Benefits Director

Cast & Crew•Burbank, CA

4d•$140,000 - $180,000•Hybrid

About The Position

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 We are seeking a strategic Benefits Director with deep operational expertise to lead the evolution of our benefits ecosystem in support of the company’s growth and broader transformation. This role sits within the People & Culture team and plays a critical role in delivering meaningful, competitive, and scalable benefits to our approximately 1,200 global employees. This is not a maintenance role. You will own our benefits strategy end-to-end, lead and optimize key external partnerships, and bring a thoughtful, builder mindset to how benefits are designed, delivered, and experienced. This role requires an individual who can deliver high-impact benefits through strong partnerships, disciplined decision-making, and a deep understanding of how to balance employee experience with business priorities. This individual will be a member of a high-performance People & Culture organization anchored in accountability, execution, collaboration, and culture, working in close partnership with Finance, Payroll, and People & Culture leadership. You will lead one direct report.

Requirements

8+ years of experience leading benefits programs in a growing, fast-paced, or evolving organization.
Proven experience managing and optimizing external partnerships.
Strong operational and analytical skills, with the ability to translate data into clear insights and recommendations.
A demonstrated track record of accountability and execution, with comfort owning outcomes from planning through delivery.
Ability to balance strategic thinking with hands-on execution in a dynamic environment.
Experience working with Workday or a comparable HRIS, with a solid understanding of benefits administration, workflow and integrations.
Advanced proficiency in Microsoft Excel and PowerPoint, with the ability to create data-driven analyses and executive-level presentations.
Ability to work holidays as needed for payroll processing.
Strong interpersonal and communication skills, with the ability to collaborate effectively across levels and functions.
A collaborative mindset and experience partnering closely with Finance, Payroll, and People & Culture colleagues.
High integrity and discretion when handling sensitive People & Culture information.

Responsibilities

Own the design, delivery, and ongoing evolution of global benefits and leave programs, including health, dental, vision, life, disability, wellness, and statutory benefits.
Lead benefits renewals, negotiations, benchmarking, and vendor evaluations to ensure offerings are scalable, well-structured, and aligned with business needs.
Translate business and workforce priorities into a clear, sustainable benefits strategy that supports growth and change.
Apply a practical, solution-oriented approach to benefits design, identifying opportunities to improve value, experience, and impact.
Lead open enrollment processes, testing, and employee communications.
Oversee the design and delivery of global wellness initiatives, including but not limited to budget, wellness fairs, companywide wellness challenges, in-person events, and related communications.
Build and present executive-level decks that drive alignment, clarity, and decision-making across the business
Oversee all leave of absence programs (including FMLA, ADA, CFRA, state, and global leaves), ensuring compliance, consistency, and a strong employee experience.
Monitor regulatory and legislative changes and proactively implement updates to programs, policies, and practices.
Serve as a subject matter expert for complex benefits and leave-related matters.
Oversee the administration of the company’s 401(k) retirement plan, working closely with financial advisors and plan providers to ensure compliance and employee engagement.
Partner with Finance and HR leadership to ensure budgeting and forecasting accuracy related to and benefits costs.
Ensure compliance with ERISA, ACA, FMLA, COBRA, and other relevant regulations, staying updated on legislative changes and implementing necessary policy adjustments.
Prepare and submit required government reports and filings related to benefits.
Maintain accurate records and documentation for benefits enrollment, payroll deductions, and related adjustments.
Oversee processing of multiple audits each payroll cycle, as well as monthly and quarterly audits and reporting.
Ensure prompt and accurate monthly, bi-weekly, and weekly billing processes.
Serve as subject matter expert on Workday benefits set ups, including file feeds, open enrollment processes, integrations, audits, data integrity, and related system configurations. You will partner closely with our Workday HRIS Analyst.
Partner closely with Payroll to ensure accurate deductions, reconciliations, and timely issue resolution.
Leverage data, systems, and process improvements to increase efficiency, accuracy, and scalability.
Stay informed on evolving benefits and People & Culture best practices relevant to growing organizations.
Be the backup support for time on day-to-day employee communications and responding to employee questions.
Work closely with Finance to support forecasting, cost transparency, and informed decision-making related to benefits programs.
Collaborate across the People & Culture team to ensure benefits programs align with culture, workforce needs, and broader people initiatives.
Communicate clearly and effectively with leaders and employees, providing guidance, context, and recommendations as needed.
Foster strong working relationships across teams and vendors to support consistent, reliable service delivery.
Model ownership, accountability, and follow-through as part of a high-performing People & Culture team.
Lead and develop one direct report, providing coaching, clear expectations, and growth opportunities.
Ensure high-quality day-to-day benefits operations while continuously improving processes and employee experience.