Episode 364AIContent StrategyPersonalization

Are You Marketing to the Wrong People?

Zach Presswood, Director of Advertiser Success at AdMarketplace, argues that the line for AI and personalization should be drawn the moment it stops feeling authentic — and shares a deeply personal story of how automated personalization sent baby congratulations emails after a tragic loss, illustrating why human judgment must remain the final filter. He recommends using AI for information management and data tasks while keeping humans in control of creative output and nuanced personalization.

Zach Presswood

Zach Presswood

Director of Advertiser Success at AdMarketplace

17 min

Key Takeaways

  • 1Draw the AI line at authenticity: the moment AI-driven personalization stops feeling authentic to the end user, you have gone too far — just because you can personalize does not mean you should
  • 295% of current business AI pilots are failing to break even according to an MIT study — the two key factors are having the right personnel to use the tools and applying them to the right business functions
  • 3AI excels at information management: data wrangling, analysis, and removing tedious repetitive tasks — these back-end applications succeed where creative and sales-facing applications fail
  • 4Personalization without human empathy can cause real harm: automated tools that scraped social media to send baby congratulations emails missed the context of a tragic loss, turning what should have been helpful into a brand-destroying moment
  • 5Use AI for seeds and iteration, not full-stack creative: come up with the core idea yourself, use AI to generate variations and accelerate brainstorming, but maintain control over both the original concept and the final output

About this episode

Challenges audience targeting assumptions and how to identify the right audience.

Topics covered

  • The ethics of AI-driven personalization
  • Where AI succeeds vs. fails in marketing applications
  • Human judgment as the final filter for AI output
  • The MIT study on AI pilot failure rates
  • Balancing automation efficiency with empathy

Notable quotes

Use technology as a way to take the things off your plate that you truly find frustrating or tedious and repetitive. That's where we know that these tools currently work really, really well.

Zach Presswood(10:55)

There are certain kinds of mistakes that AI or personalization tools or LLMs can make that a human just wouldn't, because of that additional layer of our lived experience and our knowledge of each other as human beings living in the world.

Zach Presswood(10:55)

Resources mentioned

  • Research

    MIT AI Pilot Study (August 2025)

    Study finding that 95% of current business AI pilots are failing to break even — with creative and sales applications showing the highest failure rates, while back-end operations and data processing show the most success

  • Framework

    The AI Authenticity Line

    Zach's principle: use AI for information management, data analysis, and removing tedious tasks, but keep human judgment in control of creative output and personalized communications — draw the line where it stops feeling authentic to the recipient

