Stop Trying So Hard and Start Automating Smarter with Jake Hildreth

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 re-checking assumptions as threats evolve.

 

Key Takeaways:
• Work smarter, not harder — Whether you’re scripting or building a career, small sustainable improvements beat grinding yourself into a corner.
• Resumable automation is a game changer — Stepper helps scripts safely pause and resume, making real-world workflows more reliable when humans or flaky APIs are part of the loop.
• Community turns into real momentum — Contributing, asking questions, and sharing feedback builds skills, friendships, and opportunities faster than trying to learn alone.

 

Guest Bio:
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.

 

Resource Links:
• Jake Hildreth’s Website – https://jakehildreth.com
• Jake's GitHub - https://github.com/jakehildreth

• Andrew's Links - https://andrewpla.tech/links

• PowerShell Spectre Console – https://pwshspectreconsole.com/
• PDQ Discord – https://discord.gg/PDQ
• PowerShell Conference Europe – https://psconf.eu
• PowerShell + DevOps Global Summit – https://powershellsummit.org
• Jake's PowerShell Wednesday – https://www.youtube.com/watch?v=YdV6Qecn9v0

The PowerShell Podcast on YouTube: https://youtu.be/rFeoTKLerkA