Craig has overall responsibility for CNA's Corporate Finance Department, which provides asset and capital management, financial planning and analysis, investor relations, treasury services, corporate accounting, financial reporting, corporate tax, ceded reinsurance, financial regulation, internal audit and compliance, and shared services to the organization. He is also responsible for CNA's non-core operations which include Life & Group Operations and Global Resource Managers which oversees CNA Re and other run-off operations.

Craig is also a member of the Chairman's Executive Committee which is responsible for strategy, results and oversight of all business units of CNA Financial Corporation, including direction of an Operating Committee.

Prior to joining CNA in 2004, Craig was president and chief executive officer of Global Run-off Operations for St. Paul Travelers. Previously, he served in several leadership positions at Travelers Property & Casualty, including Chief Operating Officer, Gulf Insurance Group; Chief Financial & Administrative Officer, Personal Lines; and Senior Vice President & Chief Financial Officer, Bond. He began his insurance career as a bond underwriter for Aetna.

Craig holds a bachelor's in history from the University of Virginia and a master's in accounting from Georgetown University. He is a Chartered Property Casualty Underwriter (CPCU).