Director, Technical Accounting

Five9

2d • $107,900 - $336,200 • Hybrid

About The Position

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.

Requirements

• Bachelor’s degree in Accounting, Finance, or a related field.
• An active CPA license is strictly required.
• 8-12 years of progressive accounting experience, ideally starting with a Big 4 public accounting firm followed by technical accounting experience within a public SaaS or high-growth technology company.
• Proven experience managing, mentoring, and developing at least one direct report.
• Deep, practical knowledge of US GAAP.
• Must have hands-on experience navigating and implementing ASC 350-40 (Internal-Use Software).
• Demonstrated ability to work closely with highly technical, non-accounting teams (Engineering, IT, Product). You must be able to translate complex accounting requirements into actionable processes for engineers.
• Exceptional written and verbal communication skills, with the ability to write clear, concise technical memos and present findings to executive leadership.

Nice To Haves

• Experience with modern cloud-based ERP systems (e.g., NetSuite) and Jira/Jellyfish (for engineering project tracking) is highly preferred.

Responsibilities

• 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.
• Lead the research, evaluation, and resolution of significant, non-routine business transactions (e.g., M&A, complex equity structures).
• Author, review, and maintain global accounting policies and technical accounting memorandums, ensuring clear communication of accounting positions to senior leadership and external auditors.
• 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.
• Direct the strategy and execution of the internal-use software capitalization process (ASC 350-40 / ASU 2025-06) and cloud computing arrangements.
• 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.
• 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.
• 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.
• 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.
• Own the technical accounting relationship with external auditors, driving the timely resolution of audit inquiries. Ensure all technical accounting processes and documentation strictly adhere to SOX internal control frameworks.
• Partner closely with the Director of SEC Reporting to ensure accurate disclosures in financial statements and assist in the preparation of quarterly reporting materials for executive and Board-level audiences.
• Collaborate with FP&A and Investor Relations to rigorously review, audit, and tie-out external financial communications, including earnings releases, investor decks, and Q&A scripts.
• Act as a trusted advisor to Legal, Corporate Development, Tax, Treasury, and Stock Administration, providing critical accounting guidance during contract negotiations and strategic business planning.
• Lead, mentor, and develop a high-performing technical accounting function (including managing external valuation specialists or accounting consultants as needed).
• Establish and manage the Company’s Finance and Accounting technical training program, elevating the overall US GAAP proficiency of the broader finance organization.
• Champion process improvements and automation within the technical accounting and reporting functions to drive efficiency and scale with the company's growth.

Benefits

• Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
• Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching.
• Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
• Generous employee stock purchase plan.
• Paid Time Off, Company paid holidays, paid volunteer hours and 12 weeks paid parental leave.

What This Job Offers

• Job Type: Full-time
• Career Level: Director