Our Team

Jeff Craig is the CEO and founder of Craig. He serves on Craig’s Board of Directors, and oversees all of the firm’s activities, including marketing, operations, strategy and research. Since obtaining a B.S.E. degree in finance from Wharton, Jeff has founded and run several profitable businesses in addition to Craig. These include a healthcare/pharmaceuticals marketing, medical patents, consulting and publishing business whose customers include many leading pharmaceutical firms, a property investment and construction firm, and consumer goods and retail services investments.

Harry Glasspiegel is an Executive Vice President and a member of Craig’s Board of Directors. He helps to set the BPO, customer relationship, marketing, and technology strategy for the Company. Harry joined Craig in 1999, after serving as the CEO of a technology strategy and investment arm of CNA Insurance. Harry co-founded the first technology outsourcing customer advisory practice in the legal services market, at Shaw Pittman (now Pillsbury Winthrop Shaw Pittman). He was a founding adviser to the Sourcing Interests Group, and is a frequent speaker and author on business process outsourcing and technology. Harry holds a B.A. from Wesleyan University in Connecticut and a J.D. from the University of Wisconsin.

Deborah J. Knox is a Senior Vice President of Craig, which she joined in 2006, after spending 28 years with Firemans Fund Insurance Company, a $5 billion multi-line insurance and financial services company and subsidiary of Allianz, a Fortune 40 financial services company. The last position she held at FFIC was Sr. Vice President, Chief Claims Officer, responsible for nationwide claims strategy and operations to service customers in the Personal, Commercial, and Specialty business units; prior to that position Deborah held a variety of escalating executive leadership positions in home office technical/product line and field operations. Recognized in 2000 by Business Insurance Magazine as one of the 100 Leading Women in Business Insurance she holds several industry designations including, CPCU, Certified Risk Manager, Certified Insurance Counselor, Senior Claims Law Associate, and a B.S. Degree from California State University.

Robert Coffee, Esq. is General Counsel and Chief Administrative Officer of Craig. Bob served in the same position for Gryphon Holding, Inc. from 1994 until its acquisition in 1999. Prior to that, he served eight years as Vice President, Corporate Secretary and Assistant General Counsel of Willis Corroon and as Associate General Counsel for 10 years with The Pittston Company, a $4 billion publicly traded energy and transportation conglomerate. He was also in private practice with Cadwalader, Wickersham & Taft, a large corporate law firm based in New York. Bob received his B.A. and J.D. degrees from Columbia University.

Kirk Young is Senior Vice President, Client Relations and Operations at Craig. He is responsible for all claims delivery including partnership selection, process and performance standards. He is also a key participant in Craig’s consulting engagements given his years of experience in significant commercial litigation for general liability and product litigation, bodily injury, property and CAT claims handling, workers compensation, special investigation, litigation strategy development and claims operations. Previously, his line and leadership experiences at both Fireman’s Fund and Liberty Mutual included serving as Director of Subrogation as well as 2nd Injury Fund, Liability Deductibles and salvage recovery.

Matthew D. Freiman, ESQ. is the Director of Large Loss Investigations and Litigation Management at Craig. His duties include the management of large loss forensic investigations including the retention of experts, the oversight and supervision of ongoing investigations, and the retention, budgeting and management of outside counsel for litigated claims. He founded and managed a specialized staff counsel office for The Kemper Insurance Companies in Chicago, Illinois, focused on national and international commercial property, boiler/machinery and marine subrogation and coverage matters. Matt previously served as coverage counsel for Zurich North America based in Chicago, Illinois. He has practiced in state and federal courts nationwide and before international arbitral tribunals. Matt served as a diplomatic security officer in the United States Department of State and is a graduate of Boston University and The John Marshall Law School in Chicago.

Board of Directors

Jeff Craig Harry Glasspiegel