Meet Our Team

Bill Jewett

William Jewett is the Chief Executive Officer of Obsidian. He has over 35 years of industry focused experience 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, CPCU, ARe, is the Chief Reinsurance Officer & Head of Strategic Initiatives of Obsidian. Stacy has over 25 years of experience in the 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 including Head of Marketing, Head Corporate Underwriting and Executive Vice President – Broker Treaty & New Products. Stacy also served on the Board of Directors for Maiden Re NA. She began her underwriting career at St. Paul Re and Zurich Re.

Andrew Aldorisio

Andrew Aldorisio is the Chief Underwriting Officer of Obsidian. He has extensive experience and a deep understanding of diverse aspects of the program insurance marketplace including delegated authority, alternative markets, captives, and traditional programs. Andrew brings a technical underwriting skillset and a broad background to developing and building profitable programs. Most recently, Andrew was responsible for managing casualty and professional lines programs, with the additional responsibility of leading business development for SCOR Re’s primary insurance Programs Business Unit. Working with MGAs and MGUs, he developed a portfolio covering over nine lines of business. Prior experience includes program business roles at Munich Re and Arch.

Kim Ho Lo

Kim Ho Lo, FCAS, MAAA is the Chief Actuary of Obsidian. He has over 20 years of experience in Pricing, Reserving, Rate Filing, and Risk Management in both Commercial and Personal Lines of insurance. Most recently, he was the Pricing Actuary leading the middle market pricing at Blackboard Insurance. Prior to that he was Vice President and Senior Pricing Actuary at Sompo International and before that Actuarial Consultant at Perr&Knight.

Scott Palladino

Scott Palladino, CPCU, MBA is the Chief Business Development Officer of Obsidian. Scott has extensive underwriting and business development experience within the program space. Most recently, he led business development at Clear Blue, where he was one of the original members of the management team. Scott started his career at Liberty Mutual, where he held various property and casualty underwriting and management positions over a 22-year period. Subsequently, Scott held leadership positions at Sompo Japan Nipponkoa, including CUO and VP of Specialty Operations. He was also a member of the board of Sompo Marine and Fire Company and a member of the U.S. mergers and acquisition team.