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Open Enrollment Jobs in Wisconsin (NOW HIRING)

CFS

Payroll & Benefits Specialist

Madison, WI

$55K - $65K/yr

... open enrollment administration and compliance-related activities across multiple states Key Responsibilities for the Payroll & Benefits Specialist: • Process and maintain new hire paperwork ...

CFS

Payroll & Benefits Specialist

Madison, WI · On-site

$55K - $65K/yr

... open enrollment administration and compliance-related activities across multiple states Key Responsibilities for the Payroll & Benefits Specialist: • Process and maintain new hire paperwork ...

DERSE INC

Human Resources Generalist

Milwaukee, WI

Assume ownership of the open enrollment process. This includes: * Working within our HRIS to build and test open enrollment site * Handle all communication to staff and answer any inquiry within a ...

DERSE, Inc.

Human Resources Generalist

Milwaukee, WI · On-site

Assume ownership of the open enrollment process. This includes: * Working within our HRIS to build and test open enrollment site * Handle all communication to staff and answer any inquiry within a ...

DERSE INC

Human Resources Generalist

Milwaukee, WI · On-site

Assume ownership of the open enrollment process. This includes: * Working within our HRIS to build and test open enrollment site * Handle all communication to staff and answer any inquiry within a ...

EK Machine

Benefits Manager

Fall River, WI

... including open enrollment • Partner with leadership on wellness and return-to-work programs Qualifications • Strong knowledge of benefits administration and compliance • Analytical and ...

EK Machine

Benefits Manager

Fall River, WI · On-site

... including open enrollment • Partner with leadership on wellness and return-to-work programs Qualifications • Strong knowledge of benefits administration and compliance • Analytical and ...

CFS

Payroll & Benefits Specialist

Madison, WI

$55K - $65K/yr

Administer employee benefits, including enrollments, changes, terminations, COBRA notifications, and open enrollment support. * Enter payroll deductions, garnishments, benefit elections, and weekly ...

Flambeau, Inc.

Human Resources Coordinator

Baraboo, WI

$19.75 - $26/hr

Provide responses to DWD related to unemployment. Assist with benefit administration, ordering insurance cards, enrollment reminders, answer basic questions, log payments, assist with open enrollment ...

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Open Enrollment information

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$12

$22

$33

How much do open enrollment jobs pay per hour?

As of Jul 30, 2026, the average hourly pay for open enrollment in Wisconsin is $22.80, according to ZipRecruiter salary data. Most workers in this role earn between $18.17 and $25.96 per hour, depending on experience, location, and employer.

What challenges might I encounter as an Open Enrollment Specialist, and how can I successfully navigate them?

One of the main challenges Open Enrollment Specialists face is communicating complex benefits information to employees with varying levels of understanding, often within tight deadlines. You may also need to handle a high volume of inquiries and manage sensitive personal information with utmost confidentiality. Success in the role involves keeping up-to-date with plan changes, maintaining excellent organizational skills, and providing clear, empathetic support to employees. By developing strong relationships with HR teams and benefits providers, you can ensure a smooth and efficient open enrollment process for everyone involved.

What are the key skills and qualifications needed to thrive in the Open Enrollment position, and why are they important?

To excel in an Open Enrollment Specialist role, you need strong knowledge of health insurance plans, benefits administration, and excellent customer service skills, typically supported by experience in HR or benefits coordination. Familiarity with benefits administration platforms, HRIS systems, and understanding of relevant state and federal regulations (such as ACA or HIPAA) are commonly required. Exceptional communication, active listening, and problem-solving skills help effectively guide employees through complex enrollment processes. These competencies are crucial for ensuring employees understand their benefits options and for maintaining compliance with organizational and legal standards.

What is an Open Enrollment job?

An Open Enrollment job typically involves assisting individuals in selecting or enrolling in health insurance and other benefits during the designated enrollment period. These roles are common in the healthcare, insurance, and HR industries, where employees help clients understand plan options, process applications, and answer coverage-related questions. Positions may be temporary or seasonal, especially during peak enrollment times, and require strong communication and customer service skills.

What are the most commonly searched types of Open Enrollment jobs in Wisconsin? The most popular types of Open Enrollment jobs in Wisconsin are:
What are popular job titles related to Open Enrollment jobs in Wisconsin? For Open Enrollment jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Open Enrollment jobs in Wisconsin look for? The top searched job categories for Open Enrollment jobs in Wisconsin are:
Open Enrollment jobs near you
Infographic showing various Open Enrollment job openings in Wisconsin as of July 2026, with employment types broken down into 77% Full Time, 17% Part Time, 1% Temporary, and 5% Contract. Highlights an 94% Physical, 1% Hybrid, and 5% Remote job distribution, with an average salary of $47,426 per year, or $22.8 per hour.

Payroll & Benefits Specialist

CFS

Madison, WI

$55K - $65K/yr

Full-time

Re-posted 5 days ago

Job description

Ready to step into a highly visible HR role where you'll own benefits administration, compliance coordination, and employee onboarding for a growing national organization? This is an excellent opportunity to join one of the largest insulation companies in the U.S. and make a direct impact as the business continues its rapid expansion.

Payroll & Benefits Specialist

Salary: $55,000 - $65,000

Why This Opportunity Stands Out:

• Join the 3rd largest insulation business in the U.S. with $230M in revenue and 29 locations across 16 states
• Be part of a family-owned organization that combines stability with an entrepreneurial mindset
• Gain broad HR exposure across benefits, payroll, onboarding, compliance, and employee administration
• Work in a casual, relaxed environment where employees are trusted to own their responsibilities
• Support a company in growth mode, with multiple expansion initiatives and new locations opening across the country
• Collaborate closely with senior HR leadership and play a key role in important HR processes
• Take ownership of open enrollment administration and compliance-related activities across multiple states

Key Responsibilities for the Payroll & Benefits Specialist:

• Process and maintain new hire paperwork, employee records, and HR documentation for hourly employees
• Administer benefits enrollments, terminations, status changes, and COBRA notifications
• Manage payroll-related deductions including benefits, garnishments, child support, and company programs
• Enter and maintain weekly payroll hours for California-based employees
• Lead the administrative components of the annual open enrollment process
• Support multi-state compliance activities, unemployment claim responses, and employee record accuracy


Qualifications for the Payroll & Benefits Specialist:

• Associates or Bachelors degree preferred with 2+ years of benefits administration experience
• Understanding of health and dental plan eligibility and enrollment processes
• Experience with onboarding documentation and employment verification requirements, including I-9s
• Experience maintaining accurate HR records and supporting compliance-related activities

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