Have you seen the X threads on how there are going to be four jobs left?
Production engineering, security, hot people, and adults. I can't believe you haven't seen this.
I haven't seen this. This is amazing. Wow. Okay, so I'm disqualified from adults right off the bat. So that's a no-go. By the way, I definitely want to be in the hot people category.
I aspire, but I think I might have to give up on that. But it goes to my, I've spent much of my career in the invisible side of work, which is now, of course, becoming more visible and decision-made.
It's going great. Yes, yes. Welcome to Context. Welcome to Context, everybody. Jess, welcome to Context.
Newly minted. Can I still say this?
You joined us as general counsel.
I think that's a... Four and a half years ago.
Four and a half years ago. Yeah.
Kicking ass and telling us to go for gold and, you know, go win things and so on ever since. Should we dive into, like, your story here? Because I feel like we should.
Let's do it. Let's do it.
It's such a word. And so, you know, I think a lot of context is about, like, in a way we talked about this earlier, but, like, it's like, you know, how did fix happen? Like matters, like what were the inputs, what organizations were important ones. And it's such an interesting time we're in and we'll get into all this, but like where did we come from?
Yes, where did we come from? All right, well, how far back should we go? What's Jess all about? Well, I think it's, you know, it's not what you expect. I think that's always been the interesting part of my journey. I have had lots of different experiences, and I think that makes me a different kind of creature in a lot of ways. Certainly, I think you and I share a very similar way of thinking about things.
The non-standard path. And I'm a deeply unsentimental human. And I actually think that has really led to great things 'cause I think about things in all sort of ways that are fairly detached, and I can think about things in lots of different kinds of first principles ways. And I don't really get attached to an idea or an outcome or something that becomes...
Have you always been like this?
I've always been like this. I've always been like that.
Is it that, do you think people become, because the role of at least the comic book sketch of an attorney is like that someone who can passionately defend any side, which I think is an enormously valuable skill. But I wonder, is it that people who can do this become lawyers? Or is it the other way around?
Good question. I don't know the answer to that. I didn't innately want to become a lawyer. My dad's a physician, and so I grew up in a very doctor-centered household, as you did, too. And so I liked the sort of critical thinking aspects of things and how to think about things always drew my attention. So I think I sort of naturally led down the path of law. And then I studied at law school with a behavioral economist.
And so I did a lot of behavioral economist work. I then went to government, and then I sort of followed that path a bit.
The nudge unit times, yeah. So I did a lot of work on nudge and other kinds of work. And that, I think, shaped quite a bit of kind of how I think about things.
Who did you? Is that a big name?
So, and he was a professor of mine and sort of deeply influenced how I think about things. And, well, very well-known behavioral economist, libertarian, and went into government, did a lot of work with him, thought about how you set things up. I wasn't a lawyer. I mean, I was a lawyer, but I didn't, I wasn't really practicing law at that time. And I've practiced law. I was in politics, as you know, for a while.
I really don't know what got into you.
I don't know what got into me either. But the common standard is really like how you think about things, right? And how you develop skills to be on your feet and really think. And this kind of goes to my theory of how the type of talent's density is really changing. I've always been a generalist and I've always been someone who thinks about lots of different things, who likes learning lots of different new spaces. And that part has always been exciting to me, learning new challenges and taking on new things that I know nothing about. As evidenced by my path here, it has grown fairly organically over the last couple of years.
One of my favorite early Jess memories is I think when you came in. So I'm like, how do you deal with this transition? And your response was, not even close to the hardest transition I had to deal with in my career.
Meaning the White House transition. White House transition was a big one.
The last one was from President Trump to President Biden. And that experience of being able to think about how would I set up things? And how do I get to create this like day one of this new administration and what we're going to do and what decisions are we going to make and what we're going to prioritize? It's actually a fairly amazing thing.
Wow, you just made being in a government sound interesting. That literally never happened to me. I would never go back. But for a moment in time, it was this amazing way of thinking about like, oh, OK, like actually, how do I set up this information architecture of like how decisions get made? Actually, can you like, so like literally, how do you do it? Like, because at some point you're like, okay, I mean, first you have to figure out what's true, then you have to figure out what to do about it. Like, I mean, this is one of the funny things in life is like, if you can just do that, you're outperforming most people, frankly, because that's a good starting point. But like, you know, like in an infinite possibility space, how do you figure out what to do?
Yeah, it's not easy. And I think there are things that have to get done. And then there are things that are like sort of discretionary choices.
Because there's like a schedule, you have to like, I mean, at some point, there's gonna be, I guess a state of union. At this point, really, you have to figure out your messaging.
Exactly. And then the question is like, how do you actually, the coolest part, right, is how do you actually get all the information from where you need to get it? How do you synthesize it? And then how do you force a decision to get made? Which is obviously a vast simplification of what that process looks like, but it's taking a massive amount of information. And basically, like my job was to go to each of the different policy members or cabinet members or whomever to sort of say, you guys aren't talking to each other. It's basically my job now in a different way.
I was like, yeah, that sounds familiar.
