Senior IT Specialist (Retail)

Comfrt

8d•$80,000 - $100,000•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 an escalation point for complex technical issues and drive improvements in our IT service delivery.

Requirements

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).
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.

Responsibilities

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.