Director of Finance

About the Role

Streets2Schools is seeking a hands-on Director of Finance to lead the financial operations and strategy of our growing organization. This role combines strong financial stewardship with forward-looking analysis, helping leadership understand where we are today and make informed decisions about where we go next.

Reporting to the CEO and working alongside fractional CFO support, the Director of Finance will oversee financial operations, planning and analysis, revenue assurance, and the continued development of scalable financial systems and processes. This person will be an important partner to leaders across the organization as we strengthen existing operations, evaluate growth opportunities, and develop new programs and services.

We are looking for someone who enjoys both sides of finance: the detail and discipline required to keep the financial engine running well, and the analysis, curiosity, and business thinking that help an organization grow thoughtfully.

What You'll Do

• Lead and actively participate in daily financial operations, including AP, AR, banking, reconciliations, cash management, and payroll-related financial activities.
• Lead budgeting, forecasting, cash-flow planning, financial modeling, and analysis of organizational performance.
• Develop financial reporting and metrics that give leadership meaningful insight into trends, risks, opportunities, and key business drivers.
• Partner with Operations, Human Resources, and Marketing to evaluate staffing models, pricing, growth initiatives, new programs and services, and potential business verticals.
• Provide financial analysis and scenario modeling to support organizational planning and strategic decision-making.
• Maintain strong working knowledge of county-funded and other contracts, including rates, billing terms, reimbursement requirements, and payment processes.
• Ensure earned revenue is accurately captured, invoiced, monitored, and collected, while identifying opportunities to strengthen revenue processes and financial outcomes.
• Maintain strong financial controls and compliance while continually improving financial workflows, systems, and technology.
• Lead and develop Finance staff while building a function that can scale alongside organizational growth.

What We're Looking For

• 5+ years of progressively responsible experience in finance, accounting, or financial operations.
• Demonstrated experience with budgeting, forecasting, financial modeling, cash-flow management, financial reporting, and accounting operations.
• Strong financial and business acumen, with the ability to connect financial results to operational activity and organizational strategy.
• An analytical and curious approach to financial leadership—you want to understand not only what the numbers say, but why and what they can tell us about what comes next.
• Experience with government contracts, public-sector funding, reimbursement programs, or complex contractual billing strongly preferred.
• Experience developing financial processes and systems within a growing or evolving organization strongly preferred.
• Previous leadership or supervisory experience preferred.
• Bachelor's degree in finance, accounting, business, economics, or a related field preferred; significant directly related experience may substitute for formal education.

You'll Be a Strong Fit If...

You enjoy being close enough to the financial details to truly understand the business, while also being able to pull back and see the larger picture. You can move from investigating a reconciliation question to modeling the financial implications of a new program—and see both as important parts of understanding the organization well.

You are collaborative, thoughtful, and comfortable bringing a financial perspective to conversations about operations, people, marketing, and growth. You ask good questions, spot opportunities for improvement, and use financial information not simply to report on the past, but to help shape sound decisions about the future.