Expeditor

The engine behind a smooth service. Our Expeditor/Host is the person who keeps drinks moving, gaps covered, and the whole floor humming — whatever the night demands.

We're looking for a quick-thinking, reliable, and team-oriented person to join our small, close-knit team. This role sits at the operational heart of our service — keeping the bar-to-table flow tight, filling in wherever the room needs it, and ensuring every shift runs without a hitch behind the scenes.

Most of your time will be spent working closely with our bar team: running/finishing drinks accurately and efficiently, anticipating the rhythm of service during live sets, and keeping things moving at pace. Beyond that, you're the person who notices what needs doing and does it — no waiting to be asked. The ideal candidate will have strong Server and Bartender skills and be available to be scheduled in those roles occasionally.

Core responsibilities

• Expedite drinks from bar to table — accurately, promptly, and in sync with the bar team's output
• Maintain awareness of the full floor during service; anticipate needs and move proactively
• Support bar staff directly during high-volume periods — stocking, clearing, organizing as needed
• Fill in across front-of-house wherever gaps arise — this is a true catch-all support role
• Assist with coat check during coat season, keeping garments organized and guests moving smoothly
• Safeguard small personal items for guests when requested
• Maintain a composed, professional presence throughout the shift, including during peak service

Hosting — as needed

On some shifts, you'll also step into a hosting role — greeting and seating arriving guests when our designated host needs support or coverage. This is occasional rather than primary, and you'll be expected to bring the same warmth and professionalism to it as everything else.

• Welcome arriving guests and coordinate seating per seating chart
• Manage the flow of arrivals during busy entry periods
• Represent the club with poise — the first impression matters

Winter's Jazz Club is one of Chicago's most beloved music venues — and one of its best-kept secrets. An intimate listening room presenting Chicago's top talent alongside national headliners, we sit tucked along the Ogden Slip in Streeterville, where the water and the music combine to create an atmosphere that's genuinely unlike anywhere else in the city. The club was specifically designed to place all attention where it rightfully belongs — on the musicians — and that same philosophy extends to our team: we believe the people who work here deserve the same care and respect we show the artists on our stage. We are intentional and proud about hiring kind, professional, and respectful people across every role, and we work hard to keep our small, close-knit team that way. Joining Winter's means coming to work somewhere that sounds beautiful, feels special, and treats you well — every shift.