Speaker 1You have to have a product that's aligned to the success of your customer and that your incentives have to be aligned. If you have that luxury, then you get to say, I'm not trying to sell you anything. I am genuinely interested in your growth. And if you grow and you succeed, I succeed.
Speaker 2Just wrapped up a great conversation with Maya Jay, Chief Revenue Officer at Stripe in their AI division. In the conversation, we talked through what made the Stripe sales team great.
Speaker 1Where we can come in and help is be their growth consultants. And we said, this is how your revenue looks globally. This is how it compares to the median AI company. Oh, that's cool. And then we gave each of them like, here's the three things you should be doing because you're leaving that money on the table here, here, and here. Our interests are so aligned. If you grow,
Speaker 2we grow. We also talked through some of the unique insights that they're seeing running billing and pricing infrastructure for some of the fastest growing AI natives.
Speaker 1Right now, two thirds of the Forbes AI 50 are doing some kind of usage-based or hybrid approach, which is some kind of either it's a platform fee, or subscription, or seats, coupled with credits and usage-based on top. Because then you get both the predictability, which matters for the company selling, but also for the company buying, but you get the usage-based on top of it.
Speaker 2And then also talked through a lot of things in the intersection of sales and awesome Stripe run that she has had for eight years.
Speaker 1I did have this big slide that says, don't sell anything, which sounds counterintuitive. It's kind of insane. Welcome to the
Speaker 2Crew Podcast, where we have conversations with the top go-to-market leaders at AI natives and SaaS startups. I'm Chris Belestris, co-founder of Crew, a go-to-market recruiting, media, and investing firm helping seed through Series D AI natives grow. Now, on to the episode. Maya J., thanks for coming on the Crew Podcast. Thanks for having me.
Speaker 1I'm so excited to be here.
Speaker 2Of course. I finally have somebody from Stripe on. I started a blog two years ago. It's called GTMBA. It was when I was at Metronome, which now is a Stripe company. And a lot of the earliest people that would read it are like the Plaid and Stripe AEs. Now, a lot of them are still at Stripe. Actually, while you're on now, one of our longtime listeners and readers, you're a CRO of Stripe AI and always very much admired the Stripe sales culture. I guess my first question is just like, I look at Stripe as a payments API. Obviously, you guys are continuing to grow at a really fast rate and adjusting to this AI native market. What even is Stripe AI? And how are you guys adjusting to this new AI native landscape from a product perspective?
Speaker 1Yeah. Stripe's building the economic infrastructure for AI is how I've always talked about it. And so that takes a few different forms and continues to evolve. I mean, for one, we partner with all the largest AI companies and all the upstarts. So whether it's been powering the payments for OpenAI, Anthropic, and Cursor, or all the fast-growing apps like you've got Higgs Field and Lovable and Manus, all that is part of our remit. Also, agentic commerce and agentic payments. And, you know, this has been something since last year we've focused on when all the protocols were launching. And now in the recent weeks, all the rise of the agent wallets. I don't know if you've tried any of the Instincts or Grokbots. It is like we're finally at magical experiences on agents being able to pay. But that's a whole other component of it. And then we also just think about like how AI companies price and the future of monetization.
Speaker 2Yeah, I definitely want to get into more of, like, I have no idea what agent-based pricing is. I just know that, I mean, I'll allow for certain permissions when I'm letting, like, Manus or something allow for certain credits and all that. But, I mean, your background, super unique background for Ciro. The one that mimics this is when we had on Nick Bogaty, who reports to Gene at Vercel. And it was the Ciro at AppDynamics prior. It was his first sales job. It kind of blew my brain a little bit of this new sort of modern Ciro. Stevie Case, who we had on, Ciro Advanta. She was like the new wave of Ciros are going to be people that don't have sales background. Yours is probably the most unique we've had. You've done, well, you started in finance for a couple of years. You're a trader.
Speaker 1I was a trader back when that was a job, like, on the floor of the stock exchange.
Speaker 2Yeah, yeah. So you did that for two years, but then you've done stints in product and strategy and marketing. You're a former CMO at Greenhouse. And now I've been in Stripe for well over eight years, which is a hell of a run. When did you say, I want to jump in the seat of, like, the sales business unit?
