Remote Director of Benefits Jobs
Remote Director of Benefits jobs are open across the U.S. at remote-first firms, distributed teams, and large enterprises in sectors like technology, healthcare, financial services, and professional services. Employers hiring remotely right now include Protos Security, The Cigna, and Kaiser Permanente. See the openings below and apply to the ones that match your experience.
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The Child Center of NY strengthens children and families with skills, opportunities, and emotional support to build healthy, successful lives. Founded in 1953, The Child Center of NY has become a powerful community presence throughout the city. With 50 locations and 100 programs in NYC’s most under-served communities, our 1,000+ results-oriented professionals make a difference for more than 40,000 children and their families each year.
Position Summary
The HR Leave and Benefits Coordinator is responsible for administering employee leave programs and managing benefits enrollment and inquiries. This role ensures compliance with federal, provincial, and local regulations, as well as collective bargaining agreements across four unions. The coordinator provides empathetic and inclusive support to employees regarding their leave and benefits options.
Essential Functions
Leave Administration
- Coordinate and manage all types of employee leaves (e.g., FMLA, ADA, parental, medical, personal, union-specific leave provisions).
- Serve as the main point of contact for employees on leave-related matters.
- Ensure accurate documentation and tracking of leave requests.
- Communicate with managers, payroll, and union representatives to ensure proper leave coding and pay adjustments.
- Maintain compliance with applicable laws, internal policies, and collective agreements.
- Assist with benefits enrollment, changes, and terminations.
- Respond to employee inquiries regarding health, dental, vision, life insurance, disability, and retirement plans.
- Liaise with benefits providers and union benefit trusts to resolve issues.
- Support annual open enrollment processes.
- Maintain accurate benefits records and ensure timely updates in HRIS.
- Ensure compliance with federal and provincial regulations (e.g., FMLA, HIPAA, COBRA, ACA) and union contracts.
- Prepare and submit required reports and documentation.
- Stay current on changes in leave and benefits laws, union agreements, and best practices.
- Provide clear, empathetic communication to employees regarding their rights and options.
- Educate employees on available benefits and leave policies.
- Conduct benefits orientations for new hires.
- Collaborate with union representatives to ensure consistent and fair application of policies.
Monday – Friday
Qualifications
- Bachelor’s degree in Human Resources, Business Administration, or related field (Preferred)
- 2+ years of experience in HR, with a focus on leave and benefits administration
- Experience working in a unionized environment (Preferred)
- Strong knowledge of FMLA, ADA, HIPAA, COBRA, and other relevant regulations
- Familiarity with collective bargaining agreements and union processes
- Excellent organizational and time management skills
- High attention to detail and accuracy
- Strong interpersonal and communication skills
- Proficiency in HRIS systems and Microsoft Office Suite
- Bilingual (Preferred)
- DayForce (HCM) (Preferred)
- Experience with Unions (Preferred)
Company Overview
The Child Center of NY strengthens children and families with skills, opportunities, and emotional support to build healthy, successful lives. Founded in 1953, The Child Center of NY has become a powerful community presence throughout the city. With 50 locations and 100 programs in NYC’s most under-served communities, our 1,000+ results-oriented professionals make a difference for more than 40,000 children and their families each year.
Position Summary
The HR Leave and Benefits Coordinator is responsible for administering employee leave programs and managing benefits enrollment and inquiries. This role ensures compliance with federal, provincial, and local regulations, as well as collective bargaining agreements across four unions. The coordinator provides empathetic and inclusive support to employees regarding their leave and benefits options.
Essential Functions
Leave Administration
- Coordinate and manage all types of employee leaves (e.g., FMLA, ADA, parental, medical, personal, union-specific leave provisions).
- Serve as the main point of contact for employees on leave-related matters.
- Ensure accurate documentation and tracking of leave requests.
- Communicate with managers, payroll, and union representatives to ensure proper leave coding and pay adjustments.
- Maintain compliance with applicable laws, internal policies, and collective agreements.
- Assist with benefits enrollment, changes, and terminations.
- Respond to employee inquiries regarding health, dental, vision, life insurance, disability, and retirement plans.
- Liaise with benefits providers and union benefit trusts to resolve issues.
- Support annual open enrollment processes.
