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Sales Roles Jobs in Chicago, IL (NOW HIRING)

Apple Roofing

Roofing Sales Representative

Chicago, IL · On-site

Previous experience in door-to-door, canvassing, or other direct-to-consumer sales roles. * Familiarity with roofing systems, materials, and terminology. Why Apple Roofing? * Industry-Leading Support ...

Wesco

Associate Specialist - Sales

Glenview, IL

For certain sales roles, Wesco also offers a commission structure that provides additional compensation based on sales results, as defined by the applicable commission plan. In addition, Wesco offers ...

Steinway Inc

Retail Salesperson

Hinsdale, IL

$80K - $130K/yr

Resolve customer issues in a timely manner These are commission-based sales roles with average annualized earnings of $80,000-130,000 for successful employees, with uncapped earnings potential. Hired ...

Steinway Inc

Retail Salesperson

Hinsdale, IL · On-site

$80K - $130K/yr

Resolve customer issues in a timely manner These are commission-based sales roles with average annualized earnings of $80,000-130,000 for successful employees, with uncapped earnings potential. Hired ...

AMBA

Inside Sales Insurance Specialist

Naperville, IL · Remote

$50K - $60K/yr

Prefer inbound-only or appointment-based sales roles * Are uncomfortable with frequent dialing or high daily call expectations * Need a highly flexible or unstructured workday * Are looking for an ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Prefer inbound-only or appointment-based sales roles * Are uncomfortable with frequent dialing or high daily call expectations * Need a highly flexible or unstructured workday * Are looking for an ...

AMBA

Inside Sales Insurance Specialist

Naperville, IL · On-site

$50K - $60K/yr

Prefer inbound-only or appointment-based sales roles * Are uncomfortable with frequent dialing or high daily call expectations * Need a highly flexible or unstructured workday * Are looking for an ...

Orkin LLC

Sales Representative

Broadview, IL · On-site

$70K - $100K/yr

If you've succeeded in home improvement, roofing, HVAC, solar, remodeling, insurance, automotive, or other consultative sales roles, Orkin offers the opportunity to build a rewarding career with a ...

AMBA

Inside Sales Insurance Specialist

Chicago, IL · Remote

$50K - $60K/yr

Prefer inbound-only or appointment-based sales roles * Are uncomfortable with frequent dialing or high daily call expectations * Need a highly flexible or unstructured workday * Are looking for an ...

AMBA

Inside Sales Insurance Specialist

Naperville, IL · Remote

$50K - $60K/yr

Prefer inbound-only or appointment-based sales roles * Are uncomfortable with frequent dialing or high daily call expectations * Need a highly flexible or unstructured workday * Are looking for an ...

Orkin

Sales Representative

Broadview, IL · On-site

If you've succeeded in home improvement, roofing, HVAC, solar, remodeling, insurance, automotive, or other consultative sales roles, Orkin offers the opportunity to build a rewarding career with a ...

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Showing results 41-60

All JobsSales Roles JobsSales Roles Jobs in Chicago, IL

Sales Roles information

See Chicago, IL salary details

$23.7K

$79K

$145.8K

How much do sales roles jobs pay per year?

As of Sep 13, 2026, the average yearly pay for sales roles in Chicago, IL is $78,992.00, according to ZipRecruiter salary data. Most workers in this role earn between $55,100.00 and $95,800.00 per year, depending on experience, location, and employer.

What is the difference between Sales Roles vs Sales Representatives?

AspectSales RolesSales Representatives
CredentialsVaries; often includes sales training or certificationsTypically requires basic sales training or experience
Work EnvironmentCan include inside sales, outside sales, account managementPrimarily direct customer interaction, field or office-based
Employer & Industry UsageUsed across industries for various sales functionsCommonly employed in retail, B2B, and service sectors
Search & Comparison IntentUnderstanding different sales roles and career pathsJob-specific inquiries for sales positions

Sales roles encompass a broad range of positions within sales teams, including account managers, sales executives, and business development specialists. Sales representatives are specific roles focused on direct customer engagement and selling products or services. While all sales representatives are part of sales roles, not all sales roles are limited to representatives. The distinction helps job seekers understand career options and job requirements within the sales industry.