Speaker 1You probably weren't expecting an actual moment, but there was. We were at our leadership offsite, I want to say a year ago, and we were talking about all the changes that are happening in the AI landscape and how we really need to be very focused from a user-facing perspective and a go-to-market perspective on how we partner with them. And in that moment, I just knew that that's where I wanted to be. Because to me, the modern CRO, as you talk about, is really like a GM of that unit, right? And so when I think about the AI companies, so much of what we're doing with them is feeding back and being an extension of the product team and partnering with products to be like, here's the latest problems they have, and we can't solve them in a year. We need to solve them last week. It is striking, really opportunities, you know, a lot of the agentic payments that we're doing and the partnerships developer platforms are like brand new business models. Like how do you think about a consumer building a company on lovable and then taking payments on lovable? Like that hadn't existed before. So you really get to, you know, yes, you're driving sales, but you're also just thinking about like, what is the business of the future with the most exciting users of the future?
Speaker 2Shout out to a sponsor of the crew podcast, MetaView. Hiring is the highest leverage thing any leader does. As they say, the team you build is the company you build. That's why over 7,000 companies from startups to the fortune 500 hire on MetaView. MetaView gives hiring teams AI agents that do the recruiting work for them. Finding candidates, reviewing every application, capturing every interview, all in one shared workspace. So teams make faster, better hiring decisions. Don't let your competitors out hire you. MetaView customers close roles 30% faster. Check them out today at metaview.ai. You have a very unique seat. What are these AI natives doing? How are they pricing? Where's the market going? There's PLG, there's SLG, and now there's like agent-led pricing, which, yeah, I'd love to like jam out a little bit. Like, what are you guys seeing at Stripe of how the AI natives are commercializing their own businesses?
Speaker 1Yeah. Well, and first, maybe just to contextualize. So a year ago, if you took a slice of the top 100 AI companies on Stripe, which is a pretty good proxy for the top 100 AI companies, they were growing 145% year-on-year on Stripe. That's wild. Guess what it is now?
Speaker 2Do you tell me? I don't know.
Speaker 1Almost 200% year-on-year, 195%. So the growth is accelerating. These companies, there's a lot of things they're doing. I'd say one on the PLG front, like that's where a lot of the growth started. One thing that's really different about what AI companies are doing versus non-AI companies, or at least like, you know, the great SaaS companies of the past, is they're so global. So 48% of the revenue from these AI companies that we see from a PLG perspective comes from outside of the U.S. or outside of their home market. You see an AI company that starts, within three years, they're operating, like really operating in 120 markets on average. And if you take that same slice of old SaaS companies, that would be like 50. So they're just much more global and have a much broader reach from a PLG perspective. That's one. Then two, PLG, SLG. I feel like 10 years ago, the playbook was you do PLG for a while, then you get to startups, and then eventually you say, okay, like now we're ready to have an enterprise sales team. I was our first head of enterprise product and engineering at Stripe, and that was four or five years ago. We had enterprise customers, but we even followed that playbook. Now they're all doing it like on day two. You're building both a PLG motion and a really robust SLG motion. I think OpenAI just said that their enterprise volume, their enterprise sales just exceeded in that month of August, I want to say, their PLG volume. And you have other companies like 11 Labs also with higher enterprise volume than PLG volume. Like you just weren't seeing that in the
Speaker 2past. I also think that like probably a big driver as to why a lot of these motions are working in tandem is because the enterprises are very hungry to buy a lot of these tools, and they're moving just as fast as sometimes these startups. What's this like agent-led growth as well? And how does that factor in to like the Stripe product suite or really just how people are thinking about commercializing an AI product?
Speaker 1Yeah. Agents are the third buyer, the new buyer. If you look, we have a really cool chart that shows traffic to Stripe Docs, which is to me is a proxy for who is implementing and using Stripe. And you could see the agent traffic and the human traffic is basically colliding to the point where now we're going to have more agent traffic to Stripe Docs than humans. Agents are making decisions. And that's like sort of on a maybe abstract macro level. Again, I was just talking earlier about all the new link agent wallet that folks are using. So in the last couple of weeks between Muse just launching by Meta, you have Grokbot, you have Instinct. Their agents now all use the link wallet to be able to do purchases on someone's behalf. And it's magical. Like if you haven't tried it, I'll send you an email. It's so cool. I'm running a lot these days and I just really needed a sport.
Speaker 2Are you training for something or what's that?
Speaker 1I'm training for a lot of things.
Speaker 2What race? It's
Speaker 1kind of insane. It's called the 777. It's seven half marathons in seven days on seven continents.
Speaker 2Oh my. How does that even work? How do you, how do you fly?
Speaker 1You basically only, you're just like airplane, land, run,
Speaker 2shower, get back on
Speaker 1the plane. Me and two other Stripe leaders.
