Sales Representative

Kick off your Roadshow journey with a $500 sign-on bonus—paid out after you successfully complete your first three shows!

True Classic is looking for enthusiastic and results-driven  Sales Representatives to bring our brand to life at in-person retail events across the Chicago metro area. In this role, you’ll be the face of True Classic—engaging directly with customers to promote and sell our premium men’s apparel. You’ll deliver exceptional in-person experiences that drive sales, build customer loyalty, and expand brand awareness.

This is a regional travel role. Candidates must live in or near Chicago, IL, and be open to traveling up to 10 days at a time to various store locations throughout the region.

About True Classic

Founded in 2019 and headquartered in Los Angeles, True Classic is one of the fastest-growing men’s apparel brands in the world. We deliver high-quality, well-fitting wardrobe essentials at accessible prices—and we give back in the process, donating thousands of shirts each month to those in need. Our mission is to help men feel confident, comfortable, and seen—one classic tee at a time.

What You’ll Do

• Represent the True Classic brand at Costco Roadshows with professionalism, energy, and enthusiasm
• Greet and assist shoppers, creating a positive and welcoming experience
• Conduct engaging product demonstrations that highlight fit, comfort, and style
• Drive sales by confidently pitching and closing transactions
• Set up and break down branded displays in coordination with Costco staff
• Maintain a clean, organized, and visually appealing booth throughout the event

What We’re Looking For

• Valid Driver’s License and reliable transportation required for regional travel
• Comfortable working on the road for up to 10 consecutive days
• Comfortable using technology (we utilize multiple apps for onboarding, communication, and event coordination)
• Prior experience in sales, product demos, or Roadshow-style retail events preferred (Costco experience is a plus)
• Exceptional communication and interpersonal skills
• Strong self-starter who can work independently and manage time effectively
• Must be available to work weekends and holidays as needed

Physical Requirements

• Ability to stand for extended periods
• Lift and carry up to 50 pounds
• Climb ladders and step stools as necessary
• Maintain energy and focus in a busy retail/warehouse setting

Compensation and Benefits

• Base pay starts at $16.50-$25/hour, dependent on experience  
• A lucrative commission structure paid out weekly based on show performance
• $500 sign-on bonus—paid out after you successfully complete your first three shows!
• Company-paid medical, dental, and vision PPO insurance (Anthem Gold PPO):
  • Employee premiums paid 100%
  • Dependent premiums paid 65%
• 401(k) plan with 3% company match

Our mission is to empower everyone to show up as their best self. We are dedicated to creating a community where creativity, curiosity, and innovation thrive; and that starts with welcoming diverse voices to our team. We believe that everyone should feel confident being exactly who they are, which is why we’re committed to being an equal opportunity employer. We celebrate and support differences in race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, and abilities. If you need assistance or an accommodation due to a disability, please reach out to Human Resources.