Director of Finance

Overview

Who We Are

Summer is a Certified B Corp® on a mission to restore financial freedom for the 46 million Americans burdened by student debt. We combine deep policy expertise with powerful technology to simplify every step of college cost planning and loan repayment. We have helped people save an average of $278 per month and more than $1.8 billion in total savings to date.

By partnering with leading employers, cities, and financial institutions, including ADP, the City of New York, Banc of California, Norton Healthcare, and the American Federation of Teachers, Summer helps millions of Americans move closer to a debt-free future.

Backed by $30 million in funding from top investors including Rebalance Capital, Semper Virens, QED Investors, General Catalyst, and Flourish Ventures, we're building the infrastructure that powers student loan relief and education affordability in America.

Summer is hiring a Director of Finance to lead the financial backbone of the business and play a meaningful role in shaping Summer's growth. This role reports directly into the COO and partners closely with Summer's leadership team owning financial execution, forecasting, and reporting, while also supporting the executive team on board, investor, and long-term strategic initiatives.

This role blends hands-on ownership with strategic influence. The Director of Finance will professionalize financial operations, strengthen controls, and build scalable reporting and forecasting infrastructure while helping leadership evaluate tradeoffs, prioritize investments, and prepare the organization for its next phase of growth.

• Lead company-wide FP&A, including budgeting, forecasting, variance analysis, and scenario modeling to support growth and resource planning.
• Partner closely with the executive team as the day-to-day finance lead, translating strategy into clear financial plans and decision-ready insights.
• Build and own financial models and reporting that inform executive decisions, product investment, organizational tradeoffs and as needed fundraising scenarios.
• Own day-to-day financial operations, including A/P, A/R, employee reimbursements, corporate cards, cash movement, and monthly close.
• Prepare monthly financial reporting for the executive team and support quarterly board and investor reporting.
• Strengthen financial controls and approval workflows across contracts, spend, and payments, serving as the internal point of accountability.
• Manage and hold accountable external partners (controller, bookkeepers, tax advisors), providing direction and pushing back when needed.
• Develop team-, product-, and revenue-level reporting to improve visibility into performance, unit economics, cost of sales, and sales efficiency.

• 8+ years of progressive finance experience, including FP&A, forecasting, and operational finance.
• Bachelor s degree in Finance, Accounting, Economics, Business, or a related field (or equivalent practical experience), Master s degree in related field preferred.
• Experience in a VC-backed SaaS, fintech, benefits, or Gov Tech company, ideally including at least one scaled startup (100–1000 employees).
• Strong financial modeling skills and the ability to translate complex data into clear insights for executives.
• Hands-on experience managing accounting operations and external partners (controller, auditors, tax providers).
• Solid understanding of GAAP, with hands-on experience supporting revenue recognition in a SaaS or recurring-revenue business (ASC 606 familiarity strongly preferred).
• A builder mindset; comfortable creating structure, improving processes, and operating in ambiguity.
• Strong judgment and communication skills, with the ability to present financial insights clearly to executive and non-finance stakeholders.
• Prior background in consulting, venture capital, investment banking, or large enterprise finance before moving into startups is a plus.
• CPA a plus, not required

Compensation: $160-190k base + equity + comprehensive benefits

Work Setup: Remote (U.S.)

Status: Full-time

Summer is a remote-first company with team members across the U.S. While we…