Windows App Deployment Engineer
About The Position
We are seeking a skilled Windows App Deployment Engineer to join our team on a contract basis. This role is responsible for designing, building, and maintaining Windows-based installers and services to support our Overlay components. You will work closely with IT teams to ensure smooth deployments in enterprise environments, implement telemetry and heartbeat mechanisms, and integrate with backend APIs. Collaboration with security and other engineering teams is crucial to meet security and compliance requirements. The role also involves creating comprehensive documentation for IT administrators and internal teams.
Requirements
- 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.
Nice To Haves
- 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.
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.
Benefits
- Equal Opportunity Employer encouraging diversity in the workplace.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