Zach Presswood (00:02) when it comes to unlocking their capabilities through AI, I encourage my team to think about technology almost in kind of a retro futurist mindset. Use technology as a way to take the things off your plate that you truly find frustrating or tedious and repetitive. That's where we know that these tools currently work really, really well, right? Ben Ard (00:48) Welcome back to another episode of content amplified today. joined by Zach. Zach, welcome to the show. Zach Presswood (00:53) Ben, thanks so much for having me. It's an absolute delight to be here and very excited about our discussion on deck today. Ben Ard (00:59) Yeah, Zach, I'm excited. This is a discussion that I think a lot of people throughout the country and world are having amongst themselves. And it's going to be fun to have this discussion on the podcast. But before we dive in, let's get to know you share with the audience a little bit about your background, work history and all that fun stuff. Zach Presswood (01:17) You bet. So my name is Zach Presswood and I currently work for a business called AdMarketplace, which is the largest vendor in the native search space. I'm the director of advertiser success there. In a prior lifetime, I actually specialized in Romantic Era Leader and Song Cycles, which is a vocal performance of music from 1850 to 1920. Turns out it's a little hard to pay the rent performing Romantic Era Leader. So I made the classic pivot in more of a tech marketing direction at the start of my career. And since then have been fortunate to spend about 12 or 13 years here in a few different dimensions of the technology and marketing space. Ben Ard (02:01) I love it. And I love the background. This is so cool. I'm excited for your insights. And like everyone right now, we're going to talk about AI, but specifically about personalization and the balance between AI driven creative and human judgment. This balancing act that we're all trying to figure out in your opinion, when you look at it, this idea of personalization. Zach Presswood (02:10) Let's do it. Ben Ard (02:26) kind of comes to the forefront and people are using AI to personalize things. Where do you feel like they should draw the line though? Where do you feel like the AI side really matters and maybe where they should say it's gone a little too Zach Presswood (02:41) It's a great question, and I think you're the nail on the head that this is something that all of us in this space, and especially marketers, are being forced to confront right now. There's an easy answer at a high level, which is that I think the line should exist when it stops feeling authentic, is the moment to stop using AI. Of course, the challenge is that actually tactically drawing that line becomes really, really difficult. ⁓ But ultimately, I think that that's the focus that we need to have as marketers is figuring out where is this a tool that's in service for us versus where are we maybe trying to force the usage of a tool when perhaps a more human centric approach might have been better. I think one analogy that I use with my team often is we recently converted a water fountain in an office of ours in a prior role where the water fountain used an iPad to get the water to flow. And if the iPad was disconnected from the internet, the water fountain didn't work. So as exciting as it was to have a touchscreen water fountain, I think that's a useful example here where just because something is maybe really new and exciting, it doesn't mean that we should forget about all of our traditional rules about things like authenticity and usability that still matter just as much now, if not even more so than before the AI revolution. Ben Ard (03:58) Okay, I love that analogy that's spot on. That's so cool. So Zach, for you in your day-to-day job and with your team, how are you practically finding that line? Because I do agree at a high level, as soon as you lose authenticity, you've lost. But in a day in and day out, how are you building that rigor? Where have you found it to be too much? Like how do you tactically apply that? Zach Presswood (04:21) Yeah, it's a great question. think that what my team has found is that when it comes to anything to do with information management, especially at scale, that's where AI is really a game changer. For me with my team, I'm in a position where I need to be helping them to improve their own skills, whether it's on a call with a client or in actually executing their work. But I can't necessarily be physically present with them 100 % of the time every day, both because it's not a great use of my time and because frankly, it would be suffocating to those team members to have me being that close to them. tools like, for example, ⁓ AI call tools, which allow you to not just create like transcripts and notes of your calls. but also provide more detailed insights. How many questions did you ask? Were you listening or speaking more? Was there a repartee with you and your audience? Those kinds of insights allow me to up-level my coaching and feedback for my team in a really dramatic way compared to before when I didn't necessarily have access to those tools. From a creative standpoint, I think that it's great when it comes to expanding on a seed that you initially plant as a human person. I don't typically recommend folks use AI for their full stack creative. I think that a savvy person, especially your digitally native millennial and Gen Z folks that are that really priority target audience for most marketers, there's a certain kind of a style that AI Gen creative has to it that those folks can pick up on really quickly. And it just kills your authenticity the moment folks pick up on that. So rather than using these tools to create AI wholesale, What I typically recommend is that folks come up with a couple of those seeds, whether it's a couple of examples of your copy pointers that you think are really strong, and use AI to help generate some variations, really as thought starters for yourself, more so than final products, so that you can accelerate kind of that middle editing and brainstorming phase faster than you might have otherwise, but you still hold the keys on both the actual root idea that's the most important factor, and also what ultimately hits the eyes and ears of your waiting audience. Ben Ard (06:30) Yeah, I love that. So there's probably people listening to this episode and I've talked to a lot of people in this, this kind of basket, like they're forced into a position where they agree with this sentiment, a hundred percent. Let me bring in that authenticity. Let me use AI to build in some efficiencies. Let's, let's kind of draw the line and be really happy about it. But then their boss is coming to him and saying, your budget's cut in half and you get half as many people because we have AI. Like, can it do everything for you? Any ideas to equip these individuals to go back to those decision makers above them to say, Hey, there is a line. Here's where we draw it. And here's why we need to be cautious. Any like tips or tricks that they could use. Zach Presswood (07:13) Yeah, absolutely. I think that one thing that comes to mind is if you're having one of those tough conversations with someone internally at your org who maybe doesn't see the same picture that you do is to bring in some third party insights where maybe there's not that emotion or bias attached to it. I thought there was a really interesting study that was just released by MIT on August 18th that speaks to this exact challenge. In that study, there was a pretty by grabbing data point that 95 % of the current business applications of AI pilots are failing, meaning they're failing to to break even or make money from a revenue perspective for those businesses. And when you dive into that data, what it revealed was that it really boils down to two key factors. One factor speaks to what you were just highlighting and it's having the right personnel to use the tool. What that study revealed is that folks who are a little bit younger or more digitally native are more able to make use of those tools than someone who maybe doesn't have that background. So simply walking up to your 45-year-old marketing executive or even someone like me in their late 30s and saying, here, take ChatGPT and replace your team, it's just not a recipe for success. The second thing that really stood out to me was more about the application of the tools. And what the study said was that when you attempted to use these things really in a sales or marketing and creative function, those were the pilots that were failing. But when you used it in a back end business capacity, think about streamlining your operations or removing outsourcing of certain business processes or kind of tedious, repetitive calculations. Those were the things that really took off. So I think there's a way to feed the instinct of our friends on the P &L side of the business who want to see those head counts under control. and say, yes, we definitely can use this, but use this kind of external academic data profile it's building as a way of shaping how it's used and saying, all right, maybe some of these functions that we need to replace, it's not so much our copy and creative minds as it is maybe some of these back end business operational things that we can alleviate using AI in the short term. Ben Ard (09:23) I love that. That makes perfect sense. So I want to double click on a couple of things you said there. So number one, I