The MarTech Matrix · 2026-07-05 · 42 min
Key moments - from our scoring
Substance score
66 / 100
Five dimensions, 20 points each
Chris Seahorn spent 25 years in digital marketing at companies like eBags, MapQuest, and Naked Wines before launching Boundless Digital, a fractional CMO agency two years ago. Drawing from his unique vantage point of evaluating tech stacks across multiple clients simultaneously, he identifies critical mistakes vendors make when selling to marketers. The core issue: overselling. Vendors deliver generic, feature-heavy pitches when they should be personalizing around specific business problems. Seahorn emphasizes that vendors who research a prospect's actual challenges, reference them in outreach, and tailor demos to two or three high-impact capabilities (rather than 20) dramatically outperform batch-and-blast approaches. He walks through his own buying process - how he evaluates measurement foundations, team capabilities, and tech stack gaps - and reveals his consistent quick-win strategy: conversion rate optimization, where even small 5% improvements per page compound to 25-30% overall lift. For fractional CMOs and in-house marketers, the episode cuts through vendor noise by explaining what separates a compelling demo from a waste of time: preparation, specificity, and genuine problem-solving rather than capability broadcasting.
Use the StoryBrand framework: position yourself as the guide, not the hero. Research the company, identify 3-4 specific problems they're facing, and propose a personalized plan with clear outcomes and timeline, rather than generic capability pitches.
Conversion rate optimization - targeting 5% improvements across key pages (homepage, product detail, cart, checkout) compounds to 25-30% overall lift without requiring new tools or major spend, and directly reduces customer acquisition cost.
Email and SMS workflows are typically set-and-forget with poor segmentation, lifecycle sequencing, and seasonal adaptation; cleaning these up in platforms like Klaviyo or Attentive generates fast, measurable revenue lifts.
Start by auditing measurement foundation and implementation - most clients have tools but don't use them correctly; fix that first, then layer in gaps in email/SMS, A/B testing, and conversion optimization before replacing platforms.
Ask pre-demo discovery questions to a key stakeholder, understand the specific problems the company is trying to solve, and tailor the presentation to 2-3 relevant capabilities with real use cases rather than running a boilerplate deck.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers solid, actionable insights for B2B operators evaluating marketing tech and vendors. Chris covers personalization in outreach, structuring demos, conversion rate optimization tactics, and vendor selection frameworks with specificity. However, much of the content treads familiar ground (personalize messaging, focus on customer problems, measure success) and spends considerable time on soft advice rather than novel frameworks or counterintuitive findings.
take the time to personalize it, but also take a time to step out of your own shoes a little bit and try to understand it from the lens of whatever client you have
the biggest thing. The biggest um, area of uh, opportunity is time management and it can become very cumbersome to like start doing the RFPs and finding all the vendors
The core advice - personalize outreach, don't oversell, focus on customer problems, measure success - is standard vendor best practices. Chris applies these competently to the fractional CMO context and offers some useful specificity on conversion rate levers (messaging clarity, landing page alignment, checkout friction), but the underlying frameworks lack contrarian edge or first-principles rethinking. The tire store checkout anecdote is a solid concrete example but doesn't represent novel thinking.
this product is going to save the world and it's the best thing that ever happened, but they're too close to it
Visual people process visuals and images 10 times faster than reading text
Chris Seahorn is a credible practitioner with 25+ years in digital marketing across scaling companies (eBags, MapQuest, Naked Wines) and now operates a fractional CMO agency advising multiple clients across categories. He speaks from repeated exposure to common vendor mistakes and implementation failures, which is more valuable than pure consulting theory. His background is directly relevant and his current role gives him real-time cross-company perspective, though he is not a founder or operator of a major enterprise.
co founder of Boundless Digital, a fractional CMO agency he started two years ago after 25 years running digital marketing at companies like ebags, MapQuest and Naked Wines
he walks into multiple companies at a time, evaluates their tech stacks and figures out what's broken fast
Chris offers concrete examples (eBags, Naked Wines, Garden, Klaviyo, Attentive, Blurbs, Claude) and specific metrics (5% per-page improvement targeting 25-30% conversion lift, $40+ AOV threshold for decision fatigue). However, he largely avoids hard numbers on implementation outcomes, pricing comparisons, or detailed case results. The tire checkout story is vivid but remains anecdotal. Many claims remain illustrative rather than evidence-backed.
I shoot for trying to have like a 5% improvement on key pages. Whether it's like homepage to product detail, page to cart. Because if you're trying to shoot for a 50% improvement on one page, it's a lot more difficult than just a 5% here and there. But by the time you get through checkout that's a pretty significant. That can be a 25 to 30% lift in conversion rate
a 25% improvement in your conversion rate, can they do 25% lower ROAS?
