How 8am Rebuilt Its Go-To-Market For the AI Age with CMO, Nate Skinner

Everyone can buy the same AI tools now. That’s the problem and the opportunity. When technology stops being scarce, differentiation comes from how you show up, how well you understand the customer, and how consistently your go-to-market system reinforces that understanding.

Kevin Kerner sits down with Nate Skinner, CMO at 8am, to unpack a full-stack transformation: rebranding from AffiniPay (a name closely tied to payments) into 8am, a platform that supports legal and accounting professionals with payments, practice management software, timekeeping, reconciliation, and embedded fintech services. Nate explains how the team anchored the rebrand in research, then backed it up with real operational change so the brand isn’t just a new logo living inside an old motion.

We also get tactical on modern growth. Nate shares how 8am shifts to audience-based selling, restructures territories and partner relationships with bar associations, and rebuilds the website around customer context. Then we dig into answer engine optimization (AEO) and why showing up in Claude, ChatGPT, and other answer engines changes content strategy, technical SEO, and what “ungating” should look like. Finally, we talk about building AI agents, combining Gong call transcripts with Claude for sharper insights, and why leaders need to use the tools themselves to set the tone while still protecting the human voice that makes a brand feel real.

Subscribe for more real-world go-to-market engineering stories, share this with a marketing leader who’s wrestling with AI adoption, and leave a review so more builders can find the show. What part of your GTM would you rebuild first?

🎧 Tech Marketing Rewired is hosted by Kevin Kerner, founder of Mighty & True.

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Transcript

Welcome, Sponsor, And Setup

Nate Skinner 0:00

In a world where everybody has access to the same technology, this is not like only the rich companies can afford it, right? I mean, you can get a cloud license for $20 a user. It should just be part of your stack if you're a startup or your GE, right? And in that world where everyone's the same thing, the difference isn't going to be how fast you move and how much you how much ground you take in a particular segment or market. The difference is going to be how you show up in a differentiated way.

Kevin Kerner 0:24

Hey guys, this is Kevin Kerner. I'm the host of the Tech Marketing Rewired Podcast. I just had a great conversation with Nate Skinner, who is the CMO at 8 a.m. Um, and uh it's a fascinating conversation because Nate um has both a very strong sales background and also customer support and um marketing, of course. He's a very well-rounded CMO. I was curious to talk to him because they 8am had recently gone through over the last year or so a rebrand. I wanted to talk to him about the rebrand, but also how they managed their go-to-market changes that they've that they've uh recently implemented from all the way through the sales side to their website to the brand itself, all the way through the whole go-to-market function. So it was a really great conversation. Um, Nate touched on why the branding happened itself, the different systems internally that they looked at, how they implemented new go-to-market functions, and really the amazing use of AI through the whole process. So it was great, really good to hear um a very detailed view of how this uh company went through this transformation over the last few months. So I'm excited for you to hear it. Before I get started, this podcast is sponsored by my company, Mighty and True. Mighty and True is a growth marketing agency that works with tech companies, and we offer a blueprint process where we will take a look at your um the gaps in your go-to-market strategy, and we will build a full plan for you at no cost and present it back to you with um findings and how you would implement those go-to-market findings yourself or have us help. If you're interested in having us do that, you can go to www.mightyintru.com. So that's about it. This is uh going to be a good one with Nate. Uh, really appreciated his time and excited for you to hear it. Let's get to it. This is Tech Marketing Rewired. All right, Nate, welcome to the podcast. Thanks for having me, Kevin. Great to be here. So I was um super interested to talk to you because um I know you guys have done so much transformation over the last maybe couple of years or so that I've seen from the outside. And so we're gonna touch on today um a lot of what you've done in modernizing your go-to market engineering side of things. It's um in our pre-call is kind of fascinating. Maybe before we get started, talk a little bit about your background and um how it's I think what's more interesting. What's really interesting to me is how it's informed what you're doing on the marketing side, given that you have this uh sales background. So give it give us a little bit of background on you.

Nate Skinner 2:47

Yeah, uh the fast version is um, you know, I've been in the technology industry since 1999. My first job was uh I left bank, I was a banker before. Um and I got into technology right as the internet was becoming mainstream and it was going to change everybody's lives. That was in 1999, really. Um, and my first job was at SDR working in a lead queue in a product called Goldmine back then, um, and for a software company. And so I spent my first 10 years from 99 until 2009 in field-facing sales roles. I was a rep, I was a sales manager, I was an SC, like doing the demos. Um, and then I was even a product manager when we got acquired by Embarcadero Technologies in 2001. Um, I was kind of the lead product expert, and so I became a product manager. Uh, that was interesting. But anyhow, that was all field-facing. And then I joined Salesforce in 2009 as a product marketer. I'll never forget being asked by George Who at the time, who was the COO, um, who still interviewed kind of senior manager and above marketing candidates. Uh, I was an employee like 3200 or something. Uh, and he said, Why do you want to be in marketing? And I said, I don't. I've always thought that marketers couldn't sell and couldn't build product, and I could do both. And uh now I thought I talked myself out of a job. And then he explained what I what I've come to learn to be true, which is marketing done properly creates space for product and sales to operate. So if you do it right, you create this kind of area behind which marketing and product and sales, sorry, um, can take advantage of what marketing has done on their behalf and out of sold. And uh I've been a marketer ever since across a number of companies, Salesforce for two times, Oracle, um, AWS, a smaller company called Campaign Monitor, and another smaller company called Onfido, which we sold last last uh 24.

