Web3 CMO Stories

Train The AI To Recommend You – with Andy Crestodina | S6 E35

Joeri Billast Season 6

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AI is quietly rewriting the rules of marketing, not by “changing SEO” but by changing how buyers choose. When a chatbot can shortlist vendors in a single conversation, visibility is no longer the finish line. Recommendability is. I sit down with Andy Crestodina, co-founder and CMO of Orbit Media, to unpack what it takes to earn AI recommendations and what most brands are missing when they chase rankings without understanding the visitor.

We get practical about how AI search optimization is really the overlap of SEO and conversion rate optimization. Andy explains why prompts are longer and more personal than classic queries, how that extra context reveals real decision criteria, and why your website still matters because it is the place you control the depth, proof, and sales answers. We also dig into why AI-sourced visitors can be far more qualified, why traffic growth is a shaky North Star, and how to stop being silently excluded by publishing the questions prospects actually ask before they will take action.

Then we go deeper on content strategy in an era of infinite “average” content. Andy makes a clear case for the formats AI cannot truly replicate: thought leadership with a strong point of view and original research rooted in real data. We also talk prompt engineering maturity, from ad hoc prompts to reusable prompts to custom assistants and tools, and what separates the revenue accountable CMO from someone who just manages AI outputs.

This episode was recorded through a Descript call on August 3, 2026. Read the blog article and show notes here: https://webdrie.net/train-the-ai-to-recommend-you-with-andy-crestodina

If you care about B2B marketing, lead generation, buyer intent, and building a brand that gets chosen, this one will sharpen your playbook. Subscribe, share this with a marketer who needs it, and leave a review with your biggest takeaway.

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Welcome And The New Search Game

Andy Crestodina

Train the AI to recommend your brand. That's it. That's the game.

Joeri Billast

Hello everyone, and welcome to the Web3 CMO Stories Podcast. My name is Joeri Billast. I'm your podcast host. And today I'm excited to be joined by Andy. Hey Andy, how are you?

Andy Crestodina

Hello, I'm good, Joeri. Thanks for having me on the show.

Joeri Billast

I'm so excited, Andy. Guys, if you are now wondering who I'm speaking to, Andy Crestodina is my guest today. He's the co-founder and CMO of Orbit Media, an award-winning digital agency that has helped more than 1,000 businesses improve visibility and lead generation with 24, maybe already 25 years of experience across SEO analytics, content strategy, and visitor psychology. Andy is also the author of content chemistry and one of the most respective voices in B2B marketing. And today, in this episode, I would like to explore how AI is changing search, buyer behavior, and what it takes for brands to become not only visible but also recommended.

SEO Meets Visitor Psychology

Joeri Billast

Andy, as my listeners know, I like to dive straight in. I just mentioned all your experience in digital marketing. Which assumptions about visibility, content, and conversion do you believe AI is forcing us to question more seriously?

Andy Crestodina

AI is a huge challenge to the SEO who has for 24 years been focused on appearing in search, just visibility, just ranking, maybe traffic. But AI changes that completely because as sort of a layer on top of the internet that people use to get answers and recommendations and to shortlist options, it isn't just about visibility. And I love the little intro there because that is exactly my thinking. The gap between what an SEO knows and what they need to do next is to better understand the visitor. Because if you don't understand the visitor, you will never properly understand their prompts, their moment of truth, the story in their life, the reason why they're in this buyer journey. So I think that is the big that's the problem with search optimizers, claiming authority over AI search is that search optimizers are famous for having a gap when it comes to conversion optimization, empathy, visitor psychology, personas, and knowing the buyer.

Becoming Recommendable In AI Search

Joeri Billast

Yeah. And so you also argue that being visible in AI search, that's not enough. And that brands need to become recommendable. So what makes an AI confidently recommend one company over the other?

