Sr. Payroll & Benefits Specialist

Role Mandate

The Senior Payroll & Benefits Specialist will serve as the functional owner of Drive Wealth’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.

• Process accurate payroll for all employees across US and Lithuania jurisdictions.
• Support the transition to a new payroll provider, ensuring data integrity and system configuration.
• Maintain adherence (and stay ahead of) to federal, state, and local payroll laws.
• Manage reporting, garnishments, and statutory filings to ensure timely submissions.
• Partner closely with benefits broker to manage day‑to‑day operations, resolve employee inquiries, and ensure seamless data syncing across our HRIS ecosystem.
• Recon with holdings to ensure accurate 401(k), HSA/FSA, and insurance funding.
• Maintain meticulous record‑keeping and data hygiene across payroll, benefits, and immigration to ensure processes are compliant, risk‑managed, and ready for external audits.
• Monitor payroll‑related costs and variances to support corporate financial reporting.
• Resolve discrepancies and inquiries with precision and responsiveness.
• Serve as the internal point person for immigration coordination—managing timelines, tracking renewal deadlines, and liaising with external legal counsel.
• 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.
• 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.
• Track record of disciplined execution in environments where accuracy and risk management are paramount.
• Certified Payroll Professional (CPP) designation highly preferred.
• Ability to prioritize ruthlessly, focusing on what’s critical to drive work to completion.
• Extremely organized with reliable tracking framework for legal deadlines and compliance requirements.
• Client‑oriented mindset with awareness of how work impacts partners.
• Strong cross‑functional partnership skills with judgment to coordinate across multiple teams.
• Bias toward transparency, accountability, and responsiveness.
• Commitment to continuous improvement and a drive to transform processes.
• Impeccable integrity, sound judgment, and respect for risk, control, and operational excellence.

Hybrid work model with expected office cadence set by the Hiring Manager/Team.

$125,000 USD – $140,000 USD.

• Competitive base pay, bonus, equity, 401(k) match, heavily subsidized benefits.
• Full insurance coverage, wellness reimbursement, company‑provided phone, and personal development allowance.
• Generous PTO, observed holidays, and extended leave.

We are an equal opportunity employer. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We encourage candidates from all backgrounds to apply.