Stephen Lewis

Managing Director, Capstone Headwaters

Stephen Lewis joined Headwaters in 2014, now Capstone Headwaters after the merger of Headwaters and Capstone in 2018, from Cross Border Strategies LLC, a boutique cross border debt advisory practice he founded. There he focused exclusively on facilitating international debt financing for middle market companies with current or planned operations outside North America. Immediately prior to founding Cross Border Strategies LLC, Stephen served for seven years as Executive Director with GE Corporate Financial Services in Chicago and London. Prior to his tenure with GE, Stephen spent 16 years in various roles for Heller Financial, Inc. where, among other things, he founded and managed Heller’s cross border lending practice.

Stephen is a 35+ year veteran of the financial services industry. Stephen has broad legal and business experience in multi-jurisdictional transactions of all types, including portfolio acquisitions, lending, structuring and re-structuring. His extensive management skills include establishing and leading “start-up” operations in Canada and the UK for US based lending institutions.

Stephen has personally lead over 100 international financing transactions involving more than $10 billion in international financing. He has completed international debt transactions in over 30 countries, including the US, Canada, Great Britain, France, The Netherlands, Spain, Germany, Italy, Japan, China, Hong Kong, Singapore, Australia, Mexico, Brazil, Argentina and Chile.

Stephen received a BA from DePauw University with high distinction and a JD from Indiana University School of Law. He is based in Chicago, Illinois.