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

Lad Lake Inc

Math Teacher

Milwaukee, WI · On-site

$46K - $60K/yr

A valid Wisconsin teaching certificate. * Experience working with students who are historically ... Lots of our current caregivers started in entry level roles and have moved up to be Unit Managers ...

Lad Lake Inc

Math Teacher

Milwaukee, WI · On-site

$46K - $64K/yr

A valid Wisconsin teaching certificate. * Experience working with students who are historically ... Lots of our current caregivers started in entry level roles and have moved up to be Unit Managers ...

Lad Lake Inc

Math Teacher

Milwaukee, WI · On-site

$46K - $64K/yr

A valid Wisconsin teaching certificate. * Experience working with students who are historically ... Lots of our current caregivers started in entry level roles and have moved up to be Unit Managers ...

Lad Lake Inc

Middle School Teacher

Milwaukee, WI · On-site

$46K - $64K/yr

A valid Wisconsin teaching certificate. * Experience working with students who are historically ... Lots of our current caregivers started in entry level roles and have moved up to be Unit Managers ...

Lad Lake Inc

Middle School Teacher

Milwaukee, WI · On-site

$44K - $61K/yr

A valid Wisconsin teaching certificate. * Experience working with students who are historically ... Lots of our current caregivers started in entry level roles and have moved up to be Unit Managers ...

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All JobsTeaching JobsEntry Level Teaching JobsEntry Level Teaching Jobs in Milwaukee, WI

Entry Level Teaching information

See Milwaukee, WI salary details

$29.1K

$48.1K

$60.6K

How much do entry level teaching jobs pay per year?

As of Aug 22, 2026, the average yearly pay for entry level teaching in Milwaukee, WI is $48,092.00, according to ZipRecruiter salary data. Most workers in this role earn between $43,400.00 and $52,200.00 per year, depending on experience, location, and employer.

What is entry level teaching?

Entry level teaching jobs are positions typically suited for individuals who are new to the teaching profession, often recent graduates or those with limited classroom experience. These roles may include teaching assistants, substitute teachers, or full-time classroom teachers handling their own classes for the first time. Entry level teachers are responsible for planning lessons, delivering instruction, managing classrooms, and assessing student progress under the guidance of more experienced educators. These positions provide valuable on-the-job training and are a common starting point for a career in education.

What are the key skills and qualifications needed to thrive as an entry level teacher?

To thrive as an Entry Level Teacher, you need a bachelor's degree in education or a related field, teacher certification, and a solid grasp of classroom management and instructional strategies. Familiarity with educational technology tools, learning management systems (LMS), and curriculum planning software is often required. Strong communication, patience, adaptability, and enthusiasm for student development are standout soft skills in this role. These competencies are crucial for creating engaging learning environments, supporting student growth, and meeting diverse classroom needs.

What are some common challenges entry level teachers face during their first year, and how can they be addressed?

Entry-level teachers often face challenges such as classroom management, adapting lesson plans for diverse learners, and balancing administrative tasks with teaching responsibilities. Building strong relationships with mentors, seeking regular feedback, and participating in professional development workshops can help address these challenges. Collaborating with experienced colleagues and utilizing available school resources also supports a smoother transition into the teaching environment.

What is the difference between Entry Level Teaching vs Teaching Assistant?

AspectEntry Level TeachingTeaching Assistant
Required CredentialsHigh school diploma or equivalent; some positions may require a bachelor's degreeHigh school diploma or equivalent; some roles may prefer additional coursework or experience
Work EnvironmentClassroom settings, responsible for delivering lessons and managing studentsSupport teachers in classroom activities, supervision, and preparation
Employer & Industry UsageSchools, educational institutions, tutoring centersPublic and private schools, educational programs

Entry Level Teaching involves directly instructing students and managing classrooms, often requiring a bachelor's degree. Teaching Assistants support teachers with classroom tasks and student supervision, typically needing less formal education. Both roles are essential in educational settings, but Entry Level Teaching has greater responsibility for lesson delivery and student engagement.

How do I get an entry level teaching job with no experience?

Entry level teaching positions often require a minimum of a bachelor's degree and may require or prefer a state-specific teaching certification or license. Gaining relevant experience through volunteer work, internships, or substitute teaching can improve your chances, and demonstrating strong communication and organizational skills is beneficial during the application process.

How to get an entry level teaching job when you have no experience?

To secure an entry level teaching position with no experience, focus on obtaining relevant certifications such as a teaching credential or substitute teaching license, and highlight transferable skills like communication and patience in your application. Volunteering or assisting in classrooms can also build experience and demonstrate commitment to education.

What are the most commonly searched types of Teaching jobs in Milwaukee, WI?

The most popular types of Teaching jobs in Milwaukee, WI are:

Entry Level Teaching jobs near you
Infographic showing various Entry Level Teaching job openings in Milwaukee, WI as of August 2026, with employment types broken down into 1% As Needed, 60% Full Time, 35% Part Time, 1% Temporary, and 3% Contract. Highlights an 83% Physical, and 17% Remote job distribution, with an average salary of $48,092 per year, or $23.1 per hour.

Entry-Level Outside Sales Representative

The Impact Insurance Agency

Germantown, WI • On-site

$65K - $85K/yr

Full-time

Medical, Life

This job post has expired today. Applications are no longer accepted.

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/