Apple @ Work is exclusively brought to you by Mosyle, the only Apple Unified Platform. Mosyle is the only solution that integrates in a single professional grade platform all the solutions necessary to seamlessly and automatically deploy, manage, and protect Apple devices at work. Over 45,000 organizations trust Mosyle to make millions of Apple devices work ready with no effort and at an affordable cost. Request your EXTENDED TRIAL today and understand why Mosyle is everything you need to work with Apple.
MacPaw spent nearly two decades building consumer software for Mac users. CleanMyMac is one of the Mac utilities on the market, and it’s my go-to when I need to free up hard drive space, uninstall apps, etc. The company is making a different kind of bet with Leebry, a Work AI platform aimed at helping IT teams.
About Apple @ Work: Bradley Chambers has been an Apple IT admin since 2009. Through his experience deploying and managing firewalls, switches, a mobile device management system, enterprise grade WiFi, 1000s of Macs, and 1000s of iPads, Bradley will highlight ways in which Apple IT managers deploy Apple devices, build networks to support them, train users, share stories from the trenches of IT management, and ways Apple could improve its products for IT departments.
The AI trust numbers
MacPaw’s 2026 AI at Work report is where you see the issue IT faces, as they found that 90% of companies deploy AI without thoroughly auditing their internal knowledge base first. That means that internal AI tools are answering employee questions based on whatever it can find, including old product docs, outdated policies, and random Reddit discussion forums.
In this survey, MacPaw found that 6 in 10 IT leaders see a real disconnect between what their C-Suite expects from AI tools (thanks to LinkedIn feeds) and what their teams can safely and accurately deliver. That gap is where most AI disappointment lives, and it’s the problem Leebry is attempting to solve for IT teams.
What Leebry actually does
Leebry began as an internal MacPaw hackathon project in 2025. The problem it was solving was employees repeatedly asking the same questions internally, even when the answers already existed somewhere in the company’s documentation, intranets, Slack threads, etc. MacPaw built a Slack bot to surface those answers and point employees to the exact source. Within a few months, it was resolving 30% of MacPaw’s own level 1 IT tickets, so that became the foundation for what they’re launching today with Leebry.
The platform automates level 1 support tickets, handles access provisioning and removal as employees join, move roles, or leave, and answers employee questions across the tools they already use. Every Leebry response links back to its source, so employees can verify the answer rather than just trust it (and prove it), and can flag stale or outdated information that could affect accuracy. That last part is the direct product response to the 90% knowledge audit problem from their own research.
One detail worth calling out for security-conscious IT folks: Leebry is permission-aware, meaning it authenticates each user and surfaces only the information they are permitted to see. That matters more than it sounds as a lot of AI tools draw on a shared knowledge pool and let users surface things they shouldn’t access. Leebry also ships with an MCP server that exposes the device management control plane to AI agents, with admin-set guardrails on every action, so teams can delegate repetitive work to agents without giving up control over what those agents can actually do.
For IT orgs that work extensively with Apple, the access provisioning aspect is interesting. Automating access changes as people move within the organization can be a huge pain point for SMBs without a dedicated IAM team. Most of the time, it’s manual, it’s slow, and departing employees end up with access that should have been revoked days earlier. I’ve run into this myself quite a bit.
“Businesses don’t need another tool to check, they need work taken off their plate, without sacrificing oversight or control,” said Dan Jaenicke, Director of B2B Product Development at MacPaw.
Wrap up
The fair question here is why an IT team should trust a consumer Mac software company to build enterprise tooling. I think the answer is actually in the product’s origin story. MacPaw built Leebry to solve their own internal IT problem first, which is a better foundation than most enterprise software gets. It wasn’t built to make money. It was built to solve a customer (even internal) problem, so it’ll work well for other teams. The reality is all orgs have docs spread out across team chat, file sharing, intranets, etc and we’re all guilty of asking for someone else to find it for us.
Leebry aims to make it easy for IT to solve the same questions folks ask over and over again.
Apple @ Work is exclusively brought to you by Mosyle, the only Apple Unified Platform. Mosyle is the only solution that integrates in a single professional grade platform all the solutions necessary to seamlessly and automatically deploy, manage, and protect Apple devices at work. Over 45,000 organizations trust Mosyle to make millions of Apple devices work ready with no effort and at an affordable cost. Request your EXTENDED TRIAL today and understand why Mosyle is everything you need to work with Apple.
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