love that there is the statistic and I, almost everyone I've talked to in marketing has like pointed to this statistic and it's really cool. That is an opportunity. mean, this is a major university with a major study and I believe there were stock market implications from this study and all sorts of stuff that happened. It's, it's been everywhere. Yeah, it's insane. But I think for a lot of people, Zach Presswood (09:27) Let's do it. It was wild, wasn't it? Ben Ard (09:51) It rang true to say, know what? That's kind of my experience. There are tools that get it and there are tools that don't. And I think that people are starting to realize that this technology will follow probably, and none of us have a crystal ball, but it will probably follow the way of all technologies where there's a peak and a trough and then a settlement at the end. I think a lot of people thought, maybe because it's artificial intelligence, it's going to avoid all those historical trends and. Data is showing us that maybe that's not the case. So when you look at it, I also love that it's about the personnel. You talked about it's about the right personnel using it. I always have this fun analogy that if you don't know what the output should look like, you should not be using AI to try to get there. Because if you tell AI, hey, help me create something, but you don't have the vision for it in the first place, AI is not going to have your vision or creativity. So for you, do you still believe that you should have individuals who are basically still owning the output, running the AI, like how are you unlocking their capabilities through AI? And when are you specifically telling them not to use AI? Zach Presswood (10:55) Yeah, what a great question. I think that when it comes to unlocking their capabilities through AI, I encourage my team to think about technology almost in kind of a retro futurist mindset. Use technology as a way to take the things off your plate that you truly find frustrating or tedious and repetitive. That's where we know that these tools currently work really, really well, right? If you're trying to, for example, disseminate and distill a giant Excel file of audience data. And you're someone who's wrangling with VLOOKUPs. And you find yourself in Google saying, how does this VLOOKUP formula work? And you keep editing it, and it keeps giving you the error. And you're like, man, this is just not my bag. That's a place where you can tell a chat GPT, do this with the data, and you can get a really solid output in a snap. So I think that those kinds of things, drilling through figuring out what is it I need to do, what does my audience like, how can I make this data useful, those kinds of challenges can be almost erased with something like AI. I think where you need to keep the keys in your hands though are on some of these actual final outputs to what you're saying, and then some of these more nuanced personalization areas. There are certain kinds of mistakes that AI or personalization tools or LLMs can make that a human just wouldn't. because of that additional layer of our lived experience and our knowledge of each other as human beings living in the world. I'll share a personal anecdote of an experience that I had with personalization where I thought maybe a brand fell a little short here when it comes to checking those outputs. This is a personal story that I'm gonna share here. for the recording editing purposes, I don't know if we are in like a trigger warning zone or what here, but. My wife and I did have our first daughter in January. Unfortunately, she passed shortly after being born. was one of those thank you, you know, it was really difficult for my wife and I. was one of those things that is like a bolt out of the blue where the doctors are assuring us, you know, it's unlikely that it would happen again, but it happens to a larger percentage of the population than you'd expect. And what was interesting there is that my wife, who is a Ben Ard (12:45) I'm so sorry to hear that. Zach Presswood (13:03) very social media savvy person has typically posted about her life as part of her own personal creative business and her own brands. She posted throughout that experience both before and we were in the run up to having a kid and then in the aftermath as a way of not only processing our feelings about this, but also helping to make other folks feel that they weren't alone if they were in this kind of situation. So what was interesting here is that now we all have these AI tools and personalization tools that especially at a big data level, will scrape pieces of social media to try and generate creative. And what we found is that a very large number of especially maybe kids clothing retailers or baby resources started sending my wife and I emails saying, congratulations on the birth of your baby girl. Here's what you need in the first week. Here's what you need in the second week. And obviously that was really tough for us because that was something we'd been looking forward to, but wasn't actually relevant to us in the moment. And if this was more of a small business approach where someone was looking at the actual posts, what's interesting is that the data was all out there. There was data that tracks the whole journey of us and our parenthood journey and where things had gone well and where things had gone wrong. So it's not that the data wasn't out there. It's just that the way these tools are framed is to look for certain things. And perhaps in this case, it was just looking for folks who mentioned recent births. But there wasn't any look back element that was saying, But hey, maybe filter out if there's these other things that could have happened. So that's a scenario where for us, we're marketing professionals, so we understand these kinds of things happen. But if you don't have that context and you've had a tragedy like that in your life, that's the kind of thing that might turn you off of a brand forever. So I find that that example is helpful in this context because it shows that just because we can maybe pull in all this information, there's an aspect of also walking the line of, is this really appropriate? for my brands to be doing? Is this something that makes sense in a marketing context? If I was someone who didn't work in advertising and I was just having my morning coffee and reading the paper and maybe going to a barbecue on Labor Day weekend, is this the kind of thing that I would expect a brand to know about and engage with me with? So I think to spring this all back home to your ultimate original question here, where I think AI is driving a lot of value right now, is in cutting through all those tedious, repetitive tasks that have to do with information management. And where I think we still need that lens of human experience is on top of that creative layer, especially when it comes to trying to have these refined personalized outputs that connect your brands to people's personal human journey. Ben Ard (15:39) I love that. That's amazing. And thank you for sharing that story. I also, oddly enough, you know, I lost my youngest son actually about a month after he was born. So I, yeah. So I've been there before at a hundred percent. There's certain things. I love the analogy of how you're, well, not the analogy, but the experience of showing the advertisements, a human looking at that would never. Zach Presswood (15:49) I'm so sorry to hear that. Ben Ard (16:02) consider sending those kinds of emails and the immediate thought is ⁓ I Know this is a bot. This is not a brand that actually cares. It's it's them doing something at scale and ⁓ Yeah, there there is something special about human to human connection And I think that that is a great experience to rely on to say okay well how would I feel if I was in their shoes and how can I make that a special experience and Zach Presswood (16:14) Exactly. Ben Ard (16:30) If AI is not going to cut it, then AI is probably not the right solution for that. You know, even if it does take that extra time and effort. Zach, Zach, thank you for sharing all of this. This is amazing. We did run out of time. The episode we have to close so we can keep people getting back to their daily grind and everything they're doing. But if anyone who listened wants to reach out and connect with you online, how and where can they find you? Zach Presswood (16:36) Absolutely. If anyone who listened wants to reach out to me, I'm always welcome to take an email. You can reach me at ZacharyPresswood at gmail.com. I am also still on Twitter slash x. You can reach me there at ⁓ ZachPresswood. And then, yeah, would be very happy to field any additional questions. This is a topic that I'm passionate about. Or hey, even if you have good music recommendations, I'm happy to dip back into my previous life as well and just chat. good concerts with you too. always happy to connect with the people in this marketing space. I think you're exactly right. one of the most, tends to collect some of the most interesting folks. Ben Ard (17:30) Yeah, I love that. Anyone listening, if you want to connect with Zach, just scroll down to the show notes. We will link to everything right there. So you just have to click on Zach's name, go to his LinkedIn profile and connect with them there. Zach, thank you. Thank you. Thank you. I really do appreciate your time and insights today. Zach Presswood (17:46) Thanks so much, Ben. It was a pleasure connecting. And hey, have a great rest of your week.

