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Redwood Software

Posted 4 Nov 2026

Package Specialist - Installation Development

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Employment
Full time
Team
IT Operations
Posted
4 Nov 2026

About the role

We are seeking a senior installation Package Specialist to own, modernize, and automate the multi-platform installer ecosystem. In this critical role, you will be responsible for end-to-end packaging engineering from developing Windows InstallShield (. msi) and Linux/Unix InstallAnywhere (. iap_xml) installer payloads to orchestrating custom build tasks in Gradle, automating database provisioning via JDBC, and ensuring seamless enterprise upgrades across thousands of mission-critical customer environments.


You will collaborate closely with Core Engineering, Security, and Quality Engineering teams to eliminate installation roadblocks, enhance silent/unattended rollout capabilities, support modern enterprise security standards (gMSA, CyberArk PAM), and maintain zero-downtime upgrade integrity.


The core responsibilities for the job include the following:

Dual-Platform Installer Development and Maintenance:

  • Windows Packaging (InstallShield MSI): Maintain and enhance InstallShield project files (. ism) for flagship Windows products.
  • Linux/Unix Packaging (InstallAnywhere): Develop and configure Revenera InstallAnywhere (. iap_xml) project files for Unix-based repo installers.
  • Custom Action Engineering: Design, write, and maintain:
  • Windows VBScript / JScript Custom Actions: Develop Immediate and Deferred custom actions (with elevated privilege handling and rollback logic) for configuration gathering, service registration, and file manipulation.
  • Java Custom Actions: Develop compiled Java classes for InstallAnywhere runtime execution to handle cross-platform setup logic.


Enterprise Security and Silent Deployment Logic:

  • Group Managed Service Accounts (gMSA): Maintain and validate installer logic for running core services under Windows gMSA credentials in both UI and Silent Response File modes.
  • Property File Retention and Upgrade Reliability: Fix complex upgrade bugs to ensure property files (master.props, db.props ) are safely backed up, migrated, and never overwritten or deleted during reinstalls/upgrades.
  • Version String Comparison Logic: Implement precise multi-digit semantic version comparison logic (e. g., 4-digit releases like 2026.3.4.19) to prevent upgrade blockage or false "newer version already installed" errors.


Database Provisioning and Schema Orchestration:

  • JDBC Engine Integration: Work with the shared DB assistant Java CLI tool to orchestrate database connectivity validation and schema deployment.
  • Multi-Dialect DDL Alignment: Ensure installer schema execution scripts correctly apply to repository tables, supporting emerging DB topologies such as Oracle Pluggable Databases (PDB), Azure SQL, and PostgreSQL.


Build System and CI/CD Automation:

  • Gradle Multi-Module Pipeline: Maintain shared custom Gradle build-logic tasks
  • Mutagen Staging Workflow: Manage local macOS/Linux staging builds that sync VM-layout payload ZIPs to Windows and Unix packaging build VMs via Mutagen.
  • GitHub Actions and Automated Testing: Build and maintain CI/CD workflows and integrate pre-initialized Docker containers (MSSQL/PostgreSQL) for automated integration testing.


Requirements:

  • Primary Focus: Installer Engineering, Packaging and Release Validation, InstallShield (MSI), InstallAnywhere, VBScript / Custom Actions, Java / JDBC, Gradle (Kotlin DSL), GitHub Actions, Active Directory / gMSA, Docker
  • Experience: 5+ years of hands-on experience in enterprise software packaging, installation engineering, and installer validation across Windows and Linux environments.
  • InstallShield Expertise: Advanced knowledge of Revenera InstallShield, Windows Installer (MSI) technology, MSI tables, sequence tables, custom action execution contexts (Immediate vs. Deferred in System Context), and rollback execution.
  • InstallAnywhere Expertise: Hands-on experience developing Linux/Unix installers using Revenera InstallAnywhere, including Java custom actions, panel rules, and response file handling.
  • Scripting Languages: Strong proficiency in VBScript, PowerShell, Bash, and/or Python.
  • Java and JDBC: Solid understanding of Java runtime configuration, JAR packaging, and JDBC database connectivity.
  • Database Fundamentals: Practical working knowledge of Microsoft SQL Server, PostgreSQL, and Oracle Database (DDL execution, user/role permissions, tablespaces/PDBs).
  • Enterprise Security: In-depth understanding of Windows Service logons, Active Directory user rights, GMSA (Group Managed Service Accounts), and ACL permissions.
  • Build Tools and CI/CD: Experience with Gradle (Kotlin or Groovy DSL), Git, and CI/CD platforms like GitHub Actions or Jenkins.


Desirable Plus Qualifications:

  • Experience with CyberArk PAM, OAuth2, or PKI certificate management for enterprise service credentials.
  • Experience with Docker for running pre-initialized integration testing database containers.

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