Mid Level Benefits Specialist Jobs

Mid level benefits specialist jobs go to professionals ready to own benefits program administration end to end, guide junior colleagues, and make plan recommendations with minimal oversight. Positions are concentrated across Technology & Software, Healthcare & Medical Services, and Consulting & Professional Services, with 29% offering remote or hybrid schedules and employers like Rippling, viaPhoton, and CandyCo hiring at this level now.

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Overview

Open roles11
Top stateMassachusetts
Top employerRippling
Top cityBoston, MA
Work type71% On-site
Top industryTechnology

Showing 5 of 11+ Mid Level Benefits Specialist jobs

Sr. Payroll & Benefits Specialist
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Added 4d 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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Sr Specialist, Member Engagement (Member Benefits Analysis) Ohio Remote
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Added 1w ago
Sr Specialist, Member Engagement (Member Benefits Analysis) Ohio Remote
Molina Healthcare
Ohio
Customer Service
Customer Success
Customer Support
$18 - $35/hr
Remote (US)
10,000+

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Payroll & Benefits Specialist (HR Generalist)
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Added 1w ago
Payroll & Benefits Specialist (HR Generalist)
viaPhoton
Naperville, Illinois
Human Resources
Human Resources (HR) — Generalist
Learning & Development
Recruiting & Talent Acquisition
$75k - $90k/yr
Bachelor's degree in business

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Senior Human Resources Specialist - Benefits
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Added 3w ago
Senior Human Resources Specialist - Benefits
Wood Mackenzie
Boston, Massachusetts
Business Development
Human Resources (HR) — Generalist
Recruiting & Talent Acquisition
$90k - $100k/yr
Hybrid
1,001-5,000

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Payroll & Benefits Specialist
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Added 1mo ago
Payroll & Benefits Specialist
CandyCo LLC
Lindon, Utah
Accounting
Bookkeeping & AP/AR
Bachelor's degree in finance

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Mid Level Benefits Specialist Job Market

Who's Hiring

Rippling2 open roles
viaPhoton1 open role
CandyCo1 open role

Top Industries Hiring

  • Technology & Software
  • Healthcare & Medical Services
  • Consulting & Professional Services
  • Food & Beverage
  • Medical Devices

Mid Level Benefits Specialist Jobs: Frequently Asked Questions

How do I get a mid level benefits specialist job?

Position yourself by highlighting direct ownership of benefits programs rather than task-level support. Emphasize experience managing open enrollment, resolving complex employee inquiries, and working alongside benefits vendors or brokers. Recruiters at this level want evidence that you've handled a program from design to delivery, so tailor your resume and cover letter to specific outcomes you drove, not just responsibilities you held.

Which companies hire mid level benefits specialists?

Companies hiring mid level benefits specialists right now include Rippling, viaPhoton, and CandyCo, based on current listings on Migrate Mate as of November 2026. Mid-sized and large employers with dedicated HR functions tend to post the most roles at this level, since they need specialists who can run programs independently without heavy senior oversight.

Are there remote mid level benefits specialist jobs?

Yes, remote and hybrid options are widely available at this level. About 29% of mid level benefits specialist openings are remote or hybrid as of November 2026, reflecting how much of the core work, vendor coordination, employee communications, and plan administration, can be done effectively outside a traditional office setting.

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

Growth from entry level into a mid level benefits specialist role comes from deepening your technical knowledge of plan types such as medical, dental, FSA, and COBRA, and taking on progressively more ownership. Volunteering to lead open enrollment cycles, managing vendor relationships, and quantifying your impact, such as error reduction or improved employee participation rates, signals to employers that you're ready for greater autonomy.

Which industries hire the most mid level benefits specialists?

Mid Level benefits specialist roles concentrate in Technology & Software, Healthcare & Medical Services, and Consulting & Professional Services, based on current listings on Migrate Mate as of November 2026. These sectors tend to employ large, geographically distributed workforces that require consistent, knowledgeable benefits administration and benefit most from specialists who can operate independently across multiple plan structures.