Director of Finance

Title:

Director of Finance

Reports to:

Founders

Location:

Remote (EST)
Status:  Exempt
Company Overview  Windsor Path is a fast-growing ecosystem of premier accounting and tax firms across the United States. We are a family office-backed platform designed to provide a long-term home for the industry’s most respected firms. We accelerate the growth trajectory of our member firms through investment in talent, technology, and operational infrastructure, while preserving their local character, brand, and autonomy.

While our member firms focus on delivering top-tier client service, the Windsor Path team is hard at work supporting key functions critical to overall growth and scale.
At Windsor Path, you’ll join a collaborative, high-energy team grounded in servant leadership and focused on reimagining how accounting firms innovate and thrive in a digital-first world.
Summary  Windsor Path is seeking a Director of Finance to help lead the day-to-day financial operations of the business. This role is responsible for owning the accuracy, structure, and usability of financial information and for partnering closely with the founders to provide reliable financial insight and support strategic decision-making as the business scales.
The Director of Finance combines the discipline of a Controller with broader responsibilities across FP&A, cash flow management, strategic analysis, and acquisition performance tracking. This role is accountable for financial integrity while also helping shape how financial data is translated into insight, priorities, and action. The role is unique in that it supports both Windsor Path’s financial operations and those of the firms within our partner ecosystem.
The emphasis of this role is execution-driven and impact-oriented: producing reliable financials, building repeatable processes, and steadily improving financial visibility and discipline as the platform grows.
This is a highly hands‑on role in a fast‑scaling environment. The ideal candidate is comfortable operating across both detail-oriented execution and higher-level analysis, building scalable financial infrastructure while actively running it.
This role is best suited for someone who enjoys being close to the work, comfortable “doing” as well as designing, and thrives in a dynamic environment.
Responsibilities  Financial Reporting & Controls   Provide direction and oversight to outsourced accounting partners to ensure timely, accurate, and well‑controlled month‑end closes across all entities
Translate financial data into straightforward insights that help business leaders prioritize near‑ and mid‑term decisions
Ensure the integrity of both cash- and accrual‑based financials to support operational visibility, planning, and decision‑making
Prepare and review monthly and annual financial packages, including variance explanations and key observations for business leaders including drivers, risks and trends behind results
Define and maintain KPIs that support performance management and decision making
M&A and Systems Integration   Lead the financial integration of newly acquired firms, including the transition from Quick Books or other legacy systems into Net Suite
Map acquired firms’ charts of accounts into a unified general ledger structure
Own the financial components of the “First 100 Days” integration process, including accounting workflows and system configuration
Develop, document, and continuously refine finance and accounting SOPs to enable repeatable, scalable integrations as the platform grows
Track post‑acquisition financial performance and flag variances or issues for discussion with business leaders
Treasury & Operational Finance   Oversee end‑to‑end AP and AR processes across the platform, including administration of Ramp for vendor payments, employee reimbursements, and corporate cards
Monitor cash flow and working capital, and drive improvements in cash collection and billing workflows across member firms
Support leadership in the development and refinement of budgeting and forecasting as the platform scales
Requirements   Bachelor’s degree in Accounting, Finance or related field. Preference for a CPA designation
8-12+ years of…