Kevin Kerner 4:43

Wow. It's almost like the perfect background for a marketer uh is to have both sales and product background. That's a good, that's a good combination.

Nate Skinner 4:52

Yeah, and and I did a two-year stint as a chief customer officer at a company called Campaign Monitor that also helped. I mean, at the end of the day, you know, what I find consistent across these different roles that I've held is is a focus on the customer. If you remain customer obsessed, kind of everything is is much makes much more sense. And where you have problems, in my experience, is when you've made decisions about your strategy, whether it's go to market or product or whatever, in the absence of the customer's point of view. Like that's where people I think run into problems.

Kevin Kerner 5:23

Yeah, yeah. So this kind of a good lead into all the restructure or uh design that you've done with the company over the last, I don't know, a year and a half, a couple of years or so. I know you rebranded from AfiniPay to 8 a.m. Well, I wanted to talk about that, dig into that. Talk about that restructure. What why did what why did you feel like you it needed to be done? What were the triggers that led you to say, okay, we need to change something here?

Rebrand Beyond Payments To 8am

Nate Skinner 5:45

Yeah, I mean, we had spent, at least since 2022, AfiniPay had been around for 20 years. And in 2022, I think, time frame, acquired some software, a software company called My Case, which had some other products inside of it. But AfiniPay's history was payments. I mean, we're still to this day, LawPay, the product, is the largest payment processor for legal professionals in North America by far. And what drove the decision to transform the company really was an observation that we were much more now than payments. And the name AfiniPay had an association with it of just payments. And we were doing things like transforming legal professionals' operation, everything from timekeeping to reconciliation to full time, full cycle financial services embedded as a fintech. And that was much more than payments. And so we did a lot of research to determine what a what a name might be. We recognized that we had really strong brand affinity for the products within our portfolio, Law of Pay, My Case, Case Pure, DocketWise, CPHR for accounting. Um, but we wanted to bring those together and amplify them as a single solution for legal and accounting professionals. And that's where 8am came from the idea that these professionals get up every day. Every day is a new opportunity for them to go out and grow their firm and get more clients and solve problems that are real systemic, you know, access to legal services, access to accounting and accounting services, these are things that that drive our audience and our customers to excel and thrive. And so the name came from that. It's really a kind of an idea, the idea that every day is a new day and you can get started as early as you'd like. I also like it because it's a simple name and number, yeah. We show up first in alphabetical lists. It's easy to remember, it's easy to spell, it's easy to say, all those benefits.

Kevin Kerner 7:34

Yeah, and you just didn't change the name. You you went ahead and started to change the go-to-market motion entirely. So you got the, and that I think is a missing component of a lot of these, like these big brand things that happen. The big brand thing happens, then the the that big brand is put in the same system that existed before, and it just kind of eventually it just sort of wanes over time. So regarding the the uh go-to-market engineering stuff that you did, or go to market, let's say, talk about what you like stepping back, like now you have to look at go-to-market. What were your considerations as you're like, okay, we are gonna have to change some things here?

Audience Based Sales And Territories

Nate Skinner 8:10

Yeah. I mean, one was we were going to market as products. We had salespeople that would call our customers and say, hey, I'm a law-pay salesperson, or I'm in my case, salesperson. Uh, we wanted to have our sales team be able to offer the entire solution as an 8 a.u. That can do all the things that our products can do, but talk about it in a solution-oriented, kind of an outside in versus inside out. And so we did a number of things on the go-to-market engineering side, including, you know, we had payments reps and we had software reps. We collapsed them. And now we have legal salespeople and accounting salespeople that know that audience and talk to that audience about their outcomes and what they're trying to do. And that's changed a lot of um our success. We have higher attach rates of multi-product sales. We have larger deals because customers understand we can do more than just one thing. But that was a lot of work. You know, we we it's one thing to say that, it's another thing to do it. And but that was major the major driver of the go-to-market changes were the customer. I mean, being customer-centric and having the customer at the center of those decisions was really the driver behind it.

Kevin Kerner 9:12

Yeah, channel, how to go you actually go to market the selling motion too. So now you're having to re when we didn't talk in the pre-call, you had to retrofit, you had to tear down a lot of things to build them back up. And there are many, many systems, obviously, systems being processes, but also technologies that you had to look at. When you step back and you look at that full go-to-market motion, how did you, how did you, what did you work on first? What was the first thing you did before you started to actually go into each one of those work streams?

