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This is How Tech Executives Will Get Hired in 2026

27m 52s

This is How Tech Executives Will Get Hired in 2026

This episode of Topline features hosts Sam Jacobs, AJ Bruno, and Asad Zaman answering a community question about how professionals in SaaS can transition into AI-first companies without prior AI experience. Sam opens by arguing that candidates must demonstrate AI fluency through practical work product, such as building agents or showing hands-on use of tools, rather than relying on a static resume. AJ adds that AI companies still need subject matter experts in sales, marketing, and demand generation, and that core business principles remain timeless even in an AI-first world. Asad frames the current platform shift as a meritocracy where limiting factors like jumpy resumes or lack of formal AI experience matter less, and potential impact matters more. The hosts stress that true AI-first believers understand both the power and limitations of AI tools, and that candidates should confidently articulate where AI works and where humans are still needed. They also discuss the importance of staying current through AI-focused social media and communities, and warn against being an AI denier. The episode concludes with advice to be hands-on with tools, demonstrate unexpected positive experiences with AI, and treat the shift as an opportunity rather than a threat.

Transcription

5330 Words, 28583 Characters

English
Speaker 1Hey, everybody. It's Sam Jacobs. I'm the CEO of Pavilion, and I'm joined by my good friends and co-hosts, AJ Bruno, the CEO of Quotapath, and Asad Zaman, the CEO of Sales Talent Agency. And this week and next week, we've got a special format of Topline for you. We've got short, impactful episodes that come from the Topline community themselves. We live in an age where AI is changing everything we do every day. There's a tremendous amount of anxiety. There's a tremendous amount of stress. But there's also a tremendous amount of opportunity. And so we want to address some of your most burning and pressing questions. We're going to tackle one question at a time for the next two weeks. If this format works, we'll continue it, of course. But for now, we want to engage the community with questions about what's happening in the world and see if we can help solve some of these problems in just 20 minutes. We can solve the world's problems in 20 minutes. Right, AJ? We only have
Speaker 219 minutes left. But, Sam, I am wearing my Quotapath Labs hoodie today. So I put my thinking suit on and I am ready to go for all the questions.
Speaker 1Let's go. But before we do, a funny joke for me. Quotapath Labs reminds me of these companies that started foundations when they raised their Series A at the height of COVID. They're like, we're starting a non-for-profit. I'm like, okay. Can I have some of the money? Just the money for the non-for-profit. I just want that money back. I always wanted to be tired of it.
Speaker 2Where's my North Face swag? Give me my North Face swag. This is QP Labs.
Speaker 1There's a teacher in Florida contributing money to the Florida Teachers Pension Union, and they invested in a VC, and then that VC invested in you so that you could start a foundation. Give the teachers money away.
Speaker 2I love it. Yes. And that's exactly the vision for Quotapath Labs.
Speaker 1Thanks, Sam. Right? Wait on that. Weird. All right, let's get started. Start your engines. Asad, over to you. Ask us a question, and we will answer.
Speaker 3We have been receiving a number of questions, and there are a few questions that have asked the same thing. So I'm paraphrasing, but the essence of the question is this. I am working in SaaS today. I have kept an eye on what's happening. I understand the world is changing. I want to move into an AI company. I've tried applying to a bunch of them. I'm not getting really far. What do I do to make myself extremely successful with these AI companies? I don't have AI experience today, but I have a lot of drive. I have a lot of desire to work in these companies. What should I do?
Speaker 1Sam. I'm going to riff. AJ is going to have better thoughts, so I will go first, because in the absence of these better thoughts, my thoughts will sound good. But they are second best, but that's why I'm going first. Here's what I think. I have been helping people find work recently. There's a few companies, including some folks that AJ knows quite well. I've been helping people find work recently. There's a few that are hiring, and I've been getting resumes for VPs of marketing. Here's what I think. I think now is the time that the concept of demonstrating your work product is really changing. If you want to move into AI from SaaS, you have to demonstrate from the beginning of the application process that you are fluent and conversant with these tools. And so instead of just a static CV, I'm seeing a lot of people and I really think what you're trying to do is demonstrate that you're capable of working with these tools, not theoretically, but practically through your conversations that you're having with hiring managers, with CEOs. I think your work product needs to speak for itself. And I think that also includes some demonstrations, maybe with something like OpenClaw, where you can show you're building your own agents, training your own agents, and leveraging your own agents. So the short answer to the question is the way that you're going to make this transition is by becoming AI fluent, and you're going to demonstrate that through work product, not through talk.
Speaker 3Yeah, I really like that. And I think there's this unique, you said it well, Sam, there's a unique opportunity today to do that in a way that wasn't possible before. Like back in the day, you would see some people do some version of it. You know, youngsters would create a website to show some of their design work. And that would be so compelling, but not everybody could do it. And now, now so many more can. AJ, what are your thoughts on this?
