Kirsten Bowersox

As president of Xroads Real Estate Advisors, Kirsten Bowersox provides custom real estate solutions to family offices, private and institutional investors and banks. As a “working” president, leader of collaborative teams, and process champion, she oversees everything from strategy to operations, client management, and business development, while providing a vision and roadmap for the company’s future.

Under her guidance over the last 12 years, the firm’s third-party property management portfolio has grown by more than 500%, with a managed portfolio now totaling over 7.5 million square feet.

During her career, Bowersox has administered the servicing, credit and workout of more than $2 billion in commercial real estate. She worked on complex CMBS financing structures and large construction loans, developing specialized servicing platforms, policies, and procedures as business needs warranted.

Additionally, Bowersox is a designated managing broker and assists in the execution of office and retail brokerage transactions, both as a tenant’s representative and an owner’s representative. Xroads provides leasing for several prominent office and retail properties in Illinois, including 4201 Lake Cook Road in Northbrook, Sunset Grove Shopping Center in Long Grove, and 1255 S. State Street in Chicago. 

Whether it’s the importance she places on building strong relationships—both business and personal—or the way she personally welcomes new hires on their first day, Bowersox leads with intention, warmth, and authenticity.

These are just a few reasons Kirsten Bowersox is among the Chicago & Midwest Connect CRE 2025 Women in Real Estate Award winners. Connect CRE’s Women in Real Estate Awards honor the achievements and inspirational stories of women who have reached respected leadership positions and taken on mentorship roles.