Director of Finance

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. Pets Best is hiring for a Director of Finance based in our Chicago, IL Office This is a hybrid role; the successful candidate will be in the Chicago area or relocating to the area.

About Doubtless Doubtless is redefining pet care by bringing together trusted pet insurance brands, innovative technology, and data-driven health solutions to help pets live longer, healthier lives. Formed through the combination of Independence Pet Holdings and Pinnacle Pet Group, Doubtless serves more than 6 million pets across North America, Europe, and the United Kingdom with a team of over 4,000 employees.

Our portfolio includes leading pet insurance brands, wellness solutions, AI-powered health tools, microchip recovery services, adoption platforms, and other technologies that support pet parents throughout every stage of their journey. About Pets Best Since 2005, Pets Best has helped pet owners access high-quality veterinary care through flexible, comprehensive pet insurance. As one of Doubtless' flagship brands, Pets Best combines insurance expertise with a commitment to making pet healthcare more affordable and accessible while delivering exceptional service and innovative products.

Position Overview The Director of Finance serves as a strategic business partner to executive leadership, providing financial insights, decision support, and commercial analysis that drive revenue growth, profitability, and long-term value creation. This leader will leverage financial modeling, forecasting, operational analytics, and business intelligence to evaluate opportunities, optimize investments, and support key strategic initiatives across the organization.

In addition, the role will oversee financial planning processes, partner closely with accounting and operational teams, and lead continuous improvement initiatives that enhance decision-making, scalability, and organizational performance. Key Responsibilities Strategic Finance & Commercial Partnership Provide financial leadership and strategic partnership to executive leadership and cross-functional stakeholders, delivering actionable insights that support business performance and long-term growth.

Develop frameworks for evaluating business opportunities, growth initiatives, market expansion strategies, new revenue streams, and key investment decisions through financial modeling and scenario analysis. Design and maintain forecasting, profitability, and decision-support models used to evaluate strategic initiatives, partnerships, marketing investments, and operational performance. Partner closely with business leaders to assess risks, identify opportunities, optimize resource allocation, and support data-driven decision making.

Deliver meaningful analyses and recommendations that improve revenue growth, operating performance, and overall financial outcomes. Financial Planning & Analysis Lead the annual budgeting process, long-range planning activities, and recurring forecasting cycles to ensure accurate, actionable financial plans. Monitor business performance against plans and forecasts, identifying trends, risks, and opportunities while recommending corrective actions as needed.

Support unit economics, customer profitability, customer acquisition cost (CAC), lifetime value (LTV), and other key operating metrics that drive business