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Transitional Training Jobs in Chicago, IL (NOW HIRING)

Sertoma Star Services

Transition Case Manager

Matteson, IL · On-site

$50K - $55K/yr

Transition Case Manager Department: Community Mental Health and Counseling Status: Full-time Who We ... Attend all agency mandated training within required timeframes. Qualifications * Bachelor's degree ...

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All JobsTransitional Training JobsTransitional Training Jobs in Chicago, IL

Transitional Training information

See Chicago, IL salary details

$12

$19

$28

How much do transitional training jobs pay per hour?

As of Aug 8, 2026, the average hourly pay for transitional training in Chicago, IL is $19.42, according to ZipRecruiter salary data. Most workers in this role earn between $15.34 and $22.31 per hour, depending on experience, location, and employer.

What is the difference between Transitional Training vs Medical Assistant?

AspectTransitional TrainingMedical Assistant
CredentialsVaries; often includes certifications or on-the-job trainingHigh school diploma; CMA or RMA certification often preferred
Work EnvironmentTraining programs, clinics, or hospitalsClinics, hospitals, physician offices
Industry UsageUsed as a stepping stone into healthcare rolesDirect patient care and administrative tasks

Transitional Training is typically a preparatory phase for individuals entering healthcare, focusing on foundational skills. Medical Assistants perform direct patient care and administrative duties, often after completing formal certification. While Transitional Training helps build necessary skills, Medical Assistants are fully qualified to perform clinical and clerical tasks independently.

What are popular job titles related to Transitional Training jobs in Chicago, IL? For Transitional Training jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Transitional Training jobs in Chicago, IL look for? The top searched job categories for Transitional Training jobs in Chicago, IL are:
Transitional Training jobs near you

Trainer & Sales Representative -- Teaching, Training, & Mentorship Experience Welcome

The Impact Insurance Agency

Crestwood, IL • On-site

$85K - $105K/yr

Full-time, Contractor

Medical, Life

Re-posted 4 days ago

Job description

Trainer & Sales Representative Teaching, Training, & Mentorship Experience Welcome

Outside Sales Representative and Trainer
Impact Insurance Agency | Full-Time | Independent Contractor | Local Territory

A New Chapter in Helping People

Many educators and coaches reach a point where they're ready for a professional path that still centers on guidance, mentorship, and meaningful connection just in a different environment. 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.

Former teachers, trainers, and education professionals often find this role to be a natural extension of the skills they already use every day: listening, educating, encouraging growth, and building trust. This isn't about leaving education behind it's about applying your strengths in a setting that offers flexibility, professional development, and long-term opportunity.

The Role

As a Trainer & Sales Representative, you'll blend relationship-driven B2B sales with mentorship and leadership. You'll meet face-to-face with business owners and employees while helping support and guide newer representatives in the field.

This independent contractor role provides autonomy over your schedule and territory, while still offering structured training, leadership support, and a collaborative, people-first culture.

What You'll Do

Build and nurture relationships with local business leaders and their teams

Educate employees on supplemental insurance solutions with clarity and professionalism

Guide enrollment conversations and provide ongoing follow-up support

Maintain organized client records and manage your territory effectively

Mentor and support newer representatives, sharing best practices and encouragement

Participate in weekly team collaboration, training, and professional development

Foster long-term partnerships built on trust, service, and consistency

Training & Professional Support

Structured onboarding for professionals transitioning from education, coaching, or training roles

Hands-on mentorship and field guidance from experienced leaders

Health & Life licensing assistance and reimbursement

Ongoing professional development focused on communication, leadership, and client care

Collaborative, supportive team culture centered on growth and encouragement

Compensation & Structure

Target annual earnings: $85,000$105,000 (draw pay, commissions, and bonuses)

Weekly draw available while growing your client base

Performance-based incentives and advancement into senior sales or leadership roles

Hybrid flexibility with local, in-person client meetings

Autonomy over your schedule while following a proven, supportive system

Ideal Background

This opportunity may resonate with you if you:


Have experience as a teacher, coach, trainer, educator, or academic leader

Enjoy mentoring others and guiding people through important decisions

Value meaningful relationships and long-term impact

Are seeking a career that blends purpose, flexibility, and professional growth

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

Why Impact Insurance Agency

Our culture is built on respect, collaboration, and mentorship. Many of our leaders transitioned from education and people-focused professions and discovered a role where their ability to teach, encourage, and lead remains at the center of their success.

Apply Today

If you're ready to explore a new chapter one that allows you to continue helping people while building a sustainable, leadership-focused career we'd love to connect.

https://www.theimpactinsuranceagency.com/