Billing & Collections Leader: Strategy, Automation, Impact

Ascot Group; Woodbridge Township (NJ); On-site; USD 200,000 - 220,000; Full time

Benefits offered by this job

Health and welfare benefits

Retirement benefits (401(k))

Paid holidays and PTO

Job summary

Ascot Group, a world‑class specialty risk underwriting organization, seeks a strategic Head of Billing & Collections. You will lead end‑to‑end invoicing, cash application, collections, and reconciliations while building scalable processes to improve working capital and service for internal and external stakeholders.

You will partner across Finance, Underwriting, Claims, Reinsurance, Treasury, and Technology, influence senior leaders, and drive automation, data analytics, and AI‑enabled tools.

Qualifications

• Bachelor’s degree in Accounting, Finance, Business Administration, or a related field; equivalent relevant experience may be considered.
• At least 10 years of progressive experience in accounts receivable, billing, collections, finance operations, insurance accounting, or a related discipline, including people leadership experience.
• Experience in insurance, reinsurance, financial services, specialty insurance, workers’ compensation, or another complex, transaction‑intensive environment is strongly preferred.
• Deep knowledge of billing operations, collection strategies, receivables management, cash application, internal controls, reconciliations, and financial reporting.
• Demonstrated ability to analyze complex account issues, identify root causes, and implement practical, well‑controlled solutions.
• Proven success leading process improvement, automation, reporting, and operational transformation initiatives.
• Strong stakeholder‑management skills and the ability to influence effectively across functions and with external partners.
• Excellent written and verbal communication skills, including the ability to explain complex issues clearly to senior leaders and business partners.
• Highly organized and detail‑oriented, with the ability to manage competing priorities in a fast‑paced, collaborative environment.
• Experience with accounting, billing, collections, ERP, workflow, or reporting platforms; Guidewire BillingCenter or comparable Guidewire experience is strongly preferred.
• Experience serving as a business subject‑matter expert or functional lead on billing‑system implementations, including requirements, process design, data conversion, user acceptance testing, training, and adoption.
• Proven ability to build trusted relationships with Finance, Operations, Underwriting, Claims, Reinsurance, Treasury, Technology, brokers, clients, and external service providers.
• Demonstrated success building and developing high‑performing teams and fostering accountability, collaboration, customer service, and continuous improvement.
• A positive, self‑motivated, customer‑centric leadership style and a commitment to developing people and improving outcomes.

Responsibilities

• Lead the end-to-end Billing & Collections function, including invoicing, cash application, payment reconciliation, collections, dispute management, unapplied cash resolution, and related receivables activities.
• Define and execute the Billing & Collections strategy, operating model—including direct, agency, and deductible billing—and target-state roadmap in support of growth, customer experience, controls, and financial objectives.
• Establish clear policies, procedures, controls, service standards, and performance metrics that enable timely, accurate, compliant, and scalable execution.
• Own receivables and working‑capital performance, improving collection effectiveness, cash conversion, aging, unapplied cash, and overall cash-flow outcomes.
• Develop risk‑based collection strategies that maximize cash realization while preserving strong relationships with brokers, clients, reinsurers, coverholders, and other partners.
• Optimize the operating model across automation, outsourced or offshore resources, and internal teams to achieve service, control, quality, and cost objectives.
• Manage outsourced billing and collections providers, holding them accountable for contractual commitments, service‑level agreements, controls, and key performance indicators.
• Use data, analytics, and predictive monitoring to identify collection risks, prioritize recovery efforts, strengthen cash‑flow forecasting, and support proactive decisions.
• Oversee the analysis and resolution of aged receivables, past‑due balances, unapplied cash, payment discrepancies, returned payments, disputes, and other complex account issues.
• Develop executive reporting and dashboards covering aging, collections effectiveness, cash‑application timeliness, dispute trends, working capital, cash flow, operational quality, receivables risk, and service performance.
• Partner with Underwriting, Claims, Reinsurance, Treasury, Finance, Operations, Technology, Legal, Compliance, and business leaders to resolve systemic issues and improve performance.
• Serve as the senior escalation point for complex broker, client, reinsurer, and internal stakeholder matters involving billing, collections, payment application, and account status.
• Drive continuous improvement, automation, and standardization, including active leadership in the Guidewire billing implementation and thoughtful use of data, technology, and AI‑enabled tools.
• Support month‑end, quarter‑end, and year‑end close by ensuring accurate receivables reporting, reconciliations, documentation, controls, and timely issue resolution.
• Build, lead, coach, and develop a high‑performing team with clear expectations, strong capabilities, career development, and accountability.
• Model The Ascot Way through inclusive collaboration, ownership, and a commitment to an engaged, high‑performing culture.

Skills

Strategic leadership

Stakeholder management

Communication

Process improvement

Team development

Education

Bachelor’s degree in accounting/finance/business administration

Tools

Guidewire BillingCenter

Job description

Ascot Group, a world‑class specialty risk underwriting organization, seeks a strategic Head of Billing & Collections. You will lead end‑to‑end invoicing, cash application, collections, and reconciliations while building scalable processes to improve working capital and service for internal and external stakeholders.

You will partner across Finance, Underwriting, Claims, Reinsurance, Treasury, and Technology, influence senior leaders, and drive automation, data analytics, and AI‑enabled tools.