May 25, 2026

Solving Problems at the Root with Mark Littlefield

50 minutes

In this episode, host Andrew Pla sits down with Mark Littlefield, VP of Product at PDQ, for a wide-ranging conversation about product management, the PowerShell community, and what it looks like to deeply learn a technical domain when you're not coming from a traditional sysadmin background. Mark shares his journey from tech support to product management, what drew him to PDQ and the challenges facing IT admins, and what surprised him about PowerShell once he started paying close attention. The two also dig into the history behind PDQ Connect's PowerShell Scanner, how product teams learn from customers, the art of storytelling as a PM and sysadmin skill, and more.

Key Takeaways:

Product management and PowerShell automation share a core philosophy: solve problems at the root, not just on the surface. Whether you're writing a script or building a feature, the goal is to eliminate a challenge entirely rather than patch around it.

Understanding your customer requires more than data — it requires immersion. Mark describes going deep into the sysadmin world through customer interviews, internal usage, and community engagement to truly understand the problems facing IT teams.

Great storytelling is a transferable skill. Andrew draws a parallel between how Jeffrey Snover used the Monad Manifesto to get internal buy-in at Microsoft and how to use narrative to align teams and push ideas forward.

Guest Bio:

Mark Littlefield is the VP of Product at PDQ, where he leads product strategy and development for PDQ Connect and the broader PDQ product suite. With over 15 years of product management experience, Mark previously served as VP of Product Management at InsideSales.com, where he oversaw product management and design across the platform. He holds a Bachelor of Science in Information Systems with a focus on Business Intelligence from Utah Valley University and is based in Salt Lake City, Utah.

Resource Links:

PowerShell Event: https://www.pdq.com/save-time-with-powershell-pdq-connect/

PDQ Connect: https://www.pdq.com/pdq-connect/

PDQ PowerShell Scanners GitHub repository: https://github.com/pdqcom/PowerShell-Scanners

The Monad Manifesto (Microsoft Learn): https://learn.microsoft.com/en-us/powershell/scripting/developer/monad-manifesto?view=powershell-7.5

Monad Manifesto blog post by Jeffrey Snover: https://devblogs.microsoft.com/powershell/monad-manifesto-the-origin-of-windows-powershell/

Mark Littlefield on LinkedIn: https://www.linkedin.com/in/mark-littlefield/

Connect with Andrew: https://andrewpla.tech/links

PDQ Discord: https://discord.gg/pdq

The PowerShell Podcast on YouTube: https://youtu.be/fo2V5LC-EZo

...more