Cowboys and Astronauts is hiring a Retail Associate Lead & Keyholder.
Cowboys and Astronauts is a standout Andersonville boutique offering Supplies for Modern Kind through a curated mix of style, utility, and personality. Rooted in character and community for nearly nine years, we bridge the refined and the rugged to create an extraordinary shopping experience.
Retail Associate Lead & Keyholder position is a leadership-track role with real ownership and upward potential for someone who can sell, move fast, think on their feet, and keep the store running smoothly while creating an excellent customer experience. We are a curated lifestyle destination serving up style, essentials, and Supplies for Modern Kind, and we believe shopping should feel like discovery: warm, personal, and a little unexpected.
We’re looking for a curious explorer who brings heart, hustle, and genuine hospitality to the floor. A leader who knows that good service starts with a warm hello, and knows how to make people feel seen not just sold to. You will help set the pace of the store day-to-day and play a direct role in sales performance, team leadership, and store events. The Retail Associate Lead & Keyholder sets the tone and this role directly impacts sales, team performance, and how customers experience Cowboys and Astronauts.
What We’re Looking For:
- 2+ years of retail leadership experience required, preferably in a specialty or brand-driven environment
- Proven ability to sell and take ownership of daily sales goals
- Fast, efficient, and organized managing multiple priorities without slowing down
- Polished, outgoing, and comfortable engaging with customers all day
- Open availability with flexibility for mornings, nights, weekends, and holidays
- Self-directed, reliable, and ready to step into more responsibility
What You’ll Do:
- Run the sales floor as Lead-on-Duty, owning the customer experience and flow of each shift
- Drive daily sales and average order value through confident, relationship-based selling
- Execute store operations quickly and efficiently, including opening and closing, task management, replenishment, and visual upkeep
- Balance selling and operations without letting either slip
- Help host and execute monthly sip-and-shops and community events, with opportunity to plan and lead future activations
- Support, coach, and potentially supervise Retail Sales Associates
- Maintain high standards for merchandising, presentation, and store readiness
- Communicate clearly with ownership around performance, priorities, and opportunities
Pay & Perks:
- $21.50-$23.00/hour based on experience and performance
- Generous employee discount
- Clear opportunity with growth
Pay: $21.50 - $23.00 per hour
Benefits:
- Employee discount
- Flexible schedule
- Paid time off
Application Question(s):
- Are you comfortable being in the store alone?
- What about Cowboys and Astronauts motivated you to apply?
- What is your availability? Are you available on weekends?
Education:
Experience:
- Retail sales leadership: 2 years (Required)
Shift availability:
Ability to Commute:
- Chicago, IL 60640 (Required)
Work Location: In person