Have you actually talked to this person because from where I sit, and it was cool, right? 'Cause I get to see everything. And so part of that role is to say what's actually important. Like, where do you pick up signal and what does that actually mean? And then how do you connect the dots? And then how do you actually make good decisions quickly? And one of the kind of superpowers is really to synthesize that information in a super simple way to be able to say, this is what's important. This is who's disagreeing or not disagreeing. And this is how you actually sort of think about a problem. So not all that dissimilar, but in a very different context.
It is funny. Yeah, like again, it's really, it's funny how fractal of Audrey is.
It is, yeah. And I do think people, I think politics and tech are actually much more similar than people give it credit for. There's a lot of pace. There's a lot of different kinds of flavors of trying to figure out problems in different ways. But I actually think it's not as dissimilar as we all might. This is probably why tech and politics get so famously well along.
Maybe, maybe. Oh, boy. Yeah. I do think though, I'd love your take on, I know at Shopify we've said there are T-shaped people.
I even remember when I was interviewed, it was very like part of my interviewing process was sort of...
We probably talked about it. I think we did talk about it. And so I'm curious for your take on, is that changing? My theory is maybe we're morphing from a T-shape to an X-shape because X-shape has two different T's in it.
Craft, you know, craft kind of still remains.
Yeah, explain that. That's fascinating.
Maybe we'll see if it sticks. But craft still remains obviously useful and obviously an important part, but it's no longer quite as singular, right? So you no longer have the vertical T and your ability to do different kinds of things, your ceiling is quite open. And so the sort of expansion up becomes even more possible. And I think part of the really special part about Shopify is we've had so many leaders in different parts of the company and jungle gyming and that kind of multidisciplinary aspect is so important at Shopify and valued at Shopify. I think we might be progressing.
Yeah, I haven't thought about this in a while, but I love, I think you're right that this is the kind of thing that's like, you know, again, as much as you want to, as much as I want to anyway, like you can't rethink everything all the time, It's just like possible. And so, but what is so good is, again, not having just the deference to the prior decisions all the time, going to rethink this. I agree with you, but clearly there's so much happened with the tools we get to use, with the way information now can be acquired. So the relative value between fluid intelligence that you bring to make a good decision given everything you've got or crystallized intelligence, which is the knowledge you have accumulated.
You know, the world has shifted enormously towards fluid intelligence again, because knowledge in many cases is a little bit... Well, I honestly don't want to dismiss it. It's still massively important. Like, oh, this is another one of those is like the most, probably most valuable thing anyone can say when something goes wrong, because then you have seen the movie before and you know what to do. But acquiring of knowledge is quite much easier. So it's really like, what it really should do is that people are more ready to step out of their roles. I really, I think this whole thing about roles is going to be not, I feel they'll come, actually, not the extreme case, but it will be much more muted. I think people are going to, like I think the entire world is going to turn into more jungle gym. If you've proven that you can do something at an excellent level in one area, you should think that you can do excellent work in most areas after.
But does that mean, but does that apply to high agency people? Or do you think that's going to apply everywhere?
I think the high agency thing is the thing we've always looked for, right? Like this has just been like the life story is really like find things that ideally we find a story where something went wrong. and then we dig into what did you do about that? Like, were you part of a, you know, that's a lot of what the life story does. We didn't have a words for it, but like we knew that people who had a good story about their particular role, then that something happened good or bad, or generally is the world happening to them or are they making a dent is, we always thought was deeply correlated with doing well at Shopify. And so this is like why this has always been good. We've been stacked up with the kinds of people who want to do this and then hopefully give them the room to actually act on this.
And I just feel like it's as Shopify systems have become more mature and code bases have like just more, you know, more age, like somewhere like, do I really want to edit something that clearly has been not been a problem for 10 years in this like do you want to change this code because yeah afterwards you're taking some responsibility for it. I get that but like and I think the incentives are to not make a new module replace the thing or whatever like work around it. I like the beautiful thing is now we can just like hey let's actually improve the thing and so I think high agency people have like the tools again to be high agency at much, much larger scale.
Yes, yes. Well, one of the things I think about too, which is, and I have a question for you in this, which is most companies call what we call talent HR, right? Which is so interesting in this moment in time because the whole point of HR is that it's human resources.
And now everything is possible in a different kind of way. We, of course, call it talent. Was that a conscious choice? Or how did, I mean, because of course the beauty of it is that everything can get rethought in this moment in time. So I'm curious where that distinction came from.
I'm actually not aware of that. It's not common in the industry. I mean, I don't know, but it would be surprised because it seems pretty, like human resources always sounded wrong to me. It just, I don't know. It sounds too much like seeing a state. It sounds too much like bureaucratic legibility. Some areas of a company have to be named after an activity. But where you can drive to an outcome, you want to name it after this. I think there's... Often these things don't matter, but I think it matters if you're... The difference... If you only have marketing teams, then you clearly get a lot of units of marketing performed in a company. But that's not an outcome. Like growth is what you want, right? So like either you have none, no growth team, or you have a growth team or you only have a growth team. Those are all valid decisions you can make. But like, I think most companies don't even are way of a choice and you do get different behaviors there. So I think talent density is the outcome that we want. And I think it's like shorting it to talent is good. But also, I think it set us up well to rethink things.
