Senior Systems Administrator Jobs in Wisconsin
Senior Systems Administrator jobs in Wisconsin are concentrated in Milwaukee, Madison, and Green Bay, where anchor employers like Fiserv, Epic Systems, and the University of Wisconsin System maintain large, complex IT infrastructures that demand experienced administrators. The work centers on Windows and Linux server management, virtualization platforms, and enterprise network security, with growing demand in healthcare IT and financial technology environments. Competition is strong at the senior level, and employers consistently look for candidates who can lead infrastructure projects and mentor junior staff. Find a role that fits below and apply directly.
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Showing 5 of 6+ Senior Systems Administrator jobs
Role Snapshot
The Senior Business Systems Administrator serves as the technical subject‑matter expert for Costpoint and related financial systems, ensuring secure, stable, and optimized performance across all finance applications and integrations. This role leads complex system configuration, integration management, advanced troubleshooting, and technical design efforts. It also retains business-analysis responsibilities to ensure system enhancements meet operational needs. The senior administrator partners with Finance, Accounting, IT, and leadership to deliver robust, scalable financial system solutions and support continuous improvement.
Salary Range
115,000-135,000
The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, and experience.
Work Location
Our first consideration will be to have this employee live in the state of Wisconsin to take advantage of Hybrid work and collaboration. Employees within 45 miles of WPS Headquarters (1717 W. Broadway in Madison, WI, 53713) will be expected to be able to be able to work Hybrid 2 days a week on a regular basis.
**As a secondary consideration, we do offer remote work in the following approved states:
Colorado, Florida, Georgia, Illinois, Indiana, Iowa, Michigan, Minnesota, Missouri, Nebraska, New Jersey, North Carolina, Ohio, South Carolina, Texas, Virginia, Wisconsin
How do I know this opportunity is right for me? If you enjoy the following:
- Serve as lead system administrator and technical owner of Costpoint, Time & Expense, Cognos, and related finance technology tools, providing expert configuration, advanced troubleshooting, and system stability oversight.
- Lead technical and functional analysis efforts, translate business needs into functional and configuration requirements, and design scalable technical solutions.
- Manage integrations and data flows, including API-based connections, middleware, ETL jobs, error handling processes, and cross-system data reconciliation.
- Identify, investigate, and resolve advanced system issues, including data structure anomalies, configuration defects, integration failures, and cross‑module impacts.
- Develop and validate complex reports, data models, and analytics, ensuring accuracy and consistency across operational and leadership reporting.
- Drive continuous improvement and automation, identify opportunities to standardize workflows, optimize configurations, reduce manual effort, and enhance system reliability.
- Mentor junior administrators, provide technical guidance, review configuration work, raise standards for documentation, testing, and system design.
- Maintain comprehensive system documentation supporting audit readiness, governance, and sustainable system knowledge.
- Support Agile/Scrum ceremonies, ensuring technical stories are well‑defined, dependencies understood, and delivery successful.
- Other duties as assigned.
Minimum Qualifications
- Bachelors degree in Information Systems, Finance, Accounting, or a related field, or equivalent combination of education and experience.
- Five or more years supporting financial systems or ERP platforms in roles involving system administration, configuration, troubleshooting, and business-analysis activities.
- Advanced expertise in Costpoint system administration, including module configuration, data structures, workflow behavior, security management, and cross‑module dependencies.
- Strong skills in business and systems analysis, including requirements gathering, gap analysis, process mapping, solution design, and translating financial operational needs into technical configurations and enhancements.
- Proven ability to design and implement system-based solutions supporting financial processes such as budgeting, forecasting, audit readiness, compliance, financial close, and operational reporting.
- Demonstrated capability to develop, validate, and interpret complex reports and financial data models; proficient with Cognos or similar BI/reporting tools.
- Deep technical understanding of ERP architecture, integrations, and API-based data exchange, including the downstream impacts of configuration changes across interconnected financial systems.
- Hands-on experience with middleware tools, ETL pipelines, automation platforms, and integration error handling that support data movement between Costpoint and other enterprise applications.
- Progressive experience in troubleshooting complex system issues, performing root-cause analysis, and designing stable technical solutions.
- Strong communication and collaboration skills, with ability to clearly articulate technical concepts, guide stakeholders, and support decision-making.
Remote Work Requirements
- High speed cable or fiber internet.
- Minimum of 10 Mbps downstream and at least 1 Mbps upstream internet connection (can be checked at https://speedtest.net (https://speedtest.net/)).
- Please review Remote Worker FAQs (https://secure.wpsic.com/files/remote-work-faqs.pdf) for additional information.
