Sr. Benefits Specialist in New York at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Sr. Benefits Specialist based in United States.

As a Sr. Benefits Specialist, you will help shape a high-quality employee experience across benefits and leave programs.
You will serve as a trusted subject matter expert for employees navigating healthcare, retirement, wellbeing, family leave, and other important life events.
The role covers benefits administration across the United States and Canada, with a strong focus on compliance, accuracy, and service excellence.
You will collaborate closely with employees, HR, Payroll, vendors, and other internal partners to resolve issues and improve outcomes.
Your analytical skills will help strengthen data integrity through audits, reconciliations, reporting, and issue resolution.
You will also contribute to process automation, employee communications, and scalable improvements within a growing People organization.
This is a remote opportunity offering meaningful responsibility, professional development, and exposure to modern technology and AI-enabled ways of working.

• Administer U.S. and Canadian employee benefit programs, including health, wellbeing, retirement, life, disability, and voluntary benefits.

• Guide employees through benefit elections, life events, eligibility changes, transitions, and other benefits-related questions with professionalism and empathy.

• Coordinate employee leave programs, including family, medical, disability, parental, accommodation-related, and statutory leave requirements.

• Partner with employees, benefits vendors, HR teams, and other stakeholders throughout the leave administration lifecycle.

• Ensure benefit and leave documentation, communications, eligibility changes, and related transactions are completed accurately and in accordance with applicable requirements.

• Support annual enrollment activities, employee education initiatives, benefits communications, and self-service resources.

• Perform audits and reconciliations covering eligibility, enrollments, payroll deductions, and vendor records.

• Investigate and resolve discrepancies in collaboration with Payroll, HR Operations, and external providers.

• Maintain accurate and secure employee data across HR systems and benefits vendor platforms.

• Review invoices and support other benefits administration and vendor management activities.

• Maintain employee-facing resources, FAQs, articles, process documentation, and operational materials.

• Develop clear communications that help employees understand benefits, leave programs, and operational changes.

• Identify opportunities to simplify processes, improve efficiency, and strengthen the overall employee experience.

• Support the implementation of automation and other technology enhancements that enable scalable benefits operations.

• Demonstrated experience administering employee benefit programs and managing employee leave processes.

• Strong knowledge of U.S. benefits regulations, leave requirements, and relevant employment regulations.

• Exposure to Canadian benefits administration is highly valued.

• Experience working with Workday or a comparable Human Resources Information System (HRIS).

• Strong analytical skills, including the ability to investigate discrepancies, interpret data, and develop practical solutions.

• Advanced attention to detail and a strong commitment to data accuracy and confidentiality.

• Proficiency with spreadsheets and reporting tools for audits, reconciliations, data analysis, and reporting.

• Excellent customer service skills and the ability to handle sensitive employee matters with discretion and empathy.

• Strong organizational and prioritization skills, with the ability to manage multiple responsibilities in a fast-paced environment.

• Excellent written and verbal communication skills.

• Ability to collaborate effectively with employees, vendors, HR, Payroll, and other cross-functional stakeholders.

• A proactive mindset and interest in using automation and AI-enabled tools to improve benefits operations.

• Valid authorization to work in the United States.

• Annual salary range of $60,000–$80,000 USD, with compensation determined by relevant qualifications, experience, and other job-related factors.

• Annual performance bonus opportunities.

• Equity participation through company stock programs.

• Medical, dental, and vision coverage.

• 401(k) retirement plan with company match.

• Employer-paid life, AD&D, short-term disability, and long-term disability insurance.

• Employee Assistance Program (EAP).

• Flexible open PTO and paid sick leave.

• Paid parental leave.

• Company holidays.

• Learning and development opportunities, including LinkedIn Learning access.

• Wellbeing resources and coaching support.

• Employee recognition programs.

• Collaborative and inclusive remote work environment.

• Opportunities for professional certifications, career progression, and cross-functional development.

• Access to modern AI-powered tools and technology-focused learning resources.

• Team events and celebrations.

• RTD EcoPass for eligible Colorado-based employees.