Best suited to candidates with dual-platform installer development expertise working in enterprise software environments. The role emphasizes collaboration with Core Engineering, Security, and Quality Engineering teams, and requires a contract commitment for 6 months.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Redwood Software via Greenhouse
Senior Installation Package Development & Validation Engineer (Contract role)
Focus Areas: MSI InstallShield (Windows) & Linux/Unix InstallAnywhere Automation
Role Type: Contractor – 6 months
Primary Focus: Installer Engineering, Packaging & Release Validation
InstallShield (MSI), InstallAnywhere, VBScript / Custom Actions, Java / JDBC, Gradle (Kotlin DSL), GitHub Actions, Active Directory / gMSA, Docker
Role Overview
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.
Key Responsibilities
Dual-Platform Installer Development & 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 & 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 & 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 & 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 & 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 & Automated Testing: Build and maintain CI/CD workflows and integrate pre-initialized Docker containers (MSSQL/PostgreSQL) for automated integration testing.
Required Qualifications & Experience
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 & 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 & 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.
If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!
THE LEGAL BIT
Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.
Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at Privacy@Redwood.com