Andy Crestodina

It is 100% based upon the user's search or their query or how they prompt. When they go to an AI model and they start talking about, I'm looking for this or for that. I'll give you an example. Tomorrow I'm taking a trip to northern Michigan, a beautiful place here in the U.S. And if you imagine looking for that place, you're going to write a long prompt. You're gonna, I've got two kids and I'm looking for a rental, but just for a week. It's gotta be near a city, someplace where there's a nice restaurant because it's my wife's birthday. We need some space, a beach would be nice. Doesn't have to be Lake Michigan, maybe one of the smaller lakes. Okay, time out. The average prompt is 30, 40, 50 words. The average query is four words. So there's the difference. What's in the extra 35 words? It's a multi-parameter search. It is based on their story. It's all the things that are happening for them. So the adaptation is very simple. It's to apply conversion optimization thinking, answering real sales questions, going deeper into details, covering things that aren't keywords at all, and really just knowing your buyer. So evidence, proof, all of what persuades them, why wouldn't they take action? So my thesis lately is that AI search optimization is the overlap between search optimization and conversion rate optimization. And if you don't put all of those things into your content, AI is not going to recommend your, in that example, short-term rental in northern Michigan or whatever your service or product is. SEOs aren't famous for knowing their buyer extremely well. Conversion optimizers obsess over visitor psychology. So it's really the over I think it the people who are sort of both cheese and mousetrap marketers will win in this era.

Your Website As AI Training Data

Joeri Billast

I love that comparison now. As more of the buyer journey happens inside the AI conversation I just mentioned, how should marketers rethink the role of their websites in building trust, closing the gap between the recommendation and action?

Andy Crestodina

Well, it's definitely true that there's an overlap here between classic search optimization and AI search optimization because really there's on-page, on-site signals. You can train the AI by writing content and putting information on the internet about your offers and your brand. And off-site, are you in the directories? Are you in the places where they're researching? Are you in the sources that AI refers to when it answers questions in your category? So similar to Classic Search, there's on page and off-site. But the website itself is the place where the marketer has total control, unlimited time and space to go deep into the details. And something like 50% of AI citations come out of brand websites. So yes, you have to be present in all the places where AI is training on your category. But when it lands and looks, and we have research that shows AI visits home pages 15 times more than any other page. If your homepage doesn't answer basic sales questions, then you haven't even tried to retrain the AI to recommend your brand, which is now our goal. Train the AI to recommend your brand. That's it. That's the game.

Why AI Visitors Convert Faster

Joeri Billast

Yeah. You mentioned your research. I know I love that you always look into the research. You have a lot of data. Research also found, I think, that visitors from AI sources are three times more likely to become leads. So what does this reveal about how buyer intent and decision making are changing these days?

Andy Crestodina

It's confirmation of my hypothesis. So everyone who ever made a buying decision was first problem aware, then solution aware, and then brand aware. So the consideration stage in the middle of the funnel is when people are really exploring options. Now that happens in the model. Not always, but for many use cases and user types and verticals, people are doing that thinking in the model. Oh yeah, that place looks pretty good, but I was looking for a rental that has these other options. What about one with the pool? They're talking to the AI. So if that consideration stage happens there, by the time they land, they're much warmer. They're ready to go. They've already shortlisted you. They're not bouncing back and forth between Google and websites. The brand is partly qualified in their mind by the time they click. So that super high conversion rate from AI sources is, to me, simply validation that AI search optimization truly is the overlap of search and conversion.

Joeri Billast

Yeah. Now, AI may send brands less traffic, but better qualified. I see this also with my own clients as a fractional CMO so that there is less people visiting, but they stay longer on the website. So now a question to you is should marketers stop treating traffic growth as a primary measure of digital success?

Stop Measuring Success By Traffic

Andy Crestodina

100%. If you think of it this way, in the pre-AI era, all of our traffic was inflated by having our analytics filled with unqualified visitors. People who were not qualified for our brands had to visit to look around and see if it, you know, this is a good option for them. So it simply removes the inflated traffic levels that we all experienced for 20 years and filters it out. So the internet's more efficient now. The marketers can target their audience more specifically. The audience can qualify brands before they click. It's a better internet. I think so traffic is lower now. But another way to think of that is that traffic was artificially high before.

