Director, Technical Accounting

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. We are seeking a highly skilled and strategic Director of Technical Accounting, reporting directly to the Chief Accounting Officer, to lead our technical accounting function. As a fast-growing SaaS company, we encounter complex and evolving accounting challenges. In this role, you will be the foremost expert on US GAAP and IFRS, ensuring our accounting policies and financial reporting is accurate, compliant, and optimized. This role will involve working with all accounting and finance functions including cross-functionally with Corp. Dev., IT, Engineering, Procurement, etc. A critical component of this role involves cross-functional leadership, specifically partnering with our Engineering and Product teams to accurately identify, track, and account for internal-use software capitalization (ASC 350-40/ASU 2025-06) . You will manage and mentor one direct report, driving a culture of continuous improvement, rigorous documentation, and collaborative problem-solving across the organization. Responsibilities Strategic Leadership & Technical Expertise Subject Matter Expert (SME): Serve as the company’s primary authority on complex US GAAP matters, with a deep focus on SaaS industry standards, including Business Combinations (ASC 805), Leases (ASC 842), Debt & Equity (Convertible Bonds, Accelerated Share Repurchases), and Consolidations. Complex Transaction Advisory: Lead the research, evaluation, and resolution of significant, non-routine business transactions (e.g., M&A, complex equity structures). Policy & Documentation: Author, review, and maintain global accounting policies and technical accounting memorandums, ensuring clear communication of accounting positions to senior leadership and external auditors. Standard Implementation: Proactively monitor, evaluate, and lead the cross-functional implementation of new FASB standards and pronouncements, assessing their impact on the company’s financial statements, policies, and systems. Engineering Partnership & Internal-Use Software (SaaS Focus) End-to-End Ownership: Direct the strategy and execution of the internal-use software capitalization process (ASC 350-40 / ASU 2025-06) and cloud computing arrangements. Cross-Functional Alignment: Establish deep partnerships with Engineering, Product Management, and IT leadership to integrate accounting requirements seamlessly into the software development lifecycle (SDLC), product roadmaps, and agile sprint cycles. Process Engineering: Design and implement scalable systems and workflows to efficiently track engineering costs, precisely differentiate R&D expense from capitalizable application development, and monitor project milestones for accurate amortization. Stakeholder Education: Act as a financial ambassador to technical teams, educating non-finance leaders on accounting requirements to ensure smooth compliance and data collection without disrupting engineering velocity. Financial Reporting, Operational Accounting & Compliance Operational Oversight: Own the review and tie-out of the month-end and quarter-end close package including tie-out for accuracy and accounting compliance of the core financial statement; plus activities for technical accounting domains (including stock-based compensation and equity), ensuring the accurate preparation and review of related journal entries and account reconciliations. Audit & SOX Leadership: Own the technical accounting relationship with external auditors, driving the timely resolution of audit inquiries. Ensure all technical accounting processes and documentation strictly adhe…