Payroll & Benefits Specialist
Creative Financial Staffing
Madison, WI · Posted November 3, 2026
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Where Madison, WI ranks
Where Madison, WI placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #8Best all-round cities for new graduates in the Great Lakes49 / 100 · of 16
- #8Best all-round cities for remote workers in the Midwest57 / 100 · of 20
- #8Best all-round cities for remote workers in the Great Lakes57 / 100 · of 16
- #10Cities with the most jobs that do not need a four-year degree in the Great Lakes56 jobs · of 36
- #11Best cities for entry-level jobs that want AI skills in the Great Lakes4% · of 38
- #11Best all-round cities for new graduates in the Midwest51 / 100 · of 20
Rankings about human resources jobs
- Best cities for HR jobs #1 New York (994 openings)
- Best cities for HR pay after cost of living #1 San Mateo ($158k)
- Most requested AI skills in HR jobs #1 AI tools in daily work (5.7%)
- Employers with the most HR jobs #1 Amazon (291 roles)
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How AI is used in this kind of work
AI use among payroll and timekeeping clerks is little observed so far. Measured exposure for payroll and timekeeping clerks: 5% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
About the job
Title: Payroll & Benefits Specialist
Salary: $60,000-$70,000
Why This Opportunity Stands Out:
This Payroll & Benefits Specialist role is far from transactional —you’ll be trusted to own the function and help shape how payroll and benefits evolve as the company continues to grow.
The Payroll & Benefits Specialist will step into a high-impact role supporting a multi-state workforce , giving you exposure and experience that goes beyond a typical single-location environment.
You’ll join a team that values longevity and stability —people stay here, and that says a lot about the culture and leadership.
Leadership is hands-off but supportive —you’ll have the autonomy to run with ideas while still having guidance when you need it.
Flexibility is built into the culture – offering a hybrid schedule and realistic expectations around workload.
Strong benefits package including:
401(k) with company match
Comprehensive health, dental, and vision coverage
Bonus potential + long-term career growth
The Payroll & Benefits Specialist will have the opportunity to drive process improvements, streamline systems, and create efficiencies —your input will truly matter.
Key Responsibilities:
Process all new hire paperwork
Administer employee benefits programs including health, retirement, and leave management
Serve as the primary point of contact for employee payroll and benefits questions
Enter payroll deductions for any benefits, child support, and wage garnishments
Qualifications:
3+ years of experience in benefits administration
Strong knowledge of payroll systems and benefits processes
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