Canadian Cross-Border CRE Transactions
Title Tenets: CRE Webinar
Canadian Cross-Border CRE Transactions
May 21, 2026 | 1:00 pm
Central Time (US and Canada)
Free Webinar for All CRE Professionals
Expanding your footprint across the border requires more than just a map—it requires a team that speaks the language of both markets. Join Stewart Title National Commercial Services and Stewart International for an exclusive, panel-based deep dive into the complexities of Canadian-U.S. commercial real estate transactions. In this collaborative session, our own Stewart experts step behind the mic to share "boots on the ground" insights. We’ll move past the basics to discuss the tactical nuances of title insurance, legal hurdles, and closing efficiencies that define successful cross-border deals.
Key Discussion Points
- The Regulatory Landscape: Understanding the primary differences in title and escrow practices between the U.S. and Canada.
- Risk Mitigation: How Stewart’s integrated network streamlines coverage for multi-jurisdictional portfolios.
- Closing with Confidence: Best practices for managing timelines and expectations in a shifting economic climate.
- Unified Expertise: A look at how our National Commercial and International teams work in tandem to support your growth.
The Panel
Featuring an all-Stewart lineup of veteran underwriters and commercial specialists, this session offers a unique opportunity to hear directly from the people managing your transactions every day.
NCS Speakers
Matt Skalka
Senior Vice President, Stewart Title NCS Energy and Infrastructure Group
Matt Skalka currently serves as Vice President and Head of Stewart Title’s National Commercial Services office in Houston. He also leads Stewart Title’s Energy and Infrastructure Group. Prior to rejoining Stewart, Matt started Thomas Title and Escrow’s Energy Services group, which Stewart acquired.
Prior to joining Thomas Title, Matt served as Associate Senior Underwriting Counsel in Stewart Title’s Houston National Commercial Services office, where he specialized in commercial, energy, industrial and international projects. He routinely acted as lead underwriting counsel providing guidance on affirmative coverages, endorsements and curative matters concerning complex, high-liability commercial transactions. Matt spends considerable time, and has developed a deep skill set, underwriting industrial, retail, multi-family, office, cell tower, utility scale renewable energy projects (solar/wind), mining operations, natural gas plants and other energy related infrastructure facilities throughout the U.S. Before returning to Houston, he spent 18 months in London underwriting commercial transactions throughout Europe. Matt also has experience as claims counsel and in Stewart’s corporate legal department.
Dawn Anderson
Vice President and Senior Underwriting Counsel, Stewart Title Guaranty Company & Energy Specialist, Stewart Title NCS Energy and Infrastructure Group
Dawn Anderson is Vice President and Senior Underwriting Counsel for Stewart Title Guaranty Company and an Energy Specialist with Stewart Title’s National Commercial Services Energy & Infrastructure Group. With more than two decades of industry experience, she is a trusted advisor on complex commercial real estate matters and one of Stewart’s leading specialists in renewable energy and infrastructure transactions nationwide. Dawn is known for delivering strategic, solutions-driven underwriting support, backed by a strong commitment to service, responsiveness, and long-term client relationships. (new paragraph) Throughout her career at Stewart, Dawn has held progressive leadership roles spanning underwriting counsel and commercial operations, including oversight of Direct Commercial Operations in Minnesota. Prior to joining Stewart in July 2012, she built a broad foundation across title and escrow with both residential and commercial experience at regional and national underwriters. Dawn is licensed to practice law in Minnesota and remains actively engaged in the industry through her involvement with the Minnesota Land Title Association where she has held board positions and committee chair positions, WRISE, and is a member of the Real Property Section of the Minnesota State Bar Association.
Karen Decker
Senior Vice President and Chief Underwriting Counsel – International Operations, Stewart Title Canada
Karen Decker is Senior Vice President and Chief Underwriting Counsel – International Operations at Stewart Title in Canada, bringing nearly 30 years of experience in the title insurance industry. She leads an industry‑leading underwriting team with deep expertise in both residential and commercial title insurance, as well as extensive knowledge of local markets and regulatory environments. In this role, Karen ensures Stewart’s lawyer and notary partners can close real estate transactions efficiently and with confidence, providing buyers and lenders with peace of mind.
In addition to overseeing complex commercial underwriting matters, Karen spearheads the development of new products and the introduction of policy enhancements and improvements. She is committed to the highest standards of ethics, transparency, and regulatory compliance in all aspects of her work. A frequent speaker at industry and educational events, Karen is widely recognized for her thought leadership in title insurance.
Karen holds a Bachelor of Commerce degree from Carleton University and an LL.B. from Osgoode Hall Law School. She was called to the bar in 1997.
