Senior IT Support Specialist

About the role

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.

Key Responsibilities

• Endpoint Management: Manage, maintain, and optimize our fleet using Microsoft Intune and MacOS MDM platforms (Mosyle). Ensure device compliance and security across all endpoints.
• Automation and Deployment: Oversee application packaging, patching, and deployment strategies utilizing desktop automation utilities and scripting to enhance efficiency and maintain consistency.
• Cloud Application Administration: Administer and maintain core collaboration and communication platforms, including Google Workspace and Microsoft 365.
• Identity and Access Management (IAM): 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).
• Technical Support: Act as the primary contact point for complex, advanced technical issues involving Mac, Windows, Android, and iOS devices, ensuring rapid resolution and minimal disruption.
• Remote Workforce Support: Develop and implement strategies to provide superior and scalable technical support for a remote and distributed workforce, leveraging remote tools and standardized processes.
• Documentation and Training: 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.

Qualifications

• 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.

Location

Based in Los Angeles, CA.

Experience

• 5+ years of progressive experience in technical support, systems administration, or a similar role, with a focus on advanced endpoint and cloud administration.
• Hands-on expertise and certification (preferred) with Microsoft Intune and dedicated experience with a major MacOS MDM platform (e.g., Jamf, Kandji).
• 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.
• Retail Technology Management: Experience providing support for retail store technology and deployments, including Point-of-Sale (POS) systems, network infrastructure, and other in-store hardware.
• Retail Technology Experience: Prior hands-on experience with retail technology deployment, support, and maintenance, particularly with POS systems and in-store networking solutions.
• VPN Evaluation & Deployment: Prior experience evaluating, deploying, and managing enterprise VPN solutions to support secure remote access for a distributed workforce.

Benefits

• Be part of a purpose-driven company that’s shaping the future of comfort and mental wellness.
• Work in a supportive, creative environment where your ideas and growth are valued.
• Enjoy Comfrt benefits such as generous paid time off, company-covered health insurance, 5% 401k match, and discounts on all Comfrt products!
• Join a passionate team making an impact on exciting projects

Equal Opportunity Employer

We are committed to building a team that represents a variety of backgrounds, perspectives, and skills.