Director of Underwriting

Established in 2021, Independence Pet Holdings is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.

We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands. 

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This is a hybrid role based out of Chicago or New York City.

We are seeking an experienced Director of Underwriting to provide strategic underwriting leadership for Doubtless’s North American insurance carriers.

This leadership role is responsible for establishing and operationalizing the carrier's underwriting philosophy, risk appetite, underwriting guidelines, and governance framework while ensuring regulatory compliance and profitable portfolio performance.

As senior underwriting authority, you will partner with executive leadership and cross-functional teams to shape underwriting strategy, oversee delegated underwriting authority, strengthen carrier governance, and drive sustainable, profitable growth across our insurance portfolio.

• Bachelor's degree in Business, Mathematics, Science, or a related discipline, or equivalent professional experience.
• 10+  years of progressive Property & Casualty insurance experience, ideally including Personal Lines.
• Minimum of 5 years in a senior underwriting leadership, underwriting operations, governance, or compliance role.
• Demonstrated experience establishing underwriting philosophy, risk appetite, governance frameworks, underwriting guidelines, and operational controls.
• Experience working with carriers, MGAs, delegated authority models, reinsurers, and fronting carrier relationships.
• Strong understanding of insurance regulatory requirements across the United States; Canadian regulatory experience is highly desirable.
• Experience leading underwriting audits, compliance initiatives, governance programs, and regulatory examinations.
• Previous leadership experience, including coaching, mentoring, and developing underwriting professionals.

• CPCU or other advanced insurance industry designation.
• Experience supporting insurance product development, product filings, or underwriting strategy for new insurance products.
• Familiarity with underwriting technology platforms, workflow automation, and operational process improvement initiatives.

• Deep expertise in underwriting strategy, carrier governance, risk management, and insurance operations.
• Exceptional understanding of insurance markets, competitive dynamics, technology trends, and evolving regulatory environments.
• Strong business acumen with the ability to balance profitable growth and disciplined risk management.
• Executive presence with the confidence to constructively challenge assumptions, influence strategic decisions, and communicate effectively across all levels of the organization.
• Outstanding analytical, organizational, and problem-solving skills.
• Exceptional written, verbal, and presentation communication abilities.
• High degree of personal integrity, professionalism, and sound judgment.
• Demonstrated ability to lead organizational change while building trust and alignment across diverse stakeholder groups.
• Ability to travel up to 20% as business needs require and possess a valid passport.