Vice President

2 weeks ago

Chicago IL, United States Cross Street Full time

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
~ Bachelor’s degree in Real Estate, Business, Finance, or related field.
~8+ years of experience in residential real estate brokerage, with a strong background in both leasing and sales.
~ Proven track record of building teams and scaling brokerage operations.
~ Strong leadership and coaching skills with a passion for developing talent.
~ Experience managing brokerage operations across multiple markets.
~ Strong understanding of brokerage systems, technology, and process optimization.
~ Excellent negotiation, relationship management, and communication skills.

What We Offer
Compensation: $175,000-$200,000 + Profit Share
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.

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