Director, Payroll Tax Compliance

401 Cast & Crew LLC; United States; Remote; USD 140,000 - 160,000; Full time

Job summary

Cast & Crew is seeking a Director of Payroll Tax to lead regulatory compliance and reporting across the United States and Canada. You will manage a team of six payroll tax professionals, partner with senior leaders, and drive process improvements while ensuring accurate tax filings and strong internal controls.

The role requires deep payroll tax expertise, strategic thinking, and hands‑on leadership to balance initiatives with daily execution.

Qualifications

• 10+ years in payroll tax with at least 5 in leadership.
• Strong knowledge of US and Canadian payroll tax regulations, filings, and compliance requirements.
• Experience managing complex payroll tax operations within large, multi‑state organizations.
• Proven ability to lead teams, develop talent, and drive organizational change.
• Strong analytical, problem‑solving, project management, and decision‑making capabilities.
• Experience operating in a high‑volume, deadline‑driven environment.

Responsibilities

• Lead, develop, and mentor a team of payroll tax professionals.
• Oversee all payroll tax filings, payments, and related compliance for US & Canada entities.
• Serve as primary contact for regulatory agencies regarding audits and inquiries.
• Develop payroll tax strategies with senior leaders to support compliance and goals.
• Identify and implement processes to improve scalability, accuracy, and efficiency.
• Oversee year‑end payroll tax processing and W‑2 reporting.
• Maintain policies and internal controls for payroll tax compliance.
• Review reconciliations and resolve tax liabilities, credits, and notices.
• Ensure documentation and cross‑training within payroll tax function.
• Monitor legislative changes and communicate impacts to stakeholders.
• Collaborate with other functions to implement system enhancements.

Skills

Payroll tax leadership

Regulatory compliance

Data analysis

AI in payroll

Multi-state tax

Education

Bachelor's degree in accounting/finance

CPA/CPP/FPC preferred

Tools

Excel

Word

MS Outlook

Oracle Financials

Job description

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

Position Overview

The Director, Payroll Tax is a strategic and operational leader responsible for overseeing payroll tax compliance, reporting, and advisory activities across the United States and Canada. Reporting to the SVP of Accounting, this role partners closely with Payroll Operations, Product Management, Technology, Human Resources, and Accounting to ensure compliance with all payroll tax regulations while driving process improvements, operational efficiency, and strong internal controls. The Director will lead and develop a team of payroll tax professionals and serve as a subject matter expert on payroll tax matters. This position requires a hands‑on leader who can effectively balance strategic initiatives on operational efficiency, including an aptitude for understanding how data flows in payroll systems, with day‑to‑day operational execution. The successful candidate will possess deep payroll tax expertise, strong analytical skills, and the ability to collaborate across multiple functions to support business objectives and regulatory compliance.

Core Responsibilities

• Lead, develop, and mentor a team of six payroll tax professionals, fostering a culture of accountability, continuous improvement, and professional growth.
• Oversee all payroll tax filings, payments, and related compliance activities for legal entities across the United States and Canada.
• Serve as the primary point of contact for regulatory agencies regarding payroll tax audits, inquiries, notices, and compliance matters.
• Partner with the SVP of Accounting and peer leaders to develop and execute payroll tax strategies that support organizational goals and compliance requirements.
• Identify and implement process improvements that enhance scalability, accuracy, efficiency, and customer service.
• Oversee year‑end payroll tax processing activities, including W‑2 and other required reporting, system updates, and regulatory filing requirements.
• Establish, maintain, and enhance policies, procedures, and internal controls related to payroll tax compliance and reporting.
• Review payroll tax account reconciliations and oversee resolution of tax liabilities, credits, refunds, and agency correspondence.
• Ensure appropriate documentation, knowledge transfer, and cross‑training across the payroll tax function.
• Monitor legislative and regulatory developments impacting payroll tax compliance and communicate business impacts and required actions to stakeholders.
• Collaborate with Payroll Operations, Product Management, Technology, and Finance teams to evaluate, prioritize, and implement system enhancements and compliance‑related changes.
• Develop business requirements and participate in testing, implementation, and validation of payroll tax system enhancements.
• Serve as a payroll tax subject matter expert for enterprise initiatives, acquisitions, system implementations, and other strategic projects.
• Build strong relationships with internal and external stakeholders, including clients, vendors, auditors, and government agencies.

