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Benefits Specialist

Admiral Talent > Jobs > Benefits Specialist

About the Opportunity

Benefits are one of the largest investments an organization makes in its people—and one of the most personal ways employees experience the organization behind their employment.

A benefits program may look straightforward from the outside. Behind it sits a sophisticated ecosystem of health plans, retirement programs, insurance providers, eligibility rules, payroll deductions, leave programs, regulatory requirements, enrollment technology, employee communications, vendor relationships, financial controls, and thousands of individual employee circumstances.

We are seeking an experienced Benefits Specialist to help operate, improve, and scale that ecosystem within a complex enterprise environment.

This position will support a broad portfolio of employee benefits and serve as a trusted subject-matter resource for employees, HR partners, Payroll, Finance, Legal, HRIS teams, and external benefits providers.

The role is intentionally broader than transactional benefits administration.

You will help ensure programs operate accurately, employees receive clear and thoughtful support, vendors deliver against expectations, benefits data remains reliable, regulatory requirements are addressed, and emerging issues are identified before they become larger operational problems.

The Benefits Specialist may support programs involving medical, dental, vision, retirement, life and disability insurance, health savings and flexible spending accounts, wellness, employee assistance, voluntary benefits, leave-related benefits, and other enterprise offerings based on the organization’s benefits portfolio.

You will also contribute to annual enrollment, benefits implementations, plan changes, acquisitions, vendor transitions, audits, employee communications, and other significant benefits initiatives.

The strongest candidate will understand that benefits work requires an unusual combination of capabilities.

You need enough technical knowledge to interpret plan provisions and eligibility requirements.

You need enough analytical discipline to recognize when enrollment or payroll data does not look right.

You need enough empathy to help an employee navigating a difficult personal situation.

And you need enough operational judgment to recognize when an individual question indicates a broader system, vendor, or process issue.

Technology is also changing this function.

We expect the Benefits Specialist to help improve the employee experience through modern HR platforms, workflow automation, analytics, digital self-service, knowledge management, and responsible AI-assisted HR operations—while recognizing that sensitive benefits decisions require privacy, accuracy, and appropriate human judgment.

Ultimately, this position will help ensure employees do not merely have competitive benefits.

They understand them, can access them, and can trust that they will work when they need them.


Essential Duties and Responsibilities

BENEFITS PORTFOLIO | Health & Welfare Programs

  • Support administration of enterprise health and welfare benefit programs.
  • Maintain accurate eligibility and enrollment processes.
  • Coordinate with employees, HR teams, payroll partners, and benefits vendors.
  • Investigate complex enrollment discrepancies.
  • Support plan changes and benefit implementations.
  • Monitor recurring employee issues for systemic patterns.
  • Maintain accurate plan documentation and operating procedures.
  • Help ensure consistent administration across employee populations.

Programs may include:

  • Medical
  • Dental
  • Vision
  • Life insurance
  • Disability coverage
  • HSA
  • FSA
  • Employee Assistance Programs
  • Wellness programs
  • Voluntary benefits

EMPLOYEE EXPERIENCE | Benefits Advisory & Resolution

  • Serve as a knowledgeable escalation resource for complex employee benefits questions.
  • Explain benefits programs in clear, understandable language.
  • Research eligibility and coverage issues.
  • Coordinate resolution with external providers.
  • Handle sensitive employee circumstances with discretion and empathy.
  • Escalate significant issues appropriately.
  • Identify opportunities to improve benefits education and self-service.
  • Maintain confidentiality of employee information.

ANNUAL CYCLE | Open Enrollment

Play a significant role in planning and executing annual enrollment.

Responsibilities may include:

  • Enrollment configuration
  • Eligibility validation
  • Plan testing
  • Employee communications
  • Benefits guides
  • Educational sessions
  • Vendor coordination
  • HRIS testing
  • Employee support
  • Enrollment audits
  • Post-enrollment reconciliation

Identify lessons from each enrollment cycle and convert them into improvements for the following year.

RETIREMENT | Savings & Financial Wellbeing

  • Support administration of retirement and savings programs.
  • Coordinate with retirement-plan administrators and internal stakeholders.
  • Research employee contribution and eligibility questions.
  • Support plan audits and compliance activities.
  • Assist with employee education.
  • Monitor data interfaces and contribution processes.
  • Help identify opportunities to strengthen employee financial wellbeing.

GOVERNANCE | Regulatory & Plan Compliance

Support benefits administration in accordance with applicable requirements, which may include:

  • ERISA
  • ACA
  • HIPAA
  • COBRA
  • IRS requirements
  • Section 125
  • FMLA coordination
  • State-specific requirements
  • Plan-document provisions

Partner with Benefits leadership, Legal, Payroll, HR, and external advisors on complex compliance matters.

Maintain appropriate records and documentation supporting plan administration.