About the guest

Zach Presswood

Zach Presswood

Director of Advertiser Success at AdMarketplace

Director of Advertiser Success at AdMarketplace, the largest vendor in the native search space. About 12-13 years in the technology and marketing space. Originally specialized in Romantic Era vocal performance before pivoting to tech marketing.

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Frequently Asked Questions

Zach Presswood says the line should be drawn the moment AI-driven personalization stops feeling authentic. He shares a personal story where automated tools scraped social media to send congratulatory baby emails after a tragic loss — illustrating how personalization without human empathy can destroy brand trust. If a person would never make that mistake, your AI should not either.

According to an MIT study Zach references, 95% of current business AI pilots are failing to break even. The two critical factors are personnel (younger, digitally native workers use AI tools more effectively) and application (back-end operations and data tasks succeed while creative and sales-facing applications show the highest failure rates).

Zach recommends AI for information management at scale: data wrangling, analysis, call transcription and coaching insights, and removing tedious repetitive tasks like complex spreadsheet formulas. He advises against using AI for full-stack creative or nuanced personalization, where human judgment and lived experience are still irreplaceable.

Zach suggests using third-party research like the MIT study to reframe the conversation. Show that AI pilots succeed in back-end operations but fail in creative functions, then redirect the cost-saving conversation toward operational tasks that AI handles well — rather than replacing the copy and creative minds that still drive marketing effectiveness.

Zach recommends using AI as a thought starter rather than a final product generator. Plant the creative seed yourself — a strong copy point or core idea — then use AI to generate variations and accelerate the brainstorming and editing phase. Keep human control over both the original concept and what ultimately reaches your audience.

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