Mid Level Benefits Representative Jobs

Mid level benefits representative jobs go to professionals ready to own open enrollment cycles, guide employees through complex claims, and advise on plan design with minimal supervision. Roles are concentrated across Insurance, Consulting & Professional Services, and Healthcare & Medical Services, with a mix of on-site, remote, and hybrid settings, and employers like USI Insurance Services, CVS Health, and Alvarez & Marsal hiring at this level now.

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Overview

Open roles72
Top stateFlorida
Top employerUSI Insurance Services
Top cityCoral Gables, FL
Work type71% On-site
Top industryInsurance

Showing 5 of 72+ Mid Level Benefits Representative jobs

Benefits Analyst
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Added 1d ago
Benefits Analyst
Bob's Discount Furniture
Hartford, Connecticut
Human Resources
Customer Service & Support
Compliance & Legal
Compensation & Benefits
On-Site
Bachelor's
5,001-10,000

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HR Generalist, Benefits & Operations
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Added 2d ago
HR Generalist, Benefits & Operations
Intellian Technologies
Rockville, Maryland
Human Resources
Corporate Training & Learning Development
Human Resources (HR) — Generalist
Compensation & Benefits
$66k - $90k/yr
On-Site
Bachelor's

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Sr. Payroll & Benefits Specialist
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Added 3d ago
Sr. Payroll & Benefits Specialist
Mevion Medical Systems Inc
Littleton, Massachusetts
Business Operations
Project & Program Management
Project Management
$90k - $105k/yr

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Senior Benefits Analyst
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Added 3d ago
Senior Benefits Analyst
KeyBank
Buffalo, New York
Human Resources
Corporate Training & Learning Development
Compliance & Legal
Compensation & Benefits
$69k - $105k/yr
Hybrid
Bachelor's
10,000+

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Manager, Human Resources & Benefits
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Added 3d ago
Manager, Human Resources & Benefits
Miami Marlins
Miami, Florida
Compensation & Benefits
Human Resources
Human Resources (HR) — Generalist
Learning & Development
Bachelor's degree in business administration

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Mid Level Benefits Representative Job Market

Who's Hiring

  • USI Insurance Services13
  • CVS Health8
  • Alvarez & Marsal4
  • Jobot3
  • Risksmith Insurance Services3

Top Industries Hiring

  • Insurance28
  • Consulting & Professional Services10
  • Healthcare & Medical Services6
  • Staffing & Recruiting4
  • Technology & Software4

Mid Level Benefits Representative Jobs: Frequently Asked Questions

How do I get a mid level benefits representative job?

Position your experience around ownership, not just task completion. Highlight benefits programs you managed end to end, claims issues you resolved independently, and any vendor or carrier relationships you handled directly. Tailor your resume to show familiarity with HRIS platforms, ACA compliance, and open enrollment coordination. Recruiters at this level want to see that you can operate without close supervision.

Which companies hire mid level benefits representatives?

Companies hiring mid level benefits representatives right now include USI Insurance Services, CVS Health, and Alvarez & Marsal, based on current listings on Migrate Mate as of November 2026. At this level, hiring tends to come from mid-size to large employers with dedicated HR or total rewards functions that need experienced professionals who can manage day-to-day benefits administration independently.

Are there remote mid level benefits representative jobs?

Yes, though availability varies by employer and role type. About 29% of mid level benefits representative openings are remote or hybrid as of November 2026, reflecting broader flexibility in HR-adjacent roles. Fully remote positions tend to favor candidates with strong experience using HRIS and benefits administration platforms, since in-person onboarding and oversight are limited.

How do I move up to a mid level benefits representative role?

Moving from entry level into a mid level benefits representative role comes from building depth in core functions over time. Focus on taking ownership of a full open enrollment cycle, developing fluency with benefits compliance requirements like COBRA, FMLA, and ACA, and demonstrating measurable impact such as error reduction or improved employee utilization rates. Consistent performance on cross-functional projects accelerates the transition.

Which industries hire the most mid level benefits representatives?

Mid Level benefits representative roles concentrate in Insurance, Consulting & Professional Services, and Healthcare & Medical Services, based on current listings on Migrate Mate as of November 2026. These sectors tend to employ large, benefits-eligible workforces and require experienced professionals who can handle the volume and complexity of ongoing plan administration, compliance tracking, and employee support at scale.