Technology Leader & Software Architect

Jayson Lindsley

I'm Jayson Lindsley, a technology leader and hands-on software architect with 15+ years across engineering, cloud infrastructure, cybersecurity, and IT operations.

As Director of Information Technology & Chief Architect at MyOutDesk, I lead the teams responsible for our software, infrastructure, and security. This is my personal website, where I share my work and write about building software and running the systems and teams behind it.

About & Experience Read the Blog

Selected Experience

What I've led and delivered

Technology leadership
I lead 4 software developers and 9 IT personnel at MyOutDesk, with responsibility for engineering, IT operations, technology budgets, and vendors. I still work directly on architecture and code.
Security & compliance
I built and own our enterprise GRC program, led our SOC 2 audit through successful completion, and led device compliance across 1,000+ endpoints.
Cloud infrastructure
I reduced AWS infrastructure spend by more than 75% through targeted optimization while aligning security baselines with CIS and AWS Foundational Security controls.
Software architecture & delivery
I architected and delivered MyTimeIn and led its modernization from Electron to Rust/Tauri. Our Windows and macOS applications support 2,000+ concurrent users.
More about my background and experience

Recent Posts

All posts
A robot chimpanzee in a "Claude Code" apron and safety goggles swinging a hammer backwards at a nail in a workshop.

Dear AI Companies: Give Me Baseline Thinking Performance

Like most people have likely noticed, there is a bit of a frenzy when a new frontier model comes out such as Fable 5, Opus 5, etc. Like clockwork, though, most users (including me) find that they degrade in quality over time.