Help Desk Specialist, Level 2 (Windows & Apple) - Rag & Bone

About rag & bone

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.

Overview:

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.

Responsibilities:

• 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.

Requirements:

• 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.

Rules we live by | Rules you live by

Be a Good Human | Be original, be authentic. Stand for diversity, equitability & inclusivity

Have No Fear | Innovate and solve problems

Own Every Decision | Work together and get results

Quality Matters | Not only with product, but we see it in our people

Make Shit Happen | Be disciplined, be competitive

Our in-office policy is in office, 4 days a week.

Benefits

• Paid Time Off
• Clothing Allowance
• Generous Employee Discount
• Paid Parental Leave
• Membership to Calm and access to other wellness benefits
• Medical, dental, vision and ancillary benefits
• 401k

Salary: The target salary for this role is between $70,000 and $80,000 based on candidates' experience and expectations.

rag & bone is an EEO/Affirmative Action Employer. No employee or applicant is discriminated against because of race, color, sex (including pregnancy), age, national origin, religion, sexual orientation, gender identity, gender expression, parental status, status as a veteran, and basis of disability or any other federal, state or local protected class.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 30 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.