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Entry Level Helpdesk Jobs in Milwaukee, WI (NOW HIRING)

Aspen Dental

Dental Assistant - Entry Level

Waukesha, WI · On-site

$18 - $20/hr

Our best-in-class training program, generous benefits package, and flexible scheduling will help you thrive in your career. When you join our team as an Entry-Level Dental Assistant , you will have ...

Northstar Loans

Loan Officer (Entry Level)

Milwaukee, WI

$15 - $18/hr

Loan Officer (Entry-Level) We're looking for a dependable, motivated Loan Officer to join our team ... If you enjoy helping people, learning new skills, and working in a supportive team environment, we ...

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Entry Level Helpdesk information

See Milwaukee, WI salary details

$12

$22

$33

How much do entry level helpdesk jobs pay per hour?

As of May 28, 2026, the average hourly pay for entry level helpdesk in Milwaukee, WI is $22.81, according to ZipRecruiter salary data. Most workers in this role earn between $18.94 and $25.58 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as an Entry Level Helpdesk Technician, and why are they important?

To thrive as an Entry Level Helpdesk Technician, you need a basic understanding of computer hardware, software troubleshooting, networking fundamentals, and often an associate degree or relevant certification like CompTIA A+. Familiarity with ticketing systems, remote desktop tools, and knowledge bases is typically required. Strong communication, patience, and problem-solving skills help you support users effectively and work well under pressure. These skills ensure prompt resolution of technical issues, high customer satisfaction, and smooth IT operations.

What are some common challenges faced by entry level helpdesk professionals, and how can they be overcome?

Entry level helpdesk professionals often encounter challenges such as managing a high volume of support tickets, troubleshooting unfamiliar technical issues, and communicating effectively with users of varying technical backgrounds. To overcome these challenges, it's helpful to develop strong organizational skills, actively seek guidance from more experienced team members, and continually expand your technical knowledge through training and hands-on practice. Building strong communication and customer service skills also goes a long way in ensuring successful interactions with end-users and colleagues.

What are entry level helpdesk jobs?

Entry level helpdesk jobs are positions in IT support where individuals assist users with basic technical issues, such as troubleshooting software, hardware, or network problems. These roles often serve as the first point of contact for customers or employees needing technical assistance. Entry level helpdesk staff typically follow scripts or guidelines to resolve common problems and may escalate more complex issues to higher-level technicians. This role provides valuable experience and foundational knowledge for those interested in advancing in the IT field.

What is the difference between Entry Level Helpdesk vs Technical Support Specialist?

AspectEntry Level HelpdeskTechnical Support Specialist
Required CredentialsHigh school diploma or equivalent; basic IT knowledgeHigh school diploma; some roles prefer certifications like CompTIA A+
Work EnvironmentHelpdesk or call center; office settingSupport teams; remote or on-site
Employer & Industry UsageIT departments, MSPs, tech companiesIT support, software companies, hardware vendors
Common Search & ComparisonYesYes

Entry Level Helpdesk roles focus on basic troubleshooting, customer service, and ticket management, often requiring minimal certifications. Technical Support Specialists handle more complex technical issues, may require additional certifications, and often have a broader technical skill set. Both roles are essential in IT support, but the Technical Support Specialist typically involves more advanced problem-solving.

What are the most commonly searched types of Helpdesk jobs in Milwaukee, WI? The most popular types of Helpdesk jobs in Milwaukee, WI are:
What cities near Milwaukee, WI are hiring for Entry Level Helpdesk jobs? Cities near Milwaukee, WI with the most Entry Level Helpdesk job openings:
Entry Level Helpdesk jobs near you
Infographic showing various Entry Level Helpdesk job openings in Milwaukee, WI as of May 2026, with employment types broken down into 1% Locum Tenens, 1% As Needed, 3% Full Time, 83% Part Time, and 12% Contract. Highlights an 18% Physical, 81% Hybrid, and 1% Remote job distribution, with an average salary of $47,443 per year, or $22.8 per hour.

Entry-Level Outside Sales Representative

The Impact Insurance Agency

Germantown, WI • On-site

$65K - $85K/yr

Full-time, Contractor

Medical, Life

Posted 13 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/