Professional Clothier


ESQ is seeking self motivated an extremely personable and self driven Professional Clothier to join our expanding team.

Our Professional Clothier role is a full-time salaried position, plus commission, for a self motivated and passionate individuals who not only love working with people, but also want to be part of a rapidly growing company. You will get exactly what you put into our Professional Clothier role, with compensation that will exceed any of our competitors. If you're self-motivated, six figures should be very realistic in year one.

While we want to reward you for your performance and we demand that our Professional Clothiers be the best at what they do, and you will be compensated accordingly.

ESQ Clothing was founded in 2012 by an attorney sick of the run of the mill ‘custom clothiers’ popping up nonstop. We are proud to offer the best quality handmade bespoke suit in the city of Chicago, more Italian and English fabric selection than any competitor, and an exclusive and loyal clientele base, from the discerning businessman to celebrities and professional athletes.


You will make an impact by:

  • Becoming a menswear specialist based on our training & development of client measurements, fabric knowledge, customization, alterations, and sales psychology

  • Proactively building a book of clients through different prospecting efforts (outreach, events, etc.) and building upon recurring client relationships

  • Setting appointments and meeting with clients in our showrooms to conduct personalized wardrobe planning for both casual and professional looks

  • Personally guiding clients through the experience, taking measurements, and helping them sort through different fabrics, collar types, pockets, buttons, embroideries, and every detail that goes into ultimately hand crafting a one-of-a-kind custom garment

  • Maintaining personal relationships with our most exclusive clients from their first interaction with ESQ through purchase, delivery and ongoing orders


As a growing professional, challenge and opportunity excites you. You have:

  • 2 to 5+ years of direct sales experience – creative & strategic in approach (outside sales preferred)

  • A charismatic personality with humility and a great sense of humor

  • Excellent client relationship skills (new business development, sales, client facing roles)

  • Prior affiliation with successful customer-facing businesses, preferably in the luxury industry; having a natural ability to connect with clients and comfortably handle all personality types

  • Strong eye for detail & organizational skills. As a custom menswear company with customizations, measurements, and custom client experiences - it's all in the details

  • World class communication & interpersonal skills; written and verbal, handling yourself with confidence internally to peers and externally to clients

  • Independent decision making skills with the ability to self-manage; whether it be your book of business, or employee growth and development

  • Proficiency with technology and Excel – ability to navigate and create basic formulas

  • Passion for the menswear industry and creating confidence with luxury clothing

  • The ability to be comfortable with being uncomfortable. In a high growth company, this is the only way we can learn from each other and improve

  • An entrepreneurial spirit - you take initiative to get things done

  • The drive to be involved and network, We are passionate about what we do, and what we do as a company, ultimately spreading the word and helping us grow as a business

  • Curiosity. With being a part of a competitive market, current and emerging trends, and having over 40,000 fabric swatches on file that can create endless customization combinations, you will always be learning


  • Compensation is a mix of base salary, industry leading commission, and bonus, depending on experience – high income potential

  • Comprehensive benefits package

  • Industry related training and development

  • Rewarding incentives for achieving your sales goals