Roadshow Sales Representative

True Classic is looking for charismatic, results-driven Roadshow Sales Representatives to bring our brand to life at in-person retail events throughout Chicago.

This isn’t your average retail role. As a Roadshow Sales Representative, you’re the face of True Classic—connecting with customers, delivering dynamic product demos, and creating memorable shopping experiences that drive real results. You’ll combine storytelling, product expertise, and performance-driven sales skills to turn everyday shoppers into loyal fans.

If you thrive in high-energy environments, love engaging with people, and are motivated by a high-earning, performance-based commission paid weekly based on performance, this is your stage.

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

What You’ll Do

• Represent True Classic at Costco Roadshows with confidence, professionalism, and high energy
• Create a welcoming, engaging experience for every shopper
• Deliver compelling product demonstrations highlighting fit, comfort, and style
• Confidently pitch, overcome objections, and close sales
• Set up and break down branded displays in partnership with Costco staff
• Maintain a polished, organized, and visually compelling booth throughout each event
• Consistently hit and exceed sales goals

What Makes You a Great Fit

• Valid driver’s license and reliable transportation for regional travel
• Comfortable traveling and working on the road for up to 10 consecutive days
• Tech-savvy and comfortable using multiple apps for onboarding, communication, and event coordination
• Prior sales, product demos, or Roadshow-style retail experience preferred (Costco experience is a plus)
• Exceptional communication and interpersonal skills
• Strong self-starter who can work independently and manage time effectively
• Available to work weekends and holidays as needed

You’re Someone Who

• Loves striking up conversations
• Feeds off the energy of a busy retail environment
• Takes ownership of results
• Enjoys turning engagement into measurable performance

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 & Benefits

• Base pay: $16.50 - $22/hour, dependent on experience
• High-earning, performance-based commission paid weekly based on performance
• $500 sign-on bonus paid after successfully completing your first three shows
• $250 annual True Classic merchandise allowance to rep the brand you sell
• Company-paid medical, dental, and vision insurance
• 401(k) plan with 3% company match

True Classic is proud to be 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 accommodation due to a disability, please contact Human Resources.

About True Classic

At True Classic, our purpose is simple: empower everyone to look good and feel good.

Founded in 2019, we’re a fast-growing apparel brand obsessed with fit, quality, and impact. But we’re building more than great products—we’re building a high-performance team where smart, driven people do meaningful work, move fast, and see the direct results of what they create.

Everything we do is guided by the True Classic Operating System (TCOS)—the principles that shape how we work, make decisions, and win together:

• Move the Needle – Our #1 value and the ultimate filter for decision-making. We focus on delivering tangible, measurable results that drive real business impact.
• Paint the Picture – We set clear vision and help others see what great looks like.
• Seek the Truth – We use data, customer insight, and curiosity to guide decisions.
• Get 1% Better – We continuously improve how we work through strong systems and small wins.
• Build Leverage – We maximize impact with the right mix of people, tools, automation, and AI.
• Crush the Challenge – We surface problems early and take ownership to solve them.
• Go Fast – We take initiative, move with urgency, and bias toward action.
• Be Creative – We challenge the norm and find better ways to win.
• Lead with Empathy – We care deeply about our customers and each other.

If you thrive in fast-paced environments, take ownership of your work, and want to build something that actually moves the needle—join us and help shape what’s next at True Classic!