Benefits
- Remote and hybrid work options available
- Performance bonus and/or merit increase opportunities
- 401(k) with a 100% match for the first 3% of your salary and a 50% match for the next 2% of your salary (100% vested immediately)
- Competitive paid time off
- Health insurance, dental insurance, and telehealth services start DAY 1
- Professional and Leadership Development Programs
- Review additional benefits: (https://www.wpshealthsolutions.com/careers/ (https://www.wpshealthsolutions.com/careers/))
Who We Are
WPS, a health solutions company, (https://www.wpshealthsolutions.com/about/index.shtml) is a leading not-for-profit health insurer and federal government contractor headquartered in Madison, Wisconsin. WPS offers health insurance plans for individuals, families, seniors and group health plans for small to large businesses. We process claims and provide customer support for beneficiaries of the Medicare program and manage benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for the people we serve for nearly 80 years (https://www.wpshealthsolutions.com/75/). Proud to be military and veteran ready.
Culture Drives Our Success
WPS’ culture is where the great work and innovations of our people are seen, fueled and rewarded. We accomplish this by creating an open and empowering employee experience. We recognize the benefits of employee engagement as an investment in our workforce—both current and future—to effectively seek, leverage, and include differing and unique perspectives that fuel agility and innovation on high-performing teams. This results in people bringing their authentic selves to work every day in an organization that successfully adapts to business changes and new opportunities.
We are proud of the recognition we have received from local and national organization regarding our culture and workplace: WPS Newsroom - Awards and Recognition. (https://www.wpshealthsolutions.com/news/?c=awards)
Sign up for Job Alerts (http://recruiting2.ultipro.com/WIS1003/JobBoard/e6da0c90-f987-63dc-99a9-fb8c9014f57e/Account/Register?cancelUrl=https%3A%2F%2Frecruiting2.ultipro.com%2FWIS1003%2FJobBoard%2Fe6da0c90-f987-63dc-99a9-fb8c9014f57e%2F%3Fq%3DWPS%26o%3Drelevance&redirectUrl=%2FWIS1003%2FJobBoard%2Fe6da0c90-f987-63dc-99a9-fb8c9014f57e%2FJobSearchAgent)
FOLLOW US!
Instagram (https://www.instagram.com/wpshealthsolutions/)
LinkedIn (https://www.linkedin.com/company/wps-health-solutions/)
Facebook (https://www.linkedin.com/company/wps-health-solutions/)
WPS Health Blog (https://www.facebook.com/WPSHealthSolutions/)
This position may from time to time provide support to federal health care programs and other governmental or regulated industries. In accordance with law and/or contractual requirements, individuals in this role are or may be subject to all applicable federal regulations, agency contract requirements, and WPS internal policies, including but not limited to standards for data security, privacy, confidentiality, and program integrity. WPS and its personnel are subject to mandatory enhanced screening and background investigation prior to being granted access to information systems and/or sensitive data in order to safeguard regulated information and government resources that provide critical services.
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights (https://www.eeoc.gov/poster) notice from the Department of Labor.
Role Snapshot
The Senior Business Systems Administrator serves as the technical subject‑matter expert for Costpoint and related financial systems, ensuring secure, stable, and optimized performance across all finance applications and integrations. This role leads complex system configuration, integration management, advanced troubleshooting, and technical design efforts. It also retains business-analysis responsibilities to ensure system enhancements meet operational needs. The senior administrator partners with Finance, Accounting, IT, and leadership to deliver robust, scalable financial system solutions and support continuous improvement.
Salary Range
115,000-135,000
The base pay offered for this position may vary within the posted range based on your job-related knowledge, skills, and experience.
Work Location
Our first consideration will be to have this employee live in the state of Wisconsin to take advantage of Hybrid work and collaboration. Employees within 45 miles of WPS Headquarters (1717 W. Broadway in Madison, WI, 53713) will be expected to be able to be able to work Hybrid 2 days a week on a regular basis.
**As a secondary consideration, we do offer remote work in the following approved states:
Colorado, Florida, Georgia, Illinois, Indiana, Iowa, Michigan, Minnesota, Missouri, Nebraska, New Jersey, North Carolina, Ohio, South Carolina, Texas, Virginia, Wisconsin
How do I know this opportunity is right for me? If you enjoy the following:
- Serve as lead system administrator and technical owner of Costpoint, Time & Expense, Cognos, and related finance technology tools, providing expert configuration, advanced troubleshooting, and system stability oversight.
- Lead technical and functional analysis efforts, translate business needs into functional and configuration requirements, and design scalable technical solutions.
- Manage integrations and data flows, including API-based connections, middleware, ETL jobs, error handling processes, and cross-system data reconciliation.