The host (Sean) asks logical follow-ups and probes specific areas (vendor reach-out, demo structure, tech stack decisions, behavioral changes), but rarely pushes back on claims or requests evidence. When Chris makes assertions (e.g., "visual people process visuals 10 times faster"), Sean accepts and pivots. The tire anecdote opens a door for deeper UX discussion but the conversation stays at a comfortable level of agreement. Questions are competent but lack sharpness and challenge.
Yeah. So in your role as a fractional cmo, you're sort of a layer in between the vendor and the client, right.
So conversion rate's an interesting one right? Because it isn't like oh I need a new ESP or I need a new this or new that.
Computed from the transcript - who did the talking, and the words that came up most.
Most vendor outreach fails before it's even opened. And most demos lose the deal before the second slide. In this episode of The Human Side of MarTech, Sean Simon sits down with Chris Seahorn, Co-founder of Boundless Digital - a fractional CMO agency he started two years ago with a longtime colleague after 25+ years in digital marketing at companies like eBags, MapQuest, Naked Wines, and others. Chris evaluates MarTech stacks across multiple clients simultaneously. He has an unusual vantage point: he sees what vendors do well, what kills deals, and what separates implementations that stick from ones that quietly die at renewal time.
Transcribed and scored by The B2B Podcast Index.
Speaker A: You are very close to your product. But, uh, remember that your, your client and your, your prospects, it's new to them and they're hearing it from five other people. Take the time to personalize it, but also take a time to step out of your own shoes a little bit and try to understand it from the lens of whatever client you have. And I, I see this a lot where it's like I, they know the product and they're like, this product is going to save the world and it's the best thing that ever happened. But they're too close to it. They need to take a step back and say, this is how people are going to perceive it. This is how they're going to evaluate it against other competitors. And these are the ways that I need to make sure that I have a better solution that is going to get them over that first hump.
Speaker B: Down with Chris Seahorn, co founder of Boundless Digital, a fractional CMO agency he started two years ago after 25 years running digital marketing at companies like ebags, MapQuest and Naked Wines. Chris has a perspective most people don't. He walks into multiple companies at a time, evaluates their tech stacks and figures out what's broken fast. So when he talks about what vendors get wrong, he's not guessing, seeing the same mistakes play out hundreds of times from the buyer's seat. And in this conversation we get into what actually gets a vendor meeting, why most demos lose the deal before the second slide, and why conversion rate is almost, almost always the fastest path to, um, proving value in a new engagement. There's also a tire store story that I think every E commerce brand needs to hear. Let's get into it.
Speaker A: Good. Sean, thanks for having me on.
Speaker B: All right.
Speaker A: Yeah, I've been really passionate about marketing for over 25 years. Um, I'll say I started my career back in like 99. I, um, joined a company called Ebags, where, um, eventually I went on to lead their global marketing business and then took some time away and did a few startups along the way, worked for some big companies. I'm going to date myself, but even like back to like MapQuest in like 2006 and then, and uh, a couple other startups along the way. And after, uh, a couple years, um, I went back to Ebags and I really am the type of marketer that loves, uh, building things. I love just seeing this digital space and how everything is fairly measurable. And when you put in a longer day, you can typically see what those efforts will pay out for in Terms of uh, roas and efficiency. So I've always been driven by this digital marketing space and creating things and seeing uh, uh, my efforts paying off. Uh, I uh, ended up going on after Ebags was bought out by Samsonite back in like 2017. I went to work for Naked Wines and another company called Garden. And I decided that even though I love marketing and being at this cmo, uh, level, I was spending a lot of time in strategy meetings and personal development, uh, and people management more so than actually doing the marketing which I love so much that I decided about two years ago that I really wanted to start my own fractional CMO consulting, uh, agency and uh, did that with a partner that I've worked with for 15 years and in a couple different companies and her and I started this company called Boundless. And it's been great. We love uh, now taking our experience and our expertise um, to a lot of companies that may not have the funds to uh, uh, have a full time cmo, but can use a couple hours of both of our time and create things and grow and solve problems and it's been great.
Speaker C: Things not get bored. Okay. This show is about the human side of Martech. Right? Um, we are immersed in a lot of different technologies and AI is just the tip of the iceberg. Right. There's just so many solutions out there, by some counts 20,000. So it's easy for people to get lost in the shuffle. Right. So um, today I wanted to ask you some, you know, some of your experiences around engaging with, with vendors and what you look for in solutions in companies when you're considering working with them. Right. So um, when a, when a vendor reaches out to you, right, and we all get, we all get outreach, what can, like what indicates to you that they actually understand the world that you're in, the business that you're working in, um, the needs that you have.
