"Agentless" is a design decision, but for Jordan Borean it also describes a career. He is a Senior Software Engineer at Red Hat in Brisbane, Australia, working on Ansible Core, where the Windows integration is largely his work. Ansible, a tool written in Python, extended in PowerShell, maintained by a Linux company, for an operating system that company doesn't sell. Nobody set out to build a job like that. Jordan grew up entirely inside the Microsoft ecosystem: Windows XP through 7, even a Windows phone. He studied IT, disliked programming, and became a sysadmin at an Australian bank running IIS, MS SQL Server and .NET. Ansible arrived only because the team wanted to stop hand-raising servers like pets. Almost nothing worked on Windows at the time — basic auth over WinRM was not an option in a bank — so he taught himself Python and started sending pull requests. Red Hat noticed and hired him. A large part of the conversation focuses on operating systems and developer preferences. Jordan talks about growing up on Windows, later trying Linux, and more recently using macOS for its hardware while still relying on a Linux virtual machine for development. The conversation turns to PowerShell, Bash, curl, and jq. Jordan says he values PowerShell for its object pipeline and interactive discoverability, but that AI tools have reduced some of the advantage it once had for REST and command-line work. He also discusses Linux’s role in the wider IT world, the business value of support contracts, and the differences between MIT and GPL licensing. Finally, we cover Ansible’s relationship with Windows features such as DSC, idempotency, extension models, and the limits of using Ansible in Windows-heavy environments. Jordan also shares his current focus on improving developer experience, debugging support, Windows integrations, and performance, and closes with advice to stay curious, question details, and keep trying new tools and languages. We close on .NET and C# — the language he loves and can't use at work — the pressure from Rust and Go, and his advice for anyone starting out: don't follow the guide, find out why it works. The interview was recorded on June 4th, 2026 in Wiesbaden (Germany).
