Director, Payroll Tax

About Us

At Cast & Crew, we’ve empowered creativity and supported the global entertainment industry for decades. Together with our family of brands - Backstage, CAPS, Checks & Balances, Final Draft, Media Services, Sargent-Disc, and The TEAM Companies – we operate as a combined entertainment technology and services provider offering industry standard screenwriting accounting software, digital payroll products, data & reporting, and a host of creative tools.  The industry continues to move faster than ever, and the need for our expertise, our technology, and our people has never been greater.  We are a production’s best ally every step of the way. #OneCastOneCrew

Reporting to the Vice President of Payroll Tax, the Director of Payroll Tax Compliance is responsible for overseeing all aspects of payroll tax compliance across the U.S. and Canada. This role manages regulatory tax updates, complex filings, tax audits, and responses to tax authority correspondence, while ensuring full legal compliance and maintaining system updates to meet ever-changing tax requirements. It is a highly impactful position that works cross-functionally throughout the organization and requires a deep passion for operational efficiency, strong systems aptitude, and a meticulous focus on compliance and internal controls. The Director oversees all payroll tax correspondence, including reconciliation of tax payments, filings, and related reporting requirements, while also assisting with day-to-day tax activities, troubleshooting issues with internal and external stakeholders, and supporting special projects such as research, system testing and implementation, process documentation, and ongoing tax rate maintenance. This position demands a highly organized, analytical, and self-motivated professional capable of managing multiple priorities while producing accurate and timely results.

Core Responsibilities

• Leads, manages, and develops a team of two or more Payroll Tax professionals, fostering growth, accountability, and operational excellence.

• Collaborates with the Payroll Tax team and Legal department to proactively monitor compliance requirements and ensure the accurate and timely filing and reporting of payroll taxes to all U.S. and Canadian government authorities.

• Serves as the primary liaison with regulatory agencies, managing correspondence and communications related to issues, audits, and changes in tax filing requirements, and ensuring timely, professional, and compliant responses and researching questions with a high degree of independence, initiative, and analytical rigor.

• Oversees all payroll tax filings, payments, and reporting obligations for all legal entities across the U.S. and Canada, ensuring full compliance with federal, state, provincial, and local regulations.

• Leads the research, documentation, and dissemination of payroll tax–related regulatory changes, working closely with Payroll Operations, Product Management, and Technology teams to implement required system updates.

• Partners with the Vice President of Payroll Tax and senior leadership to identify and execute process improvements that enhance departmental efficiency, quality, and overall effectiveness.

• Oversees the maintenance and accuracy of payroll tax rates and ensures all system calculations remain up to date and compliant.

• Ensures compliance with all withholding, year-end tax documents, and electronic filing requirements as mandated by the IRS, CRA, Revenue Québec, and other applicable government tax authorities.

• Directs the year-end tax process, including system enhancements, production of tax documents, and submission of time-sensitive filings to relevant regulatory agencies.

• Prepares, reviews, and approves account reconciliations related to payroll tax liabilities, managing refund requests and correspondence with tax authorities as needed.

• Performs other related duties and special projects as assigned.

Key Qualifications

• 10 years of experience with a minimum of 5 years specific to payroll tax compliance and management

• Entertainment production experience preferred

• Experience with complex payroll systems with a deep familiarity with driving ongoing compliance and management of the related liabilities

• Knowledge of US and Canadian Payroll tax laws, including ERC credits processing and Canadian tax waivers

• Experience with large enterprise financial systems, preferably Oracle Financials (including Accounts Payable module)

• Proven experience delivering in a high volume, deadline oriented, ever changing and fast-paced environment

• Effective