Head of Billing and Collections

Ascot Group • Hartford, CT

11h • 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 bring operational expertise, sound judgment, people leadership, and the ability to influence across Finance, Underwriting, Claims, Operations, Reinsurance, Treasury, Technology, brokers, and other partners.

The Head of Billing & Collections will be a key business leader in implementing, adopting, and optimizing Ascot’s new Guidewire billing system. This includes ensuring that requirements, workflows, controls, reporting, data conversion, testing, training, and user readiness are effectively represented. The role is expected to work confidently alongside AI-enabled tools, use sound judgment when interpreting insights, and adapt as technology evolves. The position follows a hybrid work schedule.

Ascot describes itself as a global specialty risk underwriting organization with a collaborative, inclusive, and entrepreneurial culture guided by its mission and “The Ascot Way.”

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 across functions and with external partners.
• Excellent written and verbal communication skills, including ability to explain complex issues clearly to senior leaders and business partners.
• Highly organized and detail-oriented, with 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 and develop high-performing teams and foster accountability, collaboration, customer service, and continuous improvement.
• Positive, self-motivated, customer-centric leadership style and commitment to developing people and improving outcomes.

Nice To Haves

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

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 that support 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 achieve 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 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 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 through 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.

Benefits

• Competitive benefits package, subject to applicable eligibility requirements.
• Medical coverage, including prescription coverage.
• Dental insurance.
• Vision insurance.
• 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.
• Paid holidays.
• Annual paid time off, including state or local paid leave where required.
• Short- and long-term disability.
• Bereavement, FMLA, adoption, maternity, military, primary caregiver, and non-primary caregiver leave.
• Contributory 401(k) savings plan.
• Annual cash bonus and other discretionary compensation may be available.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior