How do you end up employed in the new world?

In my experience, the people who get hired into roles that don't have a playbook yet tend to share three traits. That's the kind of work I hire for now at Sutter Hill, dropping someone into a startup where they have to grab the ball and start calling plays.

First, they're very hands-on. Nobody is going to hand you a tidy process doc, so you need to be comfortable just building things. In the current moment, that means actually using the AI tools, not just having opinions about them.

Second, they can operate at both the top and the bottom. The top is understanding what we're doing and why it matters. The bottom is the nitty-gritty execution. You need both, because if you can't articulate the big picture, it's really hard to judge whether pixel A or pixel B is the right call. "I like this one" is a useless conversation. "This one accomplishes the goal" is a useful one.

Third, high craft. I've had success teaching people interaction, structure, and systems. But taste is really hard to teach. And when AI can generate output at a furious pace, knowing what good looks like matters more, not less.

How do you build those traits when things change month to month? Looking back, what moved my own career from one thing to the next was always being interested in learning and sharing what I learned, and using that as a feedback loop. If you're curious about something, take the steps to learn about it. You'll be surprised how many people are interested in teaching you.

It also pays to show up early. Back in the mid-2000s, I can't tell you how many times people told me "nobody's ever going to do blank on mobile." Now the opposite is true. Nobody knew exactly how it would play out, but that's the fun part, and you get to be part of it if you get in early enough as opposed to too late. AI feels a lot like that right now.

When you do find opportunities, judge them on who you'd work with, how you'd work with them, and then what you'd work on. Be honest about whether a role is a real stepping stone or just more of the same. And use the feeling test I stole from Bill Scott: go somewhere that gives you a race in your heart and a queasiness in your stomach. If you don't feel both, keep looking.