Senior IT Support Specialist (Remote)

About Comfrt:
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.

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 an escalation point for complex technical issues and drive improvements in our IT service delivery.

• Retail Technology Management: Provide comprehensive support for retail store technology and deployments, including Point-of-Sale (POS) systems, network infrastructure, and other in-store hardware.
• 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 Productivity Suite 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).
• Tier 3 Technical Support: Act as the primary escalation point for complex, advanced technical issues involving Mac, Windows, and Android operating systems, 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.

• Platform Expertise: Deep proficiency and advanced troubleshooting skills across Mac, Windows, and Android operating systems in an enterprise environment.
• Modern Deployment: Extensive experience with configuration profiles, policy enforcement, and implementing zero-touch deployment methodologies in a Mobile Device Management (MDM) environment.
• IT Automation: Strong scripting capabilities using languages such as PowerShell, Bash, or Python to automate repetitive tasks, manage configurations, and improve operational efficiency.
• Security and Identity Mastery: Mastery of Identity Management (IdP) systems (e.g., Okta, Azure AD) and a thorough understanding of 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.

• 5+ years of progressive experience in technical support, systems administration, or a similar role, with a focus on advanced endpoint and cloud administration.
• Direct, hands-on experience in retail technology deployment, support, and maintenance, particularly with POS and in-store networking solutions.
• Hands-on expertise and certification (preferred) with Microsoft Intune and dedicated experience with a major MacOS MDM platform (e.g., Jamf, Kandji).

Browse our curated collection of remote jobs across all categories and industries, featuring positions from top companies worldwide.

• Proven track record supporting and securing a geographically diverse and remote workforce at scale.
• Demonstrated experience in a Tier 3 support capacity, handling major escalations and complex systems issues.

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, all while enjoying the flexibility and collaborative support of a fully remote environment
  

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