VENDOR ECOSYSTEM | Performance & Service Management

Partner with benefits providers, brokers, consultants, administrators, and technology vendors.

  • Monitor service performance.
  • Track unresolved issues.
  • Coordinate escalations.
  • Participate in regular vendor reviews.
  • Identify recurring service failures.
  • Validate implementation requirements.
  • Support vendor transitions.
  • Maintain accountability for agreed deliverables.
  • Help ensure vendor relationships translate into strong employee experiences.

DATA | Benefits Analytics & Reconciliation

Use benefits data to identify operational issues and support better decisions.

Analyze areas such as:

  • Enrollment
  • Eligibility
  • Participation
  • Utilization
  • Employee inquiries
  • Vendor performance
  • Payroll deductions
  • Program adoption
  • Enrollment trends
  • Benefits costs
  • Service issues

Perform regular reconciliations between HR, payroll, benefits administration, and vendor systems.

Investigate discrepancies through resolution rather than simply reporting them.

SYSTEMS | HRIS & Benefits Technology

Support benefits processes across platforms such as:

  • Workday
  • UKG
  • ADP
  • Oracle HCM
  • SAP SuccessFactors
  • Benefitfocus
  • Businessolver
  • Alight
  • Fidelity
  • Empower
  • Comparable enterprise HR and benefits platforms

Participate in system configuration, testing, integrations, implementations, and process improvements as appropriate.

CONTROLS | Data Integrity & Audit Readiness

  • Maintain accurate employee benefits records.
  • Perform eligibility audits.
  • Review enrollment files and vendor feeds.
  • Validate payroll deductions.
  • Support internal and external audits.
  • Investigate control exceptions.
  • Maintain documentation supporting benefits processes.
  • Identify opportunities to strengthen preventive controls.

COMMUNICATION | Employee Benefits Education

Partner with Communications and HR teams to create clear benefits information.

Develop or support:

  • Enrollment materials
  • Employee guides
  • FAQs
  • Knowledge-base content
  • Benefits announcements
  • Educational webinars
  • Decision-support materials
  • New-hire benefits resources
  • Life-event guidance

Translate technical plan language into information employees can realistically understand and use.

LEAVE & LIFE-EVENT COORDINATION

  • Support benefits implications associated with qualifying life events.
  • Coordinate appropriately with leave, disability, payroll, and HR teams.
  • Help employees understand how changes affect coverage.
  • Resolve discrepancies involving benefits continuation.
  • Maintain accurate documentation.
  • Ensure sensitive situations receive appropriate attention.

DIGITAL TRANSFORMATION | Automation & AI

Identify opportunities to improve benefits operations through technology.

Potential initiatives may include:

  • Workflow automation
  • Employee self-service
  • Intelligent knowledge search
  • Automated reconciliation
  • Benefits analytics
  • Case categorization
  • AI-assisted knowledge management
  • Personalized benefits education
  • Digital enrollment support

Ensure technology is implemented with appropriate attention to employee privacy, data security, accuracy, compliance, and human oversight.

ENTERPRISE PROJECTS | Benefits Transformation

Contribute benefits expertise to major organizational initiatives, potentially including:

  • Mergers and acquisitions
  • HRIS transformations
  • New benefits implementations
  • Vendor migrations
  • Geographic expansion
  • Workforce restructuring
  • Plan redesign
  • Payroll transformation
  • Employee experience programs
  • Benefits harmonization

Represent benefits requirements throughout planning, testing, implementation, and stabilization.


Job Qualifications and Requirements

  • 5+ years of progressive experience in employee benefits, benefits administration, total rewards, HR operations, benefits consulting, or a related discipline.
  • Strong working knowledge of U.S. health and welfare benefits.
  • Experience administering medical, dental, vision, life, disability, retirement, or related employee programs.
  • Experience resolving complex benefits issues.
  • Strong understanding of employee eligibility and enrollment processes.
  • Familiarity with ERISA, ACA, HIPAA, COBRA, and related benefits requirements.
  • Experience supporting annual open enrollment.
  • Strong data reconciliation and analytical skills.
  • Experience working with benefits vendors and administrators.
  • Strong attention to detail and documentation.
  • Ability to handle confidential employee information appropriately.
  • Strong written and verbal communication capabilities.
  • Experience operating within a complex, multi-stakeholder organization.
  • Bachelor’s degree in Human Resources, Business Administration, Finance, Management, or a related discipline preferred.

Experience That Will Stand Out

We particularly value candidates with experience involving:

  • Large employee populations
  • Multi-state workforces
  • Workday Benefits
  • Benefits administration platforms
  • Retirement-plan administration
  • Benefits audits
  • Vendor implementations
  • M&A benefits integration
  • HRIS transformations
  • Benefits analytics
  • Payroll reconciliation
  • Self-funded health plans
  • Leave and disability coordination
  • Global or multinational organizations
  • Benefits communications
  • Employee self-service transformation

Professional credentials such as CEBS, SHRM-CP, SHRM-SCP, PHR, SPHR, or comparable benefits/HR certifications are valued but not required.


