Outside Sales Professional - Chicago

Build Your Career. Build Your Clientele. Build Your Income.

What if you could build a career around relationships, personal growth, and uncapped earning potential—with guaranteed pay during your first two years as you establish yourself? 

As an Outside Sales Professional with Tom James, you'll build and manage your own clientele of successful professionals, providing custom clothing and personalized service at their offices and homes. You'll receive comprehensive training, mentorship, and financial support as you build your business—and as your clientele grows, so does your earning potential.

What You Can Expect

• Company-paid training and ongoing mentorship

• Strong client relationships

• W-2 employment with comprehensive benefits

• Typical 1st-Year Earnings: $70K

• Guaranteed Training Pay: Receive guaranteed pay throughout your first two years as you learn the business, build your clientele, and develop the skills to succeed. 

• Uncapped Commission: No ceiling on your commission earnings—your income potential grows with your performance and clientele. 

• Top 1st-Year Performers: $125K–$175K

• Employee ownership opportunities, 401(k) match, and profit sharing

• Leadership opportunities and incentive trips

What You'll Do

• Build and develop your clientele through prospecting, referrals, networking, and relationship development

• Schedule appointments and meet clients at their offices and homes

• Conduct personalized sales presentations 

• Develop long-term relationships that build your repeat clientele

• Manage your in-office and in-field activities daily

• Deliver a highly personalized client experience from initial meeting through ongoing service

Build Your Own Clientele and Sell Through Relationships

You'll learn how to identify prospects, generate referrals, network, and develop relationships that can become a loyal clientele throughout your career.

You'll work directly with successful, busy professionals who value convenience, quality, and personalized service. Rather than working from a traditional retail environment, you'll meet clients at their offices and homes and become a trusted advisor.

 

 

Company-paid Training

Our comprehensive, company-paid training program teaches you how to prospect, sell, measure, fit, and service custom clothing. Training and mentorship continue well beyond your initial six-month development period.

Who Thrives Here

• This opportunity is a strong fit for someone who:

  • Is ambitious, resilient, and motivated by performance-based rewards

  • Enjoys building genuine, long-term professional relationships

  • Manages their time effectively and consistently executes daily activities

  • Welcomes coaching and is willing to learn a proven sales process

About Tom James

Tom James Company is the world's largest retailer and manufacturer of custom clothing. With nearly 60 years of experience in direct selling, we've grown from a single store into a global company with locations across four continents and more than $500 million in sales.

Our vertically integrated business allows us to maintain control over the quality of the garments we provide. Our sales professionals build long-term relationships with successful professionals who value convenience, quality, and exceptional service.

At Tom James, you're not just taking a sales job. You're building a clientele, a career, and a business of your own—with the training and support to help you succeed.

careers.tomjames.com