Apprenticeship Insurance Jobs in Chicago, IL (NOW HIRING)

We are looking for a motivated, high-energy Insurance Insurance Sales Apprentice to join our team. In this role, you will be the driving force behind new business growth, helping individuals and families protect what matters most. This is a fast-paced, competitive position designed for someone who thrives on building relationships and hitting performance milestones,

The ideal candidate is a persuasive communicator who can navigate complex conversations with ease and turn a "maybe" into a "yes." Whether you are a seasoned sales professional or looking to launch a lucrative career in the insurance industry, we provide the tools and support needed to succeed.

If you’re looking for a rewarding career with advancement opportunities, competitive compensation, and a supportive environment, this could be the right fit. No prior insurance experience is required — we provide training.

What We’re Looking For

Passionate and self-driven mindset

Highly motivated and competitive attitude

Strong verbal and written communication skills

Adaptable and coachable

Desire to build a long-term career

What We Offer

Competitive compensation: Base salary + commission + performance bonuses with unlimited earning potential

Comprehensive training: Hands-on support and mentorship in a collaborative team environment

Career growth: Advancement opportunities within the organization

Flexible schedule: PTO, paid holidays

Additional perks: Professional development opportunities, and modern technology tools

If you’re ready to build a rewarding career in insurance with a team invested in your success, apply today.

If you’re looking for a rewarding career with strong earning potential, advancement opportunities, and a supportive team environment, this could be the perfect fit. Bilingual candidates (Spanish preferred) are encouraged to apply. No prior insurance experience is required — we provide training.

What We’re Looking For

Passionate and self-driven mindset

Highly motivated and competitive attitude

Strong verbal and written communication skills

Adaptable and coachable

Desire to build a long-term career

What We Offer:

Competitive compensation: Base salary + commission + performance bonuses with unlimited earning potential

Comprehensive training: Hands-on support and mentorship from an experienced team

Career growth: Advancement opportunities within the organization

Work-life balance: PTO, paid holidays, and flexible scheduling

Additional perks: professional development opportunities, and modern technology tools

If you’re ready to build a rewarding career in insurance with a team that supports your success, we encourage you to apply today.

Key Responsibilities

Develop customized insurance solutions for clients, including Auto, Home, Business, and Life coverage

Build and maintain strong client relationships by serving as a trusted advisor

Conduct risk assessments and provide recommendations tailored to individual client needs

Leverage technology and digital tools to improve efficiency and enhance the client experience

Work toward performance milestones and agency goals tied to bonus opportunities

Collaborate with team members and participate in ongoing training and professional development

Why Join Diana Castaneda-Torres Farmers Insurance Agency?

At Diana Castaneda-Torres Farmers Insurance Agency, we are committed to building long-term client relationships while creating a supportive, flexible workplace for our team. As a Sales Producer, you’ll join an agency that values collaboration, innovation, and work-life balance, giving you the resources and support needed to succeed professionally.

We foster an inclusive, positive culture where every team member has the opportunity to grow, contribute, and make a meaningful impact. Our environment empowers you to align your career with your personal goals while helping drive the continued success of an agency that prioritizes both its people and its clients.

Qualifications

Willingness to learn and obtain required insurance licenses (licensing support provided)

Sales experience or client-facing background preferred

Demonstrated reliability, integrity, and strong ethical standards

Excellent verbal and written communication skills

Enthusiastic, coachable, and goal-oriented mindset

Spanish bilingual preferred

Frequently Asked Questions

What kind of training will I receive?

We provide award-winning training in sales strategies and product knowledge, along with ongoing mentorship to support your success.

Is prior insurance experience required?

No. We offer comprehensive training for candidates new to the insurance industry.

Will I need to be licensed?

Yes. We assist you through the licensing process and provide guidance every step of the way.

Is this a commission-only role?

No. This position includes a base salary plus uncapped commission and performance bonuses.

What can I expect to earn in my first year?

With strong performance, first-year earnings of $70,000+ are achievable through a combination of base pay, commissions, and bonuses.

Ready to grow your sales career? Apply today to join Diana Castaneda-Torres Farmers Insurance Agency.