- Maintain accurate benefits records and ensure timely updates in HRIS.
- Ensure compliance with federal and provincial regulations (e.g., FMLA, HIPAA, COBRA, ACA) and union contracts.
- Prepare and submit required reports and documentation.
- Stay current on changes in leave and benefits laws, union agreements, and best practices.
- Provide clear, empathetic communication to employees regarding their rights and options.
- Educate employees on available benefits and leave policies.
- Conduct benefits orientations for new hires.
- Collaborate with union representatives to ensure consistent and fair application of policies.
Monday – Friday
Qualifications
- Bachelor’s degree in Human Resources, Business Administration, or related field (Preferred)
- 2+ years of experience in HR, with a focus on leave and benefits administration
- Experience working in a unionized environment (Preferred)
- Strong knowledge of FMLA, ADA, HIPAA, COBRA, and other relevant regulations
- Familiarity with collective bargaining agreements and union processes
- Excellent organizational and time management skills
- High attention to detail and accuracy
- Strong interpersonal and communication skills
- Proficiency in HRIS systems and Microsoft Office Suite
- Bilingual (Preferred)
- DayForce (HCM) (Preferred)
- Experience with Unions (Preferred)
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Who's Hiring
What Employers Look For
The qualifications that appear most often in remote director of benefits jobs.
- 7 or more years of progressive benefits administration and program management experience
- Deep working knowledge of ERISA, ACA, COBRA, HIPAA, and FMLA compliance requirements
- Experience managing self-funded or self-insured medical and prescription benefit plans
- Proficiency with HRIS platforms and benefits administration systems
- CEBS, CBP, or PHR/SPHR certification strongly preferred or required
- Bachelor's degree in human resources, business administration, or a related field
Tips for Your Remote Director of Benefits Job Search
Apply early to remote roles that fit
Migrate Mate lists remote director of benefits openings from across the U.S. in one place. Search for roles that match your program scope and apply directly, without digging across multiple sources. Remote roles at distributed companies often move fast once posted.
Show async communication in your materials
Remote benefits directors manage brokers, vendors, and HR partners entirely in writing. Highlight examples of benefits communications you have written for employees, executive summaries you have delivered to leadership, or compliance documentation you have produced independently.
Demonstrate remote benefits program ownership
Remote employers want to see you have run a benefits program without daily oversight. Call out specific outcomes you owned, such as a benefits renewal you led, a carrier migration you managed, or an open enrollment you coordinated for a distributed workforce.
Name the platforms and systems you work in
Remote benefits directors are expected to operate independently in HRIS and benefits administration platforms from day one. Explicitly list the systems you have used, such as Workday, Benefitfocus, or ADP, so hiring managers can see you will not need hands-on onboarding.
Remote Director of Benefits Jobs: Frequently Asked Questions
How do I get a remote director of benefits job?
Target companies that already operate with distributed HR teams, including remote-first tech firms, insurance carriers, and large professional services organizations. Remote employers screen hard for self-direction, clear written communication, and the ability to manage broker relationships and open enrollment cycles without in-person oversight. Candidates who can demonstrate experience owning a benefits program end-to-end, including vendor negotiations and compliance reporting, have a clear edge.
Which companies hire remote director of benefits?
Companies hiring remote director of benefits right now include Protos Security, The Cigna, and Kaiser Permanente, based on current remote listings on Migrate Mate as of November 2026. Remote-first technology companies, national insurance carriers, and distributed professional services firms are among the most active hirers of this role outside a physical office.
Can you get a remote director of benefits job with no experience?
Yes, but remote director of benefits roles are senior positions, so true entry-level openings are rare and require extra proof of independent capability. Candidates breaking in remotely do best by building experience managing benefits programs in a coordinator or manager role first, then demonstrating results through quantifiable outcomes, such as cost reductions or improved enrollment rates, that speak for themselves without in-person context.
Do you need a degree for remote director of benefits jobs?
Not always. Many remote employers weigh demonstrated program management experience, benefits compliance knowledge, and certifications like CEBS or PHR as heavily as a formal degree. Candidates without a degree who can show a history of managing complex benefits portfolios, navigating ACA and ERISA requirements, and leading open enrollment for large employee populations are competitive for remote roles.
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