Answer Real Sales Questions Anywhere

Joeri Billast

Yeah, absolutely. And so if AI is effectively shortlisting companies before the buyers ever visit the websites, what information must brands make feasible to ensure that they are considered rather than silently excluded?

Andy Crestodina

Joeri, this is where there's a deficiency between the SEO mindset and the way the internet works now. The FAQ section. Makes sense. Answer people's questions. Whatever people need to know. That's why you have a page, that's why you have a visitor. But what SEOs sometimes do is they think that adding an FAQ itself is the job. Just paperclip this in at the bottom of the page and you know, job done. No. FAQs must answer real sales questions that people actually have before they're willing to take action. Right? It's like so I'm getting a place of this vacation I'm taking, I'm keep using as an example. Is the internet fast? Because I have to give a webinar. I won't book unless the internet's fast. The SEO would probably miss that detail because they're using tools and Google's People also AskBox and competitors' websites as the source for thinking about what questions to really ask. Instead, we should be listening directly to our prospects. A lot of people have this as recorded sales calls. If the short-term rental for this little vacation place has talked to many prospects and people seem to ask that question, they need to stop what they're doing, put that on their website, because that's likely another people's props. And without that, it will prevent the AI from recommending that that company, that option would people search. So FAQ is a great example of how marketers are a bit too lazy about it, yet it is the perfect opportunity for empathy, even if it's not an FAQ section, doesn't have to be in it. There's something magic about those letters, FAQ. Except the first letter, frequently asked, what do people frequently ask? Just put that in the flow, just build out the page, just explain that in detail. That's how you're going to win an AI search.

Joeri Billast

Yeah. I think on an earlier moment, someone said to me, you need to have an FAQ on every page of your website, or is that maybe a bit exaggerated?

Andy Crestodina

The goal isn't to have an FAQ on every page. The goal is to make sure your pages are answering the questions people really ask. It doesn't have to be a page block with expandable accordion areas with irrelevant questions. The job of the site is to train the internet to recommend your brand. So answer the questions wherever and however. Why would you put an FAQ on an about page? Are you answering sales questions there? Like that page is about your story, your values, your people, why you exist. You can answer those questions in a format that flows nicely for the human visitor. Yeah. There's no magic in adding an FAQ section, but there is deep and real power in making sure your pages answer all of the actual questions that people truly ask you.

Joeri Billast

Yeah. Yeah, it makes sense. You know, people are always looking for hacks, right? To to show up in the AI and then so on. Now I think you said somewhere, because I've been looking at you know, following you on LinkedIn and so on, marketers need to train AI to become a sales representative for their brands. But then I'm thinking where is the line between influencing an accurate recommendation and trying to manipulate the system?

Andy Crestodina

If you're manipulating the system, you may attract visitors who are not qualified. Is that what you want to do? You may drive traffic that never converts. Is that what we're here for? You may trigger citations that no one clicks. What good does that do you? Why are we here? I mean, what is the goal? If you're a full funnel marketer, you don't want unqualified leads in your pipeline. You don't want traffic that doesn't convert, do you? Not on your sales pages, maybe on your blog posts, right? Content marketing is one thing, but no. Why would we try to trick a robot into recommending us to people that don't need what we do? That's absurd.

Joeri Billast

Yeah. Yeah, it makes sense. But you and I know there are so many people that look at vanity metrics, right? As marketers, you know, so many impressions. I see it all the time. Let's talk about the content creation with AI. I'll talk about emitex.co that's now so easy to create content.

Content AI Cannot Truly Create

Joeri Billast

And AI makes average content almost effortless to produce. So I'm wondering what will distinguish content that generally earns attention, trust, and authority.

