Biography

TRANSWESTERN ROLE

Carolyn Brennan is a Vice President within the Asset Services group. Working with receivership properties, Carolyn assists in the oversight of several million square feet of commercial assets, along with multifamily assignments totaling in the hundreds. As part of her role, Carolyn communicates with the on-site building teams, reviewing operational projects and property activity. Carolyn also confirms that Transwestern remains pursuant to the court order stipulations for receivership properties, ensures teams stay within the approved budget, and spearheads national initiatives that help buildings deliver best-in-class services. Additionally, Carolyn acts as a liaison between the property teams and special servicers, and she leads training sessions to educate on-site teams on the intricacies of receivership management.

CAREER HIGHLIGHTS

Before her current role, Carolyn was the Property Manager at 332 S. Michigan Avenue. Carolyn onboarded the receivership asset into the Transwestern portfolio, reconciling tenant billing and budgetary numbers. Managing a staff of 12, she handled several litigation issues and managed repair projects totaling approximately $100,000. Carolyn and her team also engaged tenants, building rapport by maintaining a robust events calendar and actively addressing tenant concerns.

Prior to that, Carolyn was a part of the on-site team at the Civic Opera Building for over three years, first as the Assistant Property Manager and then as the Property Manager. As part of the onboarding team for the receivership property, Carolyn audited property files, leases, tenant accounts, and service contracts. Improvements during Carolyn’s tenure made building operations more efficient and significantly reduced operating expenses through contract analysis and bidding. She also helped resolve several inherited code violations and other legal discrepancies.

Earlier in her career, Carolyn was the Tenant Services Coordinator and Assistant Property Manager at 100 N. LaSalle and 29 N. Wacker, respectively. Before Transwestern, Carolyn worked for a third-party company that was hired by property management firms to manage conference centers, run concierge services, and organize building lobby customer service representatives.

PROFESSIONAL AFFILIATION / RECOGNITION

  • National Connect CRE Next Generation Award Winner, 2025
  • BOMA International’s Rising Star Award, 2023
  • BOMA Emerging Leaders committee, member
  • Boys and Girls Club of Chicago, Young Profession Board member May 2019- February 2023
  • Transwestern’s National Recognition Take Flight Altitude Award, 2024

EDUCATION

Carolyn earned her bachelor’s degree from Eastern Illinois University. She is a licensed real estate broker in the state of Illinois.