Speaker A: Yeah, I think, I think the first thing that I'll say is that um, in the world of uh, being able to find everyone's contact information, reach out on LinkedIn, getting inundated with emails if you're in a sales role, it's really tough for someone that is looking even for your services to be able to really go through all the clutter and all the outreach that we're receiving every single day. And it gets to a point that even if you do want to respond, um, or even if I want to respond, it goes into this, this back and forth where it just takes up so much time. And one of the things that I have found that is really successful, not even in my own outreach is, uh, there's a branding book that I, that I really like, and I've actually just leaned into it for a lot of parts of my marketing. And I also think this works a lot for sales teams, but it's called building a story brand. And the basis of this concept is that in all things marketing, you have a protagonist, which is your consumer. Uh, and then you inherently are, uh, they have a problem they're trying to overcome, and you inherently are this guide that is helping them to solve and overcome this problem. And a lot of times what happens, like in a sales role, it's like, do you need to, um, grow sales while improving your marketing efficiency? I have the perfect tool for that. Well, everybody has that. Like, it's, it's so cookie cutter that it doesn't resonate or it stand stands out in the way that it needs. But if someone said, hey, Chris, I see that you either work at this company and based on just a little bit of research, these are the four things that I think we can overcome. And so they gave me, they become the guide and then they gave me a plan for what success looks like and then a, uh, time frame and an idea of what that's going to resonate with. So it becomes, it's not a lot of work, but it becomes a lot more personalized and it resonates a lot more than 99% of the emails that I'm getting that I can tell are just like the batch and blast or, uh, very, just, very, just generic. And that's not going to get through kind of my first filter, even if I do need that, that type of a product. So my first thing is find the clients that you really want to work with and do just a little bit of due diligence to personalize the message to a problem that, you know, they're trying to solve. And I think, the other thing that I think is kind of interesting is salespeople are getting really creative and there's a little bit of a creep factor where they're doing research and they're finding the name of my dog. They know vacations that I've been like, things that I don't post publicly and then they'll want to talk about it. And it's not things I'm putting on LinkedIn. So I'm like, you guys are doing research that's creeping me out, but I would rather you do the research on the company issues and spend a little bit of time. But I Think the disconnect is sometimes salespeople are sort of. They have a script, they have a boilerplate deck, and it's like what they present. And it's kind of the same for a lot, uh, their outreach, when really what we're looking for is personalized communications that are trying to solve a problem that is real.
Speaker C: Yeah, I mean, I totally hear you. It's a theme we hear a lot. Um, it's still easier said than done, I think. Um, it starts with the subject line. Right. Or actually, I would say it's even before that. It starts with Google Gmail filters or whatever email filters you have on your computer.
Speaker A: Right.
Speaker C: How do you break through those so that you can even get into the inbox to be considered? Am I going to open it or not? Um, so there's a lot of technical issues to get there. Um, but I hear you. I mean, you got to do your homework. So, you know, when someone does open the email, even if it's only 30% of the time, um, you're making. You're making an impression. Um, so when you. Let's fast forward that conversation so you agree to take the meeting with someone. Um, what separates sort of, um, you know, a good vendor call to a bad vendor call. Like, what are you looking for? Ah, initial meeting really set the tone of the relationship.
Speaker A: Yeah, I think once you have your foot in the door, this is. This is a really important time to shine. And, uh, I applaud anyone that has that first foot in the door. And what I would say is that's where what I find is a, like separates the good from bad is when, uh, it's a presentation that is just like throwing the entire kitchen sink. And I, I think it's okay to say this is the capabilities of my product and this is what we can do. But if you don't sort of refine it, uh, just a little bit to say this is based on what I'm seeing and some of the things I found, these would be. Even though we can do these 20 things in my presentation, I'm going to focus on these top three, and then I'm going to show you some of the capabilities of those. And if they're interested, you can dive into it. But what I see is, is. And I, And I see this a lot with. Representing a lot of different clients now is that they glaze over and they see, like, if there's so much information, it's like analysis paralysis. And everyone's kind of saying the same, and we feel like we're we're kind of cutting through the BS and saying, okay, what does sales speak versus what is this thing actually able to do? And the other key thing is really detailed. It doesn't have to be in the first demo, but a follow up with use cases and detail summaries is important because at face value, everyone can create a beautiful deck, everyone can, uh, make their product look amazing. But when it really comes down to the use cases and the step by step of how this is going to work, that's really what we want to see. And getting through that without having a two hour meeting or really significant onboarding is important because time is money and we're all trying to move pretty fast. So what I would say is it goes back to personalization, but it also goes back to trying not to speak so high level and throwing the entire kitchen sink to really kind of focus on a couple things that are really going to matter and be very specific about those things.
