Stop trying so hard and start automating smarter with Jake Hildreth
Aired January 26, 2026 | 55 min
Principal security consultant and community favorite Jake Hildreth returns to The PowerShell Podcast to talk about building smarter automation, leveling up through community, and creating tools that solve real problems. Andrew shares his “stop trying so hard” theme for the year, how working smarter applies directly to scripting and security, and why getting involved with others is one of the fastest ways to grow in your career.
The conversation dives into Jake’s recent projects including Deck, a Markdown-to-terminal presentation tool built on Spectre.Console, and Stepper, a resumable scripting framework designed for long-running workflows that can’t be fully automated end-to-end. They also explore presentation skills, avoiding “death by PowerPoint,” and why security work requires constantly rechecking assumptions as threats evolve.
Meet our guest
Jake Hildreth is a principal security consultant at Semperis, Microsoft MVP, and longtime builder of tools that make identity security suck a little less. With nearly 25 years in IT (and the battle scars to prove it), he specializes in helping orgs secure Active Directory and survive the baroque disaster that is Active Directory Certificate Services. He’s the creator of Locksmith, Stepper, Deck, BlueTuxedo, and PowerPUG!, open-source tools built to make life easier for overworked identity admins. When he’s not untangling Kerberos or wrangling DNS, he’s usually hanging out with his favorite people and most grounding reality check: his wife and daughter.
Meet our host
Andrew Pla
Andrew Pla, a seasoned IT professional with over 10 years of experience, has spent the last 5 years mastering PowerShell. An ardent member of the PowerShell community and a Microsoft MVP, he loves sharing his knowledge and leveraging automation to solve complex problems. You can always find him connecting with others on the PDQ Discord and troubleshooting, with the firm belief that a problem shared is a problem halved.