- Identify, investigate, and resolve advanced system issues, including data structure anomalies, configuration defects, integration failures, and cross‑module impacts.
- Develop and validate complex reports, data models, and analytics, ensuring accuracy and consistency across operational and leadership reporting.
- Drive continuous improvement and automation, identify opportunities to standardize workflows, optimize configurations, reduce manual effort, and enhance system reliability.
- Mentor junior administrators, provide technical guidance, review configuration work, raise standards for documentation, testing, and system design.
- Maintain comprehensive system documentation supporting audit readiness, governance, and sustainable system knowledge.
- Support Agile/Scrum ceremonies, ensuring technical stories are well‑defined, dependencies understood, and delivery successful.
- Other duties as assigned.
Minimum Qualifications
- Bachelors degree in Information Systems, Finance, Accounting, or a related field, or equivalent combination of education and experience.
- Five or more years supporting financial systems or ERP platforms in roles involving system administration, configuration, troubleshooting, and business-analysis activities.
- Advanced expertise in Costpoint system administration, including module configuration, data structures, workflow behavior, security management, and cross‑module dependencies.
- Strong skills in business and systems analysis, including requirements gathering, gap analysis, process mapping, solution design, and translating financial operational needs into technical configurations and enhancements.
- Proven ability to design and implement system-based solutions supporting financial processes such as budgeting, forecasting, audit readiness, compliance, financial close, and operational reporting.
- Demonstrated capability to develop, validate, and interpret complex reports and financial data models; proficient with Cognos or similar BI/reporting tools.
- Deep technical understanding of ERP architecture, integrations, and API-based data exchange, including the downstream impacts of configuration changes across interconnected financial systems.
- Hands-on experience with middleware tools, ETL pipelines, automation platforms, and integration error handling that support data movement between Costpoint and other enterprise applications.
- Progressive experience in troubleshooting complex system issues, performing root-cause analysis, and designing stable technical solutions.
- Strong communication and collaboration skills, with ability to clearly articulate technical concepts, guide stakeholders, and support decision-making.
Remote Work Requirements
- High speed cable or fiber internet.
- Minimum of 10 Mbps downstream and at least 1 Mbps upstream internet connection (can be checked at https://speedtest.net (https://speedtest.net/)).
- Please review Remote Worker FAQs (https://secure.wpsic.com/files/remote-work-faqs.pdf) for additional information.
Benefits
- Remote and hybrid work options available
- Performance bonus and/or merit increase opportunities
- 401(k) with a 100% match for the first 3% of your salary and a 50% match for the next 2% of your salary (100% vested immediately)
- Competitive paid time off
- Health insurance, dental insurance, and telehealth services start DAY 1
- Professional and Leadership Development Programs
- Review additional benefits: (https://www.wpshealthsolutions.com/careers/ (https://www.wpshealthsolutions.com/careers/))
Who We Are
WPS, a health solutions company, (https://www.wpshealthsolutions.com/about/index.shtml) is a leading not-for-profit health insurer and federal government contractor headquartered in Madison, Wisconsin. WPS offers health insurance plans for individuals, families, seniors and group health plans for small to large businesses. We process claims and provide customer support for beneficiaries of the Medicare program and manage benefits for millions of active-duty and retired military personnel across the U.S. and abroad. WPS has been making healthcare easier for the people we serve for nearly 80 years (https://www.wpshealthsolutions.com/75/). Proud to be military and veteran ready.
Culture Drives Our Success
WPS’ culture is where the great work and innovations of our people are seen, fueled and rewarded. We accomplish this by creating an open and empowering employee experience. We recognize the benefits of employee engagement as an investment in our workforce—both current and future—to effectively seek, leverage, and include differing and unique perspectives that fuel agility and innovation on high-performing teams. This results in people bringing their authentic selves to work every day in an organization that successfully adapts to business changes and new opportunities.
We are proud of the recognition we have received from local and national organization regarding our culture and workplace: WPS Newsroom - Awards and Recognition. (https://www.wpshealthsolutions.com/news/?c=awards)
Sign up for Job Alerts (http://recruiting2.ultipro.com/WIS1003/JobBoard/e6da0c90-f987-63dc-99a9-fb8c9014f57e/Account/Register?cancelUrl=https%3A%2F%2Frecruiting2.ultipro.com%2FWIS1003%2FJobBoard%2Fe6da0c90-f987-63dc-99a9-fb8c9014f57e%2F%3Fq%3DWPS%26o%3Drelevance&redirectUrl=%2FWIS1003%2FJobBoard%2Fe6da0c90-f987-63dc-99a9-fb8c9014f57e%2FJobSearchAgent)
FOLLOW US!
