Help Desk Specialist, Level 2; Windows & Apple

From our origins in New York in 2002, rag & bone was founded on a belief of uncompromising ideals: a commitment to doing things the right way, not the easy way. To making things that are as original as they are timeless. To being true to ourselves, even when that truth sets us apart from the mainstream.

We still believe in the same principles we started with: the easy elegance of classic British tailoring, the authenticity of American workwear, and the originality of our home city, New York. As New Yorkers, community and authenticity have become synonymous with our brand. An inclusive environment at rag & bone upholds our original values by encouraging employee connection and empowering each individual to have a voice on policy, process and collaboration for a more equitable future.

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.

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…