Speaker 2I actually, a couple months ago, I had lunch with a sales leader, a good friend of mine is a sales leader at CoreWeave. So more in the infrastructure, AI.
Speaker 1Yeah. Earnings announcements today, I believe.
Speaker 2That, well, they did. And that, this was a little bit before, this is a totally different world when I had lunch with him. And he had just joined. I asked him this exact question. I'm like, how do you get a job at an AI like first company like CoreWeave infrastructure? And his response kind of surprised me. He said, the funny thing about it is they don't have any clue what they're doing at the B2B world. They don't actually understand sales whatsoever. And he, he likened, he worked for a PLG company in 2019 that did really, really well, GitLab. And it was very similar feeling when he joined GitLab. It was all about, he was the expert and was teaching all of them. So he didn't actually lean away from what he knew. He actually used that as a positive and then thought about the evolution of, okay, exactly to Sam's point, how do I get embedded involved and didn't try to be someone that he wasn't and let his experience speak to it. Because you hear a lot of like, oh, traditional SaaS is dead or this is going away. But the reality inside these companies is they're actually looking for subject matter experts. It's in the very thing that you probably know. So you want to actually push that forward.
Speaker 3Can I pull that thread a little bit? Because is what you're saying that there's two sides of it. One is the thing you do. You're a sales leader, you're a marketing leader, you're a demand gen person. And these companies, like every company in history, need people that know how to do that job. And so they need you to be proficient and really good at that and bring a skill set in that they're missing and feel a lot of trust that you are really good at that thing. But then on top of that, what Sam is saying, if you layer that on, it seems like, and we need to know that you're going to do that thing with AI, with an AI first mentality. And so if you're a demand gen person, you have the principles of demand gen from all of your experience, but you are adding on this AI layer and saying, well, then how do I do this with one eighth that a human headcount that I would have needed just two years ago? Is that kind of the core message there?
Speaker 2Look at our good friend, Matt Braley, who joined Elise AI, a booming AI first product. And I know you've talked to him, Asad, and I've talked to him. And through that process, it felt like his expertise was just missing. He could see the gaps in some of those conversations he was having with their team, the sales, the individual contributors, and say, hey, why aren't you just thinking about it this way? And I was like, aha. Moment. Piece of it.
Speaker 3Right. Classical principles of business actually are quite long lasting, right? Like the idea of a value proposition is pretty timeless. Like a value proposition had the same key components 50 years ago.
Speaker 2Customer value is customer value, no matter if you're an AI first company or if you're selling paperclips, which I don't know who's selling paperclips, but maybe that's not the right relevant thing. But it always boils down back to customer value. And you don't want to be someone not when you're having these conversations with AI first companies.
Speaker 3What would you say to this?
Speaker 1What I would say is I think I've got something for the listeners. And I know we've got some oldsters. We got some oldsters out there listening. You're on the treadmill. You're huffing and puffing. You're a few pounds overweight. You're looking at that and you're like, working out.
Speaker 2Sam, are you talking to me right now? Are you staring into my soul right now?
Speaker 1You're in great shape. I'm trying to really empathize and put myself in the shoes of the listeners. And the listener is a middle-aged person just like me. But here's my point. Because on the one hand, it's like, as you said, AJ, I can't present that I'm some 25-year-old GTM engineer that is friends with Varun and Kareem from Clay and can build all these enrichment water flows by hand. On the other hand, you're worried that if you just show who you are, you're a seasoned vet and you don't have a point of view on AI that you're going to be laughed out of the room. So what's the balance? And here's here's my answer to you everybody um i think the way you position this talk track is first you do use you have to use the tools and you have to use the tools so that you can do the following which is clearly and confidently talk about their limits i think if you can go into a conversation and you say it's great i've used claude i've used tofu for content creation or writer or grammarly like i've used these tools i know what the tools are i've used them here's where they work here's where they don't work and here's where their limits are i think that really shows that you because that's what we're seeing right everybody's trying to understand where is the limit of claude will claude replace salesforce or will claude just interact with salesforce and you'll still need salesforce nobody actually knows the answers to these questions and every hiring manager every ceo wants somebody that says yes they're part of my tools toolkit in this way specifically but i'm not going to use my toolkit for here this is where i'm going to use the humans if you can even if you're completely full of poop but if you say that confidently if you draw that distinction i think that's what people are looking for. What do you think, Arsit?
