Senior Endpoint Automation Engineer

Job title: Senior Endpoint Automation Engineer
Location: REMOTE

Position Overview:
We are seeking an experienced Senior Endpoint Automation Engineer for a six-month contract engagement focused on improving endpoint management health, vulnerability patching, and operational automation across enterprise Windows and macOS environments.
This is a highly hands-on engineering position designed to address persistent operational challenges through root-cause analysis, advanced scripting, data correlation, and automated remediation.
The successful candidate will work across Microsoft Intune, Iru/Kandji, Tenable, CrowdStrike, and related platforms to identify why endpoints fall out of management, diagnose patching failures, reconcile inconsistent compliance data, and implement automated solutions that prevent issues from recurring.
This is not a traditional endpoint administration, support, or architecture role. We are looking for an engineer who can investigate complex issues, build effective automation, and deliver measurable operational improvements.

Key Responsibilities:
Endpoint Management & Device Health
Investigate Windows and macOS devices that stop communicating with endpoint management platforms.
Establish automated monitoring to identify endpoints that fail to check in within defined timeframes.
Diagnose root causes involving agent health, connectivity, identity, certificates, configuration, and device state.
Develop automated workflows to identify, classify, and remediate inactive or noncompliant devices.
Automate the identification and removal of retired devices across MDM, directory, identity, and security platforms.
Improve endpoint inventory accuracy and eliminate stale or conflicting device records.

Patching & Vulnerability Management
Investigate operating system and application patching failures across Windows and macOS environments.
Identify and resolve the underlying causes of devices remaining unpatched beyond established SLAs.
Correlate data across Microsoft Intune, Iru/Kandji, Tenable, CrowdStrike, and inventory platforms to validate patch compliance.
Investigate discrepancies between endpoint management, security, and vulnerability reporting systems.
Build automated remediation, monitoring, and escalation workflows for patching failures.
Establish reliable compliance reporting that accurately reflects endpoint security and vulnerability exposure.

Automation & Process Improvement
Design, develop, and implement scalable automation using PowerShell, Python, Bash, APIs, and existing enterprise tooling.
Replace repetitive manual processes with reliable, repeatable workflows.
Automate endpoint cleanup, agent remediation, patch troubleshooting, and compliance reporting.
Develop scripts and integrations to identify recurring issues and initiate corrective action.
Incorporate appropriate error handling, logging, validation, and exception management into automated workflows.
Document automated solutions and transfer knowledge to permanent engineering teams.

Data Analysis & AI-Assisted Engineering
Analyze large datasets from endpoint management, security, vulnerability, and ITSM platforms.
Correlate information across multiple systems to identify technical patterns and systemic failures.
Validate data accuracy rather than relying solely on existing dashboards or platform reporting.
Leverage AI-assisted engineering tools for investigation, scripting, analysis, and workflow development.
Ensure AI-generated solutions are technically validated and aligned with organizational security requirements.
Develop meaningful metrics and reporting to demonstrate improvements in endpoint health, compliance, and operational efficiency.

Required Qualifications:
Strong enterprise-level endpoint engineering experience across Windows and macOS environments.
Advanced hands-on experience with Microsoft Intune.
Experience with Iru/Kandji, Jamf Pro, or comparable macOS management platforms.
Experience with Tenable, CrowdStrike, or similar vulnerability management and endpoint security tools.
Strong scripting and automation skills using PowerShell, Python, and/or Bash.
Demonstrated experience working with APIs and integrating data across multiple enterprise platforms.
Strong understanding of endpoint patch management, vulnerability remediation, and device compliance.
Experience troubleshooting endpoint agent failures, device communication issues, and inconsistent inventory records.
Proven ability to develop automated remediation workflows rather than relying on manual endpoint administration.
Experience analyzing and reconciling large, complex datasets from multiple management and security platforms.
Practical experience using AI-assisted tools to improve engineering, automation, and analysis workflows.
Excellent root-cause analysis, technical troubleshooting, and problem-solving skills.
Ability to independently own technical challenges from initial investigation through implementation and measurable resolution.

Preferred Qualifications:
Experience developing automated device lifecycle management and decommissioning processes.
Experience integrating endpoint management, vulnerability management, identity, and security tooling.
Familiarity with enterprise ITSM platforms and automated incident or remediation workflows.
Experience building operational dashboards, compliance reporting, and automated exception management.
Relevant Microsoft, Apple, endpoint management, security, or automation certifications.

What Success Looks Like:
By the end of the engagement, the successful candidate will have delivered measurable improvements in three key areas:
1. Reliable Endpoint Visibility
Endpoints consistently check in within defined management windows.
Devices that fail to check in are automatically identified and classified by root cause.
Retired devices are automatically removed from relevant management, identity, and security platforms.
Stale records and unexplained device management gaps are eliminated or substantially reduced.

2. Accurate Patch Compliance
Patching failures are investigated and corrected at the root cause.
Conflicting data across endpoint management, vulnerability, and security platforms is reconciled.
Compliance reporting accurately reflects defined SLAs and provides leadership with reliable metrics.
Devices exceeding remediation deadlines are automatically identified and routed for corrective action.

3. Sustainable Automation
Repetitive cleanup, remediation, and reporting activities are automated.
Common agent failures, stale records, and patching issues are addressed through reusable workflows.
Manual intervention is limited to genuine exceptions.
Permanent engineering teams inherit documented, maintainable solutions that significantly reduce ongoing operational effort.

The Ideal Candidate:
You are a hands-on endpoint engineer who enjoys solving complex technical problems and eliminating them through automation. You don't simply report what a dashboard says. You investigate the underlying data, identify why something is failing, and develop solutions that prevent it from happening again.
You are equally comfortable troubleshooting Windows and macOS management issues, writing scripts, integrating APIs, and validating information across multiple security and management platforms.
Most importantly, you are a builder and problem solver who measures success by the issues permanently resolved and the manual work eliminated.