60 Key Jobs Hiring in Chicago, IL

We make objects for people who are curious about the world.
We make fountain pens, notebooks, watercolors, leather goods, house shoes, sunglasses, and other tools that help people think, create, travel, and live with greater attention.

We believe the most important moments rarely begin with certainty. They begin with a question, a blank page, a wrong turn, or a thought not yet fully formed.

To be lost is not always a problem to solve. It is often where discovery begins. We make tools for those moments.

A pen to discover what you think. Paper to give shape to an idea. Watercolors to slow down and see more carefully. Objects to carry through the world. House shoes that mark the transition from the outside world to the sanctuary of home.

As a Japanese company, many of these rituals are inspired by Japanese life, where simple acts are elevated through repetition, attention, and care.

Designed between Boston and Tokyo, our products are developed with exceptional makers, craftspeople, and industrial designers around the world. We seek lasting materials, enduring construction, and timeless utility—not because objects are meant to be admired, but because they are meant to be used.

Our shops are found in some of the world’s great creative neighborhoods. More than stores, they are places to discover tools, exchange ideas, attend workshops, and spend time with others who share a love of making, writing, drawing, and thoughtful living.

The best tools earn their place quietly and become more valuable with time.

Key Holder – Role Overview
As a Key Holder at Topdrawer, you are a frontline leader who helps bring our brand to life through exceptional customer experiences, deep product knowledge, and day-to-day store support. You lead by example, take ownership of opening and closing responsibilities, and support the team in creating a thoughtful, inspiring environment. Whether sharing the story behind a fountain pen or helping a customer discover a new creative ritual, you serve as a trusted guide and ambassador of quiet design. This role is ideal for someone passionate about creativity, service, and growing into a future leadership position.

Key Responsibilities

Customer Experience & Community

• Deliver a welcoming, educational, and personalized customer experience

• Model Topdrawer’s values in every interaction, from storytelling to service follow-up

• Support the store team in building lasting relationships with customers and local partners

Team Support & Leadership

• Lead by example on the sales floor and during peak periods

• Assist in onboarding, coaching, and mentoring new team members

• Help maintain a positive, inclusive, and collaborative team environment

Store Operations & Merchandising

• Perform opening and closing procedures with a high level of responsibility

• Assist with inventory receiving, restocking, and visual merchandising

• Uphold visual standards that highlight Topdrawer’s curated and elegant assortment

Sales & Business Support

• Contribute to achieving daily sales, conversion, and average order value goals

• Support monitoring of store performance and share opportunities for improvement

• Maintain store standards in cleanliness, presentation, and customer care

• Stay up to date on product knowledge, new arrivals, and promotions

You Are

• A thoughtful, hands-on leader with 2+ years of retail or key holder experience

• Passionate about creativity, sustainability, and intentional living

• Detail-oriented and operationally strong, with a deep appreciation for beautiful, functional tools

• Warm, dependable, and energized by building lasting customer relationships

• Curious and committed to continuous learning and improvement

• Experienced or eager to grow in visual merchandising and product storytelling

Be part of a global creative community rooted in timeless, functional design. Work for a mission-driven company that values originality, sustainability, and meaningful connection. Join a team where your creativity, leadership, and ideas truly matter.

Benefits Part-Time:

• Part-time (hourly)

• Generous Employee Discount

• Flexible Spending Accounts (FSA) for Health and Dependent Care

• 401(k) Retirement Plan (IRA) with Company Matching

• Commuter Benefits

• Monthly Sales Commission Opportunities

• $18-$22/hour

Topdrawer is an Equal Opportunity Employer and is proud to promote equal opportunity for all applicants without regard to race, color, religion, sex, sexual orientation, national origin, age, disability, military status, or any other applicable legally protected characteristic.

Physical Requirements: This role may require standing for extended periods and regularly lifting or moving items up to 50 lbs. Reasonable accommodations will be made to enable individuals with disabilities to perform essential job functions. If you need a reasonable accommodation during the application or hiring process, please contact HRadmin@topdrawershop.com.

Topdrawer will consider for employment all qualified applicants, including those with criminal histories, in a manner consistent with the requirements of applicable state and local laws, including the City of Los Angeles Fair Chance Initiative for Hiring Ordinance, the San Francisco Fair Chance Ordinance, and the California Fair Chance Act.

Applicants must be legally authorized to work in the United States. Topdrawer does not provide visa sponsorship for this position.