Head of Billing and Collections

Ascot Group•Hartford, CT

4h•$200,000 - $220,000•Hybrid

About The Position

Ascot Group is seeking a strategic, hands-on Head of Billing & Collections to lead billing, cash application, collections, reconciliations, and related receivables operations across the organization. The role is responsible for building disciplined, scalable processes that support 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 operational expertise, sound judgment, and people leadership with the ability to influence partners across Finance, Underwriting, Claims, Operations, Reinsurance, Treasury, Technology, brokers, and other groups. The role is also a key business leadership position in implementing, adopting, and optimizing Ascot’s new Guidewire billing system, representing requirements, workflows, controls, reporting, data conversion, testing, training, and user readiness. The position follows a hybrid work schedule. Ascot is embedding artificial intelligence and automation across the organization. The role requires working confidently with AI-enabled tools, applying judgment when interpreting insights, and adapting as technology evolves. The position may be filled at a different level depending on the selected candidate’s experience and qualifications.

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.
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 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.
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.
Positive, self-motivated, customer-centric leadership style and commitment to developing people and improving outcomes.
Ability to work confidently alongside AI-enabled tools, exercise sound judgment when interpreting insights, and adapt as technology evolves.

Nice To Haves

Experience in insurance, reinsurance, financial services, specialty insurance, workers’ compensation, or another complex, transaction-intensive environment is strongly preferred.
Guidewire BillingCenter or comparable Guidewire experience is strongly preferred.

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 policies, procedures, controls, service standards, and performance metrics for timely, accurate, compliant, and scalable execution.
Own receivables and working-capital performance, improving collection effectiveness, cash conversion, aging, unapplied cash, and cash-flow outcomes.
Develop risk-based collection strategies that maximize cash realization while preserving relationships with brokers, clients, reinsurers, coverholders, and other partners.
Optimize the operating model across automation, outsourced or offshore resources, and internal teams to meet service, control, quality, and cost objectives.
Manage outsourced billing and collections providers and hold 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 analysis and resolution of aged receivables, past-due balances, unapplied cash, payment discrepancies, returned payments, disputes, and 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 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 commitment to an engaged, high-performing culture.