Nate Skinner 9:42

Yeah, I mean, the first I'm gonna sound like a broken record. The first thing was looking at our customers. Where are they? How big are they? Which how many of them have more than one solution? Do they even know that we offer more than one solution? Because we went to them two years ago or three years ago and said, hey, I'm a law pay sales rep, and that's all they know. And so with that, it's the center anchor, the customer. We surrounded that with the approach that we now have today, which is you go to our website and you find your solutions by your audience. If you're a legal professional, here's all that we do. If you're an accounting professional, here's all that we do. Our sales team is organized around those audiences as well. We also instituted territories which we hadn't had before because we were just kind of, you know, taking it around as we got it. And we said, look, we have 130 bar associations, both for legal and accounting, whether it's a CPA association or the, you know, Illinois or Georgia Bar Association, we should have direct relationships with those, not just at our affinity level, which is a team of folks that we have that have built those relationships over time, but also at the territory level. So I mentioned when I was a seller uh as a rep back in 2000 time, uh, aging myself a little bit here, but um my territory was Texas Mountain. And so I would travel between Denver and Tech, Dallas, and Austin, and Houston, and kind of sell in that territory. And I remember feeling like I could do better for my customers if I just had Colorado or if I just had Dallas. And here we didn't have that concept. And what we wanted to do is create a deeper relationship with the network of customers and partners in a particular territory. And so now all those 130 affinity association partners are working directly with our sales team. So if you're where I live in Georgia, the Georgia Bar Association is a partner of ours. And now the rep who has that as a territory can talk to them directly about how we can help their members. If they're having a dinner, can we sponsor it? Can I come in and show them what we can do and who 8 AM is? And it's really increased our efficiency per person while driving more value to the end customers at the end of the day.

Kevin Kerner 11:46

Yeah. You start with customer, but then a lot of the changes you've made have been sales structure related, sort of how you talk to the customer. The next point of meeting the customer, maybe the actual salesperson, there's got to be a lot of marketing infrastructure that supports all that. Talk to me about how did you look at that now as like, okay, I have to, there's a lot of old school ways of doing things here. I'm gonna have to pick some of these and fix them.

Answer Engine Optimization That Works

Nate Skinner 12:17

Yeah. I mean, uh the the main one is, you know, in the age of gen AI and agentic AI, we have a lot of tools at our disposal. And the question wasn't like which ones we use, because you could use all of them for all kinds of things. It was what are we trying to accomplish? And the answer to that was reach our customers with the right message at the right time in their context where they search. And so you you probably know well, and your audience knows well about answer engine optimization, you know, the perplexities and chat GPTs and and clods of the world are a lot of where everyday people get information and type in something like, what's the best software for a five-person law firm? And if they do that in those engines, we needed to show up. And so one of the adjustments we made, it was not just the audience-centric stuff I talked about before, but it was also let's make sure we're present where our customers are searching for us and finding solutions like ours. And that is a whole different animal, right? We use technology like profound, we use technical SEO skills from old to recapture that market and show up in those engines. This whole practice area around answer engine optimization is a skill that you have to either learn or know. And we've really put a lot of time and energy into making sure that we show up in those places and drive the people who are finding the answer to our website and then from that point connecting with them on the issues that they're face and talking to them problem-centric, not feature-centric, right? Um, customers I've always known, you know, they're very good at describing their problem. They're not often good at connecting their problem to your product. And so we spend a lot of time making sure we're talking about the outcomes customers are trying to drive, not our product or our features.

Kevin Kerner 13:59

Yeah. Yeah, I totally agree. What's what has surprised you? What type of wins have you had on the AEO side? What surprised you that actually worked? And are there some things that you've done that you'd try over again?

Nate Skinner 14:09

Yeah. Well, I mean, one that surprised me was when you search 8 a.m., it the results now say things like 8 a.m. is 8 o'clock in the morning anti-meridian time. And then it also says, but it also could be a technology company in the legal tech. Like that's pretty cool, right? So um I don't know how many people actually search what is 8 a.m., but uh, you know, they're searching for us, they're finding us. So that was a surprise. Uh, the other that was surprising was, you know, you have to ungate all these answer engines, they use the open internet and the what's available. They don't search inside of Facebook, they don't search inside of these closed wall gardens. They aggregate and search across open access points. So marketplaces like G2, which is recently uh combined with Captera and others, those are a really important place to show up. You know, kind of what is old is new again. You know, listicles and long form is very good for AEO. You know, writing out the answer in terms of the way people think of the question, that's very, very useful. Ungating content. We have a an annual legal research report we put out, and we've always had that gated, but now we we don't. I mean, the full report is gated, but a lot of it is available on our website now because we need to show up when people search, you know, how much AI is being adopted by attorneys. We want you to find our research as the source of that truth. So there's a lot of tactical things, but also ultimately it's about helping those engines find your service and your content and prioritizing it based on the fact that almost everyone else is looking at it as well.

Kevin Kerner 15:40

Yeah, in terms of the AEO side of things, did you did you have to reskill or was the team did you have the team in place that could reskill for these things? Yes. Yeah. Yeah. That's what I found is like a lot of a lot of what needs to be done is just a a next step on the stuff that's already being done. It's not a completely new skill set.