Speaker C: Yeah. So in your role as a fractional cmo, you're sort of a layer in between the vendor and the client, right. So, um, um, and personalizing that presentation for you as that sort of fractional person is different than personalizing it for the client.
Speaker B: Right?
Speaker C: Because you're looking over two or three different clients at the same time. Um, and that changes, you know, every so often. Do you, do you ever work with the vendors to say, look, before we get on the call with my client, I want to give you some information to help you focus your conversation with the client to make sure that it's a good use of time. Do you, do you have those kinds of talks?
Speaker A: Yeah. I think just for me is I don't want the vendor to be pitching me as an agency. I want to like the way that I look at it is I'm an extension of the teams of the companies that I'm at, so I'm an extension of their marketing team and I'm evaluating their tech stack and their solutions, um, as if I was a full time employee, a full time CMO for that company. So looking at it that way, I have them pitching the specific company and I will, I think it's really important that um, the vendor, before they get in front of my client, I try to really make sure that the vendor understands what my client is looking to see in the problems that we have. And so this is, this is a part that even before the uh, the demo, knowing what the requirements are and having a little back and forth with like a decision maker or a key stakeholder in the company is good because before I want this vendor to represent, I want them to have a, like a professional good experience. And if I'm opening the door to my clients, I want the presentation to be good. And so I also know that I don't want to waste anybody's time. And even if I wasn't a fractional CMO and I was uh, at ah, uh, any of my other companies, I don't want to waste my tech time, my employees time, my boss's time. So I'm going to take just enough time to make sure that this demo that's being presented is going to be as good of a presentation and resonate with the audience than to just have a boilerplate where everyone walks away and says, why did I just waste an hour of my time? So I think it is important that you ask questions as a salesperson, uh, ahead of time to a key stakeholder and that helps you to personalize the demo. And there's been even some recent use cases where there was a, uh, demo that was scheduled. There was a demo that was scheduled with one of my clients last Wednesday. And I talked to the person and said this is exactly what they need. And she asked, will you give me another week? Because I don't, based on what you're saying, I don't want to walk in and fumble this one. I want to make my um, really, really matter. And so we're going to do it, uh, tomorrow instead. And postponing it a week was fine for this client and it gave her enough time to really make it a much more impactful presentation because, like, I can assure you, if it, she didn't do that, it probably wouldn't have had a second meeting. So it's, it's important to take that time and make sure it's, it's going to resonate with the problems that this client is supposed to solve.
Speaker C: That's, that's good, that's good advice. And if the person can't give you the time or there isn't enough time, even just an email with some questions. Right. Or a form with questions just to get some color on what is top of mind for that client. Okay, so in a fractional role, which is, you know, not that it's new, but it's becoming more popular, um, and you're walking into different companies on a somewhat regular basis for the first time, trying to understand what, um, it is they need from you. Right. Or what it is you can help with. So when you step into those businesses, um, what is the first thing you're trying to understand so that you can figure out, okay, this is what I, this is what I need to be doing here.
Speaker A: Yeah, it's uh, there's different use cases. Like some will come to me and say, I have a very specific problem that I want you to look into. Whether it's conversion rate optimization, uh, looking at why our meta, uh, campaigns or overall marketing mix isn't delivering what we're expected to do. Like, there's, there's usually like a use case. But I will say that a lot of times what will happen is, is they're like, we, we just don't have a, a, we're growing, but we've stalled out a little bit and we don't have someone that knows digital marketing, uh, that has the experience. We've had some really good people and some great employees, but we don't have just the background knowledge. So we want you to come in and, and really just open the hood and complement, um, our team and, and be a team member with them. And so what I, what I will do in that case is, is I, even before I will um, start charging anything or any like, even come on board, I actually do like a first assessment. And what's important for me on this one is I want to make sure that what I can do is something that is going to have measurable results in that the client is going to look back and be like, wow, I'm so happy that we brought Chris on board. And like my contracts, I go monthly. So it's, it's, I don't want to lock anyone into a yearly contract, but typically what I do is come up with a couple projects right away that I know are going to be wins by looking at their Google Analytics, their Shopify data, their triple Whale or North Beam, getting into their metas and Googles. And uh, for me personally it's like I'd rather do that than, uh, jump into something and then use my time and like, and it doesn't take me a lot just to do a first assessment. I can come up with a couple things pretty quickly and tends to be honestly very similar problems, um, with efficiencies and marketing that I can, I can know right out of the gate there'll be a couple wins. But what I would say is, is the first thing is really to look at the data and understand it and then I come back and say this is what I think it's going to cost and this is the time it's going to take. And we work through the details of that and then the reality is what happens is there's always something that's next. So you get through those two and then another thing comes and then the, just keeps every months kind um, of moving on to something else and making progress along the way.