Speaker 3I think that's really, really on point because all of these tools, and I spend a lot of time in them, they have such limitations, but they're so powerful as well. And if you can be the one that articulates that, yesterday I was having dinner with my mother and she was talking about the limitations of chat GPT when using it for health because she's recovered from cancer. She's going through heart failure right now. She has lots of tests, lots of results, lots of medication. And she's not like a technologist, but she's cute and funny. And she's always trying to make this stuff work. And she understands the limitations. And so she's like, sometimes it loses its mind. And I have to come back to it and start fresh and ask the same questions again so that I'm getting different responses. And then I can kind of triangulate which one from there. And that's like close to an 80-year-old woman who's figured that out. And that was really compelling to hear. It was like, oh, you are AI first then as a human being if you are thinking like this. And so I think it's compelling to hear when you see a person talk about limitations or something. I think to add to this conversation, I think a lot about the environment. How do you define the environment we're in? And then how does that dictate a little bit of your thinking and how you operate within it? And I think one of the things that is important to keep at the back of our minds is, that whenever there is a platform shift, I feel like everything becomes more of a meritocracy. The value of experience goes down a little bit. It doesn't disappear, but it goes down a little bit. And if you are a younger person, if you're a director or below, that's exciting for you because you can move up faster if you present in a very compelling manner because people are not looking at titles the same way. They're trying to assess your potential impact. Are you AI first? Do you have the right balance of the core skillset with AI? Can you do this for us? And we're willing to give you a position maybe one or two steps ahead of what we would have given you before. I think the same thing goes for if you're later in your career. A jumpier resume, if you're in your 40s or 50s and you have a couple of short stints, three years ago, that would have been a bigger limiting factor than it is today. And I think whenever you are in a true meritocracy it should be exciting for people because limiting factors, they kind of go away and you can now navigate and create opportunities that were just not available for you a little while ago. And so that's something I've been thinking about a lot.
Speaker 1Do you think it's overblown a little bit, Asif, the worry? You have people saying, how am I going to transition to AI when my experience, Matt Braley is not, he didn't have any specific AI background. He's just a really good revenue leader. Yeah. Right. And that's what Elise needed. And go ahead.
Speaker 3It's so dependent on when you make that transition. I think as soon as the platform shift happens, there's no one in the new world. So everyone has to come from the old world. And so there's more opportunity to transition. It's easier. I think every year that goes by, the friction increases. And so then what you have to do to be able to make that transition into a high quality organization, that bar just gets higher. And so I think right now, there's still, there's still many more people in SaaS than there are in AI. And if you talk to any AI company and you say, hey, what's your biggest limiting factor? What's your number one problem? It's hiring. Like we cannot hire fast enough. We need less people per stage, but we can't hire the ones that we need. Like we're so behind. And so there's still so much opportunity to transition, but it's a little bit harder than it was a year ago. And next year will be harder than it is this year.
Speaker 2I love this limitation piece of it. I think that to add to this and just kind of thinking and riffing off of what you all, what you all are throwing down right now, unexpected experiences also can go a really long way. When is a time where something, the tool that you're using did something in a positive way that was unexpected? It can be really small. I mean, just for example, I built a website for my daughter's basketball tournament for all the teams next weekend. And when I built it, it said, hey, by the way, I can just create an admin panel so that you can see and you can update all the scores in real time at the day of the games. Is that you want to do that? I was like, sure. Of course I want to do that. And it built a full admin panel to change the coaches, the contact information, the rules, the scores, everything in 30 seconds. And that I loved that experience. And so if you walk in and you talk about these limitations, but you also talk it, talk about it in a positive way, an experience that you was completely unexpected, that can be a really great part of the conversation. That could lead to places that you didn't even think would happen.
Speaker 3Yeah, because I think it is very important to call out that no one's looking to hire an AI denier, right? Into an AI company. Like what they're looking for is a true believer. And what they're trying to understand is a true believer is, A, you understand its power, but then you also understand its limitations. Getting that right is so important because if you come across as like, hey, these tools are cool, but here's all the things they can't do. And like humans are still really important. And like, what's old is new again. And like, if you, if you see, if you go too far down that path, I think you create a lot of friction for yourself. So you have to be very careful that you're still an AI first person, but a true AI first person understands how to use AI today. Because like, it's not just mentality, right? It's not like, oh, we're saying, hey, we want to be an AI first organization, hence we will be. It's like, okay, then we need to go and find the tools. Then we need to map them to our processes and our systems. Then we need to know how much AI to use and not to use and that find that balance. And that balance keeps evolving every six months because the tools keep getting better every six months. So can you stay one step ahead of everyone else? Are you that person? That's what they're trying to figure out, which is why what Sam said and what Lemkin has been saying, which is like, if you are a VP or a CMO or CRO and you have not tried to create an agent or truly like wrestle with these tools, the world will pass you by. Like, this is not a moment where you can delegate this to your RevOps team and just sit back and be like, I'm pushing the right mandate. You've got to be hands on keyboard a little bit.
