Job Description

We Love Pop Ups | Chicago, IL (On-Site) | Seasonal, Full-Time & Part-Time Roles

 Hourly Pay: $20–$30/hour

If you’re a natural leader with a bar or event management background and thrive in fast-paced, high-volume environments—this one’s for you.

Jack’s Pumpkin Pop-Up is looking for experienced Managers and Assistant Managers to join our team for the fall season. This is not your typical admin-heavy festival role. We’re looking for confident, charismatic operators who can handle real bar management, staff leadership, and high-pressure situations with ease. You’ve worked in nightclubs, bars, or festival-style events before. You know how to keep things moving, keep teams motivated, and handle a crowd.

Who This Role Is For:

• You’re an experienced GM, AGM, or bar/event manager with a background in nightlife, hospitality, or large-scale pop-ups.
• You’re sharp under pressure, approachable but firm, and people naturally want to follow your lead.
• You can handle ordering, inventory, reporting, sales numbers, staff scheduling, hiring, and team management—without missing a beat.
• You’re cool with weekend and evening-heavy hours and fully outdoor work.

What You’ll Be Doing:

• Managing bar and FOH operations for Jack’s Pumpkin Pop-Up: a major fall pop-up in Chicago.
• Leading and overseeing a large team—ensuring smooth shifts, strong sales, and top-tier guest experience.
• Coordinating inventory, ordering, and supply management with accuracy and accountability.
• Handling schedules, hiring, and training seasonal staff members as needed.
• Reporting sales numbers and troubleshooting issues as they arise.

Must-Haves:

• 21+
• Weekend and evening availability (this is peak season hospitality work!)
• Proven bar, nightclub, festival, or event management experience
• Personable, customer-focused, calm under pressure, and detail-oriented
• Familiarity with Square POS, inventory systems, staffing platforms, and basic reporting

Bonus Points:

• Kitchen management or BOH leadership experience
• Experience working in high-volume outdoor environments

If that sounds like you, hit us up. We're ready to start hiring now for the upcoming season.

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