

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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.