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.