Benefits Lead

Charlie Health•New York City, NY

3d•$70,000 - $100,000•Hybrid

About The Position

We are looking for a Benefits Lead to join our growing People team! As our Benefits Lead, you will play a critical role in owning and optimizing Charlie Health’s benefits programs, ensuring our offerings support the wellbeing and needs of our team as we scale. This role is both strategic and hands-on — overseeing all aspects of benefits administration, vendor relationships, compliance, and employee support. You’ll also manage all leaves of absence and play a key role in process improvement and employee experience initiatives. This is a great opportunity for someone who is detail-oriented, passionate about employee wellbeing, and ready to take the next step in their HR career by leading and evolving our benefits function.

Requirements

Located within a 45-minute commute of New York City and able to work 4 days a week out of our New York City office
Bachelor’s degree preferred.
At least 3–5+ years of experience in Human Resources, with at least 1–2 years in a benefits-focused role.
Experience managing leave of absence processes and communicating with employees with care and clarity.
Strong understanding of core benefits programs and related regulations (HIPAA, COBRA, ACA, FMLA, ADA).
Experience conducting audits and partnering with payroll to ensure accurate benefits deductions.
Strong communication and organizational skills with a focus on employee experience.
High attention to detail and the ability to juggle multiple priorities in a fast-paced environment.
Experience using HRIS and benefits platforms (e.g., UKG, BSwift, Sequoia) preferred.

Responsibilities

Serve as the main point of contact for all benefits-related inquiries from employees, including health, dental, vision, HSA/FSA, 401(k), and wellness offerings.
Manage all types of employee leaves of absence (FMLA, parental, medical, personal, etc.) from intake through return-to-work, ensuring compliance and a supportive experience.
Administer benefits enrollment, life event changes, and offboarding processes in UKG and BSwift, ensuring timely and accurate updates.
Support open enrollment planning and execution, including systems setup, employee communications, and vendor coordination.
Maintain strong relationships with vendors and brokers (e.g., Sequoia, Fidelity) to ensure high-quality service and troubleshoot employee issues.
Conduct regular audits of benefits data and partner with Payroll to ensure accurate deductions and data integrity.
Ensure compliance with relevant federal and state regulations (e.g., ACA, COBRA, HIPAA, FMLA).
Lead benefits orientation for new hires and ensure a seamless onboarding experience.
Maintain and update internal benefits documentation and support knowledge sharing via internal tools like Confluence.
Identify opportunities for process improvements and contribute to scaling benefits programs that meet the evolving needs of our growing team.
Support compliance documentation and assist with annual audits and filings (e.g., ACA, Form 5500, 401k audit).