If you look at my resume without context, it probably raises some questions.
Engineer. Technical program manager. Engineering ops. Chief of Staff. Product manager. Operations leader.
On paper it looks like I couldn't make up my mind. In reality, every single pivot was intentional.
Early in my career I noticed something: the people who had the clearest view of what to build, when to build it, and how to make it successful weren't the ones who'd gone deepest in one lane. They were the ones who'd navigated enough different roads to understand how the whole map fit together.
So I made a choice. Instead of optimizing for the fastest path up one ladder, I'd deliberately collect perspectives. I wanted to know what it felt like to write the code, manage the program, run the ops, sit next to the executive, own the product, and drive the business — to understand how each one shapes the others.
That curiosity looks like inefficiency from the outside. It isn't. Taking the time to go deeper, to understand a function from the inside rather than observe it from a distance, changes the quality of every decision you make downstream. You ask better questions. You spot the disconnects faster. You know which problems are actually people problems dressed up as process problems. It's not slowing down. It's building a more accurate map.
Here's what I know now that I couldn't have known staying in one lane: building and delivering software successfully is relentlessly cross-functional. It requires someone who can hold the vision and sweat the execution detail in the same breath. Someone who can sit in a monetization conversation in the morning and a product roadmap review in the afternoon and connect the thread between them. Someone who understands that strategy without delivery is fiction, and delivery without strategy is chaos.
That person isn't a specialist. That person is a well-rounded generalist who has done the work to understand the whole system.
Here's where it gets interesting for all of us right now.
AI is compressing the value of narrow, repeatable expertise faster than most people expected. The tasks most contained within a single domain — defined inputs, defined outputs, deep but bounded knowledge — are exactly where AI performs well and is improving fastest. That's not speculation, it's already visible in how knowledge work is changing across software, finance, law, and medicine.
What's harder to automate is judgment in ambiguous, high-context situations. The ability to walk into a room where the strategy and the execution are misaligned and immediately understand why. To translate between the technical and the commercial when both sides think the other doesn't get it. To know which of the ten things on the list is actually the one thing that matters. That kind of judgment doesn't come from going deep in one place. It comes from having operated across enough of the system to recognize the patterns.
None of this means specialization is dead — depth still matters, and the most resilient profiles combine genuine expertise with the ability to connect across domains. But if you've been told that the winding road is a liability, I'd push back on that. Breadth built with intention is its own kind of expertise. And right now, that expertise is in high demand.
The winding road used to be something you explained away in interviews. I think AI is changing that calculus in ways we're only starting to understand, and I'd love to know if others are seeing the same thing.
If you're a seasoned leader: is breadth getting more credit in your organization, or is the bias toward specialization still winning the hiring conversation?
If you're earlier in your career and feeling pressure to pick a lane: I'd encourage you to think carefully about what you're trading away. What's shaping the choices you're making right now?
Have thoughts? We'd love to hear them — drop us a note at executionsuite@gmail.com.