Benefits & Leave of Absence (LOA) Contractor

Handshake•San Francisco, CA

10h

About The Position

We are seeking an experienced Benefits & LOA Contractor to support the administration of our employee benefits and leave of absence programs. This role partners closely with People, Payroll, and external vendors to ensure employees receive timely support and programs run smoothly and compliantly.

Requirements

3+ years of experience in benefits administration, HR operations, or total rewards.
Experience managing leave of absence programs, including FMLA and state leave laws.
Experience working with Workday.
Strong knowledge of U.S. benefits programs and compliance requirements.
Experience managing vendor relationships and troubleshooting employee issues.
Strong attention to detail and ability to manage confidential information.
Excellent communication and employee support skills.
Comfortable working in a fast-paced, evolving environment.

Nice To Haves

Experience supporting open enrollment for mid-size or high-growth companies.
Experience supporting companies with multi-state leave requirements.
Background in fast-growing or tech organizations.

Responsibilities

Administer day-to-day operations of employee benefit programs including health, dental, vision, wellness, and others.
Manage end-to-end Leave of Absence (LOA) processes including employee guidance, documentation tracking, system updates, and coordination with leave vendors.
Serve as the primary point of contact for employee questions related to benefits and leaves.
Support benefit enrollments, life events, eligibility audits, and status changes in Workday.
Partner with Payroll to ensure accurate deductions, leave pay coordination, and vendor payments.
Coordinate with third-party leave administrators on FMLA, state leaves, disability claims, and return-to-work processes.
Assist with open enrollment planning, system configuration, employee communications, and vendor coordination.
Ensure compliance with applicable federal and state regulations including FMLA, ADA, COBRA, ERISA, and ACA.
Document processes and recommend improvements to streamline benefits and leave administration.
Support reporting related to benefits utilization, leave trends, and program costs.