Andy Crestodina

I've been thinking about this all weekend because I'm a content marketer and I have an article too. Today I had to ship it. And the topic of the article is there are two things that AI cannot make. And I make a strong case that there's really just two formats that are human-only formats for content. One of them is thought leadership. Most of the sentences we've spoken so far on this show, AI could never write. I am taking a stand. I'm drawing a line to the sand, I'm saying that's right, that's wrong. AI never does that. It's an averager. AI joke should stand for average information. It beautifully summarizes the internet and it tries to be correct. It doesn't ever state strong opinions because it has no worldview. It has no perspective. It has no experiences. Everything I've said so far today are things that I've said based on my views and experience as 25 years in digital. The other format for content that AI can't make is new original research and studies. And you mentioned one of these already. To find out what the conversion rate was from AI traffic sources, I had to extract, using AI actually to write the code, extract data out of 97 Google Analytics accounts. I had to manually tag the types of conversions as high or low intent. It was almost 20 hours of research. AI can't make that. It doesn't have access to those analytics accounts. You can find correlations after you export. But so new original research surveys, data from inside your own business. You know, a lot of people are sitting on piles of data but never use it for in their content program. So yes, strong opinion and original research. Those are the two formats for content that are forever, they were always effective, but they are forever differentiated from AI.

Joeri Billast

Yeah, it makes a lot of sense. Actually, I have the podcast, of course. I have a lot of conversations like the one we're having today, asking questions. So I have often strong opinions from people like you. And that's how I wrote my book, The Future CMO, based on what everyone said and try to make sense of that. This gives me a world through, right? By talking to all those. Like I said, I've been checking out your content. You said you are a content marketer, and I think recently you described the evolution from ad hoc prompts to reusable prompts and AI assistance. So, how can marketers determine which part of their expertise should be automated and which

From Prompts To Assistants To Tools

Joeri Billast

should actually remain deeply human?

Andy Crestodina

I think that the people who write the best prompts and who make the best assistance and who create the best AI tools are subject matter experts. We should all be using AI for the things that we're very good at and experienced with. If you're telling yourself, I don't need AI for that because I'm already a pro at that format or topic or channel, and then you're gonna miss opportunities, you are probably the best person to write a high-performing prompt or to build an extremely useful assistant or to vibe code a powerful tool. So, first of all, yes, we should be using AI for the things that we're expert at. But the trick is to break through this and get to that tipping point where your mindset changes from I'm writing ad hoc prompts to I'm creating reusable, tested, shareable prompts to I combine these prompts into an assistant that's a custom GPT or a Cloud Project or a Gemini Gem or a copilot agent. And then finally, I'm building an actual tool that runs on my in my browser, if not on the internet, that has a user experience and goes through a multi-step process and it just saves data and can go grab things from the web. If you don't think that you have the skills to build a tool using a open AIS codex or clawed code, if you think that sounds hard, you just haven't tried it yet. Anyone who has tried this is alarmed by how empowering it is. Anyone can build things now. I'm not technical at all, and I could show you tools I've built that have incredible utility. But I think I had an advantage because some of these are like in my deepest areas of expertise.

Joeri Billast

Yeah. And you also have data, probably have systems to feed the AI and to give the AI the right context, right? Before you start building that with codecs and others. Totally agree with you. It's so easy these days. And uh, you know, now even like to build a website. Now I log in on ChatGPT, it already says create a new website, right? So it will go so easy. Now I mentioned my book at a future CMO. I explore how marketing leaders become orchestrators

The Revenue Accountable CMO Mindset

Joeri Billast

across technology, data, creativity, and trust. And so, what capabilities for you will separate the most valuable CMOs from those who are just managing AI tools?

