Head of Billing and Collections

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

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.

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.

• 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…