Sr. Payroll Specialist

About Us

Drive Wealth is on a mission to make investing easier. We believe that everyone should have the ability to control their financial future, and that access to financial markets should not be limited by geography, wealth, or legacy systems. We are a global B2B financial technology organization dedicated to democratizing access to financial independence around the world. Our mission is realized through an API-based platform, empowering our partners to offer seamless investing and trading experiences to clients worldwide, all from their mobile devices.

Our technology provides partners with a modern, extensible toolkit, enabling traditional investment workflows and innovative techniques like fractional share ownership. Drive Wealth has evolved into a global platform offering trading of US equities, mutual funds, ETFs, fixed income, and options.

There’s never been a better time to build a category-defining business and there has rarely been a team better positioned for this opportunity. Our culture blends the pace and agility of a fintech start-up with the impact, stability, and discipline of Wall Street. We encourage creativity and experimentation while ensuring institutional-grade execution and regulatory compliance in everything we do. Join us and help build the future of global investing!

The Senior Payroll Analyst will serve as the functional owner of Drive Wealth’s payroll, focusing on day to day operations and staying ahead of payroll compliance. You will be responsible for the end-to-end execution of our domestic and international payrolls, while concurrently managing our migration to ADP to modernize and automate our operations. Success in this position requires a tech-forward approach to scaling multi-state operations, ensuring rigorous compliance with tax and regulatory standards, and maintaining precision in benefits accounting and GL reconciliations.

You will bridge the gap between payroll, accounting, and technology to build a scalable, audit-ready foundation for our next phase of growth. This role will be based in our Chicago office.

• Payroll Execution
  :
  Process accurate payroll for all employees across US and Lithuania jurisdictions.
• ADP Implementation
  :
  Support the transition to ADP, ensuring data integrity and system configuration.
• Regulatory Compliance
  :
  Maintain adherence (and stay ahead of) to federal, state, and local payroll laws.
• Tax & Filings
  :
  Manage reporting, garnishments, and statutory filings to ensure timely submissions.
• Benefits Accounting
  :
  Recon with holdings to ensure accurate 401(k), HSA/FSA, and insurance funding.
• Audit & Documentation
  :
  Maintain comprehensive records in accordance with controls and audit.
• Financial Analysis
  :
  Monitor payroll-related costs and variances to support corporate financial reporting.
• Issue Resolution
  :
  Resolve discrepancies and inquiries with a focus on precision and responsiveness.
• Process Optimization
  :
  Implement procedures to enhance payroll efficiency and automation.

• 6–8+ years of progressive payroll experience within Financial Services or a regulated Fintech environment.
• Bachelor’s Degree in Accounting, Finance, or a related business discipline.
• ADP Proficiency:
  Experience implementing or managing ADP in a multi-state environment.
• Strong knowledge of NY payroll regulations and experience scaling to multi state and global locations
• Understanding of accounting principles as they relate to payroll, including accruals and benefit funding reconciliations.
• A track record of disciplined execution in environments where accuracy and risk management are paramount.
• Professional Certification:
  Certified Payroll Professional (CPP) designation is highly preferred.
• A track record of ownership and disciplined execution in high-stakes environments
• The ability to prioritize ruthlessly, focussing on what’s critical versus important to drive work to completion
• A client-oriented mindset with an understanding of how your work impacts partners
• Strength in cross-functional partnership with the judgment to coordinate across multiple teams
• A bias toward transparency, accountability, and responsiveness in everything you do
• You’re committed to…