"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).
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