Senior Payroll Specialist

DraftKings • Boston, MA

3d

About The Position

At DraftKings, AI is becoming an integral part of both our present and future, powering how work gets done today, guiding smarter decisions, and sparking bold ideas. It’s transforming how we enhance customer experiences, streamline operations, and unlock new possibilities. Our teams are energized by innovation and readily embrace emerging technology. We’re not waiting for the future to arrive. We’re shaping it, one bold step at a time. To those who see AI as a driver of progress, come build the future together. The Crown Is Yours As a Senior Payroll Specialist, you’ll own end-to-end payroll operations across the U.S. and Canada, ensuring accuracy, compliance, and a seamless employee experience. You’ll partner across teams to support payroll accounting, audits, and evolving regulations while operating in a fast-paced, multi-entity environment. Your work will drive efficiency, strengthen processes, and keep payroll running at scale.

Requirements

• A Bachelor’s Degree in Business Administration, Finance, Accounting, Human Resources, or equivalent experience.
• At least 5 years of progressive payroll experience, including multi-state payroll processing for organizations with 1,000+ employees.
• Experience processing U.S. payroll, with exposure to Canadian payroll strongly preferred.
• Proficiency in Workday Payroll, including system enhancements, testing, and troubleshooting.
• Experience with payroll accounting, reconciliations, and supporting audit processes.
• Strong knowledge of federal, state, provincial, and local payroll tax regulations.
• Analytical and problem-solving skills, with the ability to resolve complex payroll and accounting issues.
• The ability to manage multiple priorities in a fast-paced, deadline-driven environment while maintaining a high level of accuracy and discretion.

Responsibilities

• Process bi-weekly U.S. and semi-monthly Canadian payroll for a multi-entity workforce, ensuring accuracy, timeliness, and compliance.
• Review, validate, and import timecard data for hourly employees while managing complex pay scenarios, including terminations and off-cycle payrolls.
• Ensure compliance with federal, state, provincial, and local payroll regulations, staying current on legislative changes and applying updates proactively.
• Serve as a primary point of contact for payroll inquiries through the JustAsk ticketing system, delivering timely and accurate resolutions.
• Process and monitor garnishments, tax levies, and other involuntary deductions with precision and confidentiality.
• Partner with Human Resources, Benefits, Equity, Finance, and Accounting teams to support payroll operations and cross-functional initiatives.
• Reconcile payroll registers, funding wires, tax payments, and benefit contributions while preparing journal entries and supporting month-end close activities.
• Support internal and external audits by preparing documentation, including materials aligned with Sarbanes-Oxley (SOX) requirements, and identifying opportunities to improve payroll processes and systems.

What This Job Offers

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