Windows App Deployment Engineer

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.

• 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.

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.

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