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 President and 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.

Nicholas Dagenais

Nicholas Dagenais is the Chief Financial Officer of Obsidian. He has extensive insurance finance and accounting experience. Immediately prior to Obsidian he was the Vice President of Finance for Arthur J Gallagher’s United States Retail Brokerage. Before joining Arthur J Gallagher, Nicholas was Zone Financial Officer at The Hanover Insurance Group where over his tenure he held a variety of roles in Investor Relations, Corporate Strategy, Capital Management, and Financial Planning and Analysis.

Jeff Wittlich

Jeff Wittlich is the Chief Underwriting Officer of Obsidian. Jeff has over 30 years of property and casualty underwriting and program management experience in the insurance and reinsurance industry. Most recently Jeff served as Senior Vice President, Head of Regional & National – MGA for Swiss Re America, establishing and managing a new specialized team focused on program business. Previously he led Swiss Re’s MGA cross functional team, Swiss Re’s Regional & National Specialty team focused on program business, E&S and mono-line specialists and alternative risk vehicles, and Swiss Re’s Workers’ Compensation portfolio.

Andrew Kempen

Andrew Kempen, FCAS, MAAA is the Chief Actuary of Obsidian. He has a significant amount of insurance industry experience which includes pricing, reserving, reinsurance, data analytics, business intelligence and enterprise risk and strategic program management. Prior to joining Obsidian, he most recently served as Senior Vice President and Chief Actuary at IFG Companies in the Excess and Surplus lines market. In addition, he has held multiple actuarial roles throughout his career in the commercial and personal lines industries for both admitted and non-admitted business.