Systems Engineer II
Paychex
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Chicago, IL · Posted November 10, 2026
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November 2026
- #1Best cities for government pay after cost of living$146k · of 18
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About the job
Paychex is reimagining how businesses manage their workforce by bringing payroll, HR, benefits, and advisory services together into a single connected HCM platform. As Paychex and Paycor come together, we're combining innovative technology, data-driven insights, AI, and human expertise to help organizations work smarter, support their people, and achieve better business outcomes. This is an exciting time to join our team as we continue to invest in innovation, simplify client experiences, and shape the future of work. At Paychex, you'll have the opportunity to grow your career, make a meaningful impact, and be part of something bigger as One Paychex. Overview
A seasoned position requiring in-depth knowledge and experience in compute system technologies. Works independently under moderate supervision responsible for troubleshooting, installing, configuring, and maintaining server hardware, operating systems, and applications in support of business requirements. Provides technical support during critical and non-critical business hours. Proactively identifies and automates the resolution to availability and performance issues throughout the environment.
This position will expose the candidate to all server based operating systems (Linux, Windows) at Paychex and will require the development of skills to support, administer, and engineer cross-platform OS solutions. The candidate will be exposed to Continuous Delivery concepts such as Version Control, Continuous Integration, Testing (smoke, sanity, regression), Automation, and Orchestration as a means to deliver and support IT systems at Paychex. Technologies like Git, Artifactory, ServerSpec, Puppet, Ansible, and many more are the means to achieve our organizations 'as code' goals and objectives. Scripting (Bash, Powershell), and non-scripting (Ruby, Python, Go) languages are leveraged to extend features/functionality within our current toolsets and further our self-service, automation, and orchestration capabilities and services. The candidate will leverage the latest technologies from Cisco, Dell/EMC, Docker, Google, Microsoft, Red Hat, VMware, and many Open Source projects in our IT environment that are critical to delivering Paychex's IT infrastructure services. The candidate will be integrated into DevOps teams (Delivery Teams) with Software Developers and Testers, Build and Release Engineers, Solution Leads, Scrum Masters, and many more, responsible for delivering new products, features/functionality, and remediating defects for Paychex's Software as a Service (SaaS) solutions. Responsibilities
Provides moderately complex technical support during critical and non-critical business hours on server hardware, operating systems, and software. Is proactive and reactive for problem alerting, analysis, resolution, and follow up to ensure platform stability.
Deploys and configuring moderately complex server operating systems and applications (Corporate and Third-Party) in physical, virtual, and containerized compute environments to corporate and vendor standards.
Performs moderately complex application and storage system upgrades (hardware/software) as well as periodic health checks in accordance with established corporate policies and procedures.
Supports cross-functional project teams to help deliver solutions as required.
Creates and maintains technical reference documentation to be used in support and training of Information Technology (IT) personnel.
Proactively identifies and automates the resolution to availability and performance failures throughout the environment.
Proactively identifies work requests that can be downshifted to Operations staff or automated via software automation and orchestration tools. Ensures that all working knowledge sets are properly documented and communicated.
Participates in the creation of corporate standards, best practices, and roadmaps for IT systems and technologies.
Participates in the creation of designs for corporate IT systems.
Qualifications
Associate's Degree in Computer related discipline and/or an IT certification in an applicable field - Preferred
4 years of experience in Infrastructure administration or support role. Applicant should have experience in IT systems administration and process management.
Troubleshooting (Problem Solving) - Preferred
Information Technology - Preferred
Operations - Preferred
Enthusiasm - Preferred
Communication - Preferred
Systems Engineering - Preferred
Automation - Preferred
Operating Systems - Preferred
Scripting - Preferred
Ansible - Preferred
Artifactory - Preferred
Git (Version Control System) - Preferred
Puppet (Configuration Management Tool) - Preferred
Business Requirements - Preferred
DevOps - Preferred
Live the Paychex Values
Act with uncompromising integrity.
Provide outstanding service and build trusted relationships.
Drive innovation in our products and services and continually improve our processes.
Work in partnership and support each other.
Be personally accountable and deliver on commitments.
Treat each other with respect and dignity.
What's in it for you?
We value your well-being: We provide over 21 comprehensive rewards, including medical coverage, virtual wellness classes, tuition reimbursement, 401(k) + employer match, adoption assistance, financial assistance, and much more.
We value your time: From paid time off to company holidays, culture days, and comprehensive work-life balance programs, we will ensure you have the flexibility you need to be your best.
We value your development: Our award-winning training and development programs empower our employees with ongoing learning opportunities to give you the building blocks to grow your career.
We value your perspective: Our company culture reflects the diversity of our employees. We want you to be you and your voice to be heard.
We value our communities: We offer paid time off for volunteerism and promote many company-wide and local initiatives that benefit organizations you care about.
Note: The benefits described apply to full-time employees. Benefits for part-time, contract, and intern roles may vary. Not sure if you meet every requirement?
At Paychex, we know that great talent comes in many forms. If you're passionate about the role but don't check every box, we still encourage you to apply. You might be the right fit - either for this position or another opportunity with us.
Paychex is an equal opportunity employer. We are committed to fostering a respectful and inclusive workplace where all individuals are treated fairly and evaluated based on their qualifications, experience, and merit. We comply with all applicable federal, state, and local laws prohibiting discrimination in employment.
Provides moderately complex technical support during critical and non-critical business hours on server hardware, operating systems, and software. Is proactive and reactive for problem alerting, analysis, resolution, and follow up to ensure platform stability.
Deploys and configuring moderately complex server operating systems and applications (Corporate and Third-Party) in physical, virtual, and containerized compute environments to corporate and vendor standards.
Performs moderately complex application and storage system upgrades (hardware/software) as well as periodic health checks in accordance with established corporate policies and procedures.
Supports cross-functional project teams to help deliver solutions as required.
Creates and maintains technical reference documentation to be used in support and training of Information Technology (IT) personnel.
Proactively identifies and automates the resolution to availability and performance failures throughout the environment.
Proactively identifies work requests that can be downshifted to Operations staff or automated via software automation and orchestration tools. Ensures that all working knowledge sets are properly documented and communicated.
Participates in the creation of corporate standards, best practices, and roadmaps for IT systems and technologies.
Participates in the creation of designs for corporate IT systems.
Associate's Degree in Computer related discipline and/or an IT certification in an applicable field - Preferred
4 years of experience in Infrastructure administration or support role. Applicant should have experience in IT systems administration and process management.
Troubleshooting (Problem Solving) - Preferred
Information Technology - Preferred
Operations - Preferred
Enthusiasm - Preferred
Communication - Preferred
Systems Engineering - Preferred
Automation - Preferred
Operating Systems - Preferred
Scripting - Preferred
Ansible - Preferred
Artifactory - Preferred
Git (Version Control System) - Preferred
Puppet (Configuration Management Tool) - Preferred
Business Requirements - Preferred
DevOps - Preferred