Speaker 2Yeah. Oh my God. Best luck. Keep going. Yeah. Yeah. Yeah. That's a whole
Speaker 1life. The sports massages are so helpful. And I couldn't remember like, who did I book it through? And their website was kind of janky and I just didn't want to go through it all. And I asked my Instinct agent, I was like, can you go on my email, find where it was and tell me if they have an appointment this weekend. And it does it all. And it comes back and it was like, yep, I can pay. Do you want me to pay? I was like, yes. All on text. Yeah. Wow. We really crossed a new threshold of magic. And just think about that is happening on the consumer side. but it's increasingly now happening on the B2B side too. Like you can be in cloud code and say, I want to spin up a database. Why should I have to like then go to another website to put in my credit card? Why don't you just have it all happen within there?
Speaker 2Big thanks to our sponsor, Attention. Sellers were hired to sell, not to fill in the CRM. Attention records and understands every sales call, then automatically updates your CRM, sends follow-ups and scores reps against frameworks like Medic, Bant or your own custom methodology. Next best actions are proactively generated from there. You get a clean pipeline, coaching on every call and forecasting you can actually trust without asking reps for more admin. Turn your call recordings into a GTM operating layer with Attention. Try them today at attention.com. I actually have never led an agent. I guess the only thing would be different is if I'm in cloud and I'm like, hey, similar to what we used to sell for Metro where it was like top off and stuff. And like, okay, hey, for certain credit, but you're saying now, people are using Rockbot and everything to have a lot of their payments saved in there, having them execute on their behalf and saying like, hey, if it's under this threshold or if it's a past thing I've already paid for, you have all right to go and pay on my behalf.
Speaker 1You can still have a human in the loop where it checks with you and you don't have to give it all the agency, but you can say rather than you then having to go to a different website, make an account, put in your credit card details, you can have the agent just do all that for you. So you have agents as buyers now too.
Speaker 2You're using Instinct. Obviously the Rockbot, I'm like testing out this weekend, finally for the first time. And finally with a bunch of folks in the innovation team at Cursor and now SpaceX. And then there's also Muse. Have you used these tools? Like, how are you using them? Is like Instinct good for, it has an iMessage integration, like that's its wedge or what? How do these tools differ? And like, how are you using them?
Speaker 1I mean, like that's like the most fun part of my job is I-
Speaker 2Just play it around.
Speaker 1I mean, I have to use all of them because I have to know what's going on. So yeah, totally. Instinct, like I said, I just use for the, for massage booking. I used it for some retail stuff. I've used things to connect to OpenTable and asked it to update reservations for me. That's cool. I was even, I have a meeting an hour after this. And so I went to Muse earlier and I just sent it a screenshot of my calendar. And I said, look at the two meetings I have and find me a coffee shop to take my call in between. Oh, that's, yeah, yeah. And it just gave me three options and said, do this one. So, so we'll see. I'll tell you afterwards. Oh yeah, no, this is good.
Speaker 2This is like motivating me. People have been more and more showing me like their phone and their apps they create. Oh, I have all these like sub box. And I feel so behind. This whole year and a half, two years, I have not felt behind. I was like early to Whisperflow and Granola. And now I feel like so behind with a lot of these like personal bots.
Speaker 1I'm not really a coder. And I started building my app with Cloud Code, I'd say three months ago. And even just between then and now, how much better everything has gotten. I have a full app in the app store that I would have never been able to do beforehand.
Speaker 2Yeah. All right. So you guys are powering a lot of, I mean, we've been doing this for a while now, but we've got a lot of things going on. We've got a couple of things going on right now. I mean, we've been doing this for a while now, but we've got a lot of things going on right now. But we've got a lot of things going on right now. We've got a lot of things going on right now. Before I move off of that, why is that? Why is it the case that this is happening now? Why didn't like happen in the SaaS era as prevalent?
Speaker 1I think part of it is that the infrastructure is just easier there now. So, you know, Stripe now has a merchant of record solution. What I mean, like all the non-payments, compliance nerds out there. It used to be a real pain in the ass to go spin up an entity in all these different countries to go sell. Well, now we can just do it for you. Like you'll still want an entity in a few places, but we'll do it for you. It used to be that it was hard to get the local currencies and local payment methods. And so you just kind of wouldn't do it. But now we make it really easy to do that. So I think a big part of it is just the infrastructure is more there. And then couple that with the AI demand. It's just been easier for them. Guess which countries have some of the highest AI usage per capita?
Speaker 2Besides the obvious ones. Yeah, I would say country Israel and Sweden and Germany.
Speaker 1Those are good.
Speaker 2If I had to guess some of the top ones, just because of where I know a lot of the startups are.
Speaker 1Yeah. How do I do?
Speaker 2What are some of the other countries that are AI hubs?
Speaker 1Some of the ones that people can't miss are Brazil and India.
