Sr. Payroll & Benefits Specialist

DriveWealth•Chicago, IL

2d•$125,000 - $140,000•Hybrid

About The Position

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.

Requirements

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
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 run a playbook—you want to optimize processes, eliminate antiquated workflows, and help build a scalable engine
Impeccable high integrity, sound judgment, and a deep respect for risk, control, and operational excellence
Applicants must possess the legal right to work in the country where the position is located at the time of application.
For US-based roles: Applicants must be currently authorized to work in the United States on a full-time basis without the need for current or future visa sponsorship.

Nice To Haves

Certified Payroll Professional (CPP) designation is highly preferred

Responsibilities

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 pings and inquiries, and ensure seamless data syncing across our HRIS ecosystem.
Recon withholdings to ensure accurate 401(k), HSA/FSA, and insurance funding.
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.
Monitor payroll-related costs and variances to support corporate financial reporting.
Resolve discrepancies and inquiries with a focus on precision and responsiveness.
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.
Implement procedures to enhance payroll efficiency and automation.