About the Senior Benefits and Leave Specialist at Headspace:

As the Senior Benefits and Leave Specialist, you will have the opportunity to support and enhance the organization’s benefits and leave programs, while learning and implementing innovative HR strategies.

Reporting to the Senior Manager, Benefits and Payroll, you will be the primary point of contact for employees with questions or needs related to benefits, leave of absence, and other perks, ensuring a seamless experience from onboarding to offboarding.

You will be an essential team member, supporting the development and execution of benefits and leave programs, managing day-to-day operations, and driving communication and employee engagement. Collaborating closely with various People Operations teams, you will champion inclusivity, change management, and the creation of a unified organizational culture.

What you will do:

• 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.

What you will bring:

Required Skills:

• 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.

Preferred Skills:

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

Pay & Benefits:

The base salary range for this role is determined by a number of factors, including but not limited to skills and scope required, relevant licensure and certifications, and unique relevant experience and job-related skills. The base salary range for this role is $67,230-$94,500.

At Headspace, cash salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, unlimited, free mental health coaching, generous parental leave, and much more. Paid performance incentives are also included for those in eligible roles. Additional details about our Total Rewards package will be provided during the recruitment process.

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together.

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace.

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent Acquisition team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

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Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment.

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice

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