Sr. Payroll & Benefits Specialist

About the role

DriveWealth is actively searching for a Sr. Payroll & Benefits Specialist to join the growing team and take ownership of the total rewards strategy as the organization continues its expansion. The successful candidate will be responsible for the oversight and execution of payroll operations across multiple jurisdictions, ensuring accuracy and timeliness in every cycle. This position requires deep involvement in the modernization of existing payroll infrastructure and the implementation of new technologies to support future growth. You will manage the full scope of benefits administration, collaborating closely with external vendors and internal stakeholders to maintain a competitive and compliant program. A key part of this role involves navigating complex domestic and international payroll requirements while maintaining strict adherence to regulatory standards. You will serve as a critical thought partner to Finance and Legal, providing insights and guidance on payroll-related matters impacting the business. This role demands a high level of ownership, where you will identify process gaps and drive initiatives to improve efficiency and control.

Key facts

What you'll do

• Orchestrate the end-to-end processing of payroll for both United States and Lithuania entities, ensuring all cycles are completed accurately and in compliance with local laws.
• Spearhead the migration and full configuration of a new payroll provider, managing the data conversion activities and validating the integrity of all transactional outputs.
• Champion the maintenance of regulatory compliance across all federal, state, and local payroll jurisdictions, proactively monitoring legislative changes.
• Execute the preparation and filing of all tax documents, manage garnishment orders, and ensure the submission of all statutory reports to government agencies.
• Partner with benefits brokers to administer health and welfare plans, providing resolution to employee questions regarding enrollments and changes.
• Reconcile all voluntary deductions for retirement plans, HSAs, FSAs, and various insurance products to ensure ledger accuracy and participant satisfaction.
• Safeguard and maintain all payroll documentation and records necessary for internal audits and the preparation for an initial public offering, including immigration and visa tracking details.
• Investigate payroll cost fluctuations and analyze variances to deliver accurate financial reporting to leadership for strategic decision-making.
• Function as the central liaison for immigration coordination, working directly with legal counsel to ensure work authorization and compliance for the global workforce.
• Develop and maintain strong relationships with external payroll vendors and legal partners to facilitate efficient issue resolution and process alignment.
• Design and implement controls within the payroll lifecycle to mitigate risk and enhance the reliability of payroll data.
• Provide subject matter expertise to support global headcount planning and workforce cost modeling initiatives.
• Lead special projects related to payroll system enhancements, process optimization, and the implementation of best practices.
• Mentor junior payroll staff on procedures and regulatory requirements to build a stronger, more capable team.

Requirements

• Possess 6 to 8 or more years of progressive payroll experience, specifically within financial services or a regulated fintech environment.
• Hold a Bachelor degree in Accounting, Finance, or a related business discipline.
• Demonstrate expert knowledge of New York payroll regulations and the ability to scale multi-state and global payroll operations.
• Show proficiency in core accounting principles as they apply to payroll, including the management of accruals and benefit funding mechanisms.
• Exhibit strong organizational abilities to manage competing priorities, legal deadlines, and complex compliance frameworks simultaneously.
• Be capable of working effectively within a hybrid office model located in Chicago, adhering to the schedule set by the hiring manager.
• Have authorization to work in the United States without the need for company-sponsored visa sponsorship.

Nice to have

• Possession of the Certified Payroll Professional (CPP) designation.

Practical notes

This position requires a hybrid presence in the Chicago office on a schedule determined by the hiring manager. DriveWealth does not provide or take over employment visa sponsorship.