Speaker C: Yeah. So I know a lot of people have their favorite solutions in a particular category but when you walk into a new, new client, how do you decide? Should I optimize the tech stack or you know, in terms of like okay, they have some partners in place, we're just going to get them working better or um, there's one or two that need to be removed and another one added in. How do you, do you have a process for that or um, are you letting the client drive that conversation?
Speaker A: Yeah. So the, the first thing that is core to any company is, is measurement. Like well how are you guys looking at your data and how do you define success and what you're trying to achieve and what are the tools that help you do that? And a lot of times what I find is that a lot of clients will have the tools but they don't either have them implemented correctly or they um, are not looking at them in a way that actually can action the business in, in a material way. So the first thing that I kind of do is I make sure that the measurement tools are going to set the standard of the foundation of how we're going to judge the business and move forward. Uh, I also look at the team and to understand sort of where are existing resources that we can really lean into and how do we may have to augment it. Like where do I have to come in and roll up my sleeves and really get into it versus where do you want me to be a mentor and kind of just uh, give a little bit more guidance to teams that you already have there and areas that we can improve. And then when it comes to tech stacks, um, really making sure they have fundamentals covered. They have the fundamentals in um, anything they need in related relation to uh, uh, like email marketing for instance email and SMS and customer lifecycle cycle management. I also look at anything that can help with conversion rate optimization and a B testing platforms to help become much more um, data focused on uh, their measurement approaches. There's a lot of subjectivity in design and UX and making sure that there's a testing mentality and there's, there's sources to do so. And then what I find is there's a lot of other sources that can be specific to various industries but really help with conversion rate um improvements or it could help with expense to new medias, new markets, new top of funnel. Uh, it kind of just depends on the client from there. And then I go out there and I try to find solutions that uh, will do that. Now, now saying that I think the tough part is as soon as you start reaching out it just becomes the biggest thing. The biggest um, area of uh, opportunity is time management and it can become very cumbersome to like start doing the RFPs and finding all the vendors and having to do all the outreach that finding sort of the right solution for certain um, areas of improvement, whether it's conversion rate or it's a B testing like this is the process that there's a lot that are out there and narrowing it down to the very best and getting the pricing and getting the exact, is where a lot of time happens today and finding ways to make that more efficient. Um, there are things, Blurbs is a great example. I've been using Claude a lot to help me delineate and find and narrow down exactly what I'm looking for. Uh, so I'm glad to see there, there are things that are happening and improvements that are happening. Uh, and referrals is another great way to find vendors but that's really how I approach it at this point.
Speaker C: Yeah, no, it's a really good point. I think I would just caveat all that by saying um, that if you're, if you're looking for a solution, referrals are a great resource but also understand um, what the problem was they were trying to solve for and what their tech stack is because what might be good for one brand might not be good for another. And that's where there's like nuances can make a big difference between what works for you and what doesn't work for you. In your experience, in your, in your experience going into multiple companies, have you found um, like is there any one short term win like you're looking for? Like okay, where's my quick win? Is there a consistency? Like everyone is a little bit deficient in one area that you can go in and fix?
Speaker A: Yeah, I mean there's, there's a, there's a few. I, I would, I would say that um, in email marketing, everything from like uh, sometimes what I find with clients is there's like a little bit of a set, set it up and forget it mentality where you put like a uh, an email capture and you have various uh, embedded places for like email and SMS capture throughout your website, but you don't really go Visit it and look at what does this mean? Like is it hurting the customer experience because you're, you're having a pop up before they even get there is what does your drip campaigns look like? How have you changed that over time? What resonates with your customers even with seasonality? So I have seen that even going through and looking at customer um, like the whole customer experience from acquisition all the way through building a loyalist like in a tool like a CMS system or customer relationship management, uh system like Klaviyo or Attentive, you can really make a lot of, of pretty quick wins right away. The other one is conversion rate. That's the tide that lifts all ships. That doesn't take a lot on looking at the full customer padding and experience to actually improve someone's uh, conversion rate. I, I shoot for trying to have like a 5% improvement on key pages. Whether it's like homepage to product detail, page to cart. Because if you're trying to shoot for a 50% improvement on one page, it's a lot more difficult than just a 5% here and there. But by the time you get through checkout that's a pretty significant. That can be a 25 to 30% lift in conversion rate. And when it comes to um, companies that are spending millions of dollars in marketing a uh, 25% improvement in your conversion rate, can they do 25% lower ROAS? And uh, that's a pretty compelling metric for a win anytime I come into an organization.
