Benefits Lead

Checkout

Hybrid (3 days in office, 2 days remote)
Benefits strategy and operations
Vendor and system management
Benefits compliance and regulations
Checkout.com is seeking a Benefits Lead to design, implement, and enhance benefits programs across the Americas, with a strong focus on the US, Canada, and Brazil. The ideal candidate will have extensive experience in benefits management, vendor relations, and strategic planning, and will thrive in a fast-paced, high-growth environment

Job Summary

  • As we continue our rapid growth, we're seeking a proactive Benefits SME to take ownership of designing, implementing, and enhancing our benefits programs across the Americas Region.
  • You'll own and execute the day-to-day operations of our regional benefits programs across the Americas, including managing enrollments, ensuring seamless payroll integrations, handling compliance, and resolving employee inquiries with a strong focus on exceptional service.
  • This is a role for a true self-starter, expected to work with a high degree of autonomy, independently managing the full scope of benefits for the Americas while ensuring both operational excellence and long-term strategic enhancements.

Matching Summary

Match Score: 85

Checkout.com is seeking a Benefits Lead to design, implement, and enhance benefits programs across the Americas, with a strong focus on the US, Canada, and Brazil. The ideal candidate will have extensive experience in benefits management, vendor relations, and strategic planning, and will thrive in a fast-paced, high-growth environment.

Skills & Requirements

Must-have

  • Benefits strategy and operations
  • Vendor and system management
  • Benefits compliance and regulations
  • Data-driven strategic planning
  • Cross-functional collaboration

Nice-to-have

  • Fast-paced, high-growth environment
  • Empathy, patience, and compassion
  • Thrive in dynamic environments

Key Requirements

  • 5+ years of Benefits Expertise
  • US and Canada benefits administration
  • US FMLA and leave administration
  • Vendor and Systems Management
  • Strategic & Analytical Skills
  • Project Leadership
  • Advanced Microsoft Excel skills
  • Workday experience

Work Rights

Not specified

Tailored Resume

Cover Letter