Senior Benefits and Leave Specialist

Summary

Join Headspace as a Senior Benefits and Leave Specialist and support the organization's benefits and leave programs. You will be the primary point of contact for employee inquiries regarding benefits and leave, ensuring a seamless experience. Responsibilities include administering health and wellness plans, managing vendor relationships, providing employee support, collaborating on plan design and compliance, and overseeing leave of absence policies. You will also lead audits, manage benefit communication, and support the development of training resources. This role requires 5+ years of experience in benefits, leave of absence, and ADA, strong customer service skills, and proficiency in Excel. Headspace offers a competitive salary, comprehensive healthcare coverage, a wellness stipend, retirement savings match, and generous parental leave, among other benefits.

Requirements

• 5+ years of Benefits, leave of absence, and ADA experience
• Knowledge of key concepts and regulations in human resources, benefits, etc
• Strong customer service skills and ability to handle issues with sensitivity, empathy, patience, and confidentiality
• Excellent organizational and follow up skills with ability to prioritize assignments and meet deliverables while handling various projects simultaneously
• An analytical thinker who enjoys problem-solving and has the ability to analyze large amounts of benefits data for invoice reconciliation, auditing, etc
• Naturally inclined to exercise good judgment within defined procedures and practices to determine appropriate action and follow general instructions on routine work and detailed instructions on new assignments
• Proficiency in Excel
• Experience with payroll, benefit, or HR systems
• Experience managing leave of absence vendors

Responsibilities

• Support the administration of Health & Wellness plans, including COBRA and ongoing program changes in collaboration with the Benefits team
• Manage relationships with outside vendors, including brokers and benefit plan administrators, ensuring smooth integration and resolution of issues (e.g., file feed and enrollment errors)
• Provide first-line and escalated support to employees and managers in partnership with the Sequoia Advocate Team
• Collaborate with the Benefits team on plan design, implementation, and compliance, including open enrollment and renewals
• Continuously review and streamline benefits policies, procedures, vendor integrations, and payroll requirements
• Lead and support audits related to FSA/HSA/Core benefits and ensure compliance with enrollment, eligibility, and other regulatory requirements
• Oversee benefit communication for new hires, ensuring a smooth onboarding experience
• Manage benefits compliance, including nondiscrimination testing, ACA, and PCORI filings
• Own the administration of Global Leave of Absence policies (including FMLA, Parental Leave, Workers’ Compensation, Disability, and ADA requests), ensuring compliance with relevant laws and regulations
• Serve as the primary point of contact for all employee and manager inquiries regarding leaves of absence and accommodation requests
• Support the development and continuous improvement of training and resources for managers on leave processes
• Review and monitor leave usage through data analytics, ensuring compliance and identifying any emerging trends
• Partner with internal stakeholders to oversee employee return-to-work plans and ensure a positive experience for returning employees

Preferred Qualifications

• Experience with UKG
• Experience with Cocoon
• Experience working within a tech and/or fast paced environment

Benefits

• Comprehensive healthcare coverage
• Monthly wellness stipend
• Retirement savings match
• Lifetime Headspace membership
• Unlimited, free mental health coaching
• Generous parental leave
• Paid performance incentives