Senior Benefits & LOA Specialist

Join us in bringing joy to customer experience.  Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.   

Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. 

The Sr. Benefits & LOA Specialist is a key member of the Benefits COE team and will be responsible for leading the day-to-day operations and delivery of Five9’s benefit programs, while also managing projects within the benefits function. To be successful in this role, you will need a strong mix of project management, strong orientation to details, and a process and systems optimization mindset. 

 Responsibilities: 

 Benefits Administration: 

• Collaborate with stakeholders to align benefit programs with company policies and global regulations. 
• Lead annual enrollment processes. 
• Review and approve new hire benefits and qualifying life event elections. 
• Calculate missed deductions for semi-monthly payroll processing. 
• Enter changes in employee retirement contributions weekly in the HRIS system for US and Canada. 

 Record Keeping and Compliance: 

• Maintain employee files and ensure timely monitoring of HR inbox and Slack for employee assistance. 
• Manage compliance data audits, required filings, and other compliance-related initiatives. 
• Conduct internal audits for benefits deductions and contributions (FSA, 401(k)) to ensure data accuracy. 

 Payroll and Vendor Coordination: 

• Work closely with the Payroll team to ensure processes are efficient and lead to accurate benefit deductions and funding (e.g., 401K, HSA, FSA, RRSP). 
• Send taxable benefit calculations to Payroll for Canada. 

• Manage Purchase Orders, invoice payments, and perform funding reconciliation and claim audits. 

 System and Process Improvement: 

• Maintain and troubleshoot data in vendor and HR systems, manage interfaces, and participate in system testing. 
• Design and implement operational processes and improvements for benefit programs, including process documentation and training. 
• Implement and manage benefit systems in partnership with the Technology team. 

 Reporting and Communication: 

• Prepare scheduled and ad hoc reports as needed. 
• Develop and deliver benefit communications through various mediums (emails, Slack, site updates). 
• Publish global holiday calendar and update HR SharePoint site with benefit information. 

 Leave of Absence and Workers Compensation: 

• Handle all aspects of Leave of Absence in compliance with laws and company policy. 
• Manage international time off accrual and utilization policies and lead the development of administrative processes for time off and LOA programs. 
• Implement and manage outsourced LOA provider services and coordinate with Workers Compensation carriers. 
• Facilitate the ADA interactive process and coordinate ergonomic processes with Facilities and other stakeholders. 

  Qualifications:

• Minimum 5 years of leave administration and benefits experience.  
• Proficiency of LOA, ADA and Worker’s Compensation Laws (Federal and State) across multiple states, including CA. International leave experience is a plus.  
• Proficiency with Microsoft office products (Word, Excel, PowerPoint, Outlook).  
• Exceptional customer service, written and verbal communication skills.  
• Strong customer service skills and ability to work independently and in a team environment.  
• Strong audit and attention to detail skills.  
• Strong organizational and multi-tasking capabilities, ability to problem solve and work effectively in a fast-paced environment.  
• Ability to maintain the highest level of confidentiality.  
• Experience with HRIS and benefits enrollment portals. Familiarity with, UKG, Plansource is a plus.  
• Ability to thrive in a constantly evolving environment. 

 

 

Remote    This role is fully remote for candidates who reside at least 50 miles away from our San Francisco or San Ramon office locations. For candidates who reside within 50 miles of our San Francisco or San Ramon locations, this role will be Hybrid. 

 

 

 

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process.  Actual compensation