Required Qualifications

• 10+ years of progressive payroll tax experience, including at least 5 in a leadership role managing payroll tax compliance functions
• Strong knowledge of U.S. and Canadian payroll tax regulations, filings, and compliance requirements
• Experience managing complex payroll tax operations within large, multi‑state and multi‑jurisdiction organizations
• Demonstrated success leading teams, developing talent, and driving organizational change
• Strong analytical, problem‑solving, project management, and decision‑making capabilities
• Proven ability to operate effectively in a high‑volume, deadline‑driven, and rapidly evolving environment.
• 10 years of experience with a minimum of 5 years specific to payroll tax compliance and management
• Expert level computer skills including Excel, Word, and MS Outlook
• Hands‑on experience using AI tools within your discipline — able to speak to specific tools used, workflow integration, and measurable business impact — with a drive to continuously experiment with and apply emerging AI capabilities.

Preferred Qualifications

• Bachelor’s degree in accounting, finance or equivalent – CPA, CPP, or FPC certification preferred
• Experience with enterprise payroll and financial systems; Oracle Financials experience preferred
• Excellent communication and relationship‑building skills with the ability to influence stakeholders across all levels of the organization
• Entertainment, media, or production industry experience preferred

Special Work Conditions

• Sedentary – Involves sitting most of the time but may involve walking or standing for brief periods of time.
• Some positions may entail exerting up to 15 lbs. of force occasionally and/or a negligible amount of force to lift, carry, push, or pull.

We take care of our people.

When you join Cast & Crew, you're backed by a benefits package built around what matters most. From comprehensive medical, dental, and vision coverage, to a 401(k) match, generous PTO, paid parental leave, health and wellness programs, tuition reimbursement, and employee discounts.

We’re committed to helping you thrive, professionally, and personally.

Benefits are subject to eligibility requirements.

Cast & Crew is an equal opportunity employer committed to hiring a diverse workforce and sustaining an inclusive culture. It is our policy to provide equal employment opportunities to all individuals based on job‑related qualifications and ability to perform a job, without regard to age, gender, gender identity, sexual orientation, race, color, religion, creed, national origin, disability, genetic information, veteran status, citizenship or marital status, and to maintain a non‑discriminatory environment free from intimidation, harassment or bias based upon these grounds.

CA residents

Your personal information may be collected in connection with certain services provided by Cast & Crew or its affiliated companies. A summary of your California privacy rights can be found at: https://www.castandcrew.com/privacy-policy/

Compensation is commensurate with various factors including, but not limited to, relevant experience, qualifications, skills, training, licensure, certifications, geographic cost of labor, and other business and organizational needs. Compensation range for candidates in other locations may differ based on the cost of labor in that location.

The compensation range for this position is: $140,000.00 - $160,000.00 per year.

At Cast & Crew, our diverse workforce is always at the heart of what we do. Our company is committed to a culture of encouraging unique perspectives and backgrounds and to ensure growth and opportunities are available for all.

Come join our team of talent that helps make magic happen.

#OneCastOneCrew

We grew from a modest small business in 1976 to be the premiere provider of entertainment technology and solutions, staying true to our mission of modernizing content production and leading the digital transformation within the industry. Our cloud‑based solutions and industry expertise help streamline the entire production lifecycle and have revolutionized how content is made. We now have a global workforce across a host of storied brands, spanning all areas of produced and live entertainment, from film, television, streaming, to advertising, live events, and short‑form.