Nate Skinner 16:00

That's right. It it isn't. I mean, there are there are new tools, you know, AirOps and Profound that really help us and we use them. But the, I think the the step back to your point, it's like, do we have the people that understand the problem and can they go solve the problem? And we do. So we we made a conscious decision, you know, early last year to say, like, we want to establish a presence in these answer engines. And and by the way, the the goalpost keeps moving, right? One minute it's it's a if you're showing up here, it's driving you know relevant results. Another minute it's actually it's over here. And so the team is constantly looking at that and using the technology to stay a step ahead of it. Um and I anticipate that that won't change. Like it's gonna continue, you know. One year ago, Kevin, if we had had this conversation, chat GPT was the place. If you show up there, you're good. Well, that's flipped. Claude is rapidly outpacing. Uh, I've got a graph and a slide that shows adoption of Claude is massively over. Yeah. And so, you know, if you were putting all your eggs in the Chat GPT basket a year ago, you you better have made a conscious decision to address the Claude platform as well.

Picking AI Tools And Building Agents

Kevin Kerner 17:04

Yeah, and I don't I'd be interested to see how you think about this from a leadership perspective. It's like for me as own in a business, it's you know, we have Gemini because we're a Google shop. We have ChatGPT, we have ChatGPT teams because we signed up for it last year and paid for the whole year. And now everyone wants a Claude subscription. And so we're sort of we're going, well, do we get Claude? So we have probably, I don't know, 10 or so Claude individual subscriptions that we pay, but we're thinking about moving to teams. But as a as a leader, I'm trying to figure out. I know for a fact that in another six months, something else will be the thing. And it will probably be one of those two. Could be perplexity, but I don't know how, you know, there do you have to buy all the things to just stay in the with the best tool? It's just so hard to figure out.

Nate Skinner 17:51

Yeah. You know, our approach is no, you don't have to buy all the tools, but you should test them as you as you approach them. As you approach that technology for your business, whether it's whether it's your internal employees or for in service of your customers, approaching should be try all, try, try it all, right? Do it, do a pilot test, try to solve a particular problem, try to understand how it could be used to help your business in a particular way, and then land on the one that's giving you the best possible outcome and the best control and compliance and protection that you feel like you can get. For us, we did that. We looked at Gemini last year. We, you know, we were kind of like where you are. We were looking at Gemini with Chat GPT. For us, it's we want Gemini for our knowledge workers, like connecting Drive, and we're a Google shop, so it's like Drive and Gmail and calendars, and just having to say, you know, what's this spreadsheet actually telling me, right? Um it's useful for our for our teams and it's not that expensive to add. But for production work and agentic things that we're doing, we're doing that with Claud Code and core.

Kevin Kerner 18:52

Yeah, interesting. Yeah. And isn't it so interesting how the terminal now has become so important, Claude Code actually in the terminal? And we're training up our creatives in terminal. All of our systems engineering people are in terminal. It's just, it's I would have never expected a year ago that we would have terminal open on so many people's desks. Yeah. Yeah, it's it's fascinating.

Nate Skinner 19:12

I mean, like I mentioned earlier, what's old is new again, right? I've got Claude uh code terminal open right now. And um the the work that it can do, especially on local file systems while I go do other things, it's it's extraordinarily powerful. And we used it to do all kinds of interesting things. Like we built our positioning and messaging GPT where all of how back to the brand, right? How we talk about our company and our solutions that we provide changed from just product pitches to solution. That was last summer. Well, we wanted to build all that positioning and messaging house into a GPT so our reps can just say, like, what's the standard value proposition of our legal solution? And it just gives them the answer. And it's the right answer in the right tone of voice. And so we built all of that on Claude and you just have it where you click the GPT and away you go.

Kevin Kerner 20:04

Yeah, isn't that incredible? I mean, do you think that there will be, because you're at you've done this, a lot of this um replatforming. Do you think they'll be at a point where you're building your own software versus relying on other software for the market, let's say marketing or sales department, little mini at TypeScript apps that are built to do a thing versus using some other thing?

Nate Skinner 20:24

Yeah, I don't, I wouldn't think of it as it's not apps as much as it's services, right? Like we're you we're we're building all kinds of agents. We have agents running all over the place. We have so many agents, we need an agent to manage them at this point. Uh but they're what they're doing is useful work that others, you know, it used to take. I would come in, look at our dashboard, ask a bunch of questions, not really get the answer, have to diagnose what the data was saying. And now I have an agent that goes and summarizes it all for me. And I wake, I come in and there's a Slack post of like, here's where you are for the month or for the quarter or for the year. Those things are absolutely like right at your fingertips if you understand how to use this stuff. But as far as like apps, internal apps, we built one. We built one called Gonzilla, where we have Gong that that records our salespeople's conversations and like helps us with insights around win rates and win reasons and loss reasons, and you know, how often does pricing come up in a conversation? But when we added the GPT and combined gong with with Claude, now it gives you things like what was the last time somebody said um, you know, tax season? Because we have a product for CPA charge for accounting. And right now, at the in March, in April, sorry, it is starting to really spike, right? It's like showing up every time. So we're talking about CPA charge with a customer, and their reason for not engaging is it's taxis. Well, we knew that, but now you can see it. We don't have to go to a board meeting and say CPA charge is slightly down because of tax season. There it's evidence, and everybody knows. And so what we're able to do back to the customer centric. Like record on repeat, we're able to tell our teams, look, understand that and build your outreach sequences and your email cadences and your call scripts accordingly, meaning, hey, I know it's tax season and I realize now is not a good time. I wanted to wish you luck and let you know I'm here when you're ready. That's a different conversation than we were having, you know, a year ago.

