Helpdesk Analyst

Cloaked is a well-funded Series B startup based in NYC, building a people-first support experience with a hybrid team. You’ll join a collaborative environment with strong benefits, flexible work options, and a modern toolset, including a new company laptop and a home office stipend when you need it.

This Tier 1 helpdesk role is the first point of contact for user issues. You’ll handle ticket intake and triage, resolve requests within SLA, and support end users across both software and hardware needs, including account lifecycle work and macOS troubleshooting.

What you’ll do

• Manage the ticket queue by handling intake, triage, and resolution within SLA.
• Answer phones and respond to email and chat, plus assist walk-ups when you’re on-site.
• Troubleshoot macOS, common business applications, and basic networking (Wi-Fi, VPN, and issues like “the internet is down for just me”).
• Complete account lifecycle tasks including password resets, group membership updates, license assignment, and MFA re-enrollment.
• Image, deploy, and recover end-user hardware such as laptops, desktops, monitors, peripherals, and mobile devices.
• Document fixes clearly. If you solved the same issue twice, create a KB article.
• Escalate appropriately when something is outside your scope or requires access, with enough context so the next person can continue without starting over.
• Support users with patience and ownership, including when users are wrong or frustrated.

Requirements

• 1+ year in a customer-facing technical support role (helpdesk, MSP, retail tech support, internship, or equivalent).
• New grads with a strong technical foundation and demonstrable side projects will be considered.
• Working knowledge of Windows 10/11 and Microsoft 365 basics (Outlook, Teams, OneDrive, SharePoint).
• Basic networking literacy, including what an IP address is, what DNS does, and how to tell if Wi-Fi is the issue.
• Writing skills that help others understand ticket notes months later.
• Patience with a genuine, non-performative approach.

Helpful experience

• MacOS support experience.
• Familiarity with Active Directory or Entra ID for tasks like resetting passwords, unlocking accounts, and checking group membership.
• Exposure to an ITSM ticketing system (any platform, transferable vocabulary).
• CompTIA A+, Network+, or equivalent hands-on knowledge.
• Some scripting exposure (PowerShell or Bash), even if you only read scripts.
• Curiosity about layers beneath the tools you support.

Benefits and perks

• Above market rate pay and equity based on the market’s best commercially available data (salary, bonus and equity).
• Comprehensive full-time US benefits: medical, dental, and vision with Cloaked covering the majority of employee premiums.
• Company-paid basic life.
• 401(k) with company match.
• Flexible work arrangements, with ability to work remotely when needed.
• Home office stipend.
• New company laptop (and other tech depending on the role).
• PTO, floating holidays, and sick days.
• Parental Leave: paid leave for all new parents (birth, adoption, or foster placement).
• Monthly wellness & meals stipend, plus lunch and coffee during the workday.
• Unlimited professional development fund and encouragement to attend conferences and industry events.

Location: New York, NY (hybrid). Pay: USD 40 - 47 per hour. Experience level: 1+ years.