Weekend Windows Systems Engineer Jobs in Pennsylvania

Company Description

With a workforce of over 25,000 people, and opportunities in more than 1,000 different job categories, the City of Philadelphia is the fifth largest city in the United States and one of the largest employers in Southeastern Pennsylvania. As an employer, the City of Philadelphia operates through the guiding principles of service, integrity, respect, accountability, collaboration, diversity and inclusion. Through these principles, we strive to effectively deliver services, to resolve the challenges facing our city, and to make Philadelphia a place where all of our residents have the opportunity to reach their potential.  

The Office of Innovation & Technology (OIT) is the central IT agency for the City of Philadelphia headed by the Chief Information Officer. This position is within the CityGeo team of OIT led by the Chief Geographic Information Officer (GIO).  The CityGeo team manages enterprise GIS operations for the city including on-prem and cloud services, large scale technology and data contracts, and governance for geodata sharing and development standards.  CityGeo is performing some of the most innovative work in municipal government on data analytics, application development, use of imagery and management of governance and multi-departmental stakeholder collaboration

Job Description

The Associate Systems Engineer is a technical role responsible for supporting, monitoring, documenting, troubleshooting, and improving systems used by the Philadelphia Department of Prisons. This position is intended for a motivated IT professional who wants to grow in systems engineering, scripting, task automation, application support, infrastructure operations, monitoring, and process improvement.

The successful candidate should have strong troubleshooting instincts, curiosity, professionalism, and the ability to learn new systems quickly. The Associate Systems Engineer will work with senior technical staff to support Microsoft Windows Server environments, application platforms, scheduled jobs, automation scripts, monitoring systems, system integrations, and escalated technical support needs.
This role may benefit from the thoughtful use of AI tools to support research, assist in reading or writing code, explore solution options, draft technical notes, and improve workflow efficiency. When used, these tools should complement existing engineering skills and judgment, not replace them.

This position is a strong fit for someone with experience in IT support, systems administration, scripting, help desk escalation, application support, infrastructure support, or technical troubleshooting who has experience with, or is willing to learn, Python, PowerShell, task automation, and system scripting.

Essential Functions

The Associate Systems Engineer will:

· Monitor and support departmental systems, applications, scheduled jobs, reports, interfaces, file transfers, automation processes, and integrations.

· Troubleshoot technical issues related to Windows servers, applications, user access, reports, network connectivity, file permissions, scheduled tasks, scripts, and automated processes.

· Review system health, job status, log files, alerts, dashboards, scheduled tasks, and error messages to identify issues and recommend next steps.

· Assist with reporting, exports, data review, and operational support tasks using approved City tools and platforms.

· Support scheduled scripts, task automation, data imports, data exports, file transfers, and integrations between internal and external systems.

· Assist with the development, maintenance, testing, and documentation of automation scripts using tools such as PowerShell, Python, batch scripting, Windows Task Scheduler, or similar automation platforms.

· Support routine system administration tasks in Windows Server environments, including service checks, scheduled tasks, event logs, application configuration, file shares, and permissions.

· Assist with account access, group membership, permissions reviews, and role-based access control in coordination with Active Directory and established data access procedures.

· Assist with report updates, dashboard support, operational validation, recurring support tasks, and process improvement efforts.

· Create, update, and maintain technical documentation, standard operating procedures, troubleshooting guides, job schedules, system inventories, and support notes.

· Assist with testing system changes, patches, application updates, report updates, database changes, and process improvements prior to implementation.

· Support vendor coordination, including issue research, log collection, testing, documentation, and communication of technical findings.

· Provide technical support to MIS staff, help desk staff, business users, vendors, and other City technology teams.

· Participate in troubleshooting calls, vendor meetings, system reviews, project discussions, and operational planning as needed.

· Escalate complex issues to senior staff while clearly documenting symptoms, troubleshooting steps, business impact, and recommended next actions.

· Learn the operations, data, reporting needs, policies, procedures, and business processes of the Philadelphia Department of Prisons.

· Maintain a professional and service-oriented approach when supporting public safety operations, staff, and technology stakeholders.

