Senior Level Benefits Representative Jobs
Senior level benefits representative jobs put experienced professionals in charge of benefits program design, compliance oversight, and the cross-functional initiatives that shape how organizations support their workforce. Hiring is concentrated across Insurance, Technology & Software, and Banking & Financial Services, with a mix of on-site, hybrid, and remote roles available and employers like The Hartford, Stripe, and Amazon hiring at this level now.
Find JobsOverview
Showing 5 of 27+ Senior Level Benefits Representative jobs
Job no: 494452
Work type: Managerial
Location: Oklahoma City
Categories: Human Resources/Legal Affairs
Pay Range: Commensurate with education and experience.
Benefits Eligible: Yes
Work Schedule: Monday – Friday, 8:00 a.m. to 5:00 p.m., may be required to work beyond normal business hours
Travel: Required
Position Introduction:
The HR Assistant Director, Benefits will provide strategic leadership and oversight for benefits operations across all three campuses. Responsibilities will include guiding day-to-day benefits administration, ensuring regulatory compliance, leading process improvement efforts, and supervising staff to deliver consistent, high-quality service to university employees. The role will also serve as a key partner to the Director of Benefits and Retirement, supporting long-range planning, vendor management, and policy development, while building institutional knowledge.
Essential Duties
- Assist the Director of Benefits and Retirement with the strategic planning, development, implementation, and administration of the university’s comprehensive employee benefits programs.
- Manage assigned benefit programs and operational functions under the direction of the Director of Benefits and Retirement, ensuring accurate, timely, and customer-focused service delivery.
- Serve as a subject matter expert on assigned benefits programs and provide guidance to employees, benefit staff, and campus partners.
- Assist with the planning and administration of the university’s annual benefits enrollment process, including system configuration, testing, employee communications, vendor coordination, data reconciliation, and post-enrollment activities.
- Support compliance with applicable requirements, including ACA, COBRA, HIPAA, IRS regulations, and other federal and state requirements affecting employee benefits.
- Monitor vendor performance and service levels and work with vendors to resolve operational issues, employee concerns, data discrepancies, and other service-related matters.
- Coordinate reconciliation of benefits eligibility, enrollment records, payroll deductions, premiums, vendor invoices, and other benefits-related financial and enrollment data.
- Assist with the development, implementation, and maintenance of benefits policies, procedures, process documentation, and internal controls.
- Research and resolve complex benefits questions and issues and escalate matters to the Director of Benefits and Retirement when appropriate.
- Develop and coordinate employee communications, educational materials, presentations, workshops, and informational sessions related to benefits programs.
- Support benefits-related projects, vendor implementations, audits, and university-wide initiatives.
- Promote consistent and high-quality customer service across benefits operations.
- Performs various duties as needed to successfully fulfill the function of the position.
Required Education and Experience:
- Bachelor's Degree
- 6 years in a related field
- 2 years of managerial experience
Hiring Contingent Upon a Background Check: Yes
Advertised: 12 Nov 2026 Central Standard Time
Applications close: 26 Jan 2027 Central Standard Time
Job no: 494452
Work type: Managerial
Location: Oklahoma City
Categories: Human Resources/Legal Affairs
Pay Range: Commensurate with education and experience.
Benefits Eligible: Yes
Work Schedule: Monday – Friday, 8:00 a.m. to 5:00 p.m., may be required to work beyond normal business hours
Travel: Required
Position Introduction:
The HR Assistant Director, Benefits will provide strategic leadership and oversight for benefits operations across all three campuses. Responsibilities will include guiding day-to-day benefits administration, ensuring regulatory compliance, leading process improvement efforts, and supervising staff to deliver consistent, high-quality service to university employees. The role will also serve as a key partner to the Director of Benefits and Retirement, supporting long-range planning, vendor management, and policy development, while building institutional knowledge.
Essential Duties
- Assist the Director of Benefits and Retirement with the strategic planning, development, implementation, and administration of the university’s comprehensive employee benefits programs.
