Managing Broker in Chicago, Illinois at Cross Street Real Estate LLC

Cross Street is hiring a Managing Broker for our Chicago office. This role is heavily involved in shaping how brokerage runs across the company. If you’re someone who thrives behind the scenes building systems, loves developing agent talent, and wants to have a lasting impact on how a growing brokerage operates, this is a good fit for you.

As Managing Broker, you’ll serve as the official Managing Broker for our Illinois operations while playing a central role in shaping how Cross Street’s brokerage functions company-wide. You’ll own broker recruiting, onboarding, training, and career development across the organization, while also building and refining the systems, processes, and compliance frameworks that keep our brokerage running at the highest level.

About Cross Street

Cross Street is a Chicago-based real estate services firm with deep roots in property operations and client service. Cross Street combines institutional-quality expertise with entrepreneurial flexibility, offering clients a full suite of brokerage and advisory services. We lead with hustle, heart, and real data, balancing creativity with strategy to drive results that matter.

What We’re Looking For

? Active Illinois real estate license with Managing Broker designation (or ability to obtain).

? 5+ years of experience in real estate, with a strong background in brokerage operations, training, or agent development.

? Strong understanding of state laws and regulatory compliance.

? Passion for mentoring others and helping people grow.

? A people-first approach that fosters collaboration, not competition.

? Comfort working in a fast-growing, startup-style environment.

? Experience with budgeting, forecasting, and using data to drive decisions.

How You’ll Stand Out

? You have strong local knowledge or a desire to learn your market inside and out

? You are proficient with Google Suite

? You have solid connections in the industry (lenders, attorneys, contractors)

? You have a 2- or 4-year college degree

What We Offer

? Base salary ($70k) + Commission + Profit Sharing Structure

? Comprehensive benefits package including Medical (BCBS), Dental and Vision Insurance

? Paid time off: 15 vacation days and 5 sick days

? Leadership opportunity to shape and scale a brokerage division.

? Oversight of a growing, multi-market platform.

? Access to Cross Street’s established network.

? A collaborative and entrepreneurial culture committed to innovation and career growth.