Sr. Payroll & Benefits Specialist

About the role

DriveWealth 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. DriveWealth 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! Role Mandate The Senior Payroll & Benefits Specialist will serve as the functional owner of DriveWealth's total rewards execution, anchoring our payroll, benefits administration, and compliance landscape as we scale our operations to the next level. You will be responsible for the end-to-end execution of our domestic and international payrolls, driving a seamless partnership with our benefits broker. Concurrently, you'll help anchor our system transitions to automate operations, eliminate manual friction, and elevate our data hygiene. Success requires a tech-forward, high-execution approach to multi-state operations, ensuring a bulletproof, audit-ready foundation for our next phase of institutional growth. This role is based in our Chicago office.

Responsibilities

• Payroll Execution: Process accurate payroll for all employees across US and Lithuania jurisdictions.
• Payroll System Implementation: Support the transition to a new payroll provider, 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 Administration & Partnership: Partner closely with benefits broker to manage day-to-day operations, resolve employee pings and inquiries, and ensure seamless data syncing across our HRIS ecosystem.
• Benefits Accounting: Recon withholdings to ensure accurate 401(k), HSA/FSA, and insurance funding.
• Audit & IPO Readiness: Maintain meticulous record-keeping and data hygiene across payroll, benefits, and immigration to ensure our processes are fully compliant, risk-managed, and structured for rigorous external audits.
• 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.
• Immigration Pipeline Management: Serve as the internal point person for immigration coordination-managing timelines, tracking critical renewal deadlines, and acting as the primary liaison between our external legal counsel and our global workforce.
• Process Optimization: Implement procedures to enhance payroll efficiency and automation.
• You Bring
• 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
• 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
• Extreme organizational hygiene-the ability to build a reliable tracking framework for legal deadlines and compliance requirements so nothing slips through the cracks
• 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 continuous improvement and implicitly believe that we > I.
• An appetite for transformation; you aren't just looking to

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