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Entry Level Outside Sales Jobs in Illinois (NOW HIRING)

Legacy Restoration LLC

Outside Sales Rep

Lombard, IL · On-site

$90K/yr

This is a great entry-level opportunity to brush up on your sales skills and learn effective new ... Our entry-level Outside Sales Reps enjoy: * Earning potential of $90,000+ per year, depending on ...

Hibu

Entry Level Outside Sales Representative

Chicago, IL · On-site

$115K - $130K/yr

What You'll Do as an Outside Sales Representative: * Partner with small businesses to provide best-in-class digital marketing solutions (websites, SEO, social ads, and more) * Prospect and cold call ...

Hibu

Entry Level Outside Sales Representative

Chicago, IL · On-site

$115K - $130K/yr

What You'll Do as an Outside Sales Representative: * Partner with small businesses to provide best-in-class digital marketing solutions (websites, SEO, social ads, and more) * Prospect and cold call ...

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Entry Level Outside Sales information

See Illinois salary details

$29.1K

$75.6K

$160.4K

How much do entry level outside sales jobs pay per year?

As of May 28, 2026, the average yearly pay for entry level outside sales in Illinois is $75,625.00, according to ZipRecruiter salary data. Most workers in this role earn between $50,900.00 and $87,200.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Entry Level Outside Sales Representative, and why are they important?

To excel as an Entry Level Outside Sales Representative, you need strong interpersonal skills, persuasive communication, and a basic understanding of sales principles, often supported by a high school diploma or bachelor's degree. Familiarity with CRM software, mobile sales tools, and product knowledge training is typically required. Initiative, resilience, and the ability to build rapport quickly are crucial soft skills for this role. These competencies are vital for generating leads, closing deals, and establishing lasting client relationships in a competitive sales environment.

What are some common challenges faced by entry level outside sales representatives and how can they overcome them?

Entry level outside sales representatives often encounter challenges such as building a client base from scratch, handling frequent rejections, and learning to manage their time effectively while on the road. To overcome these hurdles, new reps benefit from proactively networking, seeking mentorship from experienced colleagues, and diligently following up with leads. Additionally, setting daily goals and consistently tracking progress can help maintain motivation and improve performance. Embracing feedback and continuously refining sales techniques are key to long-term success in this role.

What is an Entry Level Outside Sales job?

An Entry Level Outside Sales job involves selling products or services to customers primarily through face-to-face interactions outside of an office setting. These professionals are responsible for generating leads, meeting potential clients, giving presentations, and closing sales. Entry level positions typically require strong communication and interpersonal skills, but not necessarily prior sales experience. Training is often provided by the employer to help new hires learn about products and effective sales techniques. The role can offer opportunities for career advancement and commission-based earnings.

What jobs make 5000 a week without a degree?

Entry level outside sales positions can sometimes generate $5,000 or more per week through commissions, especially in industries like real estate, insurance, or high-value B2B sales. Success depends on sales skills, product value, and commission structures, with many roles requiring strong communication and persistence rather than formal education.

What is the difference between Entry Level Outside Sales vs Entry Level Inside Sales?

AspectEntry Level Outside SalesEntry Level Inside Sales
Work EnvironmentField-based, traveling to client locationsOffice-based, remote or in-office
Customer InteractionFace-to-face meetings with clientsPhone or online communication
Required SkillsCommunication, persuasion, travel readinessCommunication, CRM proficiency, multitasking
Common IndustriesRetail, manufacturing, wholesaleSoftware, telecommunications, services

Entry Level Outside Sales involves traveling to meet clients face-to-face, focusing on building relationships and closing sales in the field. In contrast, Entry Level Inside Sales primarily involves remote communication from an office, handling inbound or outbound calls. Both roles require strong communication skills, but outside sales emphasizes travel and in-person interaction, while inside sales centers on digital and phone-based engagement.

What are the most commonly searched types of Outside Sales jobs in Illinois? The most popular types of Outside Sales jobs in Illinois are:
What cities in Illinois are hiring for Entry Level Outside Sales jobs? Cities in Illinois with the most Entry Level Outside Sales job openings:
Entry Level Outside Sales jobs near you

Entry-Level Outside Sales Representative

The Impact Insurance Agency

Fairfield, IL • On-site

$65K - $85K/yr

Full-time, Contractor

Medical, Life

Posted 12 days ago

Job description

Entry-Level Outside Sales Representative

Company: Impact Insurance Agency
Schedule: Full-Time | Independent Contractor
Industry: Supplemental Insurance | B2B Outside Sales
Location: Local Territory | In-Person

A Career Path Built for Educators Who Love Helping People

Many teachers, coaches, and education professionals reach a point where they want to continue making a difference while also exploring new opportunities for growth, flexibility, and long-term income potential.

At Impact Insurance Agency, we partner with local businesses to provide supplemental insurance solutions that help employees and families feel supported during life's unexpected moments. Professionals from education often thrive here because the role draws on familiar strengths: communication, mentorship, leadership, and the ability to guide others through important decisions.

This isn't about leaving education behind it's about applying your experience in a new environment where your voice, structure, and people skills continue to matter.

The Opportunity

This entry-level outside sales role focuses on education-based conversations, relationship-building, and ongoing client support. You'll meet with business owners and employees face-to-face, helping them understand benefit options in a clear and approachable way.

As an independent contractor, you'll manage your own local territory while working within a structured system that provides training, mentorship, and consistent support even if you've never worked in sales before.

What You'll Do

  • Connect with local businesses and introduce supplemental insurance solutions

  • Lead enrollment-style conversations that feel educational, not high-pressure

  • Break down complex information into clear, easy-to-understand guidance

  • Build long-term relationships through follow-up and consistent communication

  • Organize your schedule, appointments, and territory activity

  • Participate in weekly training, collaboration, and professional development

Training Designed for Education Professionals

  • Structured onboarding with step-by-step support

  • Hands-on field training and mentorship

  • Health & Life licensing assistance and reimbursement

  • Coaching focused on communication, leadership, and relationship skills

  • A collaborative team culture that values encouragement and growth

Compensation & Structure

  • Commission-based income with performance bonuses

  • Average first-year income: $65,000$85,000 (performance-based)

  • Optional 6-week base draw while building your client base

  • Flexible daytime schedule with autonomy over your territory

  • Long-term advancement into training, leadership, or mentoring roles

Ideal Background

This opportunity may resonate with you if you:

  • Have experience as a teacher, coach, trainer, educator, or mentor

  • Enjoy presenting, guiding conversations, and helping people learn

  • Communicate with clarity, patience, and professionalism

  • Thrive in relationship-focused environments

  • Are looking for a career path that blends purpose with growth potential

  • Are willing to obtain a Health & Life Insurance license (support provided)

Why Impact Insurance Agency

Our culture is built on mentorship, collaboration, and steady development. Many of our leaders began in entry-level roles and grew through consistency, encouragement, and a genuine desire to help others succeed. We believe strong relationships not pressure drive long-term success.

Apply Today

If you're ready to take your communication and leadership skills beyond the classroom and into a professional role where you can continue helping people every day, we'd love to connect.

https://www.theimpactinsuranceagency.com/