Helpdesk Analyst

Cloaked is building a cyber expert at your side - one that watches, advises, and acts to keep you safe and private in the age of AI. 600k+ paying members already use Cloaked to take back control of their data, their identity, and who can reach them: masked emails, phone numbers, and payment cards, data removal from broker sites, and an AI voice agent that screens calls before they ring through. We've protected 10M+ identities, screened 50M+ calls, and removed 1B+ records from the data brokers who profit off personal information. Backed by a $375M Series B, we're now building the agents that turn detection into action - for individuals, families, and the companies that want to protect their people. About the Role You're the first person our users talk to when something's broken. Password resets, laptops that won't wake up, printers that hate Mondays, "my email is doing a weird thing" — that's the job. Some of it is routine. Some of it is a genuine mystery. All of it matters to the person on the other end of the ticket. This is a Tier 1 role with room to grow. If you like solving problems, learning new tools, and helping people who don't share your comfort with technology, you'll do well here. What will you do?

• Work the ticket queue: intake, triage, and resolve within SLA.
• Answer phones, respond to email/chat, and handle walk-ups when you're on-site.
• Troubleshoot macOS, common business apps, and basic network issues (Wi-Fi, VPN, "the internet is down for just me").
• Handle account lifecycle tasks: password resets, group membership, license assignment, MFA re-enrollment.
• Image, deploy, and recover end-user hardware (laptops, desktops, monitors, peripherals, mobile devices).
• Document what you fix. If you solved it twice, write the KB article.
• Escalate cleanly when something is over your head or your access — with enough context that the next person doesn't have to start from zero.
• Show up for the user. Even when the user is wrong. Especially when the user is frustrated.

What skills and experiences will help you?

• 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 (Outlook, Teams, OneDrive, SharePoint basics).
• Basic networking literacy: what an IP address is, what DNS does, how to tell if Wi-Fi is the problem.
• Writing skills that pass the "can I understand this ticket note six months from now?" test.
• Patience. Genuine, non-performative patience.

What's nice to have?

• MacOS support experience.
• Familiarity with Active Directory or Entra ID — enough to reset passwords, unlock accounts, and check group membership.
• Exposure to an ITSM ticketing system (any of them — the vocabulary transfers).
• CompTIA A+, Network+, or equivalent hands-on knowledge.
• Any scripting exposure (PowerShell, Bash) — you don't need to be a developer, but reading a script is useful.
• Curiosity about the layer under the one you work at.

What Success Looks Like

• 30 days:You've cleared onboarding, know the ticketing system cold, and are resolving straightforward tickets independently.
• 90 days:You're closing tickets within SLA consistently, contributing to the KB, and picking up more complex work.
• 12 months:You've grown into the harder Tier 1 work, and either you're the go-to person for a specific area or you're ready to move into Tier 2 / a specialization.

What This Job Isn't

• Sitting behind a screen ignoring people. This is a people job that happens to involve computers.
• Endless password resets forever. We'll invest in you if you invest in the work.

What we offer

Cloaked is a well-funded Series B startup based out of NYC.

Although we are a distributed team, the NYC team operates with a hybrid model. We have two floors of our building, with two state of the art kitchens packed with drinks, snacks and everything else you'd need to get through the day.

The Cloaked team has diverse interests and so we frequently embark on team outings and go out for socials!

Compensation and Benefits

We offer above market rate pay and equity based off of the market's best commercially available data. Your compensation will be a combination of salary, bonus and equity.

For full-time US employees, we offer a comprehensive benefits package: medical, dental and vision with Cloaked covering the majority of employee premiums, company-paid basic life, and a 401(k) with company match.

While this role has in-person requirements, we offer flexible work arrangements and the ability to work remotely when needed. Cloaked provides a home office stipend in addition to a new company laptop (and other tech depending on the role).

Perks

🌴 Competitive PTO: PTO, floating holidays and sick days - and we push people to actually use them. We see time off as a preventative burnout measure, not a balance to hoard. 👶 Parental Leave: Paid leave for all new parents - birth, adoption, or foster placement - because the people building privacy deserve time with their families. 🤸 Monthly wellness & meals stipend: Used for any kind of physical, mental or emotional care you'd like to take for yourself, be it a gym membership, a meditation app, or time with a personal trainer - plus lunch and coffee during the workday. 🧠 Professional Growth: Opportunities for career development and personal growth are provided to all employees who seek to further their knowledge and capabilities through an unlimited professional development fund. Additionally team members are encouraged to regularly attend conferences and industry events. We are really excited about having you join our mission-driven team and help us build the future of online privacy!