What does it take to modernize a 30-year-old software product without breaking everything in the process?
In this episode of CTO2CTO, Forte Group’s CTO Lucas Hendrich sits down with Jeff Miller, VP of Engineering at LinenMaster (and former CTO at Yellow and NCSA), to talk about building resilient teams, wrangling legacy codebases, and using AI where it actually counts.
If you’re a technology leader dealing with legacy systems, technical debt, or evolving org structure in the age of generative AI—this one’s for you.
From hardware store roots to SaaS leadership
Jeff’s journey started in a small Iowa town, working at his family’s hardware store. a place where entrepreneurial spirit and roll-up-your-sleeves work ethic were daily habits. That mindset stayed with him as he moved into engineering leadership, and it’s one of the throughlines of this conversation.
“If there’s a job to be done and no one’s around to do it, you just do it. That’s something I carry into engineering every day.”
The reality of working with legacy code
At LinenMaster, Jeff oversees a codebase that goes back to 1995, including C++ wrapped in .NET and running in hybrid cloud environments across industrial laundries. Sounds messy? It is. But the team isn’t trying to rewrite the whole thing.
Instead, they’re applying a “strangler” pattern: incrementally refactoring key components while avoiding unnecessary risk to their customers, many of whom run 24/7, mission-critical operations.
“You don’t shut down invoicing at a laundry business. You can’t afford to break production.”
AI isn’t a silver bullet, but a strategy
Rather than falling for AI hype, Jeff’s team uses a two-track approach:
- Trusted AI tools for production work
- Experimental AI for innovation, code analysis, and summarization
From summarizing field notes to parsing legacy endpoints, AI is deployed where it can help, not just where it sounds flashy.
“We’re not trying to replace engineers. We’re trying to free them up to focus on the hard stuff.”
Hiring in the AI era
Jeff's take on technical interviews? He doesn’t care if a candidate uses an LLM—as long as they can explain their thinking.
“It’s like an interrogation. I want to hear how they reason through problems—not just the right answer.”
That philosophy extends to how his teams are structured: focusing less on raw output, more on connectors and communicators—the glue people who drive collaboration.
Why ownership matters more than ever
At the core of Jeff’s leadership style is a single principle: Extreme Ownership.
“Every challenge is an opportunity to ask: what can I do to influence this outcome?”
It’s a mindset that scales across engineering, hiring, stakeholder communication, and culture, and one that Jeff believes will matter more as ambiguity in tech work continues to rise.
Tune in
This is a conversation full of real talk, practical insights, and sharp observations from someone who’s seen it all—from PE-backed scale-ups to legacy SaaS platforms. Whether you’re modernizing tech, leading teams, or navigating the AI shift, there’s something here for you.
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