THE TEAM

Bill Jewett

Obsidian will be led by William Jewett, Chief Executive Officer, who has over 35 years of industry focused on building and managing insurance and reinsurance companies. His most recent executive position within the industry was with Bermuda-based Insurer and Reinsurer Endurance Specialty, where he was President and  a Member of the Board of Directors.

Craig Rappaport

Craig Rappaport is the Chief Financial Officer & Chief Operating Officer of Obsidian.  He has over 20 years of industry experience focused on building and managing program focused insurance companies.  Prior to Obsidian, he was the COO of Specialty Property & Casualty for the Hanover Insurance Group where he led a specialty program division as well as an E&S business.  He was also an original founding team member of AIX Group, a private equity funded program insurance company. 

Emily Canelo

Emily Canelo is the Chief Legal Counsel of Obsidian.  She is a seasoned attorney with broad and deep experience in legal, regulatory, claims and transactional work in the fields of insurance and reinsurance. Prior to joining Obsidian, Emily served as Chief Counsel and Executive Vice President for the Worldwide Reinsurance and Insurance segments of Endurance Services Ltd., the service company for Endurance Specialty Insurance Ltd.

Stacy Armstrong

Stacy Armstrong is the Chief Client Officer of Obsidian. She has over 25 years of experience in the Reinsurance and Insurance Industry, and has extensive experience in the underwriting of property, casualty, and specialty portfolios.  Most recently she served as Executive Vice President, Underwriting, M&A, and TPA Management at Cranmore, a unit of Enstar Group. Prior to that she was at Maiden Re for 20 years,  where she served in various leadership positions.