Kevin Kerner 22:23

Yeah, it's amazing. This is one of my favorite use cases for these AI in sales and marketing is art is voice data, any type of transcript data. It's just the best thing to use. There's just a time lip.

Nate Skinner 22:35

Yeah, I mean, nothing substitutes the actual words of a customer. Like you can you can write down and record, you know, sit in the meeting and write down what they said, but hearing them say it and being able to hear, see it kind of show up hundreds of times. I mean, we have, you know, hundreds of opportunities. Our customers are 280,000 legal professionals around the country and 80,000 accounts, like firms. And when you hear them say the words, that helps us turn our positioning messaging into something that's more meaningful for them. So we're using their language to speak to them. It's it's changed a lot.

Kevin Kerner 23:08

The Gonzilla idea synthesizing all these conversations in addition to other skills files and all the context that you're getting. Does that funnel down farther into your marketing workflow or sales workflow, email uh sequences, ad serving? Like, have you have you built it out to that degree?

Nate Skinner 23:28

Yeah, that's kind of like so the fun part about this stuff, right, Kevin, is like you pick a problem you want to solve. We have all this Gong data, but what we can't do is ask it questions. You can say transcribe, you can say, you know, whatever. Well, the GPT plus Gong gives us the ability to say, how many times did this happen? How many times did that happen? And it tells you. Now, kind of iteration number two is already having prompts and agents that run those kinds of analysis for us. And our product team uses it. So they'll say, you know, over the last quarter, how many times did feature X show up in a conversation around the reason they picked our solution? And if, you know, compared to the previous year, like that flow down through not just marketing and our messaging and our email copy from Gong plus GPT, but into product, into our competitive insights and product insights, into validating it kind of validates the quant with the qual, right? Like we think it's because of tax season. Here's quantitative data that says that's actually exactly what it is. It's a game changer.

Kevin Kerner 24:30

Yeah. So awesome. And can you imagine having that data for a couple of years now? I mean, so you really get trend data, the the brain, that brain. We're building this brand brain that we use for clients now. And it's really interesting to see how a stated brand will change over time through Slack conversations and transcripts and all these other things. And there might be things that happen in all those conversations that may actually change the brand in some way. Yeah. If you added your gonzilla into it, it would be it would be even further customer data that would do those type of things.

Nate Skinner 25:01

Yeah, I mean, that that's the thing. It's like all that, all those calls have we've had them, we've had gong for years. So now we just added the GPT and now it's all accessible. Like this is the thing that I mean, everybody that pays attention to Gen AI knows that the value of it really does rely on the quality of your data. And we have a very robust data set. So uh that's years and years in the making. So now it it's it's not only like I'll tell you an example where that what you just said came through. It was like we keep saying the wrong word. There was a there was a feature we were using and referring to, it was basically timekeeping. And we were talking calling it something else. And the customer kept on having to do the mental gymnastics themselves. So we basically changed the our GPT positioning and messaging to say when you're talking about this issue, talk about timekeeping. That's the way they talk about it. And boom, it's changed the the outcome of the conversation. We even we even can catch now if an AE or a set of reps, if their tone changes, like if they're super positive, like I'm I tend to be an overly excitable person, and all of a sudden I'm not overly excitable, it comes through. It says, like, hey, you know, Nate seems to have had a difference in his tone over the last seven days. That's crazy. Like we could never have done that before. Where where it shows up in real application is in the end of the year, last year, just because we've had Gonzilla since probably September, and it's it's gone through it durations and evolution. But in December, a sales team for most technology companies, and most any companies, I'm sure, if you're on a fiscal calendar, they're tired. Like they're they're they've been going all year, they're trying to get to their number, and they start to get a little tired. They start looking at the holidays and the new year, and we get a sense that you could set you could tell the energy was down. And so we paused, gave everybody an afternoon off, kind of celebrated the progress made in the year, and everybody kind of reset, and then we finished the year strong. So, like that kind of insight was just not possible.

Kevin Kerner 26:59

Synthesis. There's no way you could synthesize that without the tools that we have today. Um, this really amazing transformation that's happening there. There has to be some team implications to it. And I'm I know a lot of CMOs are struggling. And I, you know, same thing on as a business that we run, getting people, it's not getting them on board, but getting people to see, to take the blinders off on what this stuff can actually do. Everyone wants everyone wants to do it. And it's it's like I like to say that you can't unsee it once you see it. Once you know what you know, then you can't not know it. Did you have to do how did you get an organization as big as you guys are to be able to like move the stuff forward, get people on the bus?

unknown 27:40

Yeah.

Kevin Kerner 27:40

What were the steps for good?

