Director of Finance

📋 Description

• • Windsor Path is seeking a highly motivated and experienced Director of Finance to spearhead the day-to-day financial operations of our rapidly expanding ecosystem of premier accounting and tax firms. Reporting directly to the Founders and operating remotely within the Eastern Standard Time zone, this exempt role is pivotal in ensuring the accuracy, structure, and usability of our financial information. You will be instrumental in partnering with the leadership team to deliver reliable financial insights and robust support for strategic decision-making as we scale our platform.
• • This position uniquely blends the rigorous discipline of a Controller with broader responsibilities encompassing Financial Planning & Analysis (FP&A), comprehensive cash flow management, in-depth strategic analysis, and meticulous tracking of acquisition performance. You will be accountable for upholding the highest standards of financial integrity while actively shaping how financial data is transformed into actionable insights, strategic priorities, and concrete actions. A key aspect of this role involves supporting the financial operations of both Windsor Path itself and the diverse array of firms within our partner ecosystem.
• • The emphasis of this role is firmly on execution and tangible impact. Your primary focus will be on producing consistently reliable financial statements, establishing and refining repeatable processes, and driving continuous improvements in financial visibility and discipline across the organization. This is a deeply hands-on role, designed for an individual who thrives in a fast-scaling, dynamic environment. The ideal candidate possesses the unique ability to seamlessly transition between meticulous, detail-oriented execution and high-level strategic analysis, building scalable financial infrastructure while actively managing its day-to-day operations.
• • Responsibilities will span across several critical areas:
• • **Financial Reporting & Controls:**
• • Provide clear direction and diligent oversight to our outsourced accounting partners, ensuring the timely and accurate completion of month-end closes across all entities, underpinned by robust internal controls.
• • Translate complex financial data into clear, concise, and actionable insights that empower business leaders to make informed decisions regarding near- and mid-term priorities.
• • Guarantee the integrity of both cash- and accrual-based financial reporting, providing essential visibility for operational planning and strategic decision-making.
• • Prepare and meticulously review comprehensive monthly and annual financial packages, including detailed variance explanations and critical observations for business leaders, highlighting key drivers, risks, and emerging trends influencing financial results.
• • Define, implement, and maintain Key Performance Indicators (KPIs) that effectively support performance management, strategic alignment, and data-driven decision-making.
• • **M&A and Systems Integration:**
• • Lead the financial integration of newly acquired firms, managing the seamless transition from legacy systems such as QuickBooks or other platforms into our core NetSuite ERP environment.
• • Skillfully map the unique charts of accounts of acquired firms into a unified, standardized general ledger structure for the entire platform.
• • Own and execute the financial components of the critical 'First 100 Days' integration process, encompassing accounting workflows, system configurations, and initial financial reporting setup.
• • Develop, meticulously document, and continuously refine finance and accounting Standard Operating Procedures (SOPs) to ensure repeatable, scalable, and efficient integrations as the platform expands.
• • Diligently track post-acquisition financial performance, proactively identifying and flagging variances or potential issues for prompt discussion and resolution with business leaders.
• • **Treasury & Operational Finance:**
• • Oversee the end-to-end Accounts Payable (AP) and Accounts Receivable (AR) processes across the entire platform, including the administration of Ramp for vendor payments, employee reimbursements, and corporate card management.
• • Actively monitor cash flow and working capital, driving proactive initiatives to improve cash collection cycles and optimize billing workflows across all member firms.
• • Support leadership in the development, refinement, and ongoing management of budgeting and forecasting processes as the platform continues its rapid scaling trajectory.
• • At Windsor Path, we are building a collaborative, high-energy team grounded in servant leadership. We are dedicated to reimagining how accounting firms innovate and thrive in a digital-first world. You will join an entrepreneurial organization operating in a true startup mode, scaling through strategic acquisitions. Our culture is hands-on, action-oriented, and built for individuals who excel in dynamic environments where priorities can evolve quickly and individual impact is clearly visible. We deeply value ownership, accountability, and collaboration, expecting team members to proactively solve problems and contribute to building scalable processes. If you are energized by working at pace, navigating ambiguity, and actively shaping operational frameworks rather than inheriting a pre-defined playbook, you will find a welcoming and stimulating environment at Windsor Path.