Rich Pleeth on AI-Driven Workforce Restructuring and the Future of Agile Organizations
Author(s): Scott Douglas Jacobsen
Publication (Outlet/Website): The Good Men Project
Publication Date (yyyy/mm/dd): 2025/09/15
Rich Pleeth is the CEO and Co-Founder of Finmile, an AI logistics SaaS company building the Finmile OS, a delivery intelligence platform optimizing routes, costs, and operations for carriers and retailers worldwide. A serial entrepreneur with extensive experience in scaling technology ventures, Rich has been at the forefront of AI-native business models that prioritize agility and efficiency. At Finmile, he has championed AI-driven automation across product development, operations, and customer support, making the company leaner and more resilient. With thirty percent of Finmile’s code already AI-written, Rich advocates for rethinking organizational structures, skill sets, and workforce strategies in an AI-first economy.
Scott Douglas Jacobsen: Why are companies like Microsoft restructuring their workforces?
Rich Pleeth: It’s not failure driving restructures, it’s efficiency. AI is displacing legacy roles and forcing companies to run leaner, more agile teams as more can be done with less. Even the biggest tech players need to show they can adapt faster to market shifts, not just scale headcount.
Jacobsen: How is AI accelerating the shift to AI workflows?=
Pleeth: AI doesn’t just automate tasks, it rewires workflows. At Finmile, thirty percent of our code is written by AI, and we use it across operations, customer support, and data analysis. Without it, our team would need to be four times the size. That’s the shift every industry is seeing.
Jacobsen: What skill sets are valuable for tech workers now?
Pleeth: The most valuable skill is systems thinking. It’s not about doing the task yourself, but knowing how to build and adapt workflows with AI. People who can bridge tools, teams, and tactics will be the ones who thrive.
Jacobsen: How should HR and workforce strategists approach reskilling?
Pleeth: Reskilling needs to move from execution to orchestration. Instead of teaching employees how to do the old job faster, companies need to train them to design, monitor, and adapt AI-driven workflows. The winners will be companies that retrain staff as AI partners, not AI casualties.
Jacobsen: How does workforce restructuring improve organizational agility?
Pleeth: Smaller teams with AI leverage can move faster than larger ones with legacy processes. That agility means quicker product cycles, tighter cost controls, and the ability to pivot when markets shift. Restructuring isn’t just about cutting headcount, it’s about building resilience.
Jacobsen: How might these changes influence job security?
Pleeth: Job security won’t come from clinging to old roles. It’ll come from adaptability. Workers who embrace AI as an amplifier, not a threat, will be in demand. Those who resist will find themselves left behind. It will be hard for some to adapt and that is where reskilling will be needed.
Jacobsen: What are the risks of over-relying on AI?
Pleeth: The biggest risk is blind trust. AI is powerful but imperfect, and if teams don’t maintain human oversight, small errors can cascade into big failures. The sweet spot is AI-first, but human-guided.
Jacobsen: What practical steps can employees take to remain competitive?
Pleeth: Everything is about experimentation. Experiment with tools, understand where they’re right and where they’re wrong, and practice adapting workflows. The most valuable employees will be the ones who test, try and experiment and can reason with AI, not just use it.
Jacobsen: Thank you for the opportunity and your time, Rich.
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