Real Estate Wholesale Apprentice

Real Estate Wholesaling Apprenticeship Opportunity

Chicago | Full-Time | Paid Apprenticeship

Heart of Chicago Homes is offering a Wholesaling Apprenticeship for someone who is serious about learning real estate and wholesale transactions from the ground up. This opportunity is designed for individuals who want to learn inside a real, operating wholesaling business with structure, mentorship, and accountability rather than trying to figure everything out on their own.

This is not a traditional Realtor role . Wholesaling requires a different skill set, a higher level of initiative, and a willingness to work directly with distressed properties and motivated homeowners. The right candidate understands that real estate investing involves problem-solving, consistent outreach, and hands-on work.

Learn From Proven Leaders

As a Wholesaling Apprentice, you will work closely with Jessica and Mackenzie , gaining direct exposure to high-performing wholesale and traditional real estate transactions .

Jessica Macey is a highly successful real estate broker with a proven track record in sales and negotiations. You will learn how to communicate effectively with motivated homeowners, evaluate property situations, structure offers, and navigate real-world challenges that arise in wholesaling. You will receive in-field, hands-on training working with sellers, buyers, and wholesale transactions from start to finish.

Mackenzie oversees operations, systems, and accountability and brings over six years of experience managing and scaling top 1% real estate teams . You will be trained on the operational side of the business, including lead management, follow-up processes, property coordination, and execution standards. This exposure is critical to understanding how transactions move from initial contact to closing.

This is not a simulated training environment. You will be learning inside an active, fast-paced business that handles real deals with real clients every day. The experience gained in this role is designed to prepare you for growth within wholesale transactions, traditional sales, and leadership opportunities over time.

Compensation :

$1,200 month base + commissions

Responsibilities :

About the Apprenticeship

This is a structured apprenticeship designed to teach you the fundamentals of real estate wholesaling from start to finish.

Throughout the program, you will be trained on :

• Working with distressed homeowners
• Prospecting through phone calls, door knocking, and follow-up
• Handling difficult conversations with professionalism and empathy
• Evaluating property condition and motivation
• Coordinating lockboxes, access, and property walkthroughs
• Assisting with property cleanup and logistics
• Supporting owner relocation services when needed
• Understanding contracts, assignments, and deal flow
• Managing leads and tracking progress through systems

This role includes both field work and phone-based work. Weekend availability is required, as real estate activity does not follow a strict weekday schedule.

What Success Looks Like

Over time, the right person will :

This apprenticeship is intended to prepare you for real responsibility, not just observation.

Qualifications :

Accountability Expectations

This program is designed for someone who shows up consistently, follows systems, tracks performance, and takes ownership of results. Accountability is a core part of the learning process and is required for growth within the role.

Compensation & Schedule

This apprenticeship is structured to provide income while you are learning, with increased opportunity tied directly to execution, consistency, and performance.

Who This Is For

This Is Not a Fit If

About Company

What We Provide

If you are hungry to learn, motivated by commission, and excited about solving problems for sellers while closing deals, we would love to hear from you.

Apply today and let’s see if this is the right fit.