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Payroll & Benefits Specialist

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Vail Systems Inc.
Full Time position
Listed on 2026-01-12
Job specializations:
  • HR/Recruitment
    Regulatory Compliance Specialist
  • Business
    Regulatory Compliance Specialist
Salary/Wage Range or Industry Benchmark: 100000 - 125000 USD Yearly USD 100000.00 125000.00 YEAR
Job Description & How to Apply Below

Who You Are:

Interested in managing payroll and benefits? As the company’s Payroll and Benefits Specialist will be the subject matter expert on payroll and benefits. You will be responsible for managing all aspects of payroll processing and ensuring compliance with relevant regulations and company policies. You would also administer and help make decisions on employee benefits programs, including enrollment communication, and resolving benefit-related inquiries.

Your success profile includes having a strong understanding of payroll and benefits administration, exceptional organizational skills, and the ability to maintain confidentiality in handling sensitive information.

What You’ll Do:
  • Responsible for the full multi-state payroll administration including but not limited to assuring accurate record of hourly pay, salaried, and PTO (Vacation, Sick, Floating, FMLA, Parental leaves).
  • Be the primary point of contact for all Payroll and Benefits interactions with employees.
  • Ensure the onboarding and offboarding process for all types of employees (full-time, contract, internship), is accurate and up to date in the payroll and benefit systems and reviewing the benefit statements are accurate for payment.
  • Analyze company policies and procedures and assist with developing documentation and policy implementation and administration.
  • Manage payroll and benefit documentation and make annual, quarterly, or monthly updates based on changes to policies or employee base.
  • Reviews monthly benefits invoices and prepares them for payment, maintains and files documentation, and creates ad hoc accounting reports.
  • Maintain accurate employee records.
  • Assist with audits and provide necessary documentation to auditors or relevant team members.
  • Update HR systems and platforms with up-to-date salary, title, and other employee-related information.
  • Takes an interest in continuous improvement including reviewing and recommending new HRIS systems.
  • Manage the open enrollment process including supporting employees, setting up changes and functions in the payroll system, working with external vendors, and propose benefit changes with corresponding costs.
  • Train team members on payroll processing and benefit administration to ensure sufficient backup support.
Qualifications

We encourage you to apply if you think your experience may be a match, even if you do not meet all of the qualifications.

  • A Bachelor’s degree in Human Resources, Accounting, or other related field (or equivalent work experience).
  • 2-4+ years of relevant work experience as a Payroll Specialist, Benefits Specialist, or similar role.
  • Proficiency with a Payroll system such as UKG Ready, ADP, etc.
  • In-depth knowledge of payroll processing, tax regulations, and benefits administration.
  • Excellent verbal and written communication skills
  • Strong attention to detail.
  • Ability to multi-task, remain organized and work both independently and with a team.
  • Can manage ambiguity and maintain composure under pressure.
  • Knowledge of basic accounting principles.
  • Knowledge of relevant federal, state, and local payroll and benefit laws and regulations.
  • Strong problem-solving skills and the ability to handle payroll and benefits-related inquiries efficiently.
  • Strong computer skills including Microsoft Office Suite (Word, Excel and PowerPoint).
  • Experience and willingness to work with an HR team on various tasks, projects, and goals.
Who We Are

At Vail, we believe in the unique power of voice interactions to create more expressive, more intimate, and more efficient interpersonal interactions. Using Vail technology, we make millions of voice interactions better every day. We process around 10% of all toll-free call traffic in the U.S.; 1 in 10 times when someone calls a customer support hotline, Vail is routing or interacting with that call.

We are rapidly growing across multiple dimensions, including our customer base, the scope of products we offer, and the size of our team. Now is the right time for a strong candidate to join and grow with us. We have a supportive culture where employees are encouraged to achieve both personal and team goals because we believe growth leads to both business impact and personal…

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