Andy Crestodina

Well, the difference between the good and the great CMOs is the bottom line performance, accountability, and strategy. So there are a lot of marketers still who are focused on a channel. We need to be more active on LinkedIn or YouTube, or they're focused on a format. We need to launch a podcast or have a webinar. And I've gone through that era myself, and I fully understand that level of thinking. But the ones who will perform the best and come through the end of this transformation on top are the ones who can connect all the dots from the topic and the channel and the frequency and the formats all the way through the funnel down to the impact in the business. They focus on the CRM. Right? Are we getting qualified leads? Which of these types of leads is converting into a deal? Which of these deals has the highest lifetime value of customer? Those aren't really always the perspective of CMOs. So I think that the revenue accountable CMO is the future of our category. If you want to be a marketing leader, how do you get there unless your goals are 100% aligned with business outcomes? It should be obvious.

Joeri Billast

Yeah, that's actually also one of the premises of the book. There needs to be a business outcome. And that's why even Philip Kotler liked it, because these days they're all the CMO. Yeah, that's one of the things I you know, what made the book also special, right? You know, Andy, um yeah, and if I just may say this, it's you know when you create something and you write something, you know, you're never sure, you know, will people like it? You know, but I had all these podcast conversations, and then I sent it to Philip Kotler, and I also mentioned this in my TEDx talk. And I just asked, you know, can you can you give a review of my book? And he didn't directly answer, and then because I sent him a summary, right? And then he said, Yes, but I'm waiting for your manuscript. And so he really read it, and he said it was the best thing he ever read about CMOs, so I'm really proud about that. You're right.

Andy Crestodina

That's an example of human of human-based marketing as well. Right? That was you know the name, you respect the personal brand, you reached out in a sensitive way, you got a human response. My book had a similar experience. You mentioned it, content chemistry. Yeah. My hero in digital is one of my oldest. I'm a big fan of Jay Bear. And so when I sent him this book, he sent back a quote. I put it on the cover. The most practical book ever written about modern digital marketing. That to me was a career highlight to get that feedback from Jay Bear. Um, I think one of the greats. Yeah.

Joeri Billast

That's also a name I want to get on my podcast because you know, now I have you. I had a common friend Mark Schaefer, Joe Poinzi, I had Philip Kotler was also on the podcast, by the way. And I had people like Chris Dot too, and I had also Gary V on the show. You know, Gary is very, very busy, also strong opinions. But because, you know, I had the Philipp Kotler story, you know, I got him on. So we also talked about AI and some of the topics that you mentioned, but then of course, from his perspective, you know what a book can bring, and they you know, it's something you work on and it creates so many opportunities.

Andy Crestodina

And again, different from AI. These are relationships, AI has zero friends, these are people with personal brands, AI has no name. Not really. Everything that we're doing now and that we're discussing are things that are literally impossible for a model to do, right? It doesn't put anything in quotations. You can't quote AI. So, yeah, it's strange to me that marketers keep grumbling and asking themselves, like, how can I differentiate my content from AI? If you're even asking that question, you're probably not publishing anything that should be published. If AI can write it, don't publish it. Doesn't make sense.

Joeri Billast

Yeah, indeed. And actually, it's good. And now that you are talking about it, it was one of the things I mentioned in my TEDx talk. So, guys, if you're not listening, check it out because some of the things that Andy just mentioned, I spoke about that. That of course, the book, that it was not AI who created that review or the testimonial, but it was the person, brand, and the relationships. Now, Andy, a lot of marketers are very busy, of course, in my conversations with people.

High Leverage Marketing When Busy

Joeri Billast

One of the challenges is that they need to decide what deserves human attention. When AI can, of course, do a lot of work and a lot can a lot of accelerating. How should resource-constrained marketers identify their highest leverage work?

