Head of Billing and Collections

This is an opportunity to join Ascot Group - one of the world’s preeminent specialty risk underwriting organizations.

Designed as a modern-era company operating through an ecosystem of interconnected global operating platforms, we’re bound by a common mission and purpose: One Ascot. Our greatest strength is a talented team who flourish in a collaborative, inclusive, and entrepreneurial culture, steeped in underwriting excellence, integrity, and a passion to find a better way, The Ascot Way.

The Ascot Way guides our people and our organization. Our underwriting platforms collaborate to find creative ways to deploy our capital in a true cross-product and cross-platform approach. These platforms work as one, deploying our capital creatively through our unique Fusion Model: Client Centric, Risk Centric, Technology Centric.

Built to be resilient, Ascot maximizes client financial security while delivering bespoke products and world class service — both pre- and post-claims. Ascot exists to solve for our clients’ brightest tomorrow, through agility, collaboration, resilience, and discipline.

Ascot is embedding artificial intelligence (AI) and automation across the organisation to enhance decision‑making, efficiency, and quality of outcomes. In this role, you will be expected to work confidently alongside AI‑enabled tools, apply sound judgment when interpreting insights, and adapt as technology continues to evolve. We value curiosity, critical thinking, and a willingness to embrace change as part of how we work.

Job Summary:

Ascot’s Finance Operations team is seeking a strategic, hands-on Head of Billing & Collections to lead billing, cash application, collections, reconciliations, and related receivables operations across the organization. This leader will build disciplined, scalable processes that drive timely invoicing, accurate cash application, effective collections, strong controls, improved working capital, and high-quality service for internal and external stakeholders.

The successful candidate will combine deep operational expertise, sound judgment, and strong people leadership with the ability to influence across Finance, Underwriting, Claims, Operations, Reinsurance, Treasury, Technology, brokers, and other partners. The role will also be a key business leader in the implementation, adoption, and ongoing optimization of Ascot’s new Guidewire billing system—ensuring that requirements, workflows, controls, reporting, data conversion, testing, training, and user readiness are effectively represented. This position follows a hybrid work schedule.

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.

Requirements:

• 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.

This position may be filled at a different level based on the selected candidate’s experience and qualifications.

Compensation:

Actual base pay may vary above or below the stated range based on factors such as experience, subject-matter expertise, and skills. Base pay is one component of Ascot’s total compensation package. Additional rewards may include an annual cash bonus and other discretionary compensation awarded by the Company.

Annualized base pay range: $200,000 - $220,000

Company Benefits:

Ascot offers a competitive benefits package, subject to applicable eligibility requirements, including:

• Health and welfare benefits: medical (including prescription coverage), dental, vision, health savings account, commuter account, health care and dependent care flexible spending accounts, life insurance, accidental death and dismemberment insurance, work-life resources (including an Employee Assistance Program), and more.
• Leave benefits: paid holidays; annual paid time off, including state or local paid leave where required; short- and long-term disability; and other leaves, including bereavement, FMLA, adoption, maternity, military, primary caregiver, and non-primary caregiver leave.
• Retirement benefits: contributory savings plan (401(k)).