AI May Make Your Career Detours More Valuable

Shopify COO Jess Hertz recently described a shift from the traditional “T-shaped” person, someone with broad capabilities and deep expertise in one area, to what she calls an “X-shaped” person. As she put it, AI requires people with “multiple spikes of expertise” who can absorb complexity, learn new spaces quickly, and become capable across several disciplines.

That idea resonated with me because my own career has moved across engineering, services, product management, product marketing, industry marketing, CMO, and GM roles. At different points, each move probably looked like a change of direction. Today, I see those experiences very differently. They give me multiple lenses through which to look at a client’s problem.

When I work with clients now in my product marketing practice, those lenses often come together in ways I couldn’t have planned. Building an ROI model isn’t just a financial exercise. My engineering and product background helps me understand where the value is created, while my marketing experience helps translate it into something a buyer will care about. Developing positioning for industries such as healthcare, manufacturing, financial services, or utilities requires understanding of the technology, but also the operating problems, buying priorities, and language of each industry. And when I work on an AI-based maturity assessments, I can look beyond the technology to the processes, organization, use cases, and business outcomes required to make AI useful.

And that makes me look at career paths differently. The move that seems sideways today may become one of your most valuable spikes tomorrow.

I see a very different version of this with my daughter Karina as she builds KarinaJ Denim. She brought experience from product management at Microsoft, banking at JPMorgan, and consulting at McKinsey to a problem far removed from corporate finance and enterprise technology: creating jeans for working women who want to feel comfortable all day and still look polished.

Her product background helped her treat the jeans almost like a product that needed continuous iteration: prototypes, customer feedback, fit changes, and refinement. Her consulting experience helped her break a broad idea like “make women’s jeans more comfortable” into specific problems to solve, test assumptions, listen closely to what customers were saying, and keep refining the proposition.

That is what I find most interesting about the idea of the X-shaped person. AI may make it easier for all of us to learn new skills. But the advantage may not come from adding one more skill to the resume. It may come from building depth in several different areas and learning how to connect them.

The career move that looks sideways today may turn out to be the experience that gives you a perspective others do not have.

What experience in your career became more valuable than you ever expected?