[Hiring] IT Systems Engineer @Thoughtful

Role Description

We're seeking an IT Systems Engineer to build, manage, automate, and continuously improve our IT infrastructure as well as our global endpoint ecosystem, which primarily consists of macOS and Windows devices. You'll be instrumental in ensuring our environment is secure, reliable, and highly automated, integrating our systems, including M365, O365, Okta, Slack, MDM solutions, and more.

This role is for an engineer passionate about integrating systems and managing endpoints, leveraging Configuration-as-Code (CaC), GitOps principles, and automation to create a connected, intelligent, and adaptive IT environment that scales with the company.

Primary tech stack:

• macOS
• Windows
• MDM solutions
• Okta
• Microsoft 365
• Python
• Bash
• Git

Key Responsibilities

• Integrate complex systems into Identity Management and implement new systems into the environment as they’re added.
• Help manage Microsoft 365 / Office 365 Services such as OneDrive, SharePoint online, and Exchange Online.
• Own and manage an MDM for device management.
• Implement, test, and maintain GitOps workflows to ensure repeatable, auditable, and version-controlled changes across the client platform.
• Develop and maintain scripts, policies, and configuration profiles to enforce compliance and automate device setup using scripting languages like Python and Bash.
• Automate IT business processes.
• Leverage APIs, webhooks, and automation to build and maintain visibility dashboards for device posture, compliance, and provisioning metrics.
• Maintain vulnerability management processes and patch cadence across platforms.
• Create technical and standard operating procedure documentation for workflows and policies.

What Success Looks Like

• The deployment and configuration of macOS and Windows endpoints are primarily managed through automated and version-controlled GitOps workflows.
• Users have a technology experience they love, the tools they need, and as consumers of an experience as possible.
• Successfully assist with complex migrations of dispersed applications to a centralized environment.
• Cross-functional collaboration with IT and Security teams results in a seamless and highly secure user experience for all employees.
• Onboarding and Offboarding workflows are optimized.

Qualifications

• 4+ years of experience as an IT Systems Engineer with a heavy hand in MDM solutions and endpoint management.
• Proficient with scripting and automation using Bash, Python, or similar languages.
• Experience managing SaaS products and configuring SSO solutions such as Okta.
• Experience with Git, CI/CD pipelines, and Infrastructure-as-Code or GitOps methodologies.
• Strong knowledge of macOS, Windows, endpoint automation, and enterprise support.
• Strong understanding of API-based integrations (e.g., REST, Graph API) for SaaS platforms.
• Experience managing Microsoft 365/Office 365 and associated services.
• Excellent troubleshooting, documentation, and communication skills.

Bonus Points

• Experience with Swift or Python for building internal tools or lightweight agent applications.
• Familiarity with compliance frameworks such as SOC 2 or ISO 27001 and working in HIPAA-regulated HITRUST environments or similar.
• Linux Client Platform Engineering experience.

Benefits

• Competitive compensation
• Equity participation: Employee Stock
• Health benefits: Comprehensive medical, dental, and vision insurance
• Time off: Generous leave policies and paid company holidays