VP of Finance

VP of Finance

Counterpart is an insurtech platform reimagining management and professional liability for the modern workplace. We believe that when businesses lead with clarity and confidence, they become more resilient, more innovative, and better prepared for what’s ahead. That’s why we built the first Agentic Insurance™ system — where advanced AI and deep insurance expertise come together to proactively assess, mitigate, and manage risk. Backed by A rated carriers and trusted by brokers nationwide, our platform helps small businesses grow with confidence. Join us in shaping a smarter future, helping businesses Do More With Less Risk®.

Counterpart is entering a new chapter of growth with strong backing from world-class investors, a growing network of distribution partners, and a passionate team of industry veterans and innovators. As Vice President of Finance, you will serve as a key financial architect, responsible for driving the company's economic strategy and performance. You will lead the development, analysis, and execution of financial plans that unlock new avenues for profitable growth, ranging from strategic partnerships and capital structure optimization to unit economics and long-range planning. Working closely with our CEO, Tanner Hackett, and external finance partners, you will own the company’s financial planning and analysis (FP&A) function, including budgeting, forecasting, scenario modeling, and cash management. You will also play a critical role in capital allocation decisions, helping ensure resources are deployed effectively across all functions. 

YOU WILL:

Finance & Strategic Planning

• Lead the development, implementation, and ongoing refinement of Counterpart’s operating and strategic financial plans.
• Manage company-wide budgeting, forecasting, financial modeling, and budget vs. actuals variance analysis to ensure robust capital allocation and planning.
• Drive the development of board, insurance carrier, and investor-facing reporting packages, providing actionable insights on performance and growth opportunities.
• Maintain and refine real-time dashboards, models, and internal systems for evaluating key performance indicators.

Risk Taking Strategy

• Architect and scale the financial infrastructure that empowers Counterpart to retain and underwrite risk directly on its balance sheet.
• Analyze opportunities to unlock additional risk capacity and optimize capital efficiency among reinsurers, fronting carriers, banks, and capital partners.
• Design and manage capital facilities (e.g., captives, quota shares, surplus lines) that enable disciplined, scalable risk-taking.
• Build systems and controls to monitor exposure, manage liquidity, and meet financial and regulatory obligations with confidence.
• Own treasury operations, ensuring proactive cash management, liquidity planning, and efficient deployment of working capital.

Insurance, Compliance & Billing Infrastructure

• Navigate the financial complexity of regulated industries by implementing systems and controls that meet the demands of compliance within the insurance space and adjacent sectors (e.g., fintech, healthcare, crypto).
• Oversee regulatory reporting, bordereaux submissions, payment processing, and audits across all carrier and reinsurance relationships.
• Lead the design and scalability of billing and backend payments infrastructure in coordination with engineering and insurance teams, ensuring seamless integration and operational excellence.

Operational Excellence & Systems

• Build and manage a high-performing finance organization, including FP&A, strategic finance, accounting, compliance, and billing operations.
• Hire, develop, and retain both onshore and offshore financial talent with an eye toward scaling infrastructure and team capabilities in alignment with company growth.
• Oversee accounting, including the monthly close process, annual audits, R&D credit, and tax filings, ensuring timely, accurate, and GAAP-compliant financial reporting.
• Evaluate and implement financial systems and tools that streamline operations and enhance cross-functional decision-making.
• Support future fundraising efforts in collaboration with executive leadership, legal advisors, and financial partners.

YOU HAVE:

• 10+ years of financial leadership experience, ideally in high-growth, venture-backed startups within regulated industries (insurance, fintech, healthcare, or crypto).
• Familiarity with and interest in designing and scaling payment and billing infrastructures, especially those supporting high-transaction environments.
• Deep familiarity with FP&A, strategic finance, accounting, and regulatory compliance frameworks within the insurance ecosystem or similar verticals.
• A strong track record of building and leading high-performing finance teams, including managing global resources and distributed teams.
• Proven track record with shaping and solving complex problems related to financial contracts, compliance infrastructure, and strategic partnership negotiations.
• Exceptional modeling and analytical skills; you use data to drive decisions and tell compelling stories to internal and external stakeholders.
• Ability to work fluidly across teams, demonstrating strong communication, adaptability, and collaborative leadership in a fast-paced environment.