Benefits & Leave of Absence (LOA) Contractor

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

• Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

Build a massive, fast-growing business with billions in revenue

About the Role

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.

Key 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.

Desired Capabilities

• 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.

Extra Credit

• 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.

Success in This Role

• Employees receive fast, accurate support on benefits questions.

• Benefits processes run smoothly with minimal errors.

• Open enrollment and ongoing administration are well organized and on schedule.

• Vendors and internal teams stay aligned and issues are resolved quickly.