Senior IT Support Specialist

Comfrt•Los Angeles, CA

1d•Remote

About The Position

We are seeking a self-motivated and well-versed Senior IT Support Specialist to join our growing Technology team. The ideal candidate will be responsible for assisting our internal employees with day-to-day break/fix issues, deploying new hardware, configuring applications and policies for deployment to the fleet, and assisting in larger company-wide initiatives. This role requires a systems-level mindset, an enthusiastic approach to problem-solving, and the ability to provide seamless, high-quality support to a diverse, remote workforce. This specialist will serve as a key contact for technical issues and drive improvements in our IT operations.

Requirements

A Bachelor’s degree in Information Technology, Computer Science, or a related field — or equivalent professional experience — is required.
Deep proficiency and advanced troubleshooting skills across Mac, Windows, and Android operating systems in an enterprise environment.
Extensive experience with asset deployment using configuration profiles, policy enforcement, and implementing zero-touch deployment configurations via a Mobile Device Management (MDM) platform.
Strong scripting capabilities using languages such as PowerShell, Bash, or Python to automate repetitive tasks, manage configurations, and improve operational efficiency.
Deep working knowledge of Identity Provider (IdP) systems (e.g., Okta, Azure AD) and a strong understanding of enterprise security protocols, including SSO, SAML, OAuth, and MFA implementation.
Proven ability to manage hardware refreshes, OS migrations, and IT infrastructure projects from planning through execution and deployment.
Solid understanding of basic networking principles (TCP/IP, DNS, DHCP, VPN) and the ability to troubleshoot connectivity issues across local and remote environments.
Familiarity with enterprise backup solutions (e.g., Veeam, Backblaze, Acronis) and experience developing or maintaining data recovery procedures aligned to defined RTO/RPO targets in a cloud or hybrid environment.
5+ years of progressive experience in technical support, systems administration, or a similar role, with a focus on advanced endpoint and cloud administration.
Proven track record supporting and securing a geographically diverse and remote workforce at scale.
Demonstrated experience in a Tier 2/3 support capacity, handling major escalations and complex systems issues.

Nice To Haves

Hands-on expertise and certification (preferred) with Microsoft Intune and dedicated experience with a major MacOS MDM platform (e.g., Jamf, Kandji).
Experience providing support for retail store technology and deployments, including Point-of-Sale (POS) systems, network infrastructure, and other in-store hardware.
Prior hands-on experience with retail technology deployment, support, and maintenance, particularly with POS systems and in-store networking solutions.
Prior experience evaluating, deploying, and managing enterprise VPN solutions to support secure remote access for a distributed workforce.

Responsibilities

Manage, maintain, and optimize our fleet using Microsoft Intune and MacOS MDM platforms (Mosyle). Ensure device compliance and security across all endpoints.
Oversee application packaging, patching, and deployment strategies utilizing desktop automation utilities and scripting to enhance efficiency and maintain consistency.
Administer and maintain core collaboration and communication platforms, including Google Workspace and Microsoft 365.
Manage and maintain the Single Sign-On (SSO) Okta platform, handle user account lifecycle administration, and ensure robust security protocols, including Multi-Factor Authentication (MFA).
Act as the primary contact point for complex, advanced technical issues involving Mac, Windows, Android, and iOS devices, ensuring rapid resolution and minimal disruption.
Develop and implement strategies to provide superior and scalable technical support for a remote and distributed workforce, leveraging remote tools and standardized processes.
Create and maintain high-quality technical documentation (e.g., knowledge base articles, runbooks) and train junior team members or end-users on new technologies and procedures.