Head Bartender/Assistant General Manager

Winter's Jazz Club | Chicago -- Head Bartender / Assistant General Manager

Winter's is looking for a Head Bartender/Assistant General Manager to join our small, close-knit team. If you're a skilled bartender who leads with warmth, thrives under pressure, and wants to help build the premier jazz club in Chicago, we'd love to meet you.

The Role

This is a five-shift-per-week position, Wednesday through Sunday, primarily scheduled as Head Bartender. When our GM is off, you'll step into AGM responsibilities — a natural extension for someone ready to grow into more ownership of how the club runs night to night.

You'll do more than make great drinks fast. You'll set the tone for the bar, anchor the guest experience, and act as an ambassador for what makes Winter's special — live jazz, upscale hospitality, and a room people come back to.

Compensation & Benefits

• Head Bartender: $17/hour + tips
• AGM: $30/hour
• Year-end bonus
• Paid holidays
• 5 PTO days
• 5 SPTO days

What We're Looking For

• A seasoned bartender/AGM who's comfortable in high-volume, fast-paced environments
• Someone who takes pride in craft and consistency behind the bar
• A collaborative, respectful presence on a tight-knit team — with guests and coworkers alike
• Genuine enthusiasm for hospitality and live music

Why Winter's

• Upscale clientele in a vibrant neighborhood
• Shorter shifts (typically 6–7 hours) with minimal side work — we don't serve food
• A professional environment where the whole team is treated with respect
• World-class live jazz, every shift

If you're excited to bring your skills to a team that takes hospitality and music seriously, we'd love to hear from you.

Responsibilities include :

• Preparing the club for opening
• Organizing and stocking the bar for the night
• Batching cocktails
• Interacting with customers, taking orders, and preparing and serving drinks.
• Assessing customer needs and preferences and making recommendations.
• Staying guest-focused and nurturing an excellent guest experience
• Keeping the bar organized, stocked, and clean
• Accurately recording and entering all beverage items into the Square POS system
• Checking guest identification to avoid serving alcoholic beverages to underage guests
• Monitoring inventory levels
• Receiving, inspecting, and putting away deliveries every other Wednesday or as needed
• Conducting preventative maintenance on the bar equipment
• Performing end of day procedures

Our ideal candidate will possess :

• 4+ years of Head Bartender-level experience at a high-volume venue
• Strong knowledge of wine, spirits, classic cocktails, and modern techniques is required
• The ability to lead and mentor
• Positive attitude and excellent communication skills
• Relevant training certificate; Basset-certified
• Ability to work a typical hospitality schedule to include weekends and holidays.
• Ability to work in a standing position for long periods of time.
• Ability to safely lift up to 25 pounds.
• Ability to work well under pressure
• A high attention to detail
• Ability to work in a fast paced environment
• Excellent listening and communication skills
• A professional appearance and demeanor
• Ability to deal effectively and interact well with guests and associates
• Ability to resolve problems/conflicts in a diplomatic and tactful manner

A background check is required.