Payroll Lead

The Lead Payroll Specialist will serve as the functional expert and operational lead for payroll, overseeing end-to-end multi-state payroll processing, compliance, and continuous improvement. This individual will be the primary subject matter expert for payroll, helping ensure accuracy, resolve complex issues, improve processes, and partner across HR, Finance, and leadership.

• Own and execute biweekly multi-state payroll processing for exempt and nonexempt employees across multiple legal entities using Workday Payroll.
• Maintain payroll data integrity by collecting, auditing, calculating, and entering payroll information with a high degree of accuracy.
• Serve as the primary escalation point for complex payroll questions and year-end payroll processing, including W2 preparation, balancing, adjustments, and amendments.
• Ensure compliance with federal, state, and local payroll regulations, including FLSA, wage and hour laws, overtime requirements, and termination pay regulations.
• Manage payroll tax obligations, including registering in new states, closing inactive accounts, and resolving tax notices with third-party providers.
• Partner with internal teams to support onboarding, offboarding, compensation changes, deductions, and benefits administration.
• Develop and maintain payroll reporting and analytics to support business and leadership needs.
• Reconcile monthly payroll bank transactions and support month-end close activities, including journal entries and general ledger reconciliations.
• Identify opportunities to automate manual payroll processes and improve operational efficiency.

• 10-15 years of payroll experience, including lead experience.
• Deep expertise in multi-state payroll processing and a strong command of federal and state compliance, tax regulations, and wage/hour laws.
• Hands-on Workday Payroll experience strongly preferred.
• Certified Payroll Professional (CPP) designation preferred.
• Experience with NetSuite or similar general ledger systems a plus.
• Strong analytical skills with proficiency in Microsoft Excel and the ability to build and interpret payroll reports.

• Technology-forward mindset actively look for ways to automate, improve, and scale payroll processes.
• Excellent communicator who can distill complex payroll topics for non-payroll stakeholders.
• Highly organized, detail-oriented, and comfortable managing competing priorities under tight deadlines.

The role operates within a dynamic financial services environment, which includes fintech, insurance, and investment sectors. The organization is a large and fast-growing entity comprising nine different companies. The headquarters is situated in a newly built office inside the Board of Trade building, reflecting the innovation across the business. The work schedule is Monday to Friday, with a hybrid model requiring on-site presence on Monday and Tuesday, which are crucial for payroll processing. The team is collaborative and values high performers, offering opportunities for growth and exposure to senior leadership.

This is a Contract to Hire position based out of Chicago, IL.

The pay range for this position is $38.00 - $47.00/hr.

Individual compensation offered for this position within this range will depend on many factors, including qualifications, skills, relevant experience, job knowledge, geographic location, internal equity, and other pertinent job-related factors.

Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: Medical, dental & vision Critical Illness, Accident, and Hospital 401(k) Retirement Plan Pre-tax and Roth post-tax contributions available Life Insurance (Voluntary Life & AD&D for the employee and dependents) Short and long-term disability Health Spending Account (HSA) Transportation benefits Employee Assistance Program Time Off/Leave (PTO, Vacation or Sick Leave)

This is a Contract to Hire position based out of Chicago, IL.

This position is anticipated to close on Nov 6, 2026.

This is a hybrid position in Chicago,IL.

About Aston Carter

Aston Carter provides world-class corporate talent solutions to thousands of clients across the globe. Specialized in accounting, finance, human resources, talent acquisition, procurement, supply chain and select administrative professions, we extend the capabilities of industry-leading companies. We draw on our deep recruiting expertise and expansive network to meet the evolving needs of our clients and talent community with agility and excellence. With offices across the U.S., Canada, Asia Pacific and Europe, Aston Carter serves many of the Fortune 500. We are proud to be a ClearlyRated Best of Staffing® Platinum Award winner for both client and talent service.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

If you would like to request a reasonable accommodation, such as the modification or adjustment of the job application process or interviewing process due to a disability, please email for other accommodation options.

San Francisco Fair Chance Ordinance: Pursuant to the San Francisco Fair Chance Ordinance, for all positions located in the city and county of San Francisco, we will consider for employment qualified applicants with arrest and conviction records.

Massachusetts Lie Detector: It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Use of Artificial Intelligence (AI): We may use Artificial Intelligence (AI) to support parts of our hiring process, including sourcing, screening, and evaluating candidates. AI helps assess applications and qualifications, but final decisions are made by our hiring team. By applying, you acknowledge and agree that your application may be reviewed using AI tools.