What types of sales roles are there?

Sales roles include positions such as inside sales, outside sales, account executive, sales development representative, and retail sales associate. These roles vary in responsibilities, with some focusing on lead generation, client relationship management, or direct product selling, often requiring skills in communication, negotiation, and familiarity with customer relationship management (CRM) tools.

What cities near Chicago, IL are hiring for Sales Roles jobs?

Cities near Chicago, IL with the most Sales Roles job openings:

Sales Roles jobs near you
Infographic showing various Sales Roles job openings in Chicago, IL as of August 2026, with employment types broken down into 77% Full Time, 21% Part Time, 1% Contract, and 1% Nights. Highlights an 76% Physical, 1% Hybrid, and 23% Remote job distribution, with an average salary of $78,992 per year, or $38 per hour.

Roofing Sales Representative

Chicago, IL • On-site

Apple Roofing
See more jobs at Apple Roofingexternal

Full-time

Medical, Dental, Vision, Retirement

Re-posted 2 days ago

Job description

On Target Earnings (Average): Year 1: 70-80K | Year 2: 90-100K | Year 3: 110K+
-- Potential to surpass listed ranges based on performance --
Your Opportunity to Raise the Roof:
Are you a natural connector, problem-solver, and go-getter who thrives on helping people? At Apple Roofing, we're not just in the business of fixing roofs - we're in the business of building trust, restoring homes, and delivering a sweeter experience from the first handshake to the final shingle.
We're looking for Roofing Sales Representatives who are ready to bring their energy, drive, and people skills to a growing company that's redefining what it means to work in the roofing industry. You'll be the face of Apple Roofing in your community - meeting homeowners, inspecting roofs, and guiding customers through the insurance and sales process with integrity and confidence.
What you'll do:
  • Scout & Serve - Identify potential clients, knock on doors, respond to referrals, and build strong local networks.
  • Own the Process - From completing roof inspections, preparing sales action plans, and securing the signed contract, you'll manage the full sales cycle while keeping clients informed every step of the way.
  • Educate & Advise - Conduct roof inspections, explain options clearly, and prepare tailored proposals that put the customer's needs first.
  • Deliver a Sweeter Experience - Deliver concierge-style service to every customer and ensure customer satisfaction
  • Stay organized - Keep accurate, up-to-date records in our CRM system and follow up consistently with leads and customers.
  • Represent Apple Roofing - Be a professional, courteous brand ambassador in person, online, and in your community.

What We're Looking For:
We're not your typical roofing company - and this isn't your average sales role. You'll love this job if you are:
  • A natural communicator who builds trust easily
  • Organized and detail-oriented, even when juggling multiple clients
  • Hungry for growth and driven to exceed goals
  • A resilient go-getter who thrives in fast-paced environments
  • Comfortable working outdoors in a variety of weather conditions
  • Must be able to lift up to 50 lbs
  • Ability to walk roofs, climb ladders/stairs, and be on your feet for extended periods
  • Willing to work in hot, cold, or rainy conditions as needed
  • Prior sales or customer service experience preferred
  • Roofing or construction background is a plus - but not required (we'll train the right person)
  • Valid driver's license

Preferred Experience:
  • Previous experience in roofing, construction, or a related field.
  • Previous experience in door-to-door, canvassing, or other direct-to-consumer sales roles.
  • Familiarity with roofing systems, materials, and terminology.

Why Apple Roofing?
  • Industry-Leading Support - Our training and tools are designed to set you up for success
  • Uncapped Commission - Sky's the limit when it comes to your earning potential
  • Team Culture - Work with motivated, collaborative professionals who take pride in what they do
  • Growth Opportunity - We promote from within and support your professional development
  • Benefits - We offer health, dental, vision, 401k, company trips, and more.

Ready to Raise the Bar with Apple Roofing? Apply now and let's build something sweeter - one roof at a time.

Apply