Senior Director, Billings and Collections

The Director of Billing and Collections will be responsible for building and leading the company's billing and collections function as we scale our Workers' Compensation and Commercial Auto Insurance business. This leader will be responsible for ensuring accurate, timely, and compliant premium invoicing and collections while reducing outstanding receivables and improving cash flow.

The ideal candidate will have deep experience in P&C insurance billing, regulatory compliance, and collections strategies. This person will drive automation, improve efficiency, and implement best practices to scale our billing operations in a high-growth environment.

How You’ll Do It

Billing & Collections Strategy & Execution:

• Own the end-to-end premium billing process, ensuring timely and accurate invoicing for Workers’ Compensation and Commercial Auto insurance policies.
• Develop and optimize collections strategies to reduce DSO (Days Sales Outstanding) and minimize bad debt exposure.
• Oversee audit premium adjustments, cancellations, and policyholder refunds, ensuring compliance with state and regulatory requirements.
• Collaborate with underwriting, policy administration, and claims teams to align billing with policy lifecycle changes.

Process Optimization & Technology:

• Automate billing & collections workflows to increase efficiency and reduce errors.
• Implement and optimize billing and payment platforms (e.g., Zuora, Guidewire, Duck Creek, One Inc, Stripe, or similar).
• Introduce AI-driven collections strategies (e.g., predictive scoring for delinquent accounts).
• Enhance customer payment experience, including self-service options and flexible payment plans.

Regulatory Compliance & Risk Management:

• Ensure compliance with state regulations governing premium billing and collections in Workers’ Comp & Commercial Auto.
• Lead audits, reporting, and reconciliation efforts to maintain compliance with NAIC, state insurance departments, and GAAP accounting standards.
• Develop and enforce collections policies, including handling of delinquent accounts and coordination with legal teams on recoveries.

Team Leadership & Cross-Functional Collaboration:

• Build and lead a high-performing billing and collections team.
• Work closely with sales and customer service teams to improve payment adherence while maintaining strong client relationships.
• Partner with finance and treasury teams to ensure accurate cash flow forecasting, financial statement reporting, subledger support and reconciliation.

The Right Stuff

• Bachelor’s degree in finance, accounting, or business required.  
• Minimum of 12 years of experience in premium billing, collections, or revenue cycle management in P&C insurance, preferably focused on Workers’ Compensation and Commercial Auto.
• Minimum of 10 years of leadership/management experience.
• Expertise in billing automation, ERP systems, and collections platforms (Guidewire, Duck Creek, One Inc, Netsuite, Workday, etc.).
• Deep knowledge of regulatory compliance (state-by-state billing laws, premium audits, cancellation & reinstatement policies).
• Data-driven approach, with experience using SQL, Tableau, or Excel to analyze billing trends and optimize collections.
• Excellent stakeholder management skills, with the ability to collaborate across Finance, Operations, Underwriting, and IT.
• Strong attention to detail.
• Excellent analytical, problem-solving, and organizational skills.
•  Strong communication and interpersonal skills.