Windows App Deployment Engineer With MSI/WiX REMOTE

Windows App Deployment Engineer Location: Remote in US Rate:$55-$60/HR C2C OR 1099 Primary Responsibilities ● Design, build, and maintain Windows-based installers (MSI/WiX or equivalent) for Overlay components, including configuration, upgrades, and uninstalls. ● Develop and operate Windows services and supporting scripts that provide machine-level telemetry, health checks, and self-healing for Overlay deployments. ● Partner with practice IT teams to support deployment via AD/GPO and Intune, including troubleshooting in locked-down, enterprise environments. ● Implement and evolve telemetry and heartbeat mechanisms, wiring metrics and logs into observability tools (e.g., SumoLogic, Datadog) for install success, configuration drift, and uninstall detection. ● Integrate installers and agents with backend APIs (e.g., license key validation, configuration fetch, metrics ingestion) in a secure, resilient way. ● Collaborate with security, desktop, and web overlay teams to ensure installers and agents meet security, compliance, and pen-test requirements. ● Create and maintain clear runbooks, IT-facing deployment guides, and internal troubleshooting documentation. Required Technical Skills ● Windows OS fundamentals: services, registry, event logs, service accounts, scheduled tasks. ● Hands-on experience building and debugging Windows desktop installers (preferably MSI/WiX) and related packaging/tooling. ● Proficiency with PowerShell for automation, deployment scripting, health checks, and log collection. ● Familiarity with enterprise software deployment patterns: Active Directory / GPO, Microsoft Intune / Endpoint Manager. ● Experience designing and instrumenting telemetry/heartbeat agents, including robust error handling and retry logic. ● Comfort working with REST APIs (auth, TLS, retries, idempotency) from Windows services/scripts. ● Solid understanding of secure handling of secrets, license keys, and configuration on Windows, plus code signing and least-privilege principles. Preferred Experience & Behaviors ● Background in endpoint or agent-style products (installers, updaters, monitoring agents, or similar). ● Experience operating in high-variability customer environments (different EHRs, hosting models, security postures). ● Strong debugging skills across local logs, remote telemetry dashboards, and practice-specific configuration. ● Clear written and verbal communication with non-engineering stakeholders (IT admins, support, deployment ops). ● Ownership mindset: comfortable with on-call participation, incident response, and continuous improvement of runbooks and monitoring.