Senior IT Support Specialist

Senior IT Support Specialist

Comfrt is one of the fastest-growing DTC apparel brands in the world, with a social presence that even industry giants envy. Founded just three years ago, we've quickly built a reputation for stylish, elevated, and functional clothing designed to deliver unmatched comfort. From subtly weighted hoodies and sweatpants to cozy blankets and even pet hoodies, every Comfrt piece is created to inspire relaxation, support well-being, and promote a positive mindset.

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.

Skills & Qualifications

• Education: A Bachelor's degree in Information Technology, Computer Science, or a related field — or equivalent professional experience — is required.
• Platform Expertise: Deep proficiency and advanced troubleshooting skills across Mac, Windows, and Android operating systems in an enterprise environment.
• Modern Deployment: Extensive experience with asset deployment using configuration profiles, policy enforcement, and implementing zero-touch deployment configurations via a Mobile Device Management (MDM) platform.
• IT Automation: Strong scripting capabilities using languages such as PowerShell, Bash, or Python to automate repetitive tasks, manage configurations, and improve operational efficiency.
• Security & Identity Management: 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.
• Project Leadership: Proven ability to manage hardware refreshes, OS migrations, and IT infrastructure projects from planning through execution and deployment.
• Networking Fundamentals: Solid understanding of basic networking principles (TCP/IP, DNS, DHCP, VPN) and the ability to troubleshoot connectivity issues across local and remote environments.
• Data Protection & Recovery: 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.
• Based in Los Angeles, CA.

Experience Requirements

• 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.

Preferred Experience

• 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.

Why Join Comfrt?

• 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

Comfrt is an equal opportunity employer. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills.