Meet the
Knighthead International^™
leadership team.

Anchored in deep experience and insurance expertise, our executive officers and board offer valuable oversight as we work towards our mission of delivering innovative solutions that chart the course to financial security.

Edward P. Massaro

Chief Executive Officer, Chief Investment Officer, and Director

Tyler Bent, CPA, CMA

Chief Operating Officer

Delia McMahon, BA, LLB, LLM

General Counsel, Chief Compliance Officer, and Company Secretary

Rob Ollins, CA, CPA

Chief Financial Officer

Jeremy Trader, FSA, FCIA

Chief Actuary

Edward P. Massaro

CEO & Chief Investment Officer, Knighthead Insurance Group (2022 – Present)
Former Partner, COO & Head of Business Development, Knighthead Capital Management (2009 – 2021)

Edward Massaro is a seasoned executive with extensive expertise in investment management, capital markets, and business development. As CEO and Chief Investment Officer of Knighthead Insurance Group, he oversees strategic investment initiatives and operational leadership for insurance products and assets. Previously, he played a pivotal role in building Knighthead Capital Management, driving business strategy, fund raising, and investor relations while spearheading the launch of Knighthead Annuity & Life Assurance Company in 2014.

Throughout his career, Edward has developed a vast global network of investors, raising over $5 billion for hedge fund products and $1 billion for direct lending real estate strategies. His leadership spans major financial institutions, including HSBC Securities, RBS Greenwich Capital, UBS Investment Bank, and Solomon Smith Barney, where he specialized in leveraged finance, high-yield securities, and institutional investment strategies.

Mr. Massaro holds an MBA in Finance from The Wharton School of Business and a BA in Chemical Engineering from Yale University.

Tyler Bent, CPA, CMA

Chief Operating Officer

Tyler has over 16 years of experience in the insurance, reinsurance and insurance administration industry. His experience and expertise spans finance & operations in the Americas, EMEA and Asia. Tyler holds a Bachelor of Commerce from St. Mary’s University in Nova Scotia and is a Chartered Professional Accountant and member of the Chartered Professional Accountants of Canada.

Delia McMahon, BA, LLB, LLM

General Counsel, Chief Compliance Officer, and Company Secretary

Delia has over 20 years professional experience as an Irish, England & Wales (Non-Practicing) and Cayman Islands qualified lawyer. Prior to joining Knighthead in 2021, she worked with several premier on-shore top-tier commercial law firms in Dublin and the Cayman Islands including William Fry, Mourant, and Conyers & Maples.

Rob Ollins, CA, CPA

Chief Financial Officer

Rob has over 22 years of experience in the insurance and reinsurance industry at an international level. He developed his expertise of US GAAP, treasury, financial modeling, ERM, and internal controls for re/insurance companies while at Deloitte, EY and PwC in Canada, Cayman, Switzerland and the UK.

Jeremy Trader, FSA, FCIA

Chief Actuary

Jeremey has over 12 years of professional experience. Prior to joining Knighthead, he worked as a Director of Financial Services Advisory at Grant Thornton in the Cayman Islands and held various roles across Great-West Lifeco.

Mike Karmilowicz

Director

Mike Karmilowicz has over 30 years of experience in the insurance industry, successfully leading, building, remediating and developing large and complex domestic and international businesses. He recently served as Chairman of Everest Global Insurance where he focused on advancing several growth initiatives including client development, building global distribution, developing the Everest brand and supporting underwriting excellence. Prior to this role, Mr. Karmilowicz served as President and CEO of Everest Insurance responsible for leading underwriting, product development and innovation, claims, sales and distribution, operations, and strategy globally. He led international expansion opening over a dozen offices worldwide including Continental Europe, Asia Pacific, and Latin America. Mr. Karmilowicz received a B.A. in Political Science from Villanova University and is a graduate of The Wharton School Executive Leadership Program.