Bookkeeper, Executive Assistant and Store Assistant

Key Responsibilities

You must be a self-starter for this role. You must be able to advance the projects allocated to you by the Owners, with autonomy and lateral thinking. Owners are available for discussion, guidance and support.

The role has the prospects of being exciting and varied. One of the first things we want is for someone to grab the bull by the horns and apply to the City for our Patio License, so our customers can enjoy an iced drink in the sunshine! Can you get this project going while balancing a number of other tasks?

While there is a significant amount of flexibility here, in the first 3 months, the role will be store-based and will act as an overspill for when the store is busy, to assist with stock management, the register and minor cleaning duties.

When applying, please set out your experience in doing a role like this.

Bookkeeping & Administrative Support (Primary Focus)

• Maintain accurate financial records, including daily bookkeeping and data entry
• Assist owners with administrative tasks, reporting, and general business operations
• Manage invoices, receipts, and basic accounting processes
• Prepare and assist with filing local and state taxes, including City of Chicago and Illinois requirements (e.g., MPEA tax, soda/sugar tax, and other applicable filings)
• Support scheduling, communications, and organizational tasks for the business
• Handle confidential information with discretion and professionalism

Store Operations Support

• Seamlessly transition from administrative work to in-store support as needed
• Jump behind the register, assist customers, or support the team during busy periods
• Deliver room service orders to residents within the building
• Provide friendly, efficient, and professional customer service
• Support general store upkeep, cleanliness, and organization

Optional Training Opportunities

• Opportunity to train on POS/register operations
• Exposure to barista skills, cocktail preparation, and general café/bar operations (optional based on interest)

Work Style & Environment

• Store-based role combining independent desk work with active floor support
• Ability to work from a laptop in a quiet space during slower periods
• Requires flexibility, awareness, and readiness to jump in when the store gets busy
• Evening availability preferred, when admin work can be the primary focus

Compensation & Benefits

• Base Pay: $17/hr
• Tips: Average $5–$6/hr, historically consistent, bringing total earnings to $22–$24/hr (and potentially higher as tips grow). Tips are tax free, so you keep more in your pocket!
• Training & Growth: Opportunity to develop bookkeeping, tax filing, and administrative skills with the owners; potential for raises as responsibilities increase
• Flexible Schedule: Part-time or full-time available; evening shifts preferred for focused admin work
• Skill Expansion: Optional cross-training in register, barista, and cocktail preparation

Pay: $21.00 - $24.00 per hour

Benefits:

• Employee discount
• Flexible schedule

Work Location: In person