Speaker 2Oh, interesting. Oh, India. I could have. Yeah, yeah. Damn.
Speaker 1Okay. They have some of the highest.
Speaker 2Brazil, Brazil. Brazil surprised me, but.
Speaker 1Yeah, apparently there's just like a huge viral aspect to how folks consume AI. And so it's almost like you have no Brazil, no Brazil, no Brazil. And then you just get it in the hands of the right person. And then it goes viral. You know, this is like for a consumer app, for example. Yeah, yeah, yeah. You get a lot of it.
Speaker 2Interesting. Okay, cool. This is a, it's good. Max cocktail party. Right, exactly. These are some good tidbits. You mentioned the company's going global faster and making a big percentage of how much money that they're making. How are people? How are people pricing AI products right now? So like when I was at Metro and it was big and like the usage based, hey, everything's going to go usage. Yes. But that comes with its own challenges because I don't think we're still fully all ready to be like, hey, you just pay for what you use. What's the split between who's still seat based, who's usage, who's hybrid, the AI needed for pricing? Like how are AI companies actually pricing their products right now?
Speaker 1I feel like we need to timestamp this conversation because whatever I say will get stale. So we're in September, 2026. I would say a year ago, everyone was having the same conversation. And at that point, folks were saying outcome based is going to be the real thing. And yes, usage based, but outcome based. And it's kind of come full circle where the market is starting to really coalesce right now. And we just had the monetize conference. So I was with all the different pricing nerds. And I say this with so much love. Like it was so fun.
Speaker 2You guys have that in Napa, right? Isn't it like a big? It was great.
Speaker 1Yeah, it was just last week. And it was amazing how many people were there and with the same question. So right now what we're seeing is two thirds of the Forbes AI 50 are doing some kind of usage based or hybrid approach. And that was less than 50%, fewer than 50% like last summer. So you see the trend to more hybrid. The majority of what I'm seeing people coalesce is this hybrid model, which is some kind of either it's a platform fee or subscription or seats coupled with credits and usage based on top. Because then you get both the predictability, which matters for the company, selling, but also for the company buying. But you get the usage based on top of it. And that's really where it seems like folks are landing on and starting to understand.
Speaker 2What happened with outcome based pricing? So that was all the crazy year ago. No one really implemented it. It's kind of like, but it was like, oh, we should do this. And then also everybody was also saying, oh, it'll be more usage based. Is it that companies have come to accept that I've just bought seat pricing for so long? Like, why can't we just fully go to usage based? Even for startups, like why are startups pushing back on like full usage?
Speaker 1Like, why are they pushing back on that? Because it was just much easier to align on like the unit of value, which is a closed ticket. What I've seen from the challenge with outcome based is that you end up really having to nail what is the outcome. And that sounds maybe simple, but like think about that negotiation that you're having on the other side.
Speaker 2Did we do it or did you do it?
Speaker 1Yeah. And beyond, was it a closed customer support ticket? Like, how do you really land on it in a way that's like really measurable? It becomes actually really hard to align on the outcome. What you really want to do is value-based pricing. And if you can't land on like, what's the exact value-based outcome, it just gets hard. And so that's where I've seen that play out.
Speaker 2You guys have been usage-based for a while. It's on an API. Now with these new AI products, I'm sure now it's like, these are even usage-based for you all. Feel free to answer this, how you guys think about AE compensation versus the AI natives that you work with. Do you have any thoughts on how to best compensate a sales team when it's usage-based pricing?
Speaker 1You have to look at the actual revenue because if you just take like a deal signed estimate, everyone could have the best of intentions and say, we think we're going to use this much and you think we're going to use this much. But at the end of the day, the AE doesn't know. The company that's buying doesn't really know. And so it's really hard to compensate anything but the actual revenue. We do, a lot of our contracts have a minimum fee commitment. So it's kind of the same concept as there's sort of a base platform fee you pay and you get a certain amount of usage and then you pay more on top of that. And that gets to be much more predictable for everyone. So when you say like, why don't people want to move to usage-based? I do think the predictability really helps again on both sides of here's how I can think about what to budget. I think the earlier stage startups, to your point, they are more pay as you go because it's so, so unpredictable. But as soon as you have some kind of steady flow, it's a lot easier to say, I can do this sort of platform fee or subscription fee.
