Endpoint Engineer (Senior)

DecisionPoint | Cortek•Chicago, IL

10h•Remote

About The Position

DecisionPoint seeks a senior Endpoint Engineer to design, maintain, secure, automate, and modernize enterprise endpoint capabilities supporting the USMEPCOM ENLIST program. The engineer owns endpoint images, application packaging, device provisioning, software deployment, endpoint patching, configuration baselines, and Virtual Desktop Infrastructure (VDI) engineering. The role develops standardized, repeatable, and secure endpoint solutions for geographically dispersed users and locations, supporting physical and virtual endpoints throughout their lifecycle—from design, testing, deployment, configuration, patching, troubleshooting, refresh, and recovery through retirement. The position coordinates closely with the Task 6 cybersecurity team while maintaining distinct responsibilities. Task 6 identifies, prioritizes, and validates security findings; the Endpoint Engineer evaluates operational impacts and implements approved endpoint configuration, software, image, patch, or remediation changes through established change-control procedures, then provides deployment evidence for cybersecurity validation. The engineer also collaborates with Service Desk, field support, Active Directory, virtualization, cloud, network, application, cybersecurity, and Government teams. This is a remote position, with Chicago-area candidates preferred. Occasional after-hours maintenance, critical incident support, on-site work, or travel may be required. By applying, candidates acknowledge and consent to having their resume included in an active competitive government contract bid.

Requirements

Active Secret clearance or higher.
Bachelor’s degree in information technology, information systems, or a related field, or equivalent professional experience where permitted by the applicable labor category.
Minimum of eight years of relevant experience in endpoint engineering, systems engineering, device management, desktop engineering, VDI engineering, or a related technical discipline.
Experience designing and maintaining enterprise endpoint images.
Experience developing, testing, and deploying application packages.
Experience supporting enterprise endpoint provisioning, deployment, patching, configuration, and lifecycle management.
Experience engineering or supporting Virtual Desktop Infrastructure.
Experience implementing approved endpoint-security or vulnerability-remediation changes.
Experience troubleshooting complex endpoint, deployment, packaging, patching, or VDI issues.
Knowledge of controlled testing, pilot deployment, phased implementation, validation, rollback, and change-management practices.
Ability to develop technical procedures, image documentation, package records, test plans, deployment plans, rollback procedures, and completion evidence.
Microsoft 365 Certified: Endpoint Administrator Associate certification when relevant to the assigned Microsoft 365 or Intune environment.
Ability to support after-hours maintenance, deployment windows, critical incidents, and endpoint recovery when required.
Strong written, verbal, analytical, and technical problem-solving skills.
Strong attention to detail and change discipline.

Nice To Haves

Experience with Microsoft Intune or Microsoft Endpoint Manager.
Experience with Microsoft Configuration Manager or System Center Configuration Manager.
Experience with Windows Autopilot and modern device provisioning.
Experience with Microsoft Defender for Endpoint.
Experience with Microsoft Entra ID and hybrid endpoint management.
Experience with PowerShell, Microsoft Graph, or other endpoint-automation technologies.
Experience packaging applications using MSI, MSIX, Win32, App-V, or comparable formats.
Experience with VMware Horizon, Azure Virtual Desktop, Windows 365, Citrix, or another enterprise VDI platform.
Experience supporting federal or Department of Defense endpoint environments.
Experience applying DISA Security Technical Implementation Guides to Windows endpoints.
Experience supporting Risk Management Framework controls, vulnerability remediation, or authorization evidence.
Experience with endpoint analytics, digital employee experience, compliance, or configuration-management tools.
Experience supporting large-scale operating-system migrations, device refreshes, or endpoint-management modernization.
CompTIA Security+ or another relevant security certification.
ITIL v4 Foundation certification.
Relevant Microsoft, VMware, Citrix, cloud, automation, or endpoint-management certification.

Responsibilities

Serve as the senior engineer for enterprise endpoint imaging, packaging, deployment, patching, configuration, and VDI capabilities.
Design, build, test, maintain, document, and validate standardized endpoint images and their components, dependencies, settings, security baselines, software, and deployment configurations.
Establish image versioning, testing, approval, rollback, release, and retirement procedures.
Develop and maintain automated deployment task sequences, provisioning workflows, configuration profiles, and enrollment processes using approved Microsoft and Government management platforms.
Support modern endpoint-management and co-management capabilities, including Intune, Configuration Manager, Windows Autopilot, or comparable technologies.
Develop, test, maintain, and deploy application packages for commercial, Government, and internally developed software.
Create package installation, detection, dependency, requirement, upgrade, repair, and removal logic; test packages for installation, detection, compatibility, security, user experience, and clean removal.
Troubleshoot software installation failures, package conflicts, missing dependencies, detection problems, and deployment errors.
Develop approved scripts and automation for packaging, provisioning, configuration, deployment, validation, and remediation; maintain automation in approved version-control and documentation repositories.
Design and administer patching processes for operating systems, approved applications, drivers, firmware, and management components.
Establish deployment rings, pilot groups, production waves, maintenance windows, deadlines, exception handling, and rollback procedures; test updates before production deployment.
Monitor patch deployment progress, failure rates, compliance, endpoint health, and exceptions; investigate failures and coordinate corrective actions, redeployment, or approved exceptions.
Engineer and support VDI capabilities, including base images, desktop pools, application delivery, user-profile configurations, policies, and endpoint-access requirements.
Monitor and troubleshoot VDI performance, availability, login, profile, application, display, peripheral, and connectivity issues; support VDI modernization, capacity planning, testing, deployment, and optimization.
Coordinate VDI dependencies with virtualization, storage, network, identity, application, and cybersecurity teams.
Support enterprise endpoint deployment and refresh projects across USMEPCOM Headquarters, MEPS, Remote Processing Substations, COOP sites, and remote users.
Develop technical implementation plans for device refreshes, operating-system upgrades, application migrations, and endpoint-management transitions.
Support endpoint provisioning, enrollment, configuration, testing, deployment, replacement, recovery, and retirement.
Provide Tier 3 and Tier 4 engineering support for complex endpoint, application-packaging, deployment, patching, and VDI incidents.
Analyze endpoint logs, deployment status, policy results, management-platform data, and other technical evidence; develop corrective actions for recurring incidents and known errors.
Support major incidents and outages involving endpoint management, software deployments, VDI, or widespread device failures; implement approved workarounds and service-restoration actions.
Coordinate with Service Desk and field-support teams to improve troubleshooting, escalation, and knowledge content, and create technical guidance for common issues.
Review Task 6 cybersecurity findings assigned to endpoint operations and assess operational impact, dependencies, testing, deployment, and rollback requirements.
Implement approved endpoint security changes and remediation involving images, software versions, patches, configurations, policies, or management settings through established change-management and release procedures.
Maintain evidence of affected populations, deployment methods, implementation status, failures, exceptions, and completion results; provide remediation evidence to Task 6 for validation and closure.
Coordinate unresolved or technically infeasible remediations with cybersecurity, system owners, vendors, and Government stakeholders.
Apply approved DISA Security Technical Implementation Guides and endpoint-security baselines.
Support endpoint compliance reporting, vulnerability remediation, configuration validation, and audit-evidence collection.
Maintain endpoint inventories, deployment records, configuration baselines, package records, patch status, VDI documentation, and technical diagrams.
Develop and maintain standard operating procedures, field guides, packaging standards, test plans, implementation plans, rollback plans, and recovery procedures.
Follow approved incident, problem, change, release, configuration, asset, security, and quality-management processes.
Provide endpoint health, deployment, patching, compliance, risk, issue, and modernization information for operational and program reporting.