How to Land Your Dream Entry Level Sales Job in Chicago: Tips and Tricks

How to Land Your Dream Entry Level Sales Job in Chicago: Tips and Tricks
10 min read


Are you a recent graduate or someone looking to switch careers? Are you passionate about sales and dreaming of starting your career in the Windy City? Chicago is home to some of the biggest corporations and businesses, offering a plethora of entry-level sales jobs. However, finding and landing your dream job can be challenging without proper guidance. In this blog post, we will provide you with tips and tricks that will help you stand out from the crowd and secure your dream entry level sales jobs Chicago. So, let's get started!

Introduction to Entry Level Sales Jobs in Chicago

Sales jobs in Chicago can be extremely rewarding, both financially and personally. If you're looking to start your career in sales, or are considering a career change into sales, then Chicago is a great place to start your search.

There are many different types of sales jobs in Chicago, from entry-level positions working in retail stores or call centers, to more advanced positions selling products or services door-to-door or over the phone. No matter what your experience level or education, there's likely a sales job in Chicago that's a perfect fit for you.

If you're not sure where to start your search for a sales job in Chicago, check out these tips and tricks:

  1. Start by taking a look at job postings online, on websites like or This will give you an idea of the types of sales jobs that are available in Chicago, as well as the skills and qualifications required for each position.
  1. Once you've identified a few potential positions that interest you, reach out to friends or family members who work in sales in Chicago and ask for their advice and recommendations. They may know of open positions that haven't been posted online yet, or could put you in touch with someone who can help you get started in your new career.
  1. Attend local job fairs and networking events specifically for sales professionals. These events are often held by professional organizations like the Sales Association of Greater Chicago.

Where to Find Job Opportunities

There are a few key places to look for job opportunities when you're trying to land your dream entry level sales job in Chicago. The first place to start is with your network of family and friends. Ask them if they know of any companies that are hiring entry level sales representatives. If they don't, try searching online or attending job fairs.

Another great place to look for job opportunities is on the website of the Illinois Retail Merchants Association (IRMA). They have a section dedicated to helping people find retail jobs in Illinois. You can also check out the website of the Chicago Association of Commerce and Industry (CACI) for job postings.

 Don't forget to utilize your school's career center. They can help you connect with employers who are looking to hire recent graduates for entry level sales positions.

Craft an Effective Resume and Cover Letter

As you embark on your job search, it's important to have a well-crafted resume and cover letter. Your resume should highlight your relevant experience and skills, and your cover letter should be tailored to the specific job you're applying for.

Here are some tips for crafting an effective resume and cover letter:

  1. Keep it simple. Don't try to cram too much information into your resume or cover letter. Stick to the essentials and make sure the information is easy to read and understand.
  1. Highlight your relevant experience and skills. Tailor your resume and cover letter to the specific job you're applying for, highlighting the experience and skills that are most relevant to the position.
  1. Be concise. In today's competitive job market, employers are bombarded with resumes andcover letters. Make sure yours is concise and to the point, or else it may get lost in the shuffle.
  1. Proofread carefully. Before you submit your resume or cover letter, proofread it carefully for any spelling or grammar errors. These can be costly mistakes that could cost you a chance at getting an interview.

Networking Strategies

If you want to land your dream entry level sales job in Chicago, you need to put yourself out there and network with as many people as possible. There are a few different ways you can go about doing this:

  1. Attend industry events: There are often industry-specific events happening in Chicago that can be great networking opportunities. Attend one of these and make sure to introduce yourself to as many people as possible.
  1. Get involved with professional organizations: There are also many professional organizations based in Chicago that can help you meet people in your industry. Consider joining one or two of these and attending their events.
  1. Connect with people online: LinkedIn is a great way to connect with other professionals in your industry, even if they don't live in Chicago. Send out some messages and see if anyone wants to meet up for coffee or lunch.
  1. Talk to people you know: Don't forget to talk to the people you already know! See if any of your family or friends know anyone working in sales in Chicago who could introduce you to the right people.

Preparing for the Interview Process

If you're looking for an entry level sales job in Chicago, you'll need to be prepared for the interview process. Here are some tips and tricks to help you land your dream job:

  1. Research the company you're interviewing with. This will help you prepare questions to ask during the interview and show that you're interested in the company.
  1. Practice your elevator pitch. You'll likely be asked to describe yourself and your qualifications during the interview, so practice beforehand so you can deliver a confident and polished answer.
  1. Dress for success. First impressions matter, so make sure you dress professionally for your interview.
  1. Be prepared to answer questions about your experience and skillset. The interviewer will want to know more about your qualifications, so be ready to talk about your previous experiences and what makes you a good fit for the job.
  1. Ask questions of your own. In addition to answering the interviewer's questions, take the opportunity to ask questions of your own about the company or position. This will show that you're truly interested in the opportunity and will help keep the conversation flowing smoothly.

Tips on Succeeding at the Interview

If you're looking for an entry level sales job in Chicago, you'll need to be prepared for the interview process. Here are some tips on how to succeed:

  1. Do your research. Before the interview, make sure you know everything you can about the company and the position you're applying for. This will help you answer questions confidently and show that you're truly interested in the job.
  1. Dress to impress. First impressions matter, so take the time to dress professionally for your interview. This will show that you're serious about the opportunity and respect the company's standards.
  1. Be ready to sell yourself. In a sales role, confidence is key. In your interview, be sure to highlight your successes and explain why you would be a great fit for the position.
  1. Be prepared to answer tough questions. Sales interviews can be challenging, so come prepared with thoughtful answers to common questions like "What are your weaknesses?" or "Why should we hire you?"
  1. Follow up after the interview. After meeting with the interviewer, send a thank-you note expressing your interest in the role and reiterating why you would be a great fit for it. This will help keep you top of mind as they make their decision.

Possible Challenges of Entry Level Sales Jobs in Chicago

There are a few possible challenges you may face when trying to land an entry level sales job in Chicago. The first challenge is the competition. With so many people wanting to enter the sales field, jobs can be hard to come by. You'll need to make sure your resume and cover letter stand out from the rest.

The second challenge is the interview process. Sales jobs can be notoriously difficult to get hired for, so you'll need to be prepared for a tough interview. Be ready to sell yourself and your skills, and don't be afraid to ask questions about the company or position.

The third challenge is the work itself. Sales can be a demanding job, so you'll need to be prepared for long hours and a lot of rejections. If you're not used to working hard or taking rejection well, it might not be the right fit for you.

Keep these challenges in mind as you start your job search, and don't let them deter you from pursuing your dream job in sales. With hard work and perseverance, you can overcome anything that stands in your way.

Final Thoughts

Sales jobs in Chicago can be extremely competitive, but there are a few steps you can take to increase your chances of landing your dream job. First, research the companies you're interested in and make sure you understand their products or services. Next, brush up on your sales skills and be prepared to demonstrate them during the interview process. Don't be afraid to sell yourself - let the employer know why you're the best candidate for the job. By following these tips, you'll be well on your way to landing that dream entry level sales job in Chicago.


Jessica Adison 197
My name is Jessica and I am a new mother, creative writer, and researcher. My aim is to assist mothers who are new to the world by giving them the knowledge the...
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