· Utilize AI tools to support troubleshooting, research, code exploration, or documentation while checking any output as part of normal technical validation.

Qualifications

· Recent graduates in STEM, technical certificate/s, military technical training, or equivalent experience in information technology, computer science, information systems, cybersecurity, data analytics, or a related field.

· Professional experience in IT support, systems administration, desktop support, help desk escalation, application support, scripting, task automation, infrastructure support, or a similar technical role.

· Experience troubleshooting technical issues in a professional, academic, military, internship, lab, homelab, or self-directed learning environment.

· Demonstrated interest in systems engineering, scripting, task automation, infrastructure support, cloud, DevOps, monitoring, cybersecurity, or application support.

· Experience or interest in using AI‑assisted tools to support scripting, documentation, or problem‑solving is a plus, but not required.

Competencies, Knowledge, Skills and Abilities

Candidates should have knowledge, experience, or demonstrated ability in several of the following areas:

· Microsoft Windows operating systems and Windows Server administration.

· PowerShell, Python, batch scripting, or similar automation tools.

· Task automation using Windows Task Scheduler, scheduled scripts, service checks, file transfers, monitoring jobs, or recurring operational processes.

· Willingness and ability to learn Python, PowerShell, scripting logic, task automation, and system administration workflows.

· Windows Server administration concepts, including services, scheduled tasks, event logs, file shares, permissions, IIS, and system configuration.

· Microsoft Active Directory concepts, including users, groups, permissions, group membership, and role-based access.

· Basic networking concepts, including IP addressing, DNS, DHCP, ports, firewalls, routing, VPNs, remote access, and connectivity troubleshooting.

· Application support, including configuration review, log analysis, vendor coordination, testing, and escalation.

· Monitoring and alerting tools, dashboards, system logs, and operational health checks.

· Technical documentation, standard operating procedures, process documentation, and troubleshooting guides.

· Data handling concepts, including file imports, file exports, validation checks, access control, sensitive data handling, and compliance awareness.

· Source control concepts using Git or similar tools.

· Containerization concepts using Docker or similar platforms.

· Ability to read, interpret, and apply technical documentation.

· Ability to analyze technical problems, document findings, and communicate recommendations clearly.

· Ability to communicate with technical staff, non-technical users, vendors, supervisors, and operational stakeholders.

· Ability to work independently on assigned tasks while knowing when to escalate.

· Strong attention to detail, accountability, judgment, and willingness to learn new systems.

· Professional judgment when working with sensitive systems, public safety data, and operational technology.

· Familiarity with modern AI‑assisted development or support tools and an interest in using them to improve troubleshooting, documentation, or workflow efficiency.

· Ability to evaluate AI‑generated responses critically and incorporate them into solutions when appropriate.

Additional Information

Salary Range: $70,000-$79,438

Salary cannot exceed $79,438

All applications must include a cover letter. Applications without a cover letter will be considered incomplete. 

Did you know?
● We are a Public Service Loan Forgiveness Program qualified employer : 25% tuition discount program for City employees (and sometimes spouses and dependents as well) in partnership with area colleges and universities

● We offer Comprehensive health coverage for employees and their eligible dependents
● Our wellness program offers eligibility into the discounted medical plan
● Employees receive paid vacation, sick leave, and holidays
● Generous retirement savings options are available

*The successful candidate must be a city of Philadelphia resident within six months of hire
Effective May 22, 2023, vaccinations are no longer required for new employees that work in non-medical, non-emergency or patient facing positions with the City of Philadelphia. As a result, only employees in positions providing services that are patient-facing medical care (ex: Nurses, doctors, emergency medical personnel), must be fully vaccinated.

The City of Philadelphia is an Equal Opportunity employer and does not permit discrimination based on race,
ethnicity, color, sex, sexual orientation, gender identity, religion, national origin, ancestry, age, disability, marital status, source of income, familial status, genetic information or domestic or sexual violence victim status. If you believe you were discriminated against, call the Philadelphia Commission on Human Relations at 215-686-4670 or send an email to faqpchr @phila.gov. For more information, go to: Human Relations Website:
http://www.phila.gov/humanrelations/Pages/default.aspx