Speaker C: Yeah, that's for sure. So conversion rate's an interesting one right? Because it isn't like oh I need a new ESP or I need a new this or new that. There's different ways you can solve for conversion rate issues. First you have to identify what is the issue or what do you think is causing the issue. Um, what are some. Are there, are there any commonalities amongst retailers where um, there's like one or two things that are always seem to be the driver of reduced um, conversion rate. Um, things that are holding the brand back.
Speaker A: Yeah. The two things that I hear that I see very often is number one
Speaker B: is
Speaker A: don't require your customer to have to overthink. Let them simplify the process as much as possible. And I mean there's just a great, so many like use cases that customers enjoy and experience if they have familiarity and they, they can just kind of go through it and not have to read a ton. Visual people process visuals and images 10 times faster than reading text. So one of the things I See is there's so much text and it's pushing everything down the page and you're trying to say everything about a specific product, uh, or service that you lose the core thing that you're trying to say. And you still can say a lot. You just got to organize it a little bit different and have primary and secondary messages. So that's the first real piece. And then the other one is really understanding kind of where your, um, how your customer journeys are in your, in your measurement platform. So what is happening with people that are coming in from your paid channels? Where are they landing? Is that the expectations that you would have? Like, a lot of people just send all their traffic to their homepage. And a lot of times, uh, if you're talking about a specific service or product, there could be a very different landing page that you have just for that specific traffic that's going to convert a lot better or get them to the next page. So I find that looking at your messaging from your ads and where they're coming from, and then understanding everything from that first page experience all the way through the product detail page to the cart, uh, and then through checkout is huge. There's so many people I know that are like, we have a leaky bar. Checkout is terrible. We're not getting it through cart, uh, to checkout. And a lot of times what that is, is you're causing a person to, once they add to cart, to not want to continue to check out. And the biggest part of that is they're either. There's coupon confusion, there is icing that they're checking that they're not like, ready to pull the trigger. There's not confidence to sort of move forward in terms of, um, warranties or free shipping or anything that kind of like makes them stall out. And the other thing is it might just be seasonal.
Speaker C: Maybe.
Speaker A: Like a lot of times use. People use their cards now as wish lists where if they're loading up for, um, this happens a lot with Black Friday is that early November. People load up their cards because they know that a Black Friday offer is gonna, gonna be coming. And if you're loading up your card on the 18th of November, you're like, I'm just going to wait a couple extra days because Black Friday deal is likely going to be better than it is today. So you just sort of have to say, okay, this is. I need to build this upper funnel. I need to make sure I'm, I'm, um, capitalizing on less expensive traffic that is coming in now. That is going to convert a little bit later. And understanding that consumer behavior is really important. I call it like just like a delayed conversion. Uh, and it happens with almost every client that has an AOV above. Like I'm talking like 40 bucks. Uh, people sometimes need to like look and have decision fatigue or they're on their phone and they're like, I just don't want to pull the trigger yet. How are you getting them back? And then how are you making sure that you understand that data so that you're prioritizing, uh, your acquisition strategy on a longer term basis?
Speaker C: Yeah, you just struck a nerve. Yesterday I was trying to buy some tires online and um, you know, I went through this whole process, had to find the right tires, you know, tires, different sizes. And I get to the checkout and it was like they were on sale and I didn't want to lose them. And um, they wanted me to log in or create an account before I could even convert. I'm like, why not just have me convert? I'm going to give you all the same information anyway. You know, my, my address, my phone number, all my credit card and then ask me if I want to create an account or just automatically create an account. Right? And then the next time I log in, but my email address and then send me a two factor authentication, like make the process easier.
Speaker A: Make the process easier.
Speaker C: Don't make me stop and have to figure out passwords and do I already have an account? Because then you put in your email address like you already have an account and like I don't know my password. It's like, I just want to check out, I just want to give you my money. Take it. Um, you brought up a good point earlier when you talked about your behavior as a, you know, as a, as a marketer has changed. You know, you're using Claude, you're using blairb's to find solutions. Are you seeing the consumer behavior change? Because they're using some of the same tools, right? They're using Claude, they're using ChatGPT. And then when you go shopping you still have this like 1999 experience, right? On a lot of E comm websites, are you starting to see consumer behavior change? In other words, are you starting to see, uh, with brands that are evolving, their experience do better than the ones that aren't evolving. What does that look like from a shopping experience perspective?
