Benefits Program Manager

Five9 • San Ramon, CA

1d • Hybrid

About The Position

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. Reporting to the VP, Global Total Rewards, the Benefits Program Manager will design, optimize, and operationalize Five9’s global benefit programs within income protection, life, voluntary benefits, time off, leave of absence (LOA), and well-being. You will drive program evolution through market insights, benchmarking, policy design, and clear, employee-centric communications. Success in this role requires strong program management capability, analytical rigor, cross-functional partnership, and the ability to translate complex benefits topics into simple, scalable solutions.

Requirements

• 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.

Responsibilities

• Project & Program Management 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.
• Benefits Communication & Experience 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.
• Benefits Governance, Compliance & Vendor Management 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).
• Program Ownership & Escalation 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.
• Annual Plan Review & Strategic Alignment 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.

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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees