Senior Specialist, Leave & Benefits

Teladoc Health is a global, whole person care company made up of a diverse community of people dedicated to transforming the healthcare experience. As an employee, you’re empowered to show up every day as your most authentic self and be a part of something bigger – thriving both personally and professionally. Together, let’s empower people everywhere to live their healthiest lives.

Summary of Position

The Senior Benefits Specialist is responsible for supporting leave of absence, workplace accommodation processes, and employee benefit administration in the U.S. and Canada. The specialist serves as a key member of the benefits team, and resource for HR Business Partners, employees, and vendors, ensuring compliance with applicable laws and internal policies, and delivering a positive employee experience.

Essential Duties and Responsibilities

Leave of Absence & Accommodation

• Work closely with the Senior Benefits Manager, HR Business Partners and the company’s third-party leave administrator on complex leave and accommodation cases.

• Support the interactive process for accommodations, including gathering documentation, coordinating with legal/HRBPs, communicating directly with employees.

• Manage leave data and status updates in the HRIS system, ensuring timely and accurate entries.

• Review and approve intermittent leave requests and escalate complex cases when necessary.

• Prepare parental and caregiving leave Top-up reports for payroll.

• Coordinate COBRA processing for non-protected leaves.

Employee Benefits

• Administer day-to-day benefits operations including life events, enrollments, EOI tracking, and eligibility maintenance.

• Manage benefit help tickets and respond to escalated inquiries in collaboration with the Benefits Helpdesk.

• Partner with vendors and internal teams to resolve issues related to benefit coverage, billing, and eligibility.

• Manage new hire onboarding activity including welcome emails and office hours / orientation.

• Assist with Open Enrollment activities, including system testing, communications, data audits, and reporting.

• Support compliance activities including ACA tracking, 1095-C preparation, FSA discrimination testing, and audit data collection.

• Help maintain accurate intranet content and assist with employee surveys and insights reporting.

• Reconcile benefits vendor invoices and assist with subsidy coordination.

Team & Administrative Support

• Provide general administrative support for leave and benefits processes including documentation management, report generation, and system data entry.

• Collaborate across the Benefits team to support cross-functional needs and coverage during peak times or team absences.

• Contribute to ongoing process improvements and documentation of procedures.

• Participate in and prepare presentations for employee and manager education and training.

Supervisory Responsibilities

No

Qualifications Expected for Position

• 5+ years of experience in employee benefits procedures, leave of absence administration and five years HR experience.

• Strong background in quantitative analysis, must be analytically inclined.

• Technical proficiency in Microsoft Office (Excel, PowerPoint, Word) and HRIS experience with Workday a plus.

• Knowledge of FMLA, PFL, CFRA, ADA, STD, LTD, company paid parental leaves, Workers Compensation and OSHA.

• Demonstrate and apply functional benefits knowledge to solve problems and identify opportunities for improvement.

• Demonstrated commitment to ethical conduct and the ability to handle sensitive information with the utmost confidentiality and professionalism, escalates issues when appropriate.

Bonus Qualifications

• Bachelor’s degree preferred.

• Excellent communication and interpersonal skills, must have the ability to collaborate effectively with stakeholders at all levels.

• Detail-oriented with a high level of accuracy and confidentiality.

• Strong ability to effectively manage multiple priorities and tasks simultaneously with close attention to details in a fast-paced environment.

• Ability to successfully work in a team environment, strong relationship building skills.

The base salary range for this position is $95,000-$115,000. In addition to a bas