O
Not Specified Permanent

Milwaukee, Wisconsin · USA job

Cash Operations Leader - Insurance - Remote

Oliver James Associates

Milwaukee, Wisconsin

Job description

Overview

In this remote leadership role, you will guide a high-volume cash operations function within a complex insurance environment, driving process modernization and automation. You will lead cash application, collections, reconciliations, and reporting while partnering with Finance, Treasury, IT, Compliance, and Audit. You'll develop teams, implement scalable improvements, and deliver dashboards that increase visibility into cash and working capital. This position offers a meaningful opportunity to shape a transformation-focused operating model and digital banking integrations in a distributed, cross-functional setting.

Responsibilities
  • Lead cash operations across identification, application, reconciliation, collections, and reporting.
  • Develop and coach a high-performing finance team and foster continuous improvement.
  • Oversee high-volume cash transactions (ACH, wires, checks, cards, etc.).
  • Drive improvements in AR, collections, unidentified cash, aged receivables, and working capital.
  • Lead reconciliation across banking platforms, billing systems, ERP, cash management, sub-ledgers, and GL.
  • Advise on automation and finance transformation to reduce manual effort and scale processes.
  • Partner with IT and cross-functional teams to deploy digital banking integrations and system enhancements.
  • Define objectives, KPIs, and success measures for transformation initiatives.
  • Establish policies, controls, and processes for cash-related activities.
  • Build dashboards and reporting for cash, collections, receivables, and ops performance.
  • Work across ERP, banking, and cash management systems to drive integration and process improvements.
  • Collaborate with Finance, Treasury, Compliance, Audit, and Accounting leadership to strengthen controls and scalable operations.
  • Provide updates to senior Finance leadership on transformation progress and KPIs.
Key requirements
  • Significant cash operations experience in the insurance industry.
  • Experience in cash application, collections, AR/AP, reconciliations, treasury, or operational finance.
  • Proven track record of leading and developing teams in a high-volume environment.
  • Strong understanding of insurance cash flows, premium receipts, receivables, reconciliations, and downstream accounting.
  • Experience leading automation, finance transformation, system implementations, or process improvements.
  • Experience with multiple ERP, banking, cash management, and financial systems.
  • Strong stakeholder management and ability to influence senior leadership across functions.
  • Strong analytical, communication, project management, and change leadership skills.
  • stakeholder management
  • change leadership
  • communication
  • ERP systems
  • banking and cash management systems
  • digital banking integrations

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