Nate Skinner 27:42

I mean, the the first step was last year we decided as a company to have a Gen AI internal initiative, like a value creation plan. You know, we're gonna measure our adoption of Gen AI across the business with the expectation that it can drive productivity gains, right? That's that's simple. It's like every engineer can have Claude help them with coding, and one engineer becomes you know three times as productive. Like that was the hypothesis. And so it was about using what they already were using and then institutionalizing that understanding by doing show and tells. We have a, we have a every couple of weeks, we have an all staff where somebody would show off the latest improvements they'd gotten from using Gen AI for whatever function across the business. And we had um we had ourselves placed, we placed ourselves on a kind of Gen AI maturity curve that we had a goal by the end of 26 to be at a certain level of maturity related to Gen AI application for internal use. Then, you know, there was lots of different tactics to drive that. But one of the most important ones was show and tell. I'll show up at an all hands and say, like, here's what we've done for brand. Here's how we're using Claude to track our brand awareness and our sentiment. And like that's one of those examples. And then people, by definition, they say, well, I should go look at how I can use it to do a show and tell. It's like just one tactical example. But the other way was to start, once we got the internal stuff we're rocking and people became more productive and we're still getting the benefits of that, we're not done by any stretch of the imagination. Uh, then we started looking at, well, applying it to our product. We've had a product strategy that included Gen AI for years. We have capabilities in our products that are Gen AI oriented. And we don't yell and scream if talk about it, what I call AI washing, because it doesn't matter to the customer. What well, it may matter because they are seeing it all with headlines and they're like, what's your gen AI? But I remember when that happened to me back across multiple hype cycles, right? What's your what's your cloud strategy? Like they'd asked a question back in 2000, right? And what they really care about is what it gives them, the outcome. And so our approach is like Gen AI and the customer experience where they don't even know it's working for them, but it is. And they have control and it's compliant and they can audit the results, and there's no mystery behind it. Uh, the internal became the external, but it amplified it. It was already underway in our product and it got accelerated because of all the learning we had through these internal projects. And that's what my my guidance to any company and and folks that I talk to all the time is like pick a couple problems, identify some opportunities to solve them, solutions and process improvements, and then take a shot at fixing one of them. Try it, see what happens, measure it for a month or a quarter. And if it has driven a dramatic improvement for either your customers or your employees, then roll it out. Like, why wait? Don't keep on messing with it, right? We're past the trial and error phase. We're in the effect and implement phase for at least 100%.

Kevin Kerner 30:35

Yeah, for sure. Um, I would argue that um I have this thing I like to talk about with our team about there's efficiency AI, where you're just trying to do stuff to get more efficient and do it faster. And you guys are like doing that well. I would argue that you guys are on the second step I like to talk about, which is opportunity AI. You're actually creating new opportunities, new ideas in the market that you wouldn't have created had you not had these tools. So you can be real efficient and do it faster and get to the outcome faster. But I believe that this stuff is going to give us opportunities that we can't even see today. That's the real, that's the real gold mine, I think, in all this stuff is looking at the opportunity AI aspect of this.

Nate Skinner 31:12

Yeah, I think that's a great differentiate, like a great way to delineate the two, right? There is efficiency, of course. And, you know, our designers used to spend a bunch of time redrawing, you know, ads in different pixel sizes for all our 130 bar associations. It was, it was not mind-numbing, terrible work that they had to do every month. Now Gen AI handles all that. So they're more efficient, to your point. Now, what they're focused on is making better creative than ever and like win awards for it and use Gen AI to help you with that too. And so we're getting prototypes out faster and we're getting looks at real out-of-home built. We just did a uh conference in Chicago called the ABA Tech Show. It's the American Boar Uh Bar Association um technology show for all these partners I just mentioned. Um and the way we showed up there with our brand and our booth and our out-of-home, we had never done before because the brands only existed in the market since August of 2025. And it looked amazing. And we were iterating on it till the very last minute because we have all this technology to your point. We had gone through the efficiency stuff. Now we were on the push the edge, push the envelope, push the color, push the copy.

Kevin Kerner 32:16

And it was amazing. Yeah. Yeah, amazing. I'm just curious because you're such a it's such a good looking brand. It's such a well done brand. Are you using it for any in any interesting ways for creative, for digital, building web pages, anything? Yeah. Starting to geek out on that a lot now because we're doing it a lot of that. And it's it's it's a huge if you spend more time on building the skills, the actual MD files that drive all the creative. But then once you have those set up and the components set up, you can literally chat with the terminal and it creates the thing that you want it to create. I don't know if you guys are experimenting with that too.

Nate Skinner 32:53

Yeah, we're experimenting with it. I mean, uh ultimately our objective is to be able to get world-class creative out faster, right? Yeah. Yeah. Have a lot of requirements on our marketing team and our designers across the business. We have a lot of products, we have a lot of audiences, we have uh, you know, internal and external. And so a lot of that work that they're exploring is about creating rapid prototypes that don't take as long as they used to. Because it used to be you want to mock up, it's one thing to show somebody a colorway, right? Like here's a here's four colors next to each other, and like that doesn't mean a lot to to you and me. But showing it on a billboard, showing it in an ad on a webpage, showing it at a booth, that was always hard because you had to mock up a fake scene. That's all fast now. That the the mock-ups are being driven by exactly what you're saying. We got the console working, we it's got our colorways in it, it's got our brand voice and our guides in it. And it's like, show me this in the front of a mall, right? Or show this to me on the side of a billboard. Show this to me in the, you know, we just announced an agreement with the Tampa Bay Buccaneers to have the 8 a.m. club inside of Raymond James. Nice. Show me the way this looks at Raymond James Stadium.