Speaker 1I would say 100%. Hi, everybody. This episode of Topline is brought to you by Pavilion. That is the company that I run. The leaders who rise fastest today aren't just great operators. They understand the business. They know how value is created and they negotiate like executives. At Pavilion, our education curriculum is built for exactly that kind of career. Learn the language of the P&L with our new P&L fluency course, which I taught today. So you can read a balance sheet, model unit economics and challenge a forecast with confidence. Master the art and science of executive compensation and negotiation taught by leaders who have sat on both sides of the table and know how real offers get structured and join a community where you don't just take courses. You apply what you learn with peers who are building companies, leading teams and shaping the future of go-to-market. So listen, if you're listening right now, you're listening right now, you're in your car, you're doing something, you're like, why don't I skip past this? But something is making you hesitate. Maybe he'll say something interesting. Maybe he'll say something that will get him fired. Maybe he will say something that will get him canceled. But you're listening. That's the point. And what I would share with you is, listen, if you're in go-to-market, you need to invest in Pavilion. You really do. This world is changing too quickly for you to navigate this on your own. And I appreciate that you might have, you know, your WhatsApp group chat with like your former boss. But like, that's, that's not enough. That's not enough. You need to be in a community with other go-to-market leaders. You need to lean in. You're not going to work at wherever you're working forever. You need to invest in yourself. Do it. Stop being, just, you need to change your mind. It's not an expense. It's an investment. Invest in your future. Pavilion is where you grow next. Email me if you have any questions. Sam at jointpavilion.com. Thanks for listening. This episode of Top Line is brought to you by Granola. You're in back-to-back meetings all day. You're trying to stay present, but you're also worried you'll forget the decision, the action item, the important next step. That's where Granola comes in. Granola is an AI-powered notepad for meetings. AJ, tell us about quota pass use of Granola.
Speaker 2So last week, half my management team had this debate. We said, hey, we need to go down to one internal conversational intelligence tool. And half the team is using Granola and the other half we're using a whole bunch of different things. And so the half the team that is using Granola made the bid and our entire management team is, as of next week, Sam, changing over to Granola. Wow. I know. It won out the use cases and ultimately what I love about Granola is it kind of just is sentient. It works in the background, hangs out. You can take snippets of pieces of a conversation and copy and paste them, throw them into GPT, wherever you want to show them. And it's great.
Speaker 3Is that what makes it better to every, because it's a busy area, right? There's so many options. Is that so many options
Speaker 2that the working in the background with it just kind of being this co-pilot is the thing that I really like about it. I use it in tangent with Whisper. Whisper is another tool. And those two together seem to be like a super, supercharged AI bot for me.
Speaker 1A supercharger. Listen, everybody, use code top line for three months of Granola for free and be like Quotapath. Head over to granola.ai forward slash top line and get a free copy of Granola. You can get three months of this tool that AJ's management team just said that they will mutiny unless everybody switches over to Granola. What a great company. company if you're out there listening and you don't use granola what are you doing granola.ai forward slash top line and use the code top line for the code top line for top line for three months of granola for free what was that was that top line i didn't catch that line top line thanks everybody also did you want to say something you haven't said anything at
Speaker 3all i i'm just excited to hear what ages said i'm thinking about it combining these two
Speaker 1things great all right bye bye granola everybody thanks for listening the other thing i i saw gary tan talking about recently which i do agree with yeah this is just a pro tip for people is prompting and meta prompting it's not even something you have to get amazing at it is just you can use ai tools in conjunction with each other so when i'm building unlovable these days i have my chat gpt open because i don't quite trust whatever llm lovable is working on all the time and so i stress test the answer that lovable gives in open ai and chat gpt and it's two tabs that are next to each other and it's basically like chat gpt is my uh counselor or my my advisor my tech advisor and then lovable is my engineer and so i go i say this is what lovable said it says tell lovable to do exactly this and so it's not just relying on one llm to drive the outcome because they have you have to triangulate because of what asa's mom said that they're not always correct but they'll always make you think that they're correct yes
Speaker 3they're very compelling at that like they're very compelling at that um the other thing that i think is also really interesting with this is that if you are leveraging these tools um and you are being you're speaking correctly one other thing that i think people are trying to understand is are you going to be able to stay ahead you sound like you're ahead today but are you going to stay ahead and i think if they find out that you're not on ai twitter or ai ads i think they're going to think you're not a serious person and i think that'll hurt you i know this is a controversial
