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. 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: • Understand the wholesale and traditional transaction process end-to-end • Communicate confidently with motivated sellers and buyers • Execute prospecting and follow-up consistently • Assist in active deals and property coordination • Develop strong sales, negotiation, and problem-solving skills • Build a foundation for long-term growth in real estate investing • Understand how to problem-solve complex transactions 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 • $1,200/month base + commissions • 40-50 hours per week • Full-time commitment • Weekend availability required 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 • Someone serious about learning real estate and wholesaling • Coachable, reliable, and accountable • Comfortable with phone work and in-person outreach • Willing to work with distressed properties and situations in all neighborhoods • Looking for long-term growth, not a short-term role This Is Not a Fit If • You are looking for a traditional Realtor role • You want minimal structure or accountability • You are uncomfortable with prospecting or direct seller conversations • You are not willing to work weekends when needed • You are only casually interested in real estate Compensation: $1,200 month base + commissions

• About the ApprenticeshipThis 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 systemsThis 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 LikeOver time, the right person will: • Understand the wholesale and traditional transaction process end-to-end • Communicate confidently with motivated sellers and buyers • Execute prospecting and follow-up consistently • Assist in active deals and property coordination • Develop strong sales, negotiation, and problem-solving skills • Build a foundation for long-term growth in real estate investing • Understand how to problem-solve complex transactionsThis apprenticeship is intended to prepare you for real responsibility, not just observation.