Broker Operations Manager (Chicago) in Chicago, Illinois at Cross Street Real Estate LLC

Job Title: Broker Operations Manager (Chicago)

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.

Job Overview:

As the Broker Operations Manager, you’ll play 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.

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.

Primary Responsibilities:

Agent Recruiting and Retention

• Own the full recruiting lifecycle: identifying candidates, leading and conducting the interview process and closing
• Execute recruiting strategies, including lead tracking, and prospecting touchpoints
• Ensure smooth transitions for incoming agents, coordinating with onboarding and operational teams
• Partner with leadership to execute retention strategies

Agent Development and Support

• Ensure agents adopt and utilize company technology, marketing platforms, and training resources
• Partner with the Learning and Development Specialist to ensure training and coaching plans are created and delivered consistently
• Educate agents on current state license laws, compliance, contracts, and best practices to ensure proper adherence

Leadership

• Carry out consistent performance standards, expectations, and accountability within the office
• Help agents adapt quickly to companywide changes and initiatives
• Provide feedback and mentorship to agents to foster growth within the organization

Qualifications:

• 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
• Strong local knowledge or a desire to learn your market inside and out
• Proficient with Google Suite
• Solid connections in the industry (lenders, attorneys, contractors)
• 2 or 4-year college degree

Availability and Work Hours:

• Must be available to handle requests as needed outside of normal business hours
• Ability to access emails and call on weekends and be available to resolve issues as needed

What We Offer

• Compensation: $80k-$100k annually + commission and profit-sharing structure
• Comprehensive benefits package including Medical (BCBS), Dental and Vision Insurance
• Eligibility for participation in a 401(k) plan
• Generous Paid time off package including vacation days and sick days
• 15 Company paid Holidays and your Birthday off
• Leadership opportunity to shape and scale a brokerage division.
• Access to Cross Street’s established network.
• A collaborative and entrepreneurial culture committed to innovation and career growth.