As its national commercial title business continues to expand, Proper Title, LLC, one of the Midwest’s fastest-growing title insurance agencies, has hired Kerry Walsh as commercial operations and underwriting manager, adding more than 20 years of legal, underwriting and litigation experience to its growing commercial platform.
In her new role, Walsh will leverage her varied experience in real estate and title law to oversee complex commercial transactions across the country, while maintaining the responsive, hands-on service Proper Title customers have come to expect. She will serve as a key technical resource for underwriting and closing operations, working with the national commercial team to identify and resolve complex title issues, manage risk and move transactions to closing.
“Kerry’s depth of experience on both the underwriting and litigation sides of the title business makes her an exceptional addition to our commercial team,” said Kim O’Donnell, executive vice president of business development at Proper Title. “Her litigation background gives her firsthand insight into the issues that can surface after a transaction closes and how they might have been avoided. That perspective will be invaluable as we help our customers identify potential risks early and find practical solutions that keep their deals moving forward.”
Most recently, Walsh served as national underwriting counsel for a major commercial underwriter in Chicago. Before that, she was underwriting counsel with a large commercial title agency based in Minnesota. Prior to moving into commercial underwriting, Walsh spent more than 15 years in real estate litigation both in private practice and, most recently, in-house as vice president and litigation counsel with another large national underwriter, representing its policyholders in litigation involving land disputes, escrow and closing services, contract enforcement and fiduciary matters while working closely with internal stakeholders to develop solutions to underwriting challenges identified through the litigation and claims process. She also spent several years in private practice as a real estate attorney.
“Having had the opportunity to view complex real estate and title issues from all sides, I’ve developed a unique, business-driven perspective on evaluating and managing risk,” said Walsh. “I’m excited to bring that perspective to Proper Title, which already enjoys a reputation for expertise, accessibility and problem solving. I’m also looking forward to working with the team of outstanding professionals that Proper Title has already assembled to build on that foundation and help our customers drive even the most complex transactions toward a successful closing.”
Walsh has a law degree from DePaul University College of Law and a bachelor’s degree in English from the University of Notre Dame. She also completed executive education programs at Harvard Business School, Cornell University and the University of California, Berkeley’s Haas School of Business.
Walsh’s appointment is the latest investment in Proper Title’s commercial platform. In February 2024, the company launched Proper Title National Commercial Services to provide title and escrow services for commercial real estate transactions nationwide. This serves clients with transactions and portfolios extending beyond Proper Title’s core Illinois and Northwest Indiana markets while providing a single point of contact throughout the title and closing process.
About Proper Title:
Headquartered in Chicago, Proper Title, LLC, is a full-service title insurance agency serving the residential and commercial real estate industries. Part of the expanded Compass, Inc. ecosystem, Proper Title operates 16 closing locations with 110 employees across Chicagoland and Northwest Indiana. In 2024, the firm launched its National Commercial Services Division to support complex, multi-state transactions with dedicated underwriting and construction escrow expertise. Founded in 2013, Proper Title has been recognized as Fidelity National Financial’s #1 issuing agent in Illinois, a Chicago Tribune Top Workplace (2022–2025) and REjournals’ Title Company of the Year. Since 2015, Proper Title has made a donation after every closing to its charitable arm Proper Giving, which to date has raised more than $500,000 for local organizations. For more information, visit propertitle.com.
Kerry Walsh has joined Proper Title as commercial operations and underwriting manager.