The Next C-Suite

One of my favorite podcasts is Silicon Valley Girl, hosted by Marina Mogilko. Lately, I’ve been recommending it a lot.

Marina sits down with the people building and running some of the most interesting companies out there, and she has a gift for getting them to talk about the parts of their careers you don’t usually hear. The detours. The lucky breaks. The decisions they weren’t sure about at the time. If you’re curious about AI, careers, or the people behind these companies, add her to your rotation. I think you’ll love it.

Lately, those conversations have had me thinking about something we don’t talk about nearly enough.

We spend a lot of time asking how AI will change everyone else’s job. The analyst. The developer. The recruiter. But what about the people at the top? What does it mean for the CEO, the CFO, the person deciding where the whole business goes next?

And maybe the bigger question: where will the next generation of those leaders come from?

One thing that jumps out when I listen is how few of these careers went according to plan. Yamini Rangan, the CEO of HubSpot, started out as an engineer and worked her way through sales strategy and customer roles before she ever ran the company. In her conversation with Marina, she made a point that stuck with me: it’s hard to plan a career around jobs that may look completely different in just a few years.

Brian Chesky, who runs Airbnb, studied industrial design. He told Marina he wishes he were twenty-six again because of what today’s AI tools make possible for someone starting a company.

I love that. Here’s someone who has already built one of the most recognizable companies in the world, and he’s a little envious of whoever is starting out right now.

It makes me wonder how many people working in AI today are getting experience that could take them somewhere they haven’t imagined yet.

I see a version of this in my own work. When you’re helping build an AI practice, the conversation rarely stays neatly inside a job description. We’re figuring out what we can offer clients and who can actually deliver it. Do we hire someone, develop the team we have, or bring in a partner? Those decisions shape the business well beyond a single role.

That’s a big part of why I love practice buildouts. You get to watch a business take shape through the people it brings in and the decisions it makes along the way.

So when I picture the future C-suite, I think about the people in the middle of that work right now. The ones building teams, getting close to customers, and figuring out why something that looked amazing in a demo is so much harder to make useful inside a real company. Some of them are getting a very practical education in how to run a business.

Now, being good at AI doesn’t automatically make someone a good CEO. I’d still want to know how they handle a tough client conversation, whether they understand the economics, and what they do when the team needs direction and there isn’t an obvious answer. But I wouldn’t assume the strongest future leader is the one following the most familiar path, either.

Another point from Yamini’s conversation stayed with me: AI leaders need to understand where workflows break down.

I think that’s going to change what the executive job looks like. If AI can pull together the analysis, model the options, and draft the strategy deck, I’d hope leaders spend more of their time working through what it would take to make that strategy succeed. Can we actually deliver it? Will customers pay for it? The answers need to hold up beyond the presentation.

Someone still has to make the call and live with the outcome.

And if people are struggling with a new tool, it’s worth understanding why. Maybe it doesn’t fit how they work. Maybe the information going into it isn’t reliable. Maybe nobody has explained what it means for their role. Those conversations can explain what an adoption dashboard alone can’t.

This is where AI and workforce strategy keep running into each other for me. Once you start changing how work gets done, you’re making decisions about people, whether you’ve invited the people team into the conversation yet or not. That includes deciding which responsibilities should stay with a person and what someone should learn next. I’m especially curious about how someone early in their career builds experience if AI is doing more of the work they used to learn from.

Those aren’t questions we can save for after the technology is in place. And they don’t belong to just one executive. The CFO needs to understand what the investment is actually producing. The head of HR needs to help rethink how roles and careers are changing. Every leader running part of the business needs to understand what they’re asking their teams to adopt. I suspect a lot of executives are already feeling that shift.

Then there’s curiosity. In his conversation with Marina, Ryan Roslansky highlighted curiosity alongside courage, creativity, compassion, and communication as skills worth developing. Curiosity is the one I keep coming back to.

It’s what I find myself watching for, too. I’m drawn to people who can explain the technology clearly and still ask good questions about the business. The ones who stick around after the exciting announcement, when the work gets complicated. I want to hear what they learned when something didn’t go as planned, and what they did differently afterward.

And I pay attention to how they treat people through all of it. It matters whether a leader can be honest about what’s changing without pretending to have every answer. People have real questions about their work and their futures. They deserve more than a slide about transformation.

So where will the next generation of executives come from? Honestly, I don’t think there’s one answer. I picture people building experience across areas that used to be easier to keep separate. Some will come from technical roles. Others will come from operations, customer-facing work, or people leadership. Each of them will have something different to learn before they’re ready.

If you lead a company, look closely at who’s showing potential in work that doesn’t fit the usual leadership pipeline yet, and think about what opportunity could help them grow.

And if you’re wondering where your own career could go, pay attention to the problems you’re getting to solve and the experience you’re quietly building. Your title may not tell the whole story.

I started listening to Silicon Valley Girl because I love hearing how people think. Now I listen with a second question in the back of my mind: who am I talking to in my work today whose story might sound like this ten years from now?

I have a feeling some of them are closer than we think.

Conversations mentioned: Yamini Rangan · Brian Chesky · Ryan Roslansky