Speaker 2Makes sense, even in that model. Okay, I just remembered, when we were selling usage-based, we would go to larger enterprises and you'd have more of a CFO that would care about cost predictability. Yeah. But even downmarket with these startups, I think that there's been maybe a pullback of YOLOing your credits. Yes. That like maybe the last year you can get away with it, but like there is starting this, this scrutiny a little. So that's interesting for you to hear that. But I think the, the, the dying question I've been wanting to ask a revenue executive at Stripe. So, so you, Maya, is the Stripe sales culture seems like one that is awesome and one that is very unique in the sense of technical, not salesy. That's how I've always viewed it. And I've always been very impressed with the reps that come out of Stripe. Tell us your story about, you just had SKO a couple of weeks ago and you had up a very counterintuitive phrase there. So how do you describe this Stripe sales culture and maybe what you preach as CRO at Stripe AI?
Speaker 1Yeah, I did have this slide and I said, okay, our strategy for this year, dot, dot, dot, and there's this big slide that says, don't sell anything, which sounds counterintuitive. Right? No, I will also say our reps are doing awesomely. They're all well above quota this year. What I mean by it is for these AI companies in particular, their number one priority is growth. they need to grow their businesses. And where we can come in and help is be their growth consultant. The beauty of the products that we have at Stripe is that whether it's the different payment methods in different countries, whether it's local currency conversion, whether it's a fraud prevention product or your financial infrastructure, we're building the economic infrastructure for AI, we're helping you grow. And so if you take an approach with these customers and these partners, I don't even call them customers, to be honest, we call them users and partners, and you say, hey, I'm here to help you with your growth, and you really act consultatively with them, they will end up buying the products, but it's just a super different dynamic. Like, okay, we were having the whole global conversation. So we did, with all of our top AI users, we sat down and we did a breakdown with all of them. Each of the AEs went out and had these conversations. And we said, this is how your revenue looks globally, like what percent comes from each country. Oh, that's cool. And this is how it compares to the median AI company. And then we gave each of them, like, here's the three things you should be doing because you're leaving that money on the table here, here, and here. To me, that's like exactly the relationship we want to have with them versus being like, buy this, buy that. And I think that mindset has really, really helped is like, our interests are so aligned. And so we're just here to help you do that.
Speaker 2Totally. It's a great model because for the most part, it's a take rate or a percentage of what they're using. So yeah, I think the benchmarking is super helpful. I think you guys ramped. There's certain, like, companies that can take a lot of this metadata and while not exposing specific client data, can use it as a really, as a trusted advisor in this way. You brought up like this one stat that was like, oh, if you just change local currency or something, what are some of these 80-20 hacks that these AI companies maybe aren't taking advantage of, but you guys can show them this and then they make a couple quick tweaks and it like spikes revenue like 10 or 20 percent?
Speaker 1Yeah, they really are hacks like that. Local currency presentment and showing the local payment methods can draw 17.8, we've seen 17.8 percent increase in overall cross-border revenue. Here's how I equate it, too. Like, imagine you go to a store here, go to the coffee shop that Muse picked out for me. Yeah. And you go to pay and you hand them a check. They won't look at you like you have three eyes. But that's literally what it's like sometimes when you're putting in a checkout experience in India and you say, pay me with your credit card. They pay in UPI. Ninety percent plus of, the population there pays in UPI. And so you really have to put yourself in the shoes of someone locally and say, how do they pay? And if you're not making that super easy for them, then it will be like the coffee shop being like, I'm sorry, we don't take your check.
Speaker 2All right, y'all, quick break. If you're getting value from this, do me a favor and hit the follow button on YouTube, Spotify and Apple. It helps way more than you think. Now back to the episode. That was a really good analogy. Help me crystallize that. What are some other things that you would know about other countries that are unique things? Okay, don't use credit card in India. Obviously, don't use a check here. Like nobody would like, what the hell are you doing? Anything else that comes to mind of unique challenges or opportunities in certain countries?
Speaker 1I'm going to China next weekend or this weekend in two days. And I was there last year for the first time in a long time. And I like to think I'm like a pretty savvy traveler, but I hadn't connected my payment method to WeChat yet. And I was getting out of the airport and I go to take a taxi and literally I couldn't pay because, they wouldn't take cash, they wouldn't take my credit card, only WePay.
Speaker 2Wow, interesting. These local like laws and jurisdictions are that, yeah, you need to follow them. Yeah, super interesting.
Speaker 1So now I have everything downloaded before I go this weekend because I don't want to get stuck in the airport again.
Speaker 2You should use instinct, be like, hey, what am I missing? I feel like this is like a good kind of partner here. You should test that use case for your seven continents. One thing that was really interesting, so I heard that Jean say this, she doesn't work at Stripe anymore, but she said this about when she was working at Stripe in her recent Lenny's podcast. And I was like, oh my God, I'm going to have to hire someone who's going to do all of these things. And I'm like, oh my God, I'm going to have to hire someone who's going to do all of these things. How would you describe the Stripe sales team? And how do you think about hiring for it? Like what is a Stripe seller versus someone who might not be a good fit at a Stripe?
