ZipRecruiter

Log In

2

Entry Level Outside Sales Jobs in Wisconsin (NOW HIRING)

Sysco

Sales Representative

Milwaukee, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

SPECTRUM

Entry Level Sales

Green Bay, WI · On-site

$27K/yr

Spectrum is building a NEW residential outside sales team--one that will drive impact for our business, customers and everyone who joins us. If you're looking for an exciting sales career and a ...

SPECTRUM

Entry Level Sales

Rhinelander, WI · On-site

$27K/yr

Spectrum is building a NEW residential outside sales team--one that will drive impact for our business, customers and everyone who joins us. If you're looking for an exciting sales career and a ...

Sysco

Sales Representative

Baraboo, WI

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco Corporation

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco Corporation

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco Corporation

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco Corporation

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco Corporation

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

Sysco

Sales Representative

Baraboo, WI · On-site

Career pathing opportunities for both entry level, and experienced individuals * Opportunity to be ... outside sales position responsible for promoting the company's products and services and for ...

previous pagenext page

Showing results 21-40

All JobsOutside Sales JobsEntry Level Outside Sales JobsEntry Level Outside Sales Jobs in Wisconsin

Entry Level Outside Sales information

See Wisconsin salary details

$30.3K

$78.8K

$167K

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

As of Aug 26, 2026, the average yearly pay for entry level outside sales in Wisconsin is $78,772.00, according to ZipRecruiter salary data. Most workers in this role earn between $53,000.00 and $90,800.00 per year, depending on experience, location, and employer.

What is an entry level outside sales?

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 are the key skills and qualifications needed to thrive as an entry level outside sales?

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 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 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.

Is it possible to get into entry level outside sales with no experience?

Entry level outside sales positions often do not require prior experience, as employers typically look for strong communication skills, motivation, and a willingness to learn. Candidates may need to demonstrate a proactive attitude and basic knowledge of sales techniques or customer service, but training is usually provided on the job.

What is the best entry-level outside sales job?

Entry-level outside sales jobs typically involve selling products or services directly to customers outside of a company’s premises, such as in retail, wholesale, or B2B environments. Successful roles often require strong communication skills, a valid driver’s license, and the ability to work independently, with many positions offering commission-based pay and opportunities for advancement.

What are the most commonly searched types of Outside Sales jobs in Wisconsin?

The most popular types of Outside Sales jobs in Wisconsin are:

What are popular job titles related to Entry Level Outside Sales jobs in Wisconsin?

For Entry Level Outside Sales jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Entry Level Outside Sales jobs in Wisconsin look for?

The top searched job categories for Entry Level Outside Sales jobs in Wisconsin are:

What cities in Wisconsin are hiring for Entry Level Outside Sales jobs?

Cities in Wisconsin with the most Entry Level Outside Sales job openings:

Entry Level Outside Sales jobs near you
Infographic showing various Entry Level Outside Sales job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $78,772 per year, or $37.9 per hour.

Outside Sales Representative Entry-Level

The Impact Insurance Agency

Sparta, WI • On-site

$65K - $85K/yr

Full-time

Medical, Life

Re-posted 13 days ago

Job description

Teachers & Educators Ready for a Different Kind of Impact

Outside Sales Representative Entry-Level
Impact Insurance Agency | Full-Time | Independent Contractor | Local Territory

Bring Your Experience Into a New Setting

If you've spent time in education or coaching, you already know how much heart, energy, and dedication it takes to guide others. Many of our representatives come from classrooms, athletic programs, and mentoring roles where they cared deeply about the people they served — but eventually started looking for a path that offered more flexibility, professional growth, and long-term earning potential.

This opportunity allows you to keep using your communication skills, leadership presence, and ability to connect with people — just in a setting where your schedule, growth, and results are more within your control.

What This Role Looks Like

Instead of lesson planning, grading, or navigating the changing demands of the education system, you'll spend your time meeting with local businesses and their teams, helping employees understand supplemental insurance options that provide real support during unexpected life events.

You won't be expected to know insurance on day one. Our training is designed specifically for individuals transitioning from teaching, coaching, and other service-focused careers.

As an independent contractor, you'll manage your own local territory with flexibility — while still having structured guidance, mentorship, and a proven system to follow.

Day-to-Day Responsibilities

  • Connect with local small and mid-sized businesses in your community
     

  • Lead clear, educational conversations about benefit options
     

  • Help employees enroll and answer follow-up questions
     

  • Maintain organized notes, scheduling, and client relationships
     

  • Attend weekly training and professional development meetings
     

  • Build long-term partnerships through trust and consistency
     

Training Designed for Career Changers

  • Step-by-step onboarding — no prior sales experience required
     

  • Field mentorship and real-world learning opportunities
     

  • Health & Life licensing support and reimbursement
     

  • Coaching focused on communication, leadership, and relationship-building
     

  • A collaborative team culture that values encouragement over pressure
     

Compensation & Flexibility

  • Commission-based earnings 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
     

  • Growth opportunities into mentoring, training, or leadership roles
     

This Could Be a Strong Fit If You…

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

  • Enjoy guiding people and explaining complex ideas in simple ways
     

  • Want a sustainable pace while still making a meaningful impact
     

  • Communicate clearly and build trust naturally
     

  • Appreciate structure but also want autonomy in your workday
     

  • Are open to obtaining a Health & Life Insurance license (we help you through it)
     

About Impact Insurance Agency

We partner with local businesses to provide supplemental insurance solutions that help employees and their families feel supported when it matters most. Our culture emphasizes mentorship, collaboration, and steady growth — and many of our leaders began by transitioning from other people-focused careers.

Interested in Learning More?

If you're exploring what comes next after education and want a role where your people skills, leadership experience, and passion for helping others still matter — we'd love to connect.

https://www.theimpactinsuranceagency.com/