Controller / Head of Finance

Job Description

Checkbook is seeking a Controller / Head of Finance to report directly to the Founder / CEO. This role is crucial for refining the financial landscape of the company and translating financial data into presentations for investors and enterprise customers. The Controller / Head of Finance will play a pivotal role in fortifying the company's financial image and contributing to the effective projection of financials.Responsibilities include:

• Overseeing all accounting operations, including general ledger, AR/AP, revenue recognition, payroll, and tax.
• Preparing timely and accurate monthly, quarterly, and annual financial statements.
• Establishing and maintaining internal controls and accounting policies in compliance with GAAP.
• Managing audits, tax filings, and relationships with external auditors and tax advisors.
• Leading the implementation and optimization of financial systems and tools.
• Supporting financial planning, fundraising, and board reporting with accurate financial data.
• Partnering cross-functionally with Legal, Compliance, Product, and Operations teams on financial and regulatory matters.
• Scaling the accounting team and processes to support rapid growth, including international expansion.

Requirements:

• 5+ years of progressive financial accounting experience, with at least 2+ years in a leadership role.
• Prior experience at a high-growth FinTech / SaaS startup (Series A-C preferred).
• Deep understanding of US GAAP and financial reporting standards.
• Experience with revenue recognition (ASC 606), consolidations, and multi-entity structures.
• Strong Accounting & FP&A systems background.
• Hands-on experience running payroll end-to-end, including tax withholdings, W-2 processing, and payroll tax filings.

Checkbook offers:

• Insurance (Medical, Dental, Vision, LTD and a variety of other programs)
• 401k
• Equity
• Catered meals (in office)
• Variable Base + Commission + Equity (based on experience)