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Benefits Director Jobs in Springfield, MA (NOW HIRING)

Trinity College

Benefits Specialist

Hartford, CT

Reporting to the Director of Benefits Administration/Operations, the Benefits Specialist is highly motivated, detail and project management minded, supporting an inclusive, collaborative, engaged ...

USA Waste and Recycling

Benefits Specialist

Enfield, CT · On-site

$55K - $65K/yr

The Benefits Specialist is responsible for supporting the administration of the employee benefits program, including health insurance, retirement plans, and other employee benefit offerings ...

CVS Health

Benefits Consultant

Hartford, CT · On-site

Position Summary The Benefits Consultantacts as anin-housesubject matterexperttoassistan internalcommunicationsteam dedicated to one of Aetna's largest plan sponsors.Theindividual in this roleneeds ...

Quest Global

Benefits Specialist

Windsor, CT · Remote

$70K - $80K/yr

Oversee day-to-day administration of employee benefit programs including medical, dental, vision, life, disability, retirement, voluntary benefits, and leave of absence programs. * Lead annual open ...

USA Waste and Recycling

Benefits Specialist

Enfield, CT · On-site

$55K - $65K/yr

Benefits SpecialistUSA Waste and RecyclingUSA Waste and Recycling, IncPosition Summary:The Benefits Specialist is responsible for supporting the administration of the employee benefits program ...

ISO New England, Inc.

Benefits Specialist

Holyoke, MA · On-site

The Benefits Specialist plays a key role in the delivery of an exceptional employee benefits experience. This position partners closely with the Total Rewards & HRIS team, Finance, Legal, and ...

USA Waste & Recycling

Benefits Specialist

Enfield, CT · On-site

$55K - $65K/yr

The Benefits Specialist is responsible for supporting the administration of the employee benefits program, including health insurance, retirement plans, and other employee benefit offerings ...

Veterans Benefits Administration

Director

Hartford, CT · On-site +1

$166K - $197K/yr

Summary The Regional Office Director leads a Veterans Benefits Administration (VBA) Regional Office, overseeing all benefits and services for Veterans, their families, and survivors. They set ...

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Benefits Director information

See Springfield, MA salary details

$31.4K

$116.5K

$175.9K

How much do benefits director jobs pay per year?

As of Aug 9, 2026, the average yearly pay for benefits director in Springfield, MA is $116,488.00, according to ZipRecruiter salary data. Most workers in this role earn between $96,200.00 and $140,000.00 per year, depending on experience, location, and employer.

What are some common challenges faced by benefits directors, and how do they address them?

Benefits Directors often face challenges such as navigating complex regulatory changes, balancing cost control with employee satisfaction, and managing multiple vendors or benefit providers. They address these by staying current on industry trends and legal requirements, leveraging technology to streamline processes, and fostering strong relationships with finance, legal, and HR teams. Effective communication and proactive planning are key to anticipating issues and maintaining a competitive benefits program. By tackling these challenges, Benefits Directors play a crucial role in attracting and retaining top talent for their organizations.

What are the key skills and qualifications needed to thrive as a benefits director?

A Benefits Director requires deep knowledge of employee benefits programs, regulatory compliance (such as ERISA and ACA), and strategic planning, typically backed by a bachelor’s degree in human resources, business, or a related field. Familiarity with benefits administration systems, HRIS platforms, and certifications like CEBS (Certified Employee Benefit Specialist) are highly valuable. Excellent interpersonal skills, negotiation, and the ability to communicate complex information clearly set top candidates apart. These qualifications are vital for ensuring legal compliance, optimal program design, and strong support for employees and business objectives.

What does a benefits director do?

A Benefits Director oversees an organization's employee benefits programs, including health insurance, retirement plans, and wellness initiatives. They ensure compliance with legal regulations, negotiate with vendors, and develop strategies to enhance employee satisfaction and retention. Additionally, they analyze benefit trends, manage budgets, and collaborate with HR leadership to align benefits with company goals.

What are the most commonly searched types of Benefits jobs in Springfield, MA? The most popular types of Benefits jobs in Springfield, MA are:
What are popular job titles related to Benefits Director jobs in Springfield, MA? For Benefits Director jobs in Springfield, MA, the most frequently searched job titles are:
What job categories do people searching Benefits Director jobs in Springfield, MA look for? The top searched job categories for Benefits Director jobs in Springfield, MA are:
What cities near Springfield, MA are hiring for Benefits Director jobs? Cities near Springfield, MA with the most Benefits Director job openings:
Benefits Director jobs near you

Benefits Specialist

Trinity College

Hartford, CT

Full-time

Re-posted 15 days ago

Job description

The Benefits Specialist is responsible for administering employee benefits programs and managing all leave of absence (LOA) processes with accuracy, ensuring compliance, and exceptional customer service. This role ensures employees receive timely support and clear guidance on benefits, disability, and all state and federal leave programs.

Reporting to the Director of Benefits Administration/Operations, the Benefits Specialist is
highly motivated, detail and project management minded, supporting an inclusive, collaborative, engaged, and diverse
workforce.

Trinity is a highly selective, independent, nonsectarian liberal arts institution located in the capital city of Hartford, Connecticut. The college maintains a rigorous academic profile complemented by a vibrant co-curricular program.  With more than 2,100 full-time undergraduate students, representing forty-three states and ninety-one countries, we consider our location in a culturally and socioeconomically diverse capital city to be among Trinity's most distinctive assets; and we cultivate strong connections with our surrounding neighbors and with institutions and organizations throughout Hartford and the region. As a preeminent liberal arts college in an urban setting, Trinity College prepares students to be bold, independent thinkers who lead transformative lives.
  • Bachelor's Degree 
  • 3-5 years of experience, 
  • 5-8 years of experience, preferred 
  • Technical knowledge: Strong understanding of benefits programs, policies, and legal regulations.  Proficiency in MS Office; knowledge of HRIS is a plus.
  • Analytical skills: Ability to evaluate benefits plans, analyze data, and provide accurate, meaningful reporting. 
  • Detail orientation: Outstanding organizational and multitasking abilities. Manage multiple tasks, maintain accurate records, and ensure compliance.  Strong attention to detail.
  • Communication: Excellent communication and interpersonal skills 

  • Benefits Administration: Administer employee benefit programs, including health, retirement savings and wellness initiatives.  Ensure accurate processing of enrolments, changes and terminations.

  • Employee Communication: Serve as advocate, educator and guide for employees regarding benefits onboarding, inquiries, and challenges.  Provide accurate, clear information and assistance
  • Data Management: Lead weekly audits of HRIS benefit data and vendor integration reports ensuring timely resolution of data challenges found.  Lead billing and invoice reconciliation progress for all benefit programs. 
  • Compliance: Ensure all benefits comply with federal and state regulations including ERISA, COBRA, ACA, FMLA AND HIPAA. Maintain accurate records and documentation

  • Cross Functional and Vendor Engagement: Work with internal and external benefit partners on a daily basis including payroll, finance, ITS and benefit vendors and brokers.

  • Open Enrollment: Key player in the annual open enrollment process, including preparing communication, educating employees, and assisting with data management and reporting.

  • Leave of Absence Management: Administer employee leaves including disability, FMLA, CTPL, parental leave, and personal leaves.  Ensure compliance with federal, state, and local leave regulations as well as internal policies.  Track leave usage, eligibility, and return to work dates, maintaining accurate records in HR systems. 

  • Perform other related duties as assigned and based on departmental need.

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