PowerShell Automation Engineer

Stefanini Group•Richmond, VA

4d•Remote

About The Position

Stefanini Group is hiring a remote PowerShell Automation Engineer on a W2 basis. The role focuses on building, maintaining, and modernizing Windows software deployment workflows, including application packaging, customization, automated testing, and release. The engineer will use AI-assisted coding tools as productivity aids while carefully reviewing, testing, and refining generated code to ensure production-ready quality. The position combines Windows application packaging and deployment with PowerShell automation. It involves creating MSI/MSIX packages and PowerShell deployment workflows, integrating automation with enterprise platforms, maintaining tests and version control, and documenting standards and processes. The engineer will collaborate with IT, security, endpoint engineering, and helpdesk teams to improve deployment processes and reduce manual work.

Requirements

At least 3 years of professional PowerShell scripting experience with PowerShell 5.1 and 7+.
Demonstrated experience using AI or agentic coding tools such as Copilot, Cursor, Claude Code, Amazon Q, or Windsurf in real development workflows.
Strong hands-on experience building, modifying, and troubleshooting MSI/MSIX packages.
Solid understanding of Windows systems administration, Active Directory, and Microsoft 365.
Experience with REST APIs and structured data formats such as JSON, XML, and CSV.
Strong knowledge of secure scripting practices, including credential management and secrets handling.
Familiarity with Git and collaborative development workflows.
Ability to evaluate, debug, and refine AI-generated code.
W2 candidates only.

Nice To Haves

Experience with Microsoft Graph API, Azure automation, and Az PowerShell modules.
Experience with Intune, Autopilot, or enterprise endpoint management automation.
Experience writing Pester unit or integration tests.
Exposure to CI/CD pipelines such as Azure DevOps or GitHub Actions for packaging and script deployment.
Python or Bash scripting experience as a complement to PowerShell.
Experience building internal tools, dashboards, or reporting workflows.
Prior experience defining or documenting AI-assisted engineering practices.

Responsibilities

Build, customize, and maintain MSI/MSIX application packages using tools such as WiX, Advanced Installer, or PSADT.
Develop PowerShell packaging and deployment scripts, including detection logic, custom actions, configuration, and uninstall routines.
Package complex enterprise applications involving MST transforms, prerequisite handling, DLL registrations, digital signing, and environment-specific configuration.
Ensure packages meet security requirements, follow internal standards, and deploy reliably through Intune, Configuration Manager, or orchestration pipelines.
Design, develop, and maintain PowerShell scripts and modules for system administration, packaging workflows, and broader IT automation.
Use agentic coding assistants to scaffold scripts, generate tests, and modernize legacy code, while rigorously reviewing generated output.
Integrate automation with platforms such as Active Directory, Microsoft Graph API, Azure, Intune, and ticketing or ITSM systems.
Build reusable, well-documented PowerShell modules following best practices for approved verbs, error handling, and comment-based help.
Write and maintain Pester tests to validate script and packaging reliability.
Collaborate with IT, security, endpoint engineering, and helpdesk teams to streamline deployment processes and eliminate manual effort.
Maintain version-control discipline using Git/GitHub, including clear commit messages and structured pull request reviews.
Document packaging standards, automation workflows, and AI-assisted development processes.