HR Generalist I * Benefits Specialist
POSITION OVERVIEW
As the Benefits Specialist, you will play a key role in supporting eAssist employees by administering and continuously enhancing our benefits programs. You will serve as the primary steward of employee benefits, ensuring our programs are competitive, compliant, cost-effective, and aligned with eAssist's mission, culture, and long-term people strategy.
In this role, you will oversee the full lifecycle of all employee benefit programs, including health and welfare plans, retirement benefits, leave administration, wellness initiatives, and related employee resources. You will analyze benefit trends, monitor program performance, recommend strategic improvements, and help shape future benefits offerings that support employee well-being, attraction, retention, and long-term organizational success.
Success in this role requires exceptional attention to detail, a passion for helping employees, and the ability to navigate complex benefits regulations with confidence. You will also serve as a trusted resource for employees by providing education, guidance, clear communication, and expert support throughout every stage of the employee experience.
This role is also responsible for completing verifications of employment and handling all leaves of absence.
KEY RESPONSIBILITIES
Live the eAssist Core Values
Demonstrate and promote the eAssist Core Values in every interaction while fostering a positive, collaborative, and employee-focused culture.
Benefits Administration
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Administer employee benefit programs, including medical, dental, vision, life insurance, and voluntary benefits, health savings accounts (HSA), health reimbursement arrangements (HRA), and retirement plans.
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Manage employee enrollments, terminations, qualifying life events, and benefit coverage changes within HRIS and payroll systems.
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Coordinate the annual open enrollment process, including system setup, testing, employee communications, and enrollment support.
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Ensure HSA/HRA employer contributions are accurately funded following each payroll cycle.
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Administer the company’s 401(k) plan, including enrollments, contributions, reporting, and vendor coordination.
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Respond to employee questions regarding benefit plans, payroll deductions, retirement programs, and eligibility with accuracy, professionalism, and empathy.
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Develop and distribute employee communications related to benefits programs, wellness initiatives, policy updates, and Open Enrollment.
Leave Administration
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Administer all Leave of Absence requests, including FMLA, personal leave, and other applicable leave programs.
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Coordinate with employees, leaders, payroll, benefit vendors, and third-party administrators to ensure accurate documentation, timely communication, and benefit continuation during approved leaves.
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Monitor leave timelines and maintain compliance with applicable federal, state, and company leave requirements.
Compliance & Program Administration
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Ensure benefit and retirement programs comply with all applicable federal, state, and local regulations, including ACA, COBRA, ERISA, HIPAA, FMLA, and Section 125 requirements.
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Stay informed of changing benefits regulations and proactively recommend and implement policy or process updates.
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Prepare and coordinate the annual form 5500 filing with partnering with auditors and third-party administrators to ensure timely and accurate submission.
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Support internal and external audits by preparing documentation, reconciliations, reports, and other compliance-related materials.
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Perform quarterly eligibility audits and insurance lookbacks to ensure employees enrolled in benefit plans continue to meet eligibility requirements.
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Partner with leaders to ensure timely communication regarding full-time and part-time status changes that impact benefits eligibility.
Systems, Reporting & Process Improvement
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Maintain accurate employee data across HRIS, payroll, and benefits administration systems.
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Prepare, review, and reconcile benefits reports to ensure data integrity and reporting accuracy.
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Participate in HRIS and benefit system implementations, upgrades, testing, and continuous process improvements.
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Identify opportunities to improve workflows, increase operational efficiency, strengthen compliance, and enhance the employee experience.
Employee Records & Administration
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Complete employment verification requests accurately and within established service timelines.
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Maintain accurate and confidential employee records related to benefits administration.
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Prepare employment-related correspondence, reports, and documentation as requested.
Collaboration & Team Support
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Build trusted relationships with employees, leaders, vendors, and external partners by providing exceptional customer service and subject matter expertise.
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Serve as a backup for other People Services functions and perform other duties as assigned.
QUALIFICATIONS
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One to two (1-2) years of experience in Human Resources preferred.
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A strong communicator who excels in both written and verbal communication and enjoys building positive relationships.
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Exceptionally organized with a knack for keeping multiple priorities moving without sacrificing accuracy or attention to detail.
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Comfortable with technology and experience using Google Workspace and other business tools to work efficiently.
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Experience administering employee benefits, including medical, dental, vision, life, disability, and 401(k) plans.
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Working knowledge of COBRA, FMLA, ACA, ERISA, HIPAA, Section 125 plans, and Form 5500 requirements.
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Experience working with HRIS/payroll systems (such as ADP) and benefits administration platforms.
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Strong analytical and problem-solving skills with the ability to interpret benefits regulations and resolve employee questions.
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Customer-service mindset with a passion for helping employees understand and maximize their benefits
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A trusted professional who handles confidential information with integrity, discretion, and sound judgment.
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Someone who takes initiative, owns their stewardship, and is always looking for ways to improve processes, strengthen the team, and make eAssist an even better place to work.
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HR Certifications: SHRM-CP or PHR and prior experience with ADP a plus
COMPENSATION
$60,000 - $68,000 annual salary (paid monthly)
TRAVEL
Remote. Travel typically less than 10%.
WHO WE ARE
At eAssist Dental Solutions, we empower dental practices by providing expert-driven, AI-powered dental billing solutions that maximize collections, streamline revenue cycle management, and allow dental teams to focus on patient care.
eAssist is the nation's leading dental billing and patient billing service provider for dental offices. We were co-founded by a dentist who understands what other dentists need. eAssist currently serves over 3000 dental practices through a unique proprietary technology platform that connects dental practices to vetted dental billing professionals, allowing practice owners to fully outsource their billing department.
eAssist was recently certified as a 2026 Top Workplace and 2025 Great Place to Work and has been featured on the Inc 5000 list of fastest-growing privately held companies in the U.S. for the last 10 years in a row! We were also just awarded #10 on Fortune's Great Place to Work for medium-sized Health Care and Biopharma!
eAssist is an Equal Opportunity Employer and considers applicants for all positions without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by law.
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