AI Support and Infrastructure Associate

We're an AI-first shop that builds almost everything with Claude Code. We need someone who loves technology more than anything: you'll keep our aviation clients running, and you'll build the tools, scripts, and fixes that make support better every week. ForIT builds software and runs IT for aviation companies: airlines, charter operators, and the businesses around them. We're a heavily AI-driven team. Most of our code is written with Claude Code, and our help desk runs on AI that drafts the first reply to most tickets. We're hiring a technologist who wants to live in that world. You'll start on support: password resets, a laptop that won't join Wi-Fi, a shared mailbox that stopped syncing, a new hire who needs accounts by Monday. AI drafts the reply; you check it, fix it, and send it. But the job doesn't stop at the ticket. When the same problem shows up twice, you build the fix: a script, an automation, a change to our own apps, or a correction to the AI's instructions. You'll work across the stack, from Entra ID and Intune to Azure, our Next.js apps, and the AI agents that tie them together. We're looking for someone who tinkers on weekends, has opinions about their setup, and gets excited when a new model or tool drops. Location: Remote (Canada), with some on-site work in Toronto Type: Subcontractor to start, at two-thirds of full time (about 27 hours a week). We plan to move to an employee model as we grow. Hours: You'll start by supporting two client companies. We're working on bringing on a third, which would make this a full-time role. Mostly weekday business hours, with some after-hours coverage when an airline needs it. Compensation: Target C$90,000-108,000 a year at full time. The role starts at two-thirds time (about C$5,000-6,000 a month), billed monthly as hourly rate x weekly hours x 4 weeks. We're an early-stage startup We're small and still early. Priorities shift, processes are still being written, and the role will grow as the client list does. That means real ownership and a say in how things get built, along with the uncertainty that comes with any young company. If you want a fixed job description and a big-company safety net, this isn't it. What the job is not It's not a call center and it's not a script. You'll support a small set of companies rather than thousands of anonymous users, so you'll know the people by name and have time to fix root causes instead of just closing tickets. About ForIT We're a small team working with regional airlines, charter operators, and aviation service companies across North America. We build websites, internal tools, and automation for them, and we run their help desk. We work remotely, and you'd be joining early enough to have a say in how support gets done. What you'll do Building with AI Use Claude Code daily to write scripts, automations, and fixes, and review what it produces before it shipsTurn repeat tickets into code: a PowerShell script, an Azure Function, or a change to our own appsHelp run the infrastructure behind our products: Azure, DNS, Entra ID, and the pipelines that deploy themSupport Answer the phone line, the text line, and the ticket queue during business hoursResolve tier 1 and tier 2 issues on Windows, macOS, iPhones, iPads, and Microsoft 365Review AI-drafted replies, correct them, and send them under your nameEscalate the rest with a clear write-up of what you triedGo on site in Toronto when a fix needs hands on a deviceAccounts and devices Create, change, and remove user accounts in Entra ID and Microsoft 365Enroll and troubleshoot devices in Intune and JamfRun the new-hire and departure checklists for client staffMaking the AI better Flag where the AI drafts go wrong, and write the correction into its instructions and knowledge baseWrite knowledge base articles and runbooks so the same question isn't answered twiceNotice repeat issues and propose the fix, whether that's a setting, a script, or a conversation with the clientWhat we're looking for You love technology, and it shows in what you build, fix, or tinker with outside of workYou use AI coding tools (Claude Code, Copilot, Cursor, or similar) and can explain where they go wrongComfortable on the command line, with Git, and with at least one scripting language (PowerShell, Python, or TypeScript)Real hands-on IT experience: Windows, macOS, and Microsoft 365 admin, whether from a job, a home lab, or running IT for friends and familyYou write clearly, and you stay calm with someone who is stressedYou understand the risks of joining an early-stage startup and are comfortable with themAvailable weekday business hours, with flexibility for the occasional evening or weekend issueAble to get to Toronto for occasional on-site workYou must already be legally entitled to work in Canada. We're not able to sponsor work permits.Nice to have Azure experience: App Service, Functions, SQL, networkingFull-stack web development, especially Next.js or TypeScriptEntra ID beyond the basics: conditional access, SSO, group managementIntune or Jamf device managementYou've supported Business Central or Dynamics 365 usersA home lab, a self-hosted project, or a GitHub profile you're proud ofExperience supporting aviation or any business that runs around the clockHow to apply Click Apply to go to our careers page at forit.io, and send your resume and a short note. Tell us: Something you built or automated with AI, and what you had to fixA time an AI tool gave you a confident wrong answer, and how you caught itYour weekday availability and how close you are to TorontoConfirm that you're legally entitled to work in Canada without sponsorshipWe review applications as they come in and reach out to set up a call.