- Manage assigned benefit programs and operational functions under the direction of the Director of Benefits and Retirement, ensuring accurate, timely, and customer-focused service delivery.
- Serve as a subject matter expert on assigned benefits programs and provide guidance to employees, benefit staff, and campus partners.
- Assist with the planning and administration of the university’s annual benefits enrollment process, including system configuration, testing, employee communications, vendor coordination, data reconciliation, and post-enrollment activities.
- Support compliance with applicable requirements, including ACA, COBRA, HIPAA, IRS regulations, and other federal and state requirements affecting employee benefits.
- Monitor vendor performance and service levels and work with vendors to resolve operational issues, employee concerns, data discrepancies, and other service-related matters.
- Coordinate reconciliation of benefits eligibility, enrollment records, payroll deductions, premiums, vendor invoices, and other benefits-related financial and enrollment data.
- Assist with the development, implementation, and maintenance of benefits policies, procedures, process documentation, and internal controls.
- Research and resolve complex benefits questions and issues and escalate matters to the Director of Benefits and Retirement when appropriate.
- Develop and coordinate employee communications, educational materials, presentations, workshops, and informational sessions related to benefits programs.
- Support benefits-related projects, vendor implementations, audits, and university-wide initiatives.
- Promote consistent and high-quality customer service across benefits operations.
- Performs various duties as needed to successfully fulfill the function of the position.
Required Education and Experience:
- Bachelor's Degree
- 6 years in a related field
- 2 years of managerial experience
Hiring Contingent Upon a Background Check: Yes
Advertised: 12 Nov 2026 Central Standard Time
Applications close: 26 Jan 2027 Central Standard Time
See All 27 Senior Level Benefits Representative Jobs
Find roles that match your experience and apply in just a few clicks.
Find JobsSenior Level Benefits Representative Job Market
Who's Hiring
Top Industries Hiring
- Insurance12
- Technology & Software4
- Banking & Financial Services3
- Retail2
- Medical Devices2
Senior Level Benefits Representative Jobs: Frequently Asked Questions
How do I get a senior level benefits representative job?
Employers at this level look for demonstrated ownership of benefits programs, not just administration. Candidates who have led open enrollment for large employee populations, managed vendor relationships, ensured compliance with ERISA and ACA requirements, and mentored junior staff stand out. A CEBS designation or comparable credential, combined with experience interpreting plan documents and advising HR leadership, gives you a clear edge over generalist applicants.
Which companies hire senior level benefits representatives?
Companies hiring senior level benefits representatives right now include The Hartford, Stripe, and Amazon, based on current listings on Migrate Mate as of November 2026. At this level, hiring tends to come from large self-insured employers, national professional services firms, and health systems that run complex multi-state benefits programs requiring deep subject matter expertise.
Are there remote senior level benefits representative jobs?
Yes, though availability varies by employer and role scope. About 79% of senior level benefits representative openings are remote or hybrid as of November 2026, reflecting broader workplace flexibility in HR and benefits functions. Roles tied to on-site workforce populations or requiring regular collaboration with brokers and carriers are more likely to have an in-person component.
What makes a benefits representative role senior level?
Senior level benefits representative roles carry ownership over program strategy, not just day-to-day administration. That means leading plan design reviews, managing broker and vendor negotiations, ensuring regulatory compliance across ERISA, HIPAA, and ACA, and advising HR and finance leadership on cost and competitiveness. Mentoring junior benefits staff and driving process improvements across the benefits function are also consistent expectations at this stage.
Which industries hire the most senior level benefits representatives?
Senior Level benefits representative roles concentrate in Insurance, Technology & Software, and Banking & Financial Services, based on current listings on Migrate Mate as of November 2026. These sectors tend to employ large, geographically distributed workforces with complex benefits needs, driving consistent demand for experienced professionals who can manage sophisticated plan portfolios and maintain compliance across multiple jurisdictions.