DriveWealth

DriveWealth

Sr. Payroll & Benefits Specialist

Office - Chicago · Senior · Contract

No sponsorship$125k-$140kDetected 15 hours ago
C++A/B TestingCompliancePipeline ManagementFinancial AnalysisAccountingProcess ImprovementHRISCadence

About the role

  • 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 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.
  • Financial Analysis: Monitor payroll-related costs and variances to support corporate financial reporting.
  • Process Optimization: Implement procedures to enhance payroll efficiency and automation.
  • 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
  • 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
  • To maintain the speed our partners expect, our New York, Chicago, and Lithuania teams work in office on a hybrid schedule.

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
  • A track record of disciplined execution in environments where accuracy and risk management are paramount
  • 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.

Nice to have

  • A track record of ownership and disciplined execution in high-stakes environments
  • 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
  • Impeccable high integrity, sound judgment, and a deep respect for risk, control, and operational excellence
  • Professional Certification: Certified Payroll Professional (CPP) designation is highly preferred

Compensation

  • $125,000 - $140,000 USD
  • To support that work, we provide competitive compensation, equity, and a 401(k) match.

Benefits

  • 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.
  • 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.
  • Understanding of accounting principles as they relate to payroll, including accruals and benefit funding reconciliations
  • 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.

Company info

  • 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!
  • 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!

Visa & 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.
Apply directly at DriveWealth →Create a free account for alerts like thisView DriveWealth immigration profile

This listing is sourced directly from DriveWealth's careers page and normalized into a canonical job model.