People Operations - Benefits & Systems

Jobtailor; New York (NY); On-site; USD 90,000 - 130,000; Full time

Job summary

Jobtailor in New York is seeking an experienced Benefits Administrator to manage global benefits programs and drive successful open enrollment. You will ensure regulatory compliance, optimize processes, and serve as the primary Rippling administrator, building reports and dashboards for the People team.

The role requires 5+ years in benefits or HR systems and hands‑on HRIS experience. You will collaborate with brokers, vendors, and internal stakeholders to keep benefits competitive and scalable

Qualifications

• 5+ years in benefits administration, HR systems, or a combination of both.
• Hands‑on experience with an HRIS.
• Solid understanding of benefits compliance requirements.
• Experience building or improving processes at a scaling company.

Responsibilities

• Manage day-to-day administration of global benefits programs (health, dental, vision & retirement).
• Build out benefit programs in new markets to maintain a consistent experience.
• Serve as main point of contact for employee benefits questions with clear, timely answers.
• Evaluate benefit plans regularly to stay competitive and take care of employees.
• Lead open enrollment from start to finish: communication, system setup, and vendor coordination.
• Partner with brokers and vendors on renewals, issue resolution, and evaluating offerings.
• Keep us compliant with regulations (ACA, ERISA, COBRA, FMLA, etc.).
• Audit benefits data to catch discrepancies before they become bigger problems.
• Serve as primary administrator for HRIS Rippling, including records, workflows, and permissions.
• Build and maintain reports and dashboards in Rippling to support People team needs.
• Configure and maintain Rippling integrations with benefits.
• Set up and manage automated workflows for onboarding, offboarding, and status changes.
• Own vendor relationships for People systems, including renewals and evaluations of new tools.
• Troubleshoot issues and be primary contact for Rippling support.
• Create documentation and process guides for proper tool usage.
• Look for ways to automate manual processes and improve updates to employees.
• Build documentation, workflows, and audit processes for benefits and systems as we grow.
• Keep data organized and accurate to support reporting, compliance, and decision-making.
• Get ahead of issues before they become employee-facing problems.
• Advise People team, managers, and employees on benefits and systems with clear guidance.
• Make complex benefits topics understandable for all levels.
• Contribute to broader People Operations work as the team grows.

Skills

Benefits administration

HRIS experience

Benefits compliance

Process optimization

Vendor management

Job description

Responsibilities

• Manage day-to-day administration of our global benefits programs, including health, dental, vision & retirement.
• Build out benefit programs in new markets giving our team a comparable Clay experience, no matter where they are located.
• Serve as a main point of contact for employee benefits questions, and make sure people get clear, timely answers.
• Evaluate our benefit plans to regularly ensure we are offering the best benefits for our team to both take care of our people and keep us competitive.
• Lead open enrollment from start to finish: communication, system setup, and vendor coordination.
• Partner with brokers and vendors on renewals, issue resolution, and evaluating our benefits offerings.
• Keep us compliant with relevant regulations (ACA, ERISA, COBRA, FMLA, and similar).
• Audit benefits data regularly to catch and fix discrepancies before they become bigger problems.
• Serve as the primary administrator for our HRIS, Rippling, including employee records, workflows, and permissions.
• Build and maintain reports and dashboards in Rippling to support People team and business needs.
• Configure and maintain integrations between Rippling and our benefits.
• Set up and manage automated workflows for onboarding, offboarding, and status changes (ex. new hires, terminations, promotions, leaves).
• Own vendor relationships for our People systems, including renewals, contract review, and evaluating new tools or add-ons.
• Troubleshoot issues and serve as the main point of contact for Rippling support.
• Create documentation and process guides so the team knows how to use these tools correctly.
• Look for ways to automate manual processes and improve how we communicate updates to employees.
• Build out documentation, workflows, and audit processes for benefits and systems as we continue to grow.
• Keep our data organized and accurate to support reporting, compliance, and decision-making.
• Get ahead of issues before they become employee-facing problems.
• Advise People team, managers, and employees on benefits and systems questions with clear, practical guidance.
• Make complex benefits and systems topics easy to understand for people at every level.
• Contribute to broader People Operations work as the team and company grow.

Requirements

• 5+ years in benefits administration, HR systems, or a combination of both.
• Hands‑on experience with an HRIS.
• Solid understanding of benefits compliance requirements.
• Experience building or improving processes at a scaling company.