Speaker 1So we had our catalyst, our president's club a couple of months ago, and I was having what we call stay conversations. It's like the opposite of an exit conversation.
Speaker 2I never heard before. Explain that what that is, actually.
Speaker 1Yeah, it's a concept that's basically, you know, when someone leaves, you have an exit conversation. Yeah. And you ask all the questions like, what could have made you stay here longer? What wasn't great? What did you like? It's such a miss to have that conversation after they've left or as they're leaving. And so the stay conversation is basically to have that same conversation, ask a bunch of the same questions, but just do it when someone's here. You know, what are you most energized in your job? What are the paper cuts that you really think, if they keep festering, would cause you to want to leave? What does great growth look like for you? Like, why wouldn't you? You want to have those conversations early and then you can make changes along the way. So I was having stay conversations with everyone on my team, and it was super interesting what they were saying to me. When I asked, what do you like most about your job? Every one of them talked to me about the relationship they have with the product team and how they love the collaboration with the product team. And so to me, there's like a is that correlation or causation? But I think the prod go to market interlock at Stripe is so tight and so good, and that's what makes the job. That much more interesting and exciting. I think that's what makes the product that much better.
Speaker 2Yeah. So I sold app layer and then I sold to developers because I sold them at Metro. I always thought it was a lot more intellectually stimulating, especially in an early stage environment, because you got to be a lot of people call it like a revenue generating product manager. I think what's interesting for you is you still are able to empower the sales team to scratch that itch. That's something that they really wouldn't want to do, because once you get to a point of a company being big enough, at least that was my experience in app layer. You don't get that. Yeah, but for what you guys sell, it's a technical. It's infrastructure, it's an API. So having that ability, I think, yeah, you guys like that's how I would define it, right? It's like you guys are technical, non salesy. The people that are wanting to stay there in the stay interview is the people that like they would care about that. And it's good that you guys empower them to be able to do that.
Speaker 1And it's not just empowering. I think it's actually part of the magic and the secret sauce. You know, Kevin leads product and engineering for payments and risk and support. And he was telling me he loves hearing from our team. And he wants the direct signals of what's happening in the market. So we run what we call like the AI SteerCo every week. And it's a combination of our senior most product leaders and my leaders on the AI go to market team. And we're literally just like bringing up all the things and solving them together. You know, I think a few years ago, and I can say this because I've sat on all parts of the org, it used to be product and engineering would build the product. I mean, they get a lot of feedback from the market, but they build the product. You put it in the new product introduction machine. And then it works. It would spit out your pitch deck and your PDF and your pricing. And then sales would take that and say, let me go sell it. That just doesn't work anymore. We're all moving way too fast. And so you need this sort of fluid relationship where you're like, OK, here's the product. And you're like, OK, great. We're having the conversations, but product, why don't you come join us and then go to market? Why don't you come join us in the pricing discussion? Because we're evolving it in real time and we're getting feedback from our users in real time to figure out, like, well, what's most important and how do we solve your next problem?
Speaker 2Yeah, you've been there over eight years now, I guess, like, in how you hire salespeople at Stripe. Has that changed at all since the time you've been there or is it pretty much the same? Like, has the archetype differed? I'd be curious on that.
Speaker 1We have so many different segments that it has to be a little bit different. Yeah. What makes a really good AI seller is different than what makes a hardcore enterprise seller is different than what makes a startup seller. So I think, yes, it's evolved, but the core DNA will always be the same.
Speaker 2All right, so you're Shiro at Stripe AI. I have to ask you, like, how are you guys using it? How are you guys using AI internally for the sales team? What are some of the tools, what are some of the points of leverage? Like, is everyone just now using Instinct and you're like, okay, we were all into that? How is Stripe internally specifically for the sales team using AI to get some, you know, leverage lifts, I guess?
Speaker 1So our internal data team has built such a good internal hub. We call it CHI. Sales has the highest weekly average users of anybody else in the company.
Speaker 2And what are some of the things that they're
Speaker 1specifically using CHI for? Anything from prepping all my briefs now and all the sales briefs are all done in CHI. You have a skill, you have the template. We spent a lot of time making sure that CHI was connected to all the different sources because the quality of the AI is basically only as good as the sources it has. So we spent a lot of time making sure that it could connect to customer informations, to Slack, to your email. Like, how do you actually get it to have all the information you need? And I think that's actually the crux is a lot of these tools are very powerful, but if they don't have access to. Gong and all the conversations you've had and the emails you've had, they're going to be pretty myopic. And so we really use our internal tool, but because it's connected to all the different pieces.
