VP of People in Chicago, Illinois at Cross Street Real Estate LLC

About Cross Street

Cross Street is a Chicago real estate firm built on relationships: with our clients, our residents, and the people showing up every day to do the work. We do property management, brokerage, and advisory work, but what we're really doing is helping owners build something lasting and making sure residents actually want to come home. Our tagline is The Corner of People and Place, and we need someone to continue to help us live up to it.

We pair institutional know-how with the kind of resourceful, figure-it-out energy that gets things done. Our team is hands-on by choice, not necessity, because we believe that showing up makes all the difference.

We move fast. We think long term. And we care a lot about the people we're building this thing with.

As we grow, we're looking for a VP of People who wants to do more than fill a seat at the table. We need someone to lead our exploration into who we are as a team, how we lead, and what kind of place Cross Street becomes for both clients and for everyone here.

The Opportunity

We’re looking for a VP of People to shape and scale the HR function into a true driver of the business.

This is a real opportunity to step into a growing organization at an inflection point. The VP of People is a strategic partner to the leadership team and a builder at heart. You’ll define how people, structure, and systems support the company’s next phase of growth while staying grounded enough in the work to ensure it comes to life. This opportunity is about building a company where high performance and strong culture reinforce each other.

You’ll lead a team of five thoughtful, capable HR professionals, each bringing different strengths across recruiting, operations, and employee experience. Your job is to bring out the best in them. Build the trust. Set the direction. Create the kind of environment where good people do their best work. The biggest areas of focus will be:

• Stabilizing and strengthening HR systems and infrastructure
• Elevating and developing the HR team into a high-performing, cohesive unit
• Bringing direction, structure, and clarity to core people processes

The right person will be energized by the opportunity to build strong teams and contribute to our growth. You’ll do well here if you take initiative, see around corners, and enjoy creating clarity where it doesn’t yet exist.

Responsibilities

• Own and lead the People function, setting clear direction and ensuring it scales effectively with the business.
• Build and develop a high-performing People team, providing strategic direction across recruiting, employee relations, learning and development, onboarding, compensation/bonus structures and people operations while raising the bar on performance and accountability.
• Strengthen the company’s people infrastructure, including systems, processes, and workflows to ensure it is reliable and scalable.
• Lead workforce planning and organizational design, ensuring the business has the right structure, roles, and talent in place to support growth.
• Partner with leadership to drive organizational clarity, including structure, role definition, and performance expectations.
• Ensure the company is operating with sound people practices and managing risk appropriately across policies, compliance, and employee matters.
• Oversee and evolve the employee experience across the lifecycle, ensuring consistency across a multi-entity organization.
• Act as a trusted partner to the CEO and leadership team, influencing decisions and practical guidance to people-related decisions.
• Proactively identify opportunities to improve how the organization operates, bringing forward innovative, strategic ideas that drive the business forward.

What Success Looks Like (6-12 Months)

• A structured and clearly defined HR function with strong ownership across the team
• Improved team performance through coaching and development
• Clean, reliable HR systems and workflows, particularly within our HRIS
• A systematic approach to financial incentives, KPIS, annual performance reviews
• Consistent and effective onboarding and employee experience across the organization
• A trusted, proactive partnership with leadership on people strategy and execution

Qualifications

• 10+ years of HR experience and history of leading and developing a People team.
• Preferred HR certification (SPHR, PHR, SHRM, CLRP, etc)
• Strong operator mindset with the ability to build and improve systems and processes in a fast-paced, evolving environment
• Ability to balance strategic thinking with hands-on execution when needed
• High level of ownership, initiative, and sound judgment
• Experience in multi-entity or multi-location organizations is a plus
• Familiarity with various HR systems