Benefits Specialist

Jobtailor; Connecticut; On-site; USD 65,000 - 85,000; Full time

Job summary

Jobtailor in Connecticut seeks an experienced Benefits Administrator to manage retirement, health, and wellness programs and partner with vendors on administration and enrollment readiness.

You will analyze benefits data, prepare reports, ensure compliance, and support annual enrollment while collaborating with HR, employees, and external partners to improve service and program outcomes.

Qualifications

• Bachelor’s degree or equivalent combination of education and experience.
• 3–5 years of experience in benefits, HR, Total Rewards, finance, or related analytic/operations role.
• Strong attention to detail and organizational skills.
• Ability to manage recurring responsibilities independently and apply sound judgment.

Responsibilities

• Support administration of retirement, medical, dental, vision, life, disability, and wellness programs.
• Resolve employee benefit questions and issues, escalating complex matters as needed.
• Monitor participant issues, identify patterns, and recommend process improvements.
• Manage invoice processing, record maintenance, and other benefits operations.
• Partner with external benefits vendors on administration, issue resolution, and service coordination.
• Monitor vendor service performance and elevate trends or concerns.
• Prepare standard, recurring, and ad hoc reports and supporting documentation.
• Develop and distribute benefits communications and education materials.
• Assist during annual enrollment with testing, employee support, and issue resolution.
• Support projects involving benefits administration, process improvement, systems enhancements, and vendor implementations.

Skills

Benefits Administration

Data Analysis

Invoice Processing

Compliance Management

Employee Support Processes

Attention to Detail

Organizational Skills

Sound Judgment

Curiosity

Growth Mindset

Education

Bachelor’s degree in Human Resources, Business, Finance, or related field

Equivalent combination of education and experience

Tools

Microsoft Office

Excel

Outlook

Case Management Tools

Benefits Administration Platforms

Job description

• Support administration of retirement, medical, dental, vision, life, disability, and wellness programs
• Resolve employee benefit questions and issues, escalating complex matters as needed
• Monitor participant issues, identify patterns, and recommend process improvements
• Manage invoice processing, record maintenance, and other benefits operations
• Partner with external benefits vendors on administration, issue resolution, and service coordination
• Monitor vendor service performance and elevate trends or concerns
• Contribute to vendor updates, annual enrollment readiness, and program changes
• Maintain compliance records, plan files, documentation, and standard process materials
• Prepare standard, recurring, and ad hoc reports and supporting documentation
• Compile and analyze benefits, vendor, and employee support data
• Review participation, utilization, and service data to improve employee experience and program effectiveness
• Develop and distribute benefits communications and education materials
• Assist during annual enrollment with testing, employee support, and issue resolution
• Support projects involving benefits administration, process improvement, systems enhancements, and vendor implementations
• Track project deliverables and contribute to assigned workstreams
• Collaborate with HR team members, employees, vendors, and internal partners

Requirements

• Bachelor’s degree in Human Resources, Business, Finance, or a related field, or an equivalent combination of education and experience
• 3–5 years of experience in benefits, HR, Total Rewards, finance, or a related analytical or operations role
• Strong attention to detail and organizational skills
• Ability to manage recurring responsibilities independently, apply sound judgment, and maintain accuracy in a detail-oriented environment
• Working knowledge of health and welfare benefits and employee support processes
• Proficiency in Microsoft Office tools, especially Excel and Outlook
• Experience supporting employee benefits, Total Rewards, HR operations, or related workforce programs preferred
• Familiarity with HR systems, case management tools, or benefits administration platforms preferred
• Foundational knowledge of artificial intelligence concepts and interest in applying AI-enabled tools preferred
• Ability to apply new technologies, including AI-enabled tools, with sound judgment, attention to data quality, and focus on improving employee experience preferred
• Interest in building broader knowledge across benefits, wellbeing, retirement, and leave programs preferred
• Demonstrated curiosity and growth mindset preferred

Core Competencies

Demonstrates expertise in benefits administration, including health and welfare benefits, employee support processes, and compliance management. Proficient in data analysis and reporting, with a strong focus on improving employee experience and program effectiveness through collaboration and process improvement.

Highest-signal resume keywords

• Benefits Administration
• Data Analysis
• Microsoft Excel
• HR Systems
• Process Improvement

Hard Skills

• Benefits Administration
• Data Analysis
• Invoice Processing
• Compliance Management
• Employee Support Processes

Soft Skills

• Attention to Detail
• Organizational Skills
• Sound Judgment
• Curiosity
• Growth Mindset

Industry Keywords

• Total Rewards
• Health Benefits
• Wellness Programs
• Retirement Programs
• Leave Programs

Tools & Technologies

• Microsoft Office
• Excel
• Outlook
• Case Management Tools
• Benefits Administration Platforms