Personal Capabilities and Qualifications

Employee Empathy

You understand that what looks like an administrative benefits question may involve an employee’s health, family, finances, or major life event.

Technical Precision

You are comfortable working with detailed plan provisions, eligibility rules, system records, and regulatory requirements.

Investigative Mindset

When two systems disagree, you want to know why—not simply which number should be manually corrected.

Discretion

You understand the sensitivity of benefits and employee information and treat it accordingly.

Operational Ownership

You follow issues through resolution rather than transferring them between teams.

Clear Communication

You can explain complicated benefits concepts without forcing employees to become benefits experts themselves.

Analytical Thinking

You can recognize patterns across employee inquiries, enrollment data, vendor performance, and operational exceptions.

Collaborative Judgment

You know when an issue belongs with Payroll, Legal, HRIS, a benefits vendor, HR leadership—or requires several of them working together.

Continuous Improvement

You consistently ask whether recurring employee questions can be prevented through better systems, processes, communications, or education.


Strategic Support

The Benefits Specialist will provide subject-matter expertise across broader People and enterprise initiatives.

Strategic involvement may include:

  • Total Rewards strategy
  • Benefits modernization
  • Employee experience
  • Workforce retention
  • HR technology transformation
  • Benefits cost management
  • Vendor strategy
  • Employee wellbeing
  • M&A integration
  • Workforce expansion
  • Benefits harmonization
  • Digital HR
  • AI-enabled HR operations
  • Benefits communications
  • Annual workforce planning

The position will help leadership understand the practical connection between benefits design, employee experience, operational execution, technology, and workforce trust.


Working Conditions

  • Hybrid or remote working arrangements may be available depending on organizational requirements.
  • Regular collaboration with Benefits, Total Rewards, HR, Payroll, Finance, Legal, HRIS, and external providers.
  • Work requires frequent use of HR, benefits, analytics, and collaboration platforms.
  • Additional availability may occasionally be required during open enrollment, major implementations, acquisitions, audits, or significant benefits transitions.
  • Collaboration across multiple U.S. time zones may be required.
  • Limited travel may be necessary for team meetings, vendor sessions, or enterprise initiatives.
  • The role involves access to sensitive employee and benefits information and therefore requires a high degree of confidentiality, judgment, and data-security awareness.

Job Function

Primary Function: Employee Benefits & Total Rewards Operations

Functional Scope: Benefits Administration + Employee Experience + Compliance + Analytics

Specialization Areas:

Employee Benefits | Total Rewards | Health & Welfare | Retirement Benefits | Open Enrollment | ERISA | ACA | HIPAA | COBRA | Benefits Analytics | Vendor Management | HRIS | Workday | Employee Experience | Benefits Compliance | Benefits Operations


Compensation & Benefits

The anticipated compensation range for this position is:

$155,000 – $215,000 annually

Final compensation will consider benefits expertise, complexity and scale of prior programs, HR technology proficiency, regulatory knowledge, enterprise experience, analytical capabilities, geographic considerations, and overall qualifications.

The broader total rewards package may include:

  • Annual performance incentives
  • Equity or long-term incentives where applicable
  • Comprehensive medical, dental, and vision coverage
  • Health savings and flexible spending programs
  • Employer-sponsored life and disability coverage
  • Retirement savings with employer contributions
  • Generous paid time off and company holidays
  • Paid parental and family leave
  • Employee assistance and wellbeing programs
  • Flexible or remote working arrangements
  • Professional certification support
  • Learning and career-development resources
  • Additional voluntary benefits according to organizational policy

Why Join Us

Benefits work becomes most visible at moments that matter.

A new employee deciding how to protect their family.

A parent adding a child to coverage.

Someone trying to understand a medical claim.

An employee planning for retirement.

A colleague navigating disability or another significant life event.

Behind every one of those experiences is an operating system that has to work correctly.

This position gives you the opportunity to improve that system at scale.

You will not be limited to processing enrollments and answering routine questions. You will have exposure to benefits strategy, enterprise technology, analytics, compliance, vendor performance, employee communications, process transformation, and major People initiatives.

You will also help modernize how employees interact with benefits—making information easier to find, processes easier to complete, and support more intelligent when circumstances become complicated.

The impact of your work will connect:

Benefits Strategy → Accurate Administration → Clear Communication → Employee Access → Trust → Workforce Experience

For a benefits professional who combines technical expertise with genuine care for the employee experience, this role offers the opportunity to make one of the organization’s most important investments in its people work better every day.