Instagram (https://www.instagram.com/wpshealthsolutions/)
LinkedIn (https://www.linkedin.com/company/wps-health-solutions/)
Facebook (https://www.linkedin.com/company/wps-health-solutions/)
WPS Health Blog (https://www.facebook.com/WPSHealthSolutions/)
This position may from time to time provide support to federal health care programs and other governmental or regulated industries. In accordance with law and/or contractual requirements, individuals in this role are or may be subject to all applicable federal regulations, agency contract requirements, and WPS internal policies, including but not limited to standards for data security, privacy, confidentiality, and program integrity. WPS and its personnel are subject to mandatory enhanced screening and background investigation prior to being granted access to information systems and/or sensitive data in order to safeguard regulated information and government resources that provide critical services.
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights (https://www.eeoc.gov/poster) notice from the Department of Labor.
See All 6 Senior Systems Administrator Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
Find JobsSenior Systems Administrator Jobs by City in Wisconsin
Where Wisconsin roles are concentrated, by current openings.
Senior Systems Administrator Job Market in Wisconsin
A snapshot from current Wisconsin openings, updated as new roles post.
Who's Hiring
What Wisconsin Employers Look For
The qualifications that appear most often in senior systems administrator jobs across Wisconsin.
- Bachelor's degree in information technology, computer science, or a related technical field
- Five or more years of hands-on experience managing enterprise servers and network infrastructure
- Active certifications such as Microsoft Certified: Azure Administrator or CompTIA Security+
- Proficiency with virtualization platforms including VMware vSphere or Microsoft Hyper-V
- Demonstrated experience with enterprise backup, disaster recovery, and business continuity planning
- Strong knowledge of Active Directory, Group Policy, and identity management in large organizations
Senior Systems Administrator Jobs in Wisconsin: Frequently Asked Questions
How do you become a senior systems administrator in Wisconsin?
Most Wisconsin employers require a bachelor's degree in information technology, computer science, or a closely related field, along with several years of progressively responsible systems administration experience. Wisconsin does not issue a state-specific license for this role, so advancement depends on industry certifications such as Microsoft Certified: Azure Administrator, VMware Certified Professional, or CompTIA Security+. Candidates who build experience in healthcare IT or financial technology environments tend to be most competitive given the strength of those industries in the state.
How much do senior systems administrators make in Wisconsin?
Senior systems administrators in Wisconsin earn a median of about $83,650 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $58,950 for the lowest 10% to over $128,580 for the top 10%. Pay rises with experience, specialty, and employer.
Which companies hire senior systems administrators in Wisconsin?
Wisconsin senior systems administrator roles are posted by BCS IS IT, Mad City Techs, and Galloway Company and others right now, based on current listings on Migrate Mate as of November 2026. Wisconsin's healthcare, financial services, and insurance sectors generate particularly consistent demand for senior-level infrastructure talent.
Which Wisconsin cities have the most senior systems administrator jobs?
Monona, Neenah, and Madison lead Wisconsin in senior systems administrator openings. Milwaukee drives the largest share of postings through its dense concentration of financial services firms, insurance carriers, and regional corporate headquarters, while Madison's openings are anchored by the University of Wisconsin System, state government agencies, and Epic Systems, and Green Bay draws demand from its manufacturing and healthcare employers.
Are there remote senior systems administrator jobs in Wisconsin?
Yes, and more than many technical roles, since configuration, monitoring, and administration tasks are well-suited to remote work. About 67% of senior systems administrator openings tied to Wisconsin are remote or hybrid as of November 2026, reflecting how much of the role can be performed off-site. Responsibilities involving physical hardware, data center maintenance, or on-site incident response are the most likely to require in-person presence.
How can I get hired as a senior systems administrator in Wisconsin with little or no experience?
The most realistic path is to start in a help desk, desktop support, or junior systems technician role at a Wisconsin employer, then build toward administration responsibilities over time. Large Wisconsin institutions such as the University of Wisconsin System, Froedtert Health, and Advocate Aurora Health regularly hire IT support staff and run internal development programs that move people into infrastructure roles. Earning an entry-level certification such as CompTIA A+ or Network+ early on signals technical seriousness and gives candidates a measurable edge when applying to organizations that promote from within.
Where can I find and apply to senior systems administrator jobs in Wisconsin?
You can find and apply to senior systems administrator jobs in Wisconsin on Migrate Mate, which lists current openings from employers across the state. Find a role that fits and apply directly.
See All 6 Senior Systems Administrator Jobs in Wisconsin
Find roles in Wisconsin that match your experience and apply in just a few clicks.
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