Mid Level Benefits Supervisor Jobs

Mid level benefits supervisor jobs go to professionals ready to own benefits program administration end to end, guide junior staff, and make enrollment and compliance decisions with limited oversight. Roles run across Insurance, Consulting & Professional Services, and Healthcare & Medical Services, with a mix of on-site, hybrid, and remote settings, and employers like USI Insurance Services, CVS Health, and Alvarez & Marsal hiring at this level now.

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Overview

Open roles71
Top stateFlorida
Top employerUSI Insurance Services
Top cityCoral Gables, FL
Work type73% On-site
Top industryInsurance

Showing 5 of 71+ Mid Level Benefits Supervisor 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 Supervisor Job Market

Who's Hiring

  • USI Insurance Services12
  • CVS Health8
  • Alvarez & Marsal4
  • Jobot3
  • Risksmith Insurance Services3

Top Industries Hiring

  • Insurance27
  • Consulting & Professional Services10
  • Healthcare & Medical Services6
  • Staffing & Recruiting4
  • Technology & Software4

Mid Level Benefits Supervisor Jobs: Frequently Asked Questions

How do I get a mid level benefits supervisor job?

Position yourself by highlighting direct ownership of benefits processes, such as open enrollment management, vendor relationships, or compliance audits you led without heavy supervision. Emphasize breadth across health, retirement, and leave programs, and show measurable outcomes like error rate reductions or improved employee utilization. Certifications such as CEBS or PHR strengthen your profile, and tailoring your resume to match the specific benefit lines each employer administers makes a real difference.

Which companies hire mid level benefits supervisors?

Companies hiring mid level benefits supervisors right now include USI Insurance Services, CVS Health, and Alvarez & Marsal, based on current listings on Migrate Mate as of November 2026. Hiring at this level tends to come from mid-size to large employers with dedicated HR or total rewards teams complex enough to need hands-on supervisory oversight of day-to-day benefits operations.

Are there remote mid level benefits supervisor jobs?

Yes, though availability varies by employer size and benefits complexity. About 27% of mid level benefits supervisor openings are remote or hybrid as of November 2026, reflecting broader flexibility in HR operations roles. Fully remote positions often appear at companies with distributed workforces or centralized benefits administration teams that operate independently of a single office location.

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

Moving into a mid level role comes from building deeper ownership over time, starting with hands-on work in benefits administration, then gradually taking on coordination of open enrollment, leave tracking, or vendor communication without needing to escalate routine decisions. Demonstrating that you can manage a full benefits cycle, spot compliance gaps, and guide less experienced colleagues positions you as ready for the step up.

Which industries hire the most mid level benefits supervisors?

Mid Level benefits supervisor 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 have large, stable workforces with complex benefit structures, which creates sustained demand for supervisors who can manage ongoing administration, support employees through enrollment, and keep programs aligned with regulatory requirements.