Sr. Payroll & Benefits Specialist

drivewealth

Office - Chicago · Chicago · Office

Posted Feb 28, 2026

Full-time
Remote
People & Communications

Apply on company site

Job description

About Us

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!

About The Role

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.

What You’ll Do

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 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

Location

This role is open to candidates in the following locations:
Chicago, IL - Hybrid

This role is expected to come into the office on a cadence set by the Hiring Manager/Team.
If you're not based in one of the locations listed above, this role is not a fit, and we cannot accommodate remote work outside these locations.
Applicants must be authorized to work for any employer in the U.S. DriveWealth does not sponsor or take over sponsorship of an employment visa at this time.

Pay Range: $125,000 – $140,000 USD

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, Chicago, and Lithuania teams work in office on a hybrid schedule. 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 Medical insurance, Dental insurance, Vision insurance, Disability insurance, and Paid Parental Leave, along with 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 Paid Time Off (PTO) and observed holidays.

Work Authorization

Applicants must possess the legal right to work in the country where the position is located at the time of application. DriveWealth requires all employees to provide original documentation verifying their work authorization on or before their first day of employment.

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. DriveWealth does not provide visa sponsorship or support for employment authorization, including transfers, at this time. Offers of employment are strictly contingent upon an individual’s ability to secure and maintain the legal right to work at the Company.

How We Think About AI

We leverage AI to work smarter and move faster. We seek AI-curious talent who are proactive about using emerging tools to increase signal quality, reduce friction, and improve outcomes to deliver products faster, provide better service to our partners, and to streamline processes. Your ability to leverage our internal tools and technology to drive results is as important to us as your core domain expertise.

Compensation

Pay is generally based on 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 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.

Agency Disclaimer

DriveWealth does not accept agency resumes. Do not forward resumes to our jobs alias, employees, or any other organization location. DriveWealth is not responsible for any fees related to unsolicited resumes.