[Hiring] Controller @Windsor Path

Role Description

Windsor Path is seeking a Controller to 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 role combines the accounting 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
• 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 QuickBooks or other legacy systems into NetSuite
  • 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

Qualifications

• Bachelor’s degree in Accounting, Finance or related field
• CPA Required
• 8-12+ years of accounting experience, ideally with multi-entity environments
• Public accounting foundation, ideally in a top national firm
• Experience working in an investment backed environment
• Strong working knowledge of month-end close processes, GL management, and financial statement preparation (cash & accrual)
• Experience supporting tax compliance & reporting in partnership with external advisors
• Experience integrating newly acquired entities into an existing chart of accounts and financial systems
• Demonstrated experience migrating accounting systems (e.g., QuickBooks or legacy GL) to an ERP environment
• Strong process documentation and SOP development skills
• Ability to partner cross functionally with internal stakeholders and external service providers
• High attention to detail with the ability to balance accuracy and speed in a fast-paced environment
• Willingness to be hands-on
• Advanced Excel skills; comfort working with financial data across multiple platforms

Compensation Information

Compensation is determined based on experience, depth of expertise, scope of responsibility, and geographic location. Windsor Path evaluates compensation holistically and aims to align pay with the complexity and impact of the role. The position is also eligible for a performance-based bonus and benefits consistent with the role.

Company Culture

Windsor Path is a fast-growing, entrepreneurial organization operating in true startup mode as we scale through acquisitions. Our culture is hands-on, action-oriented, and built for people who thrive in a dynamic environment where priorities evolve quickly and impact is visible. We value ownership, accountability, and collaboration, and we expect team members to roll up their sleeves, solve problems, and help build scalable processes as we integrate new firms and grow the platform. If you enjoy working at pace, navigating ambiguity, and helping shape how things are done rather than inheriting a finished playbook, you’ll feel at home at Windsor Path.

At Windsor Path, we believe great work happens when people feel welcomed, respected, and supported. We value diverse backgrounds and perspectives and encourage everyone to show up as their authentic selves.