Apply on Employer Site

Five9 · 4 days ago

Benefits Program Manager

United States

Full-time

Remote

Senior Level

$80K/yr - $223K/yr

7+ years exp

Five9 is a leading provider of cloud contact center software, dedicated to enhancing customer experience. The Benefits Program Manager will design and optimize global benefit programs, ensuring effective communication and compliance while driving program evolution through market insights and strong cross-functional partnerships.

Call CenterCustomer ServiceEnterprise SoftwareSaaSSales

Growth Opportunities

Responsibilities

Lead benefits projects from concept through delivery, applying best practices in program governance, risk management, and cross-functional coordination

Co-lead United States open enrollment

Manage timelines, deliverables, resources, and vendor engagement to ensure accurate and on-time delivery and implementation

Balance multiple complex initiatives, ensuring alignment with Total Rewards strategy and business needs

Develop and maintain policy documents, benefits content, and employee-facing materials across Five9’s channels (e.g., SharePoint, Freshservice KB)

Own well-being calendars, campaigns, and communications that support employee understanding and engagement

Deliver benefits training and support to partner teams (HRBPs, People Ops, TA) and vendors

Monitor federal, state, and international regulations affecting income protection, life, LOA, time off, and wellbeing programs; recommend updates as required

Oversee compliance tasks (e.g., welfare 5500 support, leave-related filings, policy updates) and collaborate with auditors, Legal, and People Ops to ensure accuracy

Conduct and interpret audit results; prioritize improvements and ensure controls are embedded in processes

Manage vendor relationships, including performance review, service guarantees, escalation resolution, and RFP processes

Implement new vendors and programs (security review, integration testing, UAT, contract coordination, and change management)

Serve as the subject matter expert for LOA, life, income protection, voluntary benefits, time off, and wellness programs

Investigate, resolve, and document complex escalations, including root-cause analysis, impact assessment, and recommendations

Partner closely with the Benefits Specialist for billing review, reconciliation, and operational support

Collaborate with Payroll, Legal, Finance, and HRBPs on benefit changes, compliance actions, and process improvements

Conduct market benchmarking to ensure programs remain competitive and aligned with Five9’s global benefits strategy

Support annual program evaluation, renewal recommendations, and cost modeling

Build strong internal partnerships (Legal, Payroll, Procurement, People Ops, HRBPs) to ensure seamless program execution and alignment with employee needs

Qualification

Benefits program managementStakeholder engagementAnalytical skillsVendor managementBenefits communicationProgram governanceOrganizational skillsCritical thinkingCommunication skillsProject management

Required

7+ years of experience managing benefit programs in a global, fast-paced environment

Demonstrated expertise in income protection, life, voluntary benefits, LOA, and time-off programs

Proven success in program management, stakeholder engagement, and benefits communication

Strong analytical and critical-thinking skills; able to use data to drive decisions and design solutions

Exceptional communication skills: clear, concise, employee-centered writing and messaging

Experience managing vendors, holding partners accountable, and driving continuous improvement

Strong organizational skills, with the ability to manage multiple complex initiatives simultaneously

Comfortable with ambiguity and adept at building structure, process rigor, and scalability

Benefits

Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.

Short & Long-Term Disability

Basic Life Insurance

401k saving plan with employer matching

Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents

Generous employee stock purchase plan

Paid Time Off

Company paid holidays

Paid volunteer hours

12 weeks paid parental leave

Company

Five9

Glassdoor4.2

Five9 is a cloud-based call center software company that specializes in sales, marketing, and customer service. It is a sub-organization of Five Rivers Solutions.

Founded in 2001

San Ramon, California, USA

1001-5000 employees