Speaker 1opinion but i it's really dependent who you're talking to i don't know the problem with these social media platforms is that they're terrible for your brain they're it's like it's like if you're not drinking poison you're not you're not you're not as cool as the rest of this is like okay i just don't want to drink poison every day
Speaker 3i know that's the tough part like i completely understand that i agree with
Speaker 2that's why i just spend all my time on mold book where agents talk to agents on reddit i feel like i'm not going to be able to do that i'm not going to be able to do that
Speaker 1what do you think about that i just think it's like i i could because i can see there's there's certain people but you know honestly we get confused between operators there's like three kinds of people yeah in this that there's operators uh subscale there's operators at scale and then there's vcs and investors and the problem is that we're like well why can't i be as hyper online as chamath or like some of these like well because that's their job like their job is to like be online looking at ideas and interpreting information they don't run the
Speaker 3company in researching like that is the job of
Speaker 1yeah and so you're like and then and then you're like well what about palmer lucky and the collison brothers like well stripe some 130 billion dollar business like yeah they've they've allocated part of their time to tweeting you know
Speaker 3and it's still like if you look at the velocity like the velocity is far less than if you look at some of the investors right like that most active investor is far more active than uh somebody like collison or somebody like palmer lucky and then some of them just have like you know they they grew up on social it's it's very instinctive for them like they're taking a dump they're throwing out four tweets like it's not the same as for somebody else no you're
Speaker 1you're absolutely right and that's what harry stubbings i do like this rubric he says like all of the great founders uh that like broken homes with damaged relationships with their fathers first generation immigrants and then they're immigrants video game players and i think that you're you're you're making an interesting point like some of them just are this is how how uh what's our cluley boy's name roy lee like this is how he lives you know his life is shit posting uh all the time and so dear listener if you are looking for a job at cluley you must be on x following posting
Speaker 2that's that's where he came down to if you can boil the tldr to this uh shit post your way to an ai job
Speaker 1so let's summarize uh for people that are out there listening you are a traditional it could be sass it could be any other kind of technology it doesn't even have to be sass you want to move into it you want to be ai first ai native what are the things you need to do you need to play with these tools and get used to them you need to understand their limitations so that you can project that confidently i would include use of the tools in your job application or interviewing or networking process which means building your own personal website building some kind of video like an roi calculator for hiring you or something but demonstrating that you know how to use these tools awesome what was your advice
Speaker 3again i think you should also be uh really online being able to speak to what is happening today like you have to show that you understand the culture of ai because that is to them a signal today that you'll be able to stay ahead because the information whenever you are so early in a platform shift i think the information is not going to be found in these old school channels it's going to be found on on a social network it's going to be found on youtube tutorials like that's where you're going to learn and so you need to be able to show that you can stay a step ahead you need to understand that this is a true meritocracy now where some of the limiting factors of before are no longer limiting factors treat that as an opportunity but also know that creates interesting competition for you i don't think cmos have traditionally thought that a junior vp or a senior director was their competition for a role i think that's their competition for a role now and so you've got to take that into account um i think those are my big two big points like understand the environment and how it plays out for you and then don't just show that you're good today show them that you'll stay ahead in a fast-moving environment and finally
Speaker 1obviously but i really do mean this everybody if you're not a part of something like pavilion i don't understand how you're going to how are you going to do this our ai and go-to-market community is the most active uh community within pavilion people are posting there every day they're demonstrating workflows you need to be in some kind of community i think pavilion is the best but if it's not pavilion it's something something where you're getting ambient exposure and to to real people that you can interact with because it's great following people on x but you can't always talk back to them you need to be in some kind of place where you can say how'd you do that let me schedule some time with you and get your hands dirty but let me leave you with this you got this take some deep breaths do some meditation go exercise we got this people nobody's too old for this moment we got it thanks for listening to our new format of top line we'll be back next week with another great question from our community goodbye
Speaker 4okay and against all odds you're still here look if you want more top line check out the top line newsletter at topline.beehive.com beehive is spelled weird it is b-e-e-h-i-ve dot com topline.beehive.com or if you're a video person because video is great check us out on youtube topline dash media is what you want have a delightful day everybody

