Sr. Payroll & Benefits Specialist

About the role

DriveWealth is seeking a specialist to oversee total rewards, payroll operations, and benefits administration as the company scales. This role focuses on modernizing systems, ensuring regulatory compliance, and managing complex domestic and international payroll processes.

Key facts

What you'll do

• Execute end-to-end payroll processing for US and Lithuania operations.
• Lead the transition to a new payroll provider, including system configuration and data migration.
• Ensure ongoing compliance with federal, state, and local payroll regulations.
• Manage tax filings, garnishments, and statutory reporting.
• Coordinate with benefits brokers to handle daily administration and resolve employee inquiries.
• Reconcile withholdings for 401(k), HSA/FSA, and insurance accounts.
• Maintain documentation for audits and IPO readiness, including immigration and visa tracking.
• Analyze payroll costs and variances for financial reporting.
• Act as the primary point of contact for immigration coordination and legal counsel liaison.

Requirements

• 6 to 8+ years of progressive payroll experience in financial services or regulated fintech.
• Bachelor degree in Accounting, Finance, or a related business field.
• Expertise in NY payroll regulations and experience scaling multi-state and global payroll.
• Proficiency in accounting principles related to payroll, such as accruals and benefit funding.
• Strong organizational skills for managing legal deadlines and compliance frameworks.
• Ability to work in a hybrid office environment in Chicago.
• Authorization to work in the US without company sponsorship.

Nice to have

• Certified Payroll Professional (CPP) designation.

Skills & tools

• Payroll systems and HRIS management
• Multi-state and international payroll processing
• Financial analysis and reconciliation
• Regulatory compliance and audit preparation

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. Benefits include medical, dental, and vision insurance, disability coverage, 401(k) match, equity, paid parental leave, wellness reimbursement, phone allowance, personal development allowance, and paid time off.