Vice President of Brokerage (Chicago)

Job Title : Vice President of Brokerage

Location : Chicago, IL (Hybrid)

Reports To : Principal / Managing Partners

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.

Position Overview

The Vice President of Brokerage will be responsible for leading and expanding Cross Street's brokerage platform across leasing and sales. This senior role will focus on driving transaction volume, implementing career development plans for brokers, overseeing managing brokers in other markets, and innovating the systems and processes that support the team. The VP will play a key role in scaling the brokerage division, developing talent, and positioning Cross Street as a market leader.

Key Responsibilities

• Leadership & Growth
• Set the vision and growth strategy for the brokerage division across sales and leasing.
• Establish clear career development paths and training programs to grow future leaders.
• Recruit, mentor, and retain top brokerage talent.
• Innovate and oversee training curriculum for the brokerage team.
• Oversee and support managing brokers in regional markets (2+ direct reports), ensuring alignment with firm-wide goals and consistent performance standards.
• Transaction Oversight
• Guide negotiation strategies, deal structures, and client presentations.
• Ensure a high standard of client service and execution excellence on every transaction.
• Ensure transaction management standard across each office / city.
• Business Development & Client Service
• Drive new client relationships and grow the firm's pipeline of residential sales opportunities.
• Develop and maintain strong relationships with developers and investors.
• Position Cross Street as a trusted advisor through market insights and creative solutions.
• Design and implement lead generation strategies.
• Innovation & Systems
• Implement tools and technologies to enhance brokerage productivity and tracking.
• Develop standardized processes for pipeline management, reporting, and client communication.
• Drive innovation in how brokerage services are marketed, measured, and delivered.
• Market Knowledge
• Stay ahead of market trends in Chicago and other key markets.
• Translate market intelligence into actionable strategies for brokers and clients.

Qualifications

What We Offer