Sr. Payroll Specialist

Role Mandate The Senior Payroll Analyst will serve as the functional owner of DriveWealth’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. What You’ll Do 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 withholdings 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. 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. 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, focusing 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 continuous improvement and implicitly believe that we > I. Impeccable high integrity, sound judgment, and a deep respect for risk, control, and operational excellence. Working at DriveWealth We do our best work when we’re in the same room. To maintain the speed our partners expect, our New York and Chicago teams work in‑office 4 days a week. We’ve found that being physically side‑by‑side is the only way to solve complex problems in real‑time and stay truly accountable to the products we ship. When you’re here, you’re working directly with the people making the decisions. To support that work, we provide competitive compensation, equity, and a 401(k) match. We also offer full insurance coverage, a wellness reimbursement, a company‑provided phone, and a personal development allowance. Finally, we value the time you spend away from the office with generous PTO, observed holidays, and extended leave. Compensation Pay is generally based upon the level, complexity, responsibility, location and job duties / requirements of the specific position. We then source candidates with the requisite skills, expertise, education, training, and experience. If you are selected for an interview, please feel welcome to speak to a recruiter about our compensation philosophy and other available benefits. This role is eligible for base, bonus, equity, 401(k) match, and heavily subsidized benefits and perks. Equal Employment Opportunity To build technology and products that are used and loved by people and solve real‑world problems, we need to build a team with many different perspectives and experiences. We are an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We encourage candidates from all backgrounds to apply. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us at View email address on click.appcast.io. #J-18808-Ljbffr