Kevin Kerner 34:00

And, you know, and it's just it's just like that. It's crazy. Yeah, isn't it great? Something to me just tickles me when I see a creative inside a terminal window. It's just so weird. And now yeah, the Figma connect, now you can do the Figma connection. It's MCP, it's just it's a beautiful thing. It's beautiful. It's ridiculous. No more drawing rectangles anymore. Just like it will just do it for you.

Nate Skinner 34:21

I still stay out of that because I I'm I'm sure I'll cause more problems than than I'll solve. But I I love that our team is looking at all those things and and it's helping us go much faster at the same level of quality, right? Without reducing quality.

Kevin Kerner 34:34

Yeah. You know, one thing that I notice with you and a few other CMOs I've had on the podcast, there's quite a few of them now that are in the tools. They're actually doing the work. And I think that's really impressive because it does take a little, it takes some time to get comfortable. Um, it's frustrating when you start, it, but then you start seeing the output and you get better at it. How important is it does it, how important is it to you that you're actually in the stuff, like know it, work it? How important is that for you as a leader and for your team to see you doing that?

Nate Skinner 35:05

Yeah, I mean, I don't think you can ask people to do something you don't fundamentally understand. I don't use it, for example, I use it to do what I need to do, my job, which is typically understanding big trends and themes across the go-to-market engine that is our company and also in the market. So I use it to do research and analysis, you know, who else is doing blah or blah, what, what, what are what are people doing to move the needle and blah or blah. Like I use it for the reasons that I need to do, use it for my own. And then I use that as an example to show other people how think about your job and what's tedious or what's necessary and how you could apply Gen AI to solve that and give you time back. Um and it's critically important. If I was sitting there saying Gen AI, everybody, and not doing it myself, it falls on deaf ears. We we have, you know, I'm a firm believer in you you lead by example. And I don't go into Figma and create mock-ups because I know that I'm just not as creative. I get in trouble. Yeah. I get in trouble with your team if you did. That's right. But I will say things like, look, I jammed this out in Claude this morning. It's kind of what I was thinking. And it's wrong, but it gives them a direction that they didn't have before because I would have had to say, well, show it to me. Let's get back together in a week and we'll look at a new version and we'll iterate and iterate, and it takes weeks, right? Now I'll be like, this is kind of what I was thinking the based on the last conversation. And it gives them such clarity that we don't have to wonder what you mean. It's it's clear. And so um, but I use Gen AI to do that. And then the expectation is when you give it back to me, we just had a meeting the other day. It was one of my perfect examples to answer. This is a long that question got me excited, Kevin. Um, yeah. We are reviewing creative for a brand campaign, and the team is already jamming through prototypes and jamming through stuff. I saw one of them and I was like, you know, I love this one, but I think the words could be something different. And I just mocked them up. I just mocked them up with Claude. It turned that around. We didn't wait a week. It was like the same afternoon. We're looking at new design creative with the new words. And so, like, that is changing the velocity at which we can operate. And again, I gotta re-emphasize while maintaining quality, like we we don't want to put AI slop out. We don't want to be automated to the point where you don't know it's human beings behind the scenes. We are all humans and our customers are very human, and we want that to come through our brand and how we show up in the world. Uh what Gen AI does is help us accelerate getting to the world-class outcome that we're trying to get to and and not reduce quality and not reduce the fun and the and the energy that people have to do the work.

Kevin Kerner 37:34

Yeah. If you're gonna do AI slot videos, you got to kind of lean into it. I saw something on YouTube, just a short, it was a own well short, the uh, I guess the the property tax company, software company. Yeah, and they had they were full on AI Slop. And I was like, oh, well, at least they're leaning into it. And they were doing it specifically because it was so silly. Yeah. You really got to lean into that stuff. So I was gonna ask one more question, then we'll get to uh our um roulette question for you. But I was you you had to sell a lot of the stuff at the CMO level to the rest of the organization, to the executive team. How has it been received? What's been done? What was the reaction? How have you how did you position it to them such that it was a win for the company?

Nate Skinner 38:20

Yeah, I mean, the good news about where the good news about 8am is all of the exec team is on the same page. We we all believe and understand for at least the last two and a half years that Gen AI can transform this company, both for for on our customers' behalf in the products and solutions we offer, but also for our employees. And so we've done all kinds of things like make sure Claude is available to everybody, make sure cowork is available to everybody, make sure Gemini is turned on for every knowledge worker across the company. So you you can't come into this company from at any level, a brand new SDR or a senior data analyst and not have it be front and setup, like right in your console and available to you immediately. So that's not really been a challenge. It's not like I've had to sell that across the company. We're all on the same page. The real fun part is celebrating the wins, right? It's not everything is a massive project. Sometimes it's small things. And celebrating those small things equally is what's really driving the energy and the enthusiasm across the company. And we have to create space to do that. And that we do that in all hands. We do it in marketing all hands. I do our retros in Claude. We do not use slides. So, like, those are some of the ways that we just keep on reinforcing that this stuff is changing the game for us and for our customers. And it's not, you know, scary, right? If I can use it, I'm not an engineer. So if I can use it, pretty much anybody can.

