Lead IT Systems Engineer - Cloud, Identity & Security

Treeline; Watertown (MA); On-site; USD 140,000 - 190,000; Full time

Job summary

Treeline seeks an experienced Principal Information System Engineer to join our IT team. You will lead complex IT initiatives, manage Microsoft 365/Entra ID/Okta, and strengthen endpoint security across multiple countries.

The role requires hands-on support, strong scripting, and collaboration with MSPs and internal engineers. Ideal candidates will have 8-10+ years in systems administration, a broad IT background, and exceptional problem-solving.

Qualifications

• Bachelor's degree in Information Technology, Computer Science, or related field or equivalent work experience.
• 8-10+ years of experience in systems administration, endpoint management, identity management, or IT operations.
• Broad IT experience across Windows, Mac, Databases, Storage, Security, Networking and public clouds.
• Hands-on experience with Microsoft 365 Administration.
• Experience with Microsoft Entra ID including Conditional Access Policies.
• Experience with Okta.
• Experience with endpoint security and device management.
• PowerShell scripting (Basic to Intermediate).
• Strong troubleshooting, problem-solving and analytical skills.
• Proven ownership in issue resolution and documentation.

Responsibilities

• Serve as the primary technical escalation point for the IT organization and provide hands-on end-user support as needed.
• Lead complex technical initiatives and provide recommendations to IT leadership on tooling and standards.
• Administer and optimize cloud-based technologies including endpoint, identity, and security management.
• Manage Microsoft 365, Entra ID, and Okta environments and implement MFA and CA policies.
• Develop PowerShell scripts to automate routine tasks and improve efficiency.
• Collaborate with in-house engineers and MSPs to support employees across departments and countries.
• Maintain accurate IT tickets, knowledge base articles, and ITSM process adherence.
• Communicate clearly with coworkers and vendors, both locally and remotely, ensuring effective collaboration.

Skills

PowerShell

M365 Admin

Okta

Entra ID

Endpoint Security

Identity Management

Troubleshooting

Documentation

ITSM

Vendor Management

Education

Bachelor's degree in IT or related field

Tools

Intune

Azure AD

MFA

Job description

Treeline seeks an experienced Principal Information System Engineer to join our IT team. You will lead complex IT initiatives, manage Microsoft 365/Entra ID/Okta, and strengthen endpoint security across multiple countries.

The role requires hands-on support, strong scripting, and collaboration with MSPs and internal engineers. Ideal candidates will have 8-10+ years in systems administration, a broad IT background, and exceptional problem-solving.