Speaker 2Got it. So you're using CHI, you guys, I'm assuming Gong, Salesforce, the typical stack as you move up the enterprise. Any like specific use cases that have stood out that you've seen in the last month that like a seller or a leader and you'd be like, okay, I need to like adopt this?
Speaker 1Something I do a lot with my team is I love after meetings. Taking a voice memo and then throwing that transcript in and getting a really crisp translation and then sending it out to the team. And so that to me has been one of the biggest hacks is, you know, like you're at a conference and you have tons of different meetings. And just after each one, instead of taking down all the notes and all the follow-ups, just like pop in there. It's a 30-second voice memo. It doesn't even have to be perfect. And then you could throw all those into, honestly, any tool of choice, Codex, Clot, and just say, write me the bullet summary that I can send to the whole account team.
Speaker 2Yeah, yeah. I'm definitely. whisper flow pill than a lot of this is like, I'm getting like, I was like handwriting, even when I hand write these. cards yeah i get like cramps because i haven't had i don't hand write stuff anymore yeah it's the same with typing i almost feel like i'm gonna start getting like cramps if i go back to like typing as much as i used to type it's like crazy how we're not doing it as much anymore and we throw in it's like we're doing voice-led sort of commands with these ai tools
Speaker 1i yeah it's kind of embarrassing my whole drive home i'm literally just back and forth with my phone talking back and forth and i get so annoyed if there's just a even a second of no reception where i can't have a conversation with my ai
Speaker 2completely agree you're the sierra of like stripe ai what is the revenue leadership structure at stripe and like are there different business units like i'm actually curious now that you guys have expanded and you're bringing on more products like yeah tell us how that works that's right so i
Speaker 1technically have two jobs i'm the sierra of ai and the zero of our revenue suite i report to our global cro and so we have regional cro's so we have amer amia and aipac and then we have the three main product areas and you joined stripe what was
Speaker 2the entry point eight years ago what was like how many employees how like yeah a thousand people yeah
Speaker 1and how many is right now over ten over ten thousand yeah
Speaker 2now heading up the sales team there like what do you see some of the best sellers do at stripe that separate them from from the rest of the team that what was the president's club name that you guys catalyst so like you have seen reps come to catalyst you see some that maybe are multi time catalyst members like what are they doing that differs from others i guess
Speaker 1well take tanner so tanner now is one of the managers on the ai team started as an ic i first met tanner a couple years ago patrick calls me on a friday and he's like i can't say the name of the customer but take very very large ag customer and it was like hey can you help on this thing that's going on i called tanner who's the ae on that account didn't know him but i was like hey sounds like there's a thing we should be working on together and monday we're there on site with that customer and i've just never seen someone take so much agency and to your point about being technical he's there guiding a workshop about how to think about do you set up a local entity here do you run it all from the us how do you think about the different api integration shapes and the pros and cons of each one of them i was like who is this guy i could not tell if he was an engineering leader at stripe or a salesperson and just ever since then he's been the guy who is really deeply understanding what's going on with the customer and user mapping their whole entire org and then coming back and being like this is the problem they have our solution can solve this part of it but it's got this gap and how do we do it to really help them and so he's just like relentlessly user focused really cares about doing right by them and then we'll just figure out how to get it done internally i love in that story
Speaker 2that tanner uh said hey here's where we're lacking here's where we're great and i feel like calling that out as a seller is such a weapon it builds trust right and it just and your job is to get to a yes or a no as fast as possible so by showing where the skeletons are you know or the bodies are buried a little bit they trust you more and you can just get to a faster answer and by the way if
Speaker 1not you have to deal with it afterwards totally i'm not in the business of overselling we have made that mistake in the past and then everybody suffers because
Speaker 2of it right and from what i uh there's been a couple of other stripe revenue leaders before who have said the way that you compensate reps we have a lot of revenue leaders who have said we have a lot of revenue leaders who have said we have a lot of revenue leaders who have said we have a lot of revenue leaders who maybe this has changed is uh yeah there's a percent on like the initial land that you'll get but it's like the year after what their actual usage is so you're aligning the incentives with the actual outcome that you want to see but really what's tying that is like customer success so that reps aren't whether it's malicious or not it's just sometimes you just miss it really comes down to like are they going to be actually using this a year later in a usage based billing this is what's great for everyone now some coin operator reps might not say that i worked with some at salesforce that would be like whether they were trying to oversell or not there was a lot of you know shelfware i guess but yeah i love that story and i think the other thing i want to ask you too is just like you've now been in the revenue seat for a little bit what's some sales advice that you either don't agree with or isn't true for stripe but could be true for something else like have you seen anything whether it's on linkedin or another podcast that you're like i don't know if i necessarily agree with that
