Payroll & Benefits Specialist

Posted:
1/2/2026, 8:06:26 AM

Experience Level(s):
Junior ⋅ Mid Level ⋅ Senior

Field(s):
Customer Success & Support

Workplace Type:
Hybrid

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. 
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 fulfillment. 

We offer competitive compensation and affordable benefits with flexibility and choice to meet individual and family (including Domestic Partnerships) needs, including:
·       Multiple medical, dental, and vision plan options 
·       Company-paid life insurance, short and long-term disability 
·       401(k) savings plan with company match (50% on first 6% of employee contribution) 
·       35 days total annual PTO 
·       Annual Bonus Program  
·       Paid maternity and paternity leave 
·       Relocation allowance 
·       Employee referral bonus 
·       Gym membership 
·       Technical and Professional Development stipend

We are striving to implement and sustain an inclusive and equitable work environment for all employees by sourcing underrepresented groups and continually empowering those individuals within our organization to further enrich Vail’s communication solutions. We recognize that equitable and unique individuals benefit our teams’ problem-solving, innovation, and development efforts. 

Our offices are located in Deerfield and Chicago, IL. Interviews and onboarding are conducted in our offices when possible. We observe a hybrid work format that provides employees flexibility to collaborate with team members based on business needs.