Speaker A: Yeah, I, I know everything like the buzzword of, of everything AI is, um, I would say that it is more of a buzzword and super widely adopted by consumers. And of course there's going to be innovators and person that are leading the uh, the charge there. But what I would see is fundamentally anything that you can do to make your shopping experience more consumer friendly, more personable. So AI has a lot of tools that help consumers improve that experience. And what I'm seeing with, uh, the ones that I, that the E commerce companies in particular, the ones that are winning, are ones that do AI recommendations really, really well. So they know what you buy and what your sort of behaviors are, and then they can recommend it. And then the other ones are ones that can kind of lean into how AI plays as a customer assistant throughout the website experience without feeling like AI or feeling intrusive, like it's more like I'm there if you have questions. And um, what I have seen that has really changed is I used to like AI bots used to be pretty impersonal and not very refined. And what I'm seeing now is that there are ways or like a live chat of a customer service rep. There's a couple places that I shop and I've worked at where uh, having like, we would staff lots and lots of people to answer very similar questions that were coming through AI chat because we knew that people wanted to talk and wanted to ask questions. But what we were finding is a lot of the questions were becoming very much the same and that the agents were starting to have just canned responses to make them a lot more efficient. And then the agent started sounding almost more like a bot than the bots themselves. So what I'm finding is there's a couple bots now that really do. They don't try to act like they're a human. They say, hey, this is, I am an agent, I'm a bot. And if you need to get a live person, I'm going to make sure that I hand it off and answer questions. But what I'm finding is a lot of people are like, wow, instead of waiting on a live chat for a response for five minutes, I can get exactly the question I was trying to answer for something that's very specific. And there's questions that I have. It's like, uh, one was like, I fly a Legion air, um, half the time out of my small regional airport. Does this bag fit luggage restrictions for that? Well, the agent's gonna go to Google, look it up, uh, half the time. And it's gonna take some time. And the bot's like doing it all and then says, yes, it will, this is why. And it like Answers are very robust. So there is a place for it. And the reason why I'm kind of bringing this up as an example. I think this line of how do you lean into AI so it becomes more of a service? But don't try to like hide behind it. Don't try to pretend too much that it's a real person or um, a lot of like, uh, AI images and videos and stuff. It's like you're not trying to fool the consumer. You're trying to really make sure that they can understand the experience better. And you're trying to do so in a way that you're being authentic, but you're also being very efficient.
Speaker C: I used to think that the only thing worse than talking to a live customer service agent was talking to their. Because it was just like it didn't understand me, it didn't speak natural language. Um, but I've experienced some lately that have just been tremendous, um, that just having a conversation. I mean, I know it's AI, but it doesn't feel like AI. But more importantly, I don't care. I'm getting the answers to my questions and it's accurate. Right? Because when you think about it, that AI, that agent can process data much more fast than human brain. Right? So if it can process my questions really fast, find me the answer, give it back to me, I can convert faster. Right? This plays right back into your, your conversion rate optimization. Um, so I think in that case
Speaker A: too, Sean is like, I just think that sometimes the adoption of it's going to take time. And it is. Some people are just going to hate AI and they're like, I want to talk to a live person right away. And you should make it as a organization easy to connect to a live person. But there are, it'll take time. Like I think about, I remember with self checkout was first starting to become a thing. Like people were frustrated, like I don't know how to scan this and like I remember like being in a self checkout line where people were like grumpy and yelling. And now I go uh, to like my sprouts and they have one checkout counter and all the rest are self checkout. So it's like it adapts and people like will learn it and like want to lean into it. But it may just take some time, uh, and give people the opportunity to have choice.
Speaker C: Well, I think in that instance they forced people to, to learn it. Right, because your choices were do it yourself or wait in a long line. Right. And so you find that balance. Um, So I have a question for you about, um, when a brand Buys software or SaaS solution, um, what causes it to succeed or fail? Like, what are the key things to make sure you have in place as an organization to make sure that, um, you're not wasting your money or time on a solution that you really need?
Speaker A: Yeah. So the number one thing that I see that fails with a solution is you don't have a internal champion in the company that is going to really, uh, lead it through success. And then the second piece that is so closely aligned with that is a definition of what success looks like. You come in and you say, the reason I'm doing this is I'm expecting X, Y and Z to happen. And these are the reasons why. And you have a roadmap of how that is going to be. But you also have a champion internally that there's a name that is held accountable for the success of that platform. I see that happen quite a bit where it's like, let's implement this.
Speaker C: We need it.
Speaker A: But then nobody either does the training or they fully don't utilize it at its capacity. And it's going, it's, it's not going to be a good experience for the vendor or for the, uh, the client. So really to kind of come in and say, what does success look like and define it in like, chunks of time and how are we going to track that and who's going to manage it? Those are, those are the key and those are the critical pieces. And of course, when I've seen that happen, by the time you get through evaluation, it usually sets both partnerships up for a much better experience and success. And of course there's a couple anomalies where, uh, you start not seeing the value after a period of time. But for the most part, those are the things that I make sure are happening on a vendor integration.