Podcast Summary

Key Points:

  1. The podcast introduces a new short-form format where the hosts answer one community question per episode over two weeks.
  2. The central question is how professionals in SaaS can successfully transition into AI-first companies without prior AI experience.
  3. Sam Jacobs advises candidates to demonstrate AI fluency through practical work product rather than just talk.
  4. AJ Bruno shares that AI companies still need subject matter experts in sales, marketing, and demand generation who can layer AI on top of core skills.
  5. Asad Zaman notes that platform shifts create a meritocracy where experience matters less and potential impact matters more.
  6. The hosts emphasize that true AI-first believers understand both the power and the limitations of AI tools.
  7. Staying informed through AI-focused social media and communities is presented as a signal of staying ahead.
  8. The episode concludes with advice to be hands-on with AI tools, join communities, and treat the shift as an opportunity.

Summary:

This episode of Topline features hosts Sam Jacobs, AJ Bruno, and Asad Zaman answering a community question about how professionals in SaaS can transition into AI-first companies without prior AI experience. Sam opens by arguing that candidates must demonstrate AI fluency through practical work product, such as building agents or showing hands-on use of tools, rather than relying on a static resume. AJ adds that AI companies still need subject matter experts in sales, marketing, and demand generation, and that core business principles remain timeless even in an AI-first world.

Asad frames the current platform shift as a meritocracy where limiting factors like jumpy resumes or lack of formal AI experience matter less, and potential impact matters more. The hosts stress that true AI-first believers understand both the power and limitations of AI tools, and that candidates should confidently articulate where AI works and where humans are still needed. They also discuss the importance of staying current through AI-focused social media and communities, and warn against being an AI denier.

The episode concludes with advice to be hands-on with tools, demonstrate unexpected positive experiences with AI, and treat the shift as an opportunity rather than a threat.

FAQs

Focus on demonstrating practical AI fluency through your work product, not just talking about it. Use tools like Claude or ChatGPT, understand their limits, and show examples such as building agents or an ROI calculator during interviews.

Highlight your core expertise—like sales or marketing—and pair it with hands-on use of AI tools. Show that you know where AI works and where humans are still needed, and demonstrate this in your application or conversations.

Yes, AI companies often lack subject matter experts in sales, marketing, and operations. Your classical business skills are timeless and highly sought after, especially when combined with an AI-first mindset.

It means using AI tools regularly, understanding their limitations, and integrating them into your workflows. It's not just a mentality—it's about staying hands-on and continuously adapting as tools evolve.

Being online and engaged with AI content can signal that you're staying current, but it's not the only way. Focus on demonstrating your knowledge and practical experience through your work and conversations.

Keep experimenting with new tools, triangulate information from multiple sources, and stay connected with communities where real practitioners share workflows and insights.

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