Senior Endpoint Systems Engineer

Jobtailor; Chicago (IL); On-site; USD 120,000 - 150,000; Full time

Job summary

Jobtailor in Chicago is seeking an experienced Endpoint Engineer to architect, optimize, and maintain our global UEM infrastructure using Intune, Jamf Pro, and Workspace ONE. You will design automated deployment and configuration workflows for Windows 10/11 and macOS at scale.

You will lead initiatives, automate complex tasks with PowerShell and Bash, and collaborate with Security to enforce baseline controls and IAM integrations, acting as escalation for advanced endpoint issues.

Qualifications

• 5–8+ years in endpoint engineering, systems admin, or infra architecture.
• Deep knowledge of Windows and macOS in enterprise deployments.
• Experience configuring Intune, Jamf Pro, Workspace ONE at scale.
• Strong automation with PowerShell and Bash/Zsh; Python a plus.
• Ability to lead projects and communicate with non-technical stakeholders.

Responsibilities

• Architect, optimize, and maintain UEM infrastructure using Intune, Jamf Pro, Workspace ONE.
• Design and scale automated deployment, provisioning, and configuration for Windows and macOS.
• Standardize deployment frameworks with Autopilot, ABM, and EDE for zero-touch provisioning.
• Develop, test, and maintain code for automation, reporting, and API integrations.
• Partner with Security to enforce endpoint baselines, encryption, and EDR deployments.
• Lead integration of endpoint platforms with IAM systems and SSO extensions.
• Act as highest escalation for complex endpoint, OS, and software issues.

Skills

Endpoint engineering

Windows

macOS

PowerShell

Bash

Python

Jamf Pro

Intune

Workspace ONE

Automation

Scripting

Tools

Microsoft Intune

Jamf Pro

Workspace ONE

Job description

Responsibilities

• Architect, optimize, and maintain our global Unified Endpoint Management (UEM) infrastructure using Microsoft Intune, Jamf Pro, and VMware Workspace ONE.
• Design and scale automated deployment, provisioning, and configuration management workflows for a balanced fleet of Windows 10/11 and macOS hardware.
• Standardize and evolve modern deployment frameworks utilizing Windows Autopilot, Apple Business Manager (ABM), and Automated Device Enrollment to achieve zero-touch provisioning.
• Develop, test, and maintain robust code repositories (PowerShell for Windows; Bash/Zsh/Python for macOS) to automate complex administrative tasks, custom reporting, and API integrations.
• Partner closely with the Security team to engineer and enforce endpoint security baselines (e.g., CIS Benchmarks), disk encryption protocols (BitLocker, FileVault), and EDR/antivirus agent deployments.
• Lead the integration of endpoint platforms with enterprise identity and access management (IAM) systems (e.g., Entra ID, Okta), including modern single sign‑on (SSO) extensions.
• Act as the highest tier of technical escalation for complex endpoint, OS, and software issues.

Requirements

• 5–8+ years of dedicated experience in endpoint engineering, systems administration, or infrastructure architecture within an enterprise environment.
• Comprehensive, expert‑level knowledge of both Windows and macOS operating systems, system internals, and enterprise deployment methodologies.
• Deep hands‑on engineering experience configuring and managing Microsoft Intune, Jamf Pro, and Workspace ONE at scale.
• Strong proficiency in PowerShell and Bash/Zsh (Python or Swift is a significant plus) for advanced automation, custom scripts, and utilizing MDM APIs.
• Proven ability to lead projects independently, collaborate across multi‑functional engineering teams, and explain complex technical concepts to non‑technical stakeholders.

Core Competencies

Demonstrates expertise in architecting and optimizing Unified Endpoint Management (UEM) infrastructures, with a strong focus on Microsoft Intune, Jamf Pro, and VMware Workspace ONE. Proficient in automating deployment and configuration management workflows for Windows and macOS environments while ensuring endpoint security and compliance.