Kevin Kerner 39:45

Yeah. It's like the question is is it fun or is it not fun? It's a lot more fun now than it was building the spreadsheets, doing the thing. I mean, it's just I was I this is why I have to tell my kids when I talk to them. They're a little bit wary of this stuff. I'm like, man, I used to have to do this stuff the hard way. I paid my dues building the spreadsheets and doing the things manually and sitting with a like a prompt, an open prompt on a page and having to write the stuff. It's like, oh my gosh.

Nate Skinner 40:11

I really do, I think it's it's we're in the kind of a renaissance of marketing and sales as as it relates to technology. I mean, I really believe that. And if you're if you're scared by it or you're concerned about it, or you just don't know where to start, I would suggest you figure it out because this is the best time to be in this career. Like honestly, I've been doing this a long time and I've never been able to imagine the things we can imagine and turn them into reality as quickly as we can now.

Kevin Kerner 40:36

Yeah, so much opportunity. It's crazy. It's uh not scared as uh as much as I am, just excited about where things are headed. It's really fun, a lot of fun. Well, this has been great. I want to ask you one more question. I'm gonna have actually I want to have Gemini ask you one question. I'm gonna put, I put just your literally just your uh just just your profile in this time. And so it's I'm gonna read the sentence to you. I'm gonna click send. Gemini's gonna give me a roulette question here. Okay, here we go. This is a and this is a little long. So as a veteran leader at Salesforce and Oracle, who now manages the complexity of legal and fintech marketing, you've mastered the art of making the rigid world of professional services feel human. Which is good. If you had to argue against your own success, what is the one enterprise best practice you spent decades building that you now believe is actually killing the soul of modern brand growth?

unknown 41:28

Hmm.

Kevin Kerner 41:29

Wow. Something you learned in your past that you think is now you gotta unlearn. Yeah, that's a great, that's a fascinating question for the Gemini that have produced.

Nate Skinner 41:38

Always does the best question. It's embarrassing. I would answer that by saying in a world where everybody has access to the same technology, this is not like only the rich companies can afford it, right? I mean, you can get a cloud license for $20 a user. It should just be part of your stack if you're a startup or you're GE, right? Um and in that world where everyone has access to the same thing, the difference isn't going to be how fast you move and how much you how much ground you take in a particular segment or market. The difference is gonna be how you show up in a differentiated way. And I said it before, it's kind of like old is new again. There's this concept of the customer experience matters. And people look at stuff and know that it it's talking to them because you understand them. That's something that I think you have to, it's easy to be like, oh, this is gonna help us all go faster. And next thing you know, you're using the same garbly-die-gook language that is meaningless as everybody else. And we fought that in the old days, you know, like how do you differentiate? How do you use words that are that matter? I'm a big fan of simple is better. You know, I'm a decomplexifier, not a complexifier when it comes to marketing messages. Um, but in a in a modern world, it's even easier to just let it do it and and like the result. We have to remember that we have to appear to be human and be different. And that's harder than ever, but also part of the fun and the challenge.

Kevin Kerner 43:00

Yeah, great answer. Yeah. It made me think too, is like it's the era of judgment now. It's not what can you build, it's what should you build. Yes. Like it's the should that should is the most important word now because you really can go fast at just about anything. Absolutely. And it'll help you get to worse faster, right? Yeah, that's right. And I've made that mistake too. I have. Like when I first got into some of this, I was like building all kinds of stuff. And then you're like, well, this isn't really gonna do anything. So you really need to make sure that you're judging what how you're using your time, because you can fill it up with fast, with a lot of stuff and a lot of stuff, more stuff than ever now.

Nate Skinner 43:36

Yeah, it's really crazy. Arab judgment is absolutely true. That's a great take. I mean, I I yeah, you know, if you're doing it poorly or doing bad things or bad behavior, it's gonna get you to bad fast. Real fast. Yep. If you're doing it right and taking the time and applying judgment, it's gonna help you get to great sooner.

Kevin Kerner 43:53

Yeah. And as leaders, we all we have to make sure our teams would keep them on that path because you could really drive them off the the Thelma and Louise them real real quick off the clip. Very true. That's it. I could talk to you for a while longer. I will keep up with the story that's going on there at 8 a.m. It's really, really pretty amazing what you guys have done. Uh people want to follow you at the 8 a.m. or you, how what's the best way they should you know get a hold of you?

Nate Skinner 44:19

Yeah, I mean I'm on LinkedIn and my email is Nate.skinner at 8 a.m. dot com. So either way.

Kevin Kerner 44:26

Cool. Thank you so much, Nate, for joining. I know you're a busy guy, so I really appreciate your time. Yeah, I appreciate you too, Kevin. Thank you. It was really fun.