Speaker C: Yeah, for my time on the vendor side, I think it's really important to make sure you're checking in with the customer on a regular basis and that they're happy and they're actually using the product to the fullest capacity. Otherwise, you know, because if they are, then it makes it really hard for them not to live with it. Right. But if they're not, then you're going to have churn. So that's some good advice. Um, moving on to the sort of final phase of our conversation, Chris, um, if you could give, um, vendors one piece of advice in terms of selling into an organization or a fractional cmo, uh, what would that be?
Speaker B: I.
Speaker A: The the biggest one, I would say, is you are very close to your product. But, uh, remember that your, your client and your, your prospects, it's new to them and they're hearing it from five other people. So take that, I'm going to go back to Slack. Take the time to personalize it, but also take a time to step out of your own shoes a little bit and try to understand it from the lens of whatever client you have. And I see this a lot where it's like, they know the product and they're like, this product is going to save the world and it's the best thing that ever happened, but they're too close to it. They need to take a step back and say, this is how people are going to perceive it. This is how they're going to evaluate it against other competitors. And these are the ways that I need to make sure that I have a better solution that is going to get them over, um, that first hump. I think the other one I'll be very transparent with is if they have the opportunity to test or trial, and it doesn't have to be a free trial, it could be a paid trial at a reduced rate. It goes a long way. And if you have a great product and it doesn't require a lot of integration, heavy lifting, like resources to commit to it, that you can say, I'm going to show you how good it is, uh, right out of the gate in some way or another. And it's a pretty low risk for you and for us that, that'll really help. I, I have a lot of, uh, companies that I see where it's like a lot of vendors I talk to and it's like, oh, no, we know our product's good, so it's going to be $10,000 in the first month. But then they have a competitor that's like, hey, I'll give you it for half that for the first 90 days. But then after the 90 days, we're going to show you that the value is like 50, $60,000 more. Uh, so your $10,000 investment is going to pay off. And I seen that, like, work so many times to get a foot in the door if the product is really good and can stand by the, uh, return on investment that they're pitching at that very first call.
Speaker C: Yeah, that one, that one can be more difficult for some, easier for others. But I think the first piece of advice is really good. I think if you, you know, to your point, step outside of your role and what, uh, makes me different, like where am I similar to my competition? Because there's going to be similarities. And I think if you can really, truly, honestly articulate what makes your product different and special and better than the competitors, I think that really helps you stand out. You don't have to tell, you know, the customer everything about your product. Like you said early on in the show, it's really what makes you stand out. Um, one last question I like to ask everybody. If you could go back to your early self at your days at, ah, Ebags, when you first started there, what piece of advice would you give yourself that you know now that you didn't know then?
Speaker A: Ah, wow, that's a good question.
Speaker C: Um,
Speaker A: I think at the very early stages, it's this mentality of, um, move fast, break things and embrace failure. That kind of early on is, is in your career, you don't want to fail. You want to do everything right. You kind of, like, are like, maybe a little bit more cautious to push an idea that you really believe in. And what I have found is when I, when I really got over, sort of maybe that, that timidness or that caution to say, we're good, we're going to kind of make sure that we have the right guardrails in place and it's not going to sink the ship or we're going to move faster, uh, in order to grow faster. It really sort of became a lot more fun and started having a lot of real change in terms of growth and projects that we were working on. But everything, um, it's not a project that you want to just say, I'm going to throw this at the wall. It's something like, I really believe in this and I have the data to support it, but I want, like, I don't need to be 100%, like, let's have some progress over perfection. Telling myself that maybe 20 years ago, um, would have been nice. And I think that it's like, trust your gut, but, like, come with the receipts and make sure that you're, uh, structured in a way that is going to be right. But you can do a lot of these and you're going to start having a lot more successes than failures.
Speaker C: That's great. Chris, thank you for being here and sharing the human side of Martech with us. Um, I think it goes a long way to, uh, help the listeners understand your position and folks like yours. So thanks again and take care. Appreciate it.
Speaker A: Thanks, Sean.
Speaker C: Take care.
Speaker B: Thanks for tuning in. If you enjoyed today's episode, subscribe on Apple Podcasts, Spotify, YouTube, or wherever you get your podcasts and Visit us@themartechmatrix.com and if you're a brand or agency trying to make smarter decisions about your marketing technology, checkout Blurbs IO it's built for buyers who want to research vendors on their own terms. No cold calls, no jargon, just straight information vendors. You'll want to be there, too. That's where the buyers are looking. We'll catch you on the next one.
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