Director of Finance

Independence Pet Holdings

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 performance.
• Provide financial analysis and decision support for strategic initiatives, investments, and business planning activities.

Reporting & Business Insights

• Develop and present executive-level financial reporting, including monthly, quarterly, and annual operating reviews, business performance updates, board materials, and ad hoc analyses.
• Translate complex financial and operational information into compelling business narratives and recommendations for senior leadership.
• Leverage data, analytics, and visualization tools to improve reporting capabilities and decision-making effectiveness.
• Ensure stakeholders have timely access to accurate financial and operational information.

Process Improvement & Business Intelligence

• Drive continuous improvement initiatives by leveraging technology, automation, and analytics to improve efficiency, scalability, and decision support capabilities.
• Identify opportunities to reimagine financial processes, reporting frameworks, and planning methodologies.
• Partner with business and technology teams to implement tools and processes that enhance financial visibility and operational effectiveness.
• Support the development of scalable reporting and analytics capabilities across the organization.

Financial Operations & Cross-Functional Collaboration

• Maintain a strong understanding of the company's financial statements, accounting processes, treasury activities, tax considerations, audit findings, and overall financial operations.
• Develop deep knowledge of the business model, operational drivers, technology environment, controls, governance processes, and reporting structures.
• Partner closely with accounting and operational teams to ensure alignment between planning, reporting, and business objectives.
• Collaborate effectively with parent company finance and accounting organizations as well as sister portfolio companies when appropriate.
• Ensure sound documentation of key financial policies, procedures, and workflows.

People Leadership

• Lead, develop, and mentor finance team members while fostering a high-performance, collaborative culture.
• Create opportunities for professional growth and skill development across the team.
• Build a culture of accountability, continuous improvement, and business partnership.
• Perform other duties as assigned.

Required Qualifications

• Bachelor's degree in Finance, Accounting, Business, Economics, or a related field.
• 5+ years of progressive finance experience with deep expertise in financial planning and analysis.
• Experience within the insurance industry is strongly preferred.
• Strong experience in financial modeling, budgeting, forecasting, long-range planning, scenario analysis, and business performance management.
• Demonstrated experience supporting strategic business decisions through financial analysis and data-driven recommendations.
• Experience evaluating unit economics, profitability drivers, customer acquisition costs (CAC), lifetime value (LTV), and growth initiatives.
• 3+ years of progressive leadership experience with a demonstrated track record of leading finance functions, developing teams, driving revenue growth, and supporting profitable business expansion.
• Proven ability to influence executive leadership and serve as a trusted business partner across multiple functions.
• Strong communication, presentation, storytelling, and stakeholder management skills.
• Strong business acumen and understanding of how financial results connect to operational performance and strategic objectives.
• Experience supporting direct-to-consumer (DTC), B2C, or high-growth consumer-focused business environments preferred.
• Advanced Excel and PowerPoint skills.
• Experience utilizing business intelligence, reporting, and analytics tools such as Power BI, Tableau, Power Query, SQL, Python, R, or similar technologies.
• Ability to leverage technology and automation to improve business processes and decision support capabilities.
• Highly organized with strong attention to detail and execution.
• Demonstrated initiative, ownership mentality, and willingness to work both strategically and hands-on when needed.
• Strong problem-solving capabilities and commitment to continuous improvement.
• Passion for building strong teams, improving processes, and driving business results.

Preferred Qualifications

• MBA, CPA, and/or CFA designation.
• Proven track record of leading strategic initiatives and delivering measurable business impact in complex, high-growth environments.
• Passion for pets and the mission of improving the lives of pet owners and their animals.

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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