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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Help Desk Specialist, Level 2 (Windows & Apple) - **Company:** rag & bone - **Location:** New York, NY, United States - **Experience:** Experienced - **Salary:** $70,000.0 - $80,000.0 - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Artificial Intelligence, Apple IOS, Apple Mac Systems, Bash Shell, System Configuration, Desktop Computing, Windows PowerShell, Scripting, Agentic-AI, Microsoft InTune, Information Technology, Apple Business Manager, Virtual Agents, Servicenow - **Published:** October 22, 2026 - **Apply:** https://www.careerjet.com/jobad/us12012b948699d0f7c331650a161bd6f6 ## About the Role * 2+ years of help desk or desktop support experience, including Level 2 troubleshooting in a mixed Windows and Apple environment, ideally in retail or fashion. * Strong knowledge of Windows, macOS and iOS systems, and proficient in diagnosing complex hardware, software, and operating system issues. * Ability to maintain and configure systems using Microsoft Intune and Apple Business Manager with Federated Apple ID. * Hands-on experience operating ITSM AI agents (such as Serval, ServiceNow, Fixify, or Ivanti), with strong AI literacy. * Experience writing clear, structured knowledge base content that works for both end users and AI agents. * Comfortable building workflows and automations; scripting experience (PowerShell, Bash, or zsh) is a plus. * Experience building or tuning ITSM AI agents is a big plus. * Analytical mindset, comfortable using ticket data and service metrics to spot trends and prioritize improvements. * Hands-on experience setting up workstations and peripherals, and comfortable with the physical side of the role, including moving and installing equipment. * Knowledge of Android systems is a plus. * Experience with Meraki network is a plus. * Bachelor's degree in computer science, Information Technology, or a related field, or equivalent experience. * Excellent verbal and written communication skills, with the ability to explain technical issues simply and stay calm with frustrated users. * Ability to work efficiently in a collaborative team environment. * Detail-oriented, organized, and able to effectively perform multiple tasks. * Flexible schedule availability during weekdays and weekends, as necessary. ## Description rag & bone's service desk now runs with an AI agent as the first line of support for our corporate and retail teams. It handles routine Level 1 requests, such as password resets, access requests, and how-to questions, and the share of requests it resolves on its own will keep growing. As our Level 2 Help Desk Specialist, you are the expert behind it. You pick up what the agent escalates, solve the harder Windows and Apple hardware and software problems, and make the agent better with every ticket by turning fixes into knowledge, workflows, and automations. You will also own the hands-on side of support at HQ: the workstations, desks, and equipment our teams work from. How the Team Works: The AI agent is the front door; you are the judgment and the hands behind it. Success in this role is measured not only by the issues you resolve, but by how much of the work you make repeatable, so the agent resolves more each quarter and the team spends its time on work that genuinely needs a person. We aim to be adaptable but have a long-term vision. We select team members based on their proven skills, character, and background. Meeting the challenges of our dynamic environment requires talent, creativity and determination. If you are interested in new challenges, looking for a career that utilizes your abilities, consider joining the rag & bone IT team., * Resolve Level 2 incidents and requests escalated by the AI service desk agent across Windows and Apple systems (PC, Mac, iPhone, iPad), including complex hardware, software, operating system, and application issues. * Serve as the human point of contact for corporate and retail staff when an issue needs a person, providing clear, patient support and training on our tools and devices. * Review escalations and AI-handled conversations to identify inaccurate answers, knowledge gaps, and missed automation opportunities, and feed findings back to improve resolution quality. * Own the knowledge base the AI agent relies on: write, update, and retire articles for Windows, macOS and iOS so answers stay accurate, current, and easy to follow. * Work closely with the AI team to design, test, and maintain AI agent workflows and automations (for example access requests, software installs, device enrollment, and onboarding and offboarding steps) * Manage Windows, macOS and iOS devices using Microsoft Intune and Apple Business Manager, including policies, configuration profiles, app deployment, and compliance. * Set up and support employee workstations and desks, including computers, monitors, docks, keyboards, phones, and other peripherals, for new hires, moves, and refreshes. * Troubleshoot and resolve onsite hardware and peripheral issues at HQ, including cabling and printers. * Track inventory of Windows and Apple systems to ensure proper refresh cycles and reliability. * Plan and execute the selection, purchase, installation, configuration, and testing of new Windows and Apple equipment. * Escalate issues beyond Level 2 to infrastructure, security, and application owners with clear documentation for a fast handoff.