Andy Crestodina

Well, I have a point of view on this. I think that performance-based marketers should go backwards from the end of the user's experience, from the end of the buyer journey. So let's say of all the things I can do today, one of them is make a video for LinkedIn. And one of them is check the performance of my calls to action. If one of those things might create some brand awareness, but the other one might identify a gap in the percentage of visitors who click to take action on the page. If I can improve the click-through rate on my call to action, that is worth one billion times more to my company and demand generation than another LinkedIn video. So I think that the question of prioritization gets forced if you simply consider like, what if I only had one hour to do marketing this month or one day, and my income is going to be totally based on my ability to create qualified leads? What would you do if you had one day only and your job was to create qualified leads? You would absolutely focus on the end of the user's experience. You'd go to the end of the buyer journey and work backwards from the contact page to the calls to action to the service page to the home page, you know. And content would be one of the last things you'd probably consider. So yeah, I think it's a lot of the AI can't make, it can't analyze your data, it can't look up your click-through rate. It can help you certainly identify gaps on your key performance pages. For that, I always develop personas first. For conversion optimization, I'm very, very focused on generating and testing and improving with sales call transcripts via personas because that uh is a wonderful tool for finding gaps on pages and unanswered questions.

Joeri Billast

Yeah, I think that's a really good tip to do that, to use AI in that way and not just giving it simple prompts. Now, Andy, let's look a couple of years ahead. I know it's difficult, but let's look five years ahead. What

Building Trust For The Next Five Years

Joeri Billast

do you believe that marketers or entrepreneurs should start building today to remain visible, trusted, and I would say chosen in an AI world?

Andy Crestodina

Well, first we should continue to build our brands because a top-of-mind brand circumvents all of the digital channels. I was recently shopping for a gift, and I went directly to that site that I knew I wanted to go to and started on their homepage and found what I wanted. So brands don't become less powerful in this era, not at all. And everyone that has a strong brand with good reputation and has some word-of-mouth marketing or top-of-mind awareness, they don't have to worry about disruption because they're already a big brand. For the rest of us, I think that we need to analyze where AI trains at our verticals. I have a fancy way of doing this where I run a whole run of synthetic prompts to analyze the sources that AI referred to to respond. Those are the places where you need to be present. We need to prioritize the formats that AI just can't create. Webinars, videos, podcasts, live events, building a community offline, conference presentations. There's lots of things AI just can't do. They're too human. But I think the digging into the connection between marketing and sales will make you safe. Understanding deeply your buyer will make you safe. Staying very focused on your CRMs, data, and metrics will make you safe. Keep training the AI to recommend you. But stay focused on the bottom line, stay focused on brand building, and prioritize the formats and topics that AI could never make.

Joeri Billast

And I think it's a really powerful message for people at the end of this podcast episode. We could talk for hours, I guess,

Where To Follow Andy And Final Ask

Joeri Billast

Andy. But if people, you know, they want to follow your work, they want to know more about you, where would you like me to send them?

Andy Crestodina

Well, people with underperforming lead generation programs, websites, visibility and recommendations can find us at orbitmedia.com. We build and optimize high-performing B2B lead gen websites. But my content program these days is mostly found on LinkedIn. So Andy Crestadina, if you find me there. I get a lot of noise on LinkedIn. So you can skip, but if you heard this show, I want to invite you to skip the blue button which says follow. Click the dots and find the connect button and just say that Joeri and I connected us and we'll we can chat there. But yeah, I have a LinkedIn newsletter. It's millions of readers a year. I've been a content marketer for a very long time, and I love teaching and sharing and conversations like this. So grateful for the opportunity.

Joeri Billast

Thank you, Andy. And I can say that Andy has really fresh content on LinkedIn on the newsletters. So be sure to follow him or to connect with him if you listened to the show. As always, there are show notes, so Andy profile and other data will be found there. Andy, it was really a pleasure to have you on the show today.

Andy Crestodina

Thank you for having me. This was great. I feel like we hit so many notes anytime.

Joeri Billast

Absolutely. Guys, what a brilliant episode! So I'm sure that you have people around you that also could benefit from this episode. So be sure to send him the podcast link. If you're not yet following the show, well, this is a really good moment to hit the subscribe button. If you haven't given me a review yet, if you give me these five stars, this really goes a long way. And of course, I would love to see you back next time. Take care. Thank you. A special thanks as well to Rio, the main sponsor of Feb3CMO Stories. Support the conversations at the intersection of Feb3 AI and the future of digital leadership.