Deployment Engineer

Job Summary:

We are seeking a skilled Windows Application Packaging and Deployment Engineer to take ownership of our enterprise software lifecycle. In this role, you will analyze, customize, package, and deploy applications across our large-scale corporate Windows ecosystem. You will ensure that all software updates, third-party utilities, and proprietary tools are engineered for silent, secure, and automated mass distribution. The ideal candidate bridges the gap between legacy packaging frameworks (MSI, EXE) and modern cloud-managed endpoint environments (Intune, MSIX), leveraging modern AI-assisted automation tools to optimize workflows and reduce deployment timelines.

Key Responsibilities

• Application Packaging & Virtualization: Convert vendor executable (EXE) source files and loose components into standardized Windows Installer (MSI, MST), Microsoft App-V, and modern virtualized packages (MSIX, Win32 app formats).
• AI-Enhanced Automation & Scripting: Develop robust, unattended, and silent installation/uninstallation routines using PowerShell, VBScript, and the PowerShell App Deployment Toolkit (PSADT). Leverage Generative AI code assistants to accelerate script development, refactor legacy code, and debug complex installation errors.
• Deployment & Endpoint Management: Configure, test, and execute enterprise-wide software distribution using Microsoft Intune and MECM/SCCM.
• Requirement Gathering & Discovery: Collaborate with software owners to define installation switches, registry modifications, custom shortcuts, and application dependencies.
• Testing & Conflict Resolution: Conduct smoke testing, UAT, and compatibility validation. Resolve DLL conflicts, system permission constraints, and OS compatibility issues (e.g., Windows 10 to Windows 11 migrations).
• Data-Driven Troubleshooting: Use AI-driven analytics, Copilot for Security, or machine learning-powered endpoint insights to proactively identify, diagnose, and resolve mass deployment failures and application conflicts.
• Patch & Lifecycle Management: Keep standard enterprise plug-ins and applications secure by orchestrating timely updates, application migration and supersedence, vulnerability remediation, and software retirement.

Required Technical Skills & Qualifications

• Experience: 5+ years of dedicated experience in software repackaging, virtualization, and desktop configuration management in an enterprise environment.
• Packaging Tools: Proficiency with industry-standard suites like Flexera AdminStudio, InstallShield, Advanced Installer, or Orca.
• Application Virtualization: Practical experience creating, sequencing, troubleshooting, and streaming virtual packages using Microsoft App-V (App-V Sequencer).
• Distribution Systems: Advanced administrative experience with Microsoft Intune / Endpoint Manager and SCCM / MECM.
• Scripting Languages: Strong command of PowerShell (highly preferred), VBScript, and batch command structures.
• AI Tooling: Hands-on experience using AI coding assistants (e.g., GitHub Copilot, Microsoft Copilot) to generate, optimize, and document complex automation scripts and packaging routines.
• Operating Systems: Deep structural knowledge of Microsoft Windows platforms (registry keys, file systems, user vs. machine contexts, and AppContainer isolation).

Preferred Qualifications

• Experience utilizing Microsoft Copilot for Security or Intune AI-driven endpoint analytics for predictive troubleshooting and device health monitoring.
• Experience managing and deploying virtual applications in Virtual Desktop Infrastructures (VDI), such as Azure Virtual Desktop (AVD).
• Relevant industry certifications (e.g., Microsoft Certified: Endpoint Administrator Associate, ITIL Foundation).

Interview Methodology:

First Round: 30 Minute MS Teams Second Round: 30-60 minutes on site at Hingham or Boston location.

Flexible work from home options available.