When AI agents do your shopping, everything changes, with Shopify’s Jess Hertz

**SPEAKER_1** (0:01)
The very best founders I know are brilliant at building systems. They connect teams, they remove bottlenecks, and they eliminate single points of failure. And yet, when it comes to their own wealth, most are running a disconnected stack. A tax accountant here and a state attorney there, a wealth manager who doesn't talk to either one of them. Creative Planning was built to fix exactly that. One integrated team of tax professionals, estate planners, investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and keeps every piece working together. Proactive tax efficiency, estate strategy, investments, all under one roof. Creative Planning, where wealth works together. Learn more at creativeplanning.com/masters of scale.
Hey folks, Jeff Berman here. I'm thrilled to share some of the new names who will be joining us at this year's Masters of Scale Summit. This may be our biggest stage yet. Reid Hastings, Meredith Whitaker, Van Jones, Amjad Masad and more will be there with us October 20th through 22nd in San Francisco. If you're building something great or you want to build something great, we want you there with us too. Join us at mastersofscale.com/apply26.
That's mastersofscale.com/apply26.

**Jess Hertz** (1:33)
We power over 14% of the US e-commerce market. And what's incredible about that is you can sit at this kind of wide aperture of commerce and you can see how competition kind of shakes out in real time.
The barrier to entry because of AI has reduced, right? So the ability to start your own business and have your first sale, that time has just compressed significantly. About 10% of new shops made their first sale within a single day of signing up, which is just incredible. What's at stake is to grow entrepreneurs everywhere. And I think that is the bet, and we are going to win or die trying.

**Bob Safian** (2:21)
That's Jess Hertz, COO of online shopping platform Shopify. As trade war erupts between the US and Canada, I wanted to talk to Jess because Shopify is a Canada-based company with most of its customers in the US., creating a potentially tense dynamic. Jess also digs in on the impact of agentic AI on e-commerce, outlining what's already real right now.
She's forthright about how chaotic the environment is, discussing when it makes sense to bring order to the chaos and when to let it ride. Even addressing Shopify's CBO, Toby Lukey's controversial memo last year, dictating the teams prove AI can't do a job before hiring any new staff. It's a fascinating guide to navigating change at the top of an internet giant. So let's get to it. I'm Bob Safian, and this is Rapid Response.
I'm Bob Safian. I'm here with Jess Hertz, CEO of Shopify. Jess, great to see you.

**Jess Hertz** (3:27)
So great to be here. Thank you for having me, Bob.

**Bob Safian** (3:29)
So I have to start with the elephant in the room. So Shopify is a Canadian company. We are. Headquartered in Ottawa. Most of its customers are in the US. You're based in DC.
There's this trade war going on between the US and Canada. What's the feeling about it within the company? Are you having to navigate?

**Jess Hertz** (3:52)
Okay. Well, let me say, as of next week, I'm actually going to be a Torontonian.
I finally decided to make the pilgrimage to Toronto, and so I'm really excited about that. And you asked about the feeling inside of the company. I actually think it's really more outside of the company, to be honest, and we definitely think of ourselves as a company rather than a country. But the tariffs are the big elephant in the room, and, you know, I think we've operated through lots of moments of uncertainty. Even when the first kind of tariffs came into place, where we had a team spending the weekend building a duties and taxes calculator. And so it is a moment to shine, even though there are lots of macro considerations happening in the world that, you know, really affect our merchants, in particular, our smaller merchants, who may not be able to kind of absorb that without the right kinds of tools to be able to adapt as needed.

**Bob Safian** (4:50)
You don't necessarily talk about Shopify as being a Canadian brand because it's a global business. But do you have conversations about that? If it were a terrorist between any countries, we would be reacting the same way.

**Jess Hertz** (5:03)
Terrorists between any countries, we would be reacting the same way.

**Bob Safian** (5:07)
You served in the Biden White House for a year. You know, your background as a lawyer, you were on the Biden-Harris transition team. Like, all this political machination doesn't make you think like, I should get back in there, you know, try to help fix things.