CHICAGO, IL - Cross Street, a Chicago-based residential real estate firm, today announced the addition of three senior leaders as the company continues to expand its national platform. Will Shew has joined the firm as vice president of property management; Karen Gaski has been named vice president of people and culture; and Drew Malter has joined as director of data and systems.
The appointments come as Cross Street continues to scale its operations in Chicago, Denver and Cleveland while expanding its recently launched property management platform following the incorporation of Peak Properties into the company’s national business earlier this year. The addition of Peak’s more than 9,000 units under management has expanded Cross Street’s leasing and management portfolio to nearly 12,000 apartments, strengthening the firm’s ability to provide integrated multifamily services.
“Will, Karen and Drew each bring a combination of expertise, leadership and perspective that will help shape the next chapter of Cross Street’s growth,” said Shane Rachman, president and founder of Cross Street. “As we continue expanding our platform and investing in new markets, it’s critical that we also invest in the people, processes and technology to support our teams and clients. Their experience aligns perfectly with our culture and mission of delivering exceptional service while remaining true to the collaborative, people-first approach that defines Cross Street.”
As vice president of property management, Shew will oversee the strategic and operational direction of Cross Street’s property management platform, ensuring consistency, performance and alignment across all markets by leaning into Cross Street’s vision of efficiency through a centralized model that supports a hospitality-driven community approach. A CAM-certified property management professional and active member of the Chicagoland Apartment Association, Shew brings extensive experience leading large-scale operations and building high-performing teams. Before joining Cross Street, he served as regional vice president of operations at RPM Living.
In her role as vice president of people and culture, Gaski will lead Cross Street's people strategy and all human resources functions, including talent acquisition, employee experience, leadership development, total rewards, organizational effectiveness, culture initiatives and HR operations. She brings more than 15 years of progressive human resources experience to Cross Street and a proven track record of building high-performing teams and fostering workplace cultures that support business growth. Prior to joining Cross Street, Gaski held HR leadership roles at companies including Rush Street Interactive and CareerBuilder.
Malter joins Cross Street as director of data and systems, supporting teams across all markets and business lines. He brings more than nine years of professional experience in data science, business intelligence and technology consulting, including four years at a workforce management software startup. Throughout his career, Malter has worked across business intelligence reporting and the implementation of artificial intelligence and machine-learning tools for both clients and internal teams.
The additions of Shew, Gaski and Malter underscore Cross Street’s ongoing investment in the operational foundation necessary to support its expanding national footprint, added Rachman. “As Cross Street continues to grow its presence in Chicago, Denver and Cleveland, these new hires will play key roles in strengthening our property management capabilities, cultivating culture and advancing the technology and systems that support clients and team members alike.”
Built on operational insight, market expertise and a person-to-person approach, Cross Street has become one of the fastest-growing real estate brands. The firm provides comprehensive guidance to help clients buy, sell, rent, develop and invest in properties, as well as integrated pre-development consulting and lease-up execution, adding value at every stage of the multifamily process.
About Cross Street: Cross Street is a full-service residential real estate firm specializing in multifamily leasing, property management, home sales and third-party developer services. Founded in Chicago in 2019 as Peak Realty and rebranded as Cross Street in early 2024, the firm has offices in Chicago, Denver and Cleveland, with exclusive listings for approximately 12,000 rental units across more than 200 properties. As a brand situated at “The Corner of People and Place,” Cross Street brings a relationship-first approach to connecting people with the spaces they call home. Cross Street’s team of more than 40 licensed brokers and leasing agents maintains close relationships with clients ranging from renters and homebuyers to the developers and owners of mid- and high-rise apartment communities. Through high-impact brands, data-driven development and marketing strategies, and best-in-class management services, the firm delivers value through superior property performance. For more information, visit www.yourcrossstreet.com