Speaker 1well it kind of goes back to what we were saying before i think the best sales people don't sell and shouldn't sell we're really there and look part of it is you have to have the right product because you have to have a product that's aligned to the success of your customer and that your incentives have to be aligned so i'm kind of taking that for granted but i also my advice to sellers would be do not go work for a company where the product isn't allied to their success so if you have that luxury then you get to say i'm not trying to sell you anything i am genuinely interested in your growth and if you grow and you succeed i succeed and i think that's just the best way to do
Speaker 2it i think so much of it as a as a former ae comes down to like is our leadership empowering us to be able to have that mentality i mean there's a lot of sellers that feel pressured sometimes to sell but when you go to an sko and it says don't sell i think that's like really speaking from the top so i give you guys a lot of credit and and kudos to y'all but i want
Speaker 1to be clear i want everyone
Speaker 2to crush their totally i think you can do both though you can do both you can do both this is this is why so can i give you uh something that a lot of people chirp me about yeah in our blog and everything is i have like i said the best reps are not coin operated yeah that doesn't mean that sales people don't care about money if you're at a sales organization and you're making no money it means you're probably not winning you should probably leave that company yeah but there's a way in which you can do where you don't have the main input as money but you can still be successful yeah financially also with customers you know the way the customer implements some people think i'm virtue signal by saying that i promise you i am not yeah i genuinely believe and that's i know that's like how you i don't want to assume but i believe that to be the case for you all where that is the byproduct of a lot of other things going right it's like different inputs of what's driving the output
Speaker 1sort of thing totally agree yeah very competitive our team is very competitive very ambitious our sellers are doing awesomely i'm excited for them we're beating all of our targets the folks are beating their targets i think that's really important you can just do both totally and then maybe the other one that's sort of implied i mean i think this is actually like pretty well known i used to think that when people were like my superpowers building relationships that it was like a little too fuzzy i've come so full circle on that oh interesting i think it is like all about the relationship i feel really lucky because we work with all these ai companies i'm on text with a lot of the founders i value those relationships so so much i just think that's so important and so i i really do think some of the crux of this and it kind of goes back to the don't sell it's like we all work for one company totally it's called silicon valley and we will have different managers over time but like we're all trying to do this thing together and the value of the relationship and being there to really help each other i just think is at the end of the day like one of the most important pieces i think
Speaker 2the thing the question i do want to ask things that you think in your eight years at stripe were bets that you guys took that maybe didn't pay off and this is natural in any business right you do 10 growth experiments you really think that one or two of those gonna work and it ends up being the other ones that where the outsize returned anything like that in like the stripe growth story that like
Speaker 1comes to mind we have so many failed bets as you should right because if you succeeded on everything what that would tell me is you didn't take enough bets right maybe two interesting ones are i think we were probably right but way too early okay was our initial foray into crypto interesting and now stable coins are huge but it kind of took a while for that really to play out and maybe on a shorter time scale and i credit patrick so much on this he really said you know agentic payments are huge and we have to win agentic payments but if you look at the chart of agentic volume for the last year we've put some of our best people on it and it's been really really flat and so i don't want to say i lost faith but a couple months ago i was definitely like okay it makes sense that agentic payments will be big but like i'm not going to inflect yeah and in the last few weeks it has just i mean the chart literally goes like this it's like flat flat flat for months and now we're here and i think we were just like a little bit ahead of the other pieces of the technology for folks to really adopt it so i think yes we have tons of examples of times that our bets didn't pay out and then there are also some where like we were maybe early or just timing wasn't quite right but i think at the end of the day like all that tells me is you have to have real conviction where the market is going and build for your users and their success and maybe it doesn't always work out timing wise maybe you got a little bit wrong but as long as you have that as your north star is like how do we help our customers be really really successful the rest
Speaker 2will follow sweet um maya j this was great
Speaker 1this was so fun awesome yeah excited to
Speaker 2see you guys continue to crush it and good luck on your 777 or wood continent i guess it's all seven continents but it's where are you specifically going you started
Speaker 1in antarctica got
Speaker 2it
Speaker 1and it goes antarctica south africa australia dubai spain brazil and then we ended miami yeah
Speaker 2wow it's amazing good luck thank you and uh awesome having you on thanks so much so fun thank you thanks for hanging with us if you like this one follow the show on spotify apple podcast and youtube and we'll see you next week cheers
PodcastTranscript AI