Windows App Deployment Engineer

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.