Contract Pet Insurance Underwriter Jobs (NOW HIRING)

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.
Independence American Insurance Company (IAIC), the insurance carrier for the Doubtless family of companies is hiring for aDirector of Underwriting
This is a hybrid role based out of Chicago or New York City.
Doubtless is one of the world's leading pet insurance and pet health organizations, bringing together the former Independence Pet Holdings and Pinnacle Pet Group into a unified global enterprise.
With more than 4,000 employees, Doubtless protects over 6 million pets across 10 markets throughout North America, Europe, and the United Kingdom. Through a portfolio of trusted pet insurance brands and innovative pet care solutions, we help pet parents protect and care for their pets throughout every stage of life.
Independence American Insurance Company (IAIC) is the insurance carrier within the Doubtless family of companies. IAIC provides underwriting expertise, governance, and regulatory oversight that support our pet insurance portfolio and strategic partnerships.
Working closely with Product Management, Actuarial, Claims, Compliance, and our MGA partners, Doubtless's North American insurance carriers balance disciplined risk management and governance with innovation to deliver sustainable, profitable growth.
Position Overview
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.
Key Responsibilities
Underwriting Strategy & Governance - Establish, maintain, and continuously evolve carrier underwriting philosophy, risk appetite, underwriting guidelines, governance framework, and administrative policies to support sustainable, profitable growth.
Carrier Underwriting Authority - Serve as underwriting authority for guideline exceptions, product approvals, underwriting philosophy, risk tolerance decisions, approval of new insurance products, product enhancements, and underwriting programs for Doubtless North America insurance carriers.
Portfolio Performance & Risk Management - Develop a deep understanding of underwriting performance, portfolio results, emerging risks, and market trends to continuously improve underwriting guidelines, and risk selection.
Regulatory Compliance & Governance - Ensure underwriting operations remain compliant with applicable insurance regulations across the United States and Canada while maintaining appropriate governance, documentation, and operational controls.
MGA Oversight & Delegated Authority - Provide carrier oversight of MGA underwriting operations, delegated authority, underwriting guideline adherence, operational enhancements, and claims process initiatives while ensuring compliance with contractual and regulatory requirements.
Underwriting Controls & Audit - Develop, implement, and monitor underwriting controls, governance processes, audit programs, corrective action plans, and operational procedures that strengthen underwriting consistency and regulatory compliance.
Enterprise Partnership - Partner closely with executive leadership and collaborate across Product Management, Actuarial, Claims, Compliance, Legal, Finance, and MGA leadership to align underwriting strategy with business objectives and regulatory expectations.
Strategic Influence - Build trusted relationships across the organization and effectively influence executive leaders, carrier partners, regulators, and external stakeholders through sound judgment, credibility, and technical expertise.
Required Experience

• 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.

Preferred Qualifications

• 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.

What You Bring

• 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.

Why Join Independence American Insurance Company?
As the underwriting leader, you'll have the opportunity to shape the underwriting philosophy, governance framework, and risk management strategy supporting one of the fastest-growing organizations in pet insurance.
You'll work alongside talented leaders across the Doubtless enterprise to influence product innovation, underwriting strategy, regulatory excellence, and sustainable business growth while helping millions of pet families access high-quality insurance protection.
If you're passionate about building best-in-class underwriting organizations, influencing enterprise strategy, and leading through expertise and collaboration, we'd love to hear from you.
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All of our jobs come with great benefits including healthcare, parental leave and opportunities for career advancements. Some offerings are dependent upon the location of where you work and can include the following:

• Comprehensive full medical, dental and vision Insurance
• Basic Life Insurance at no cost to the employee
• Company paid short-term and long-term disability
• 12 weeks of 100% paid Parental Leave
• Health Savings Account (HSA)
• Flexible Spending Accounts (FSA)
• Retirement savings plan
• Personal Paid Time Off
• Paid holidays and company-wide Wellness Day off
• Paid time off to volunteer at nonprofit organizations
• Pet friendly office environment
• Commuter Benefits
• Group Pet Insurance
• On the job training and skills development
• Employee Assistance Program (EAP)

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