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Real Estate Agent (Leasing & Sales) — Chicago | Mentorship-Focused Brokerage

Pioneer Realty Group, Chicago, IL, United States


Overview Location: Chicago (Roscoe Village office)

Position Type: Full-Time | Commission-Based

Pioneer Realty Group – Real Estate, Done Differently

Most real estate careers don’t fail because of effort. They fail because there’s no structure, no guidance, and no clear path forward.

At Pioneer Realty Group, we take a different approach. We focus on helping agents build long-term, sustainable businesses by starting with real clients, developing real relationships, and growing through consistency — not shortcuts. Agents typically begin with leasing, using it as a way to build a client base that turns into future buyers, sellers, and referrals. This creates a business that grows over time — not one that resets every month.

What Makes PRG Different

Real mentorship - You’ll work directly with experienced professionals who are active in the Chicago market and involved in your development.

Access to exclusive inventory - Over 20,000 rental units not listed on the MLS, allowing you to start working with clients immediately.

Structured growth - We guide agents from leasing into sales at the right time, with support throughout the process.

Professional, team-oriented environment - We are collaborative, not competitive. The focus is on long-term success, not short-term numbers.

Who This Is For

This opportunity is best suited for individuals who:

Are serious about building a long-term career in real estate

Value mentorship, structure, and consistency

Are willing to put in the time to develop their business the right way

Take pride in providing a high level of service to clients

Requirements

Illinois real estate license (or willingness to obtain)

Strong communication and interpersonal skills

Reliable transportation, smartphone, and laptop

Ability to manage your own schedule and work with clients in the field

What You Can Expect

Commission-based earnings with no desk fees

Hands-on mentorship and ongoing support

Access to exclusive rental inventory and client opportunities

Training in leasing, sales, and relationship-based business development

Flexibility and autonomy with real guidance

Next Step If you’re exploring your options in real estate and want to understand how this approach works, we’re open to having a conversation.

You can apply directly or reach out to start a discussion.

Apply here: chicagoprg.com/work-with-us

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