How to Lead Marketing Through the AI Shift with Bill Glenn (SVP of Marketing at Esper)

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0:00

For anyone listening today, I'm Jess Lytle, I'm hosting the Exit 5 podcast and I'm joined by Bill Glenn is the SVP of Marketing at ESPER and out of Bellevue. And Bill, do you want to tell us a little bit about ESPER and what you guys do?

1:39

Yeah, absolutely. And Jess, thanks for having me. First of all, this is awesome to be part of the X5 community and just really enjoy being part of the CMO type of conversation about, you know, where is the market headed, where is AI headed? Like, love that you're doubling down here on AI and I think it's going to be really helpful for the community. So thank you for that.

1:53

Yeah, thanks for being here.

2:12

ESPER is an eight year old company. Now, we are privately held, but we are one of the fastest growing mobile device management companies in the world and we are in the business of trying to create exciting customer experiences through our partners and customers. And the way in which we do that is we build software that powers hardware devices at any industry that you can think of. But mostly we've been serving restaurants and retail locations. So by way of example, your point of Sale systems and restaurants, your menu boards. If you go into a fast food chain, most likely Esper is powering that menu board behind the scenes. So we're a little bit like an intel inside where most people don't know our brand. But when you start to look around you at all the different types of hardware devices like in your fitness centers, we have customers that are driving some of the largest fitness centers in the world. And when you go in there and you see a screen of like what do you do for your workout? Or actually the software that's powering that particular what you might call a dumb screen or terminal. But it's a fun business because we have to think about the uptime and just the experience that all those devices power. And most people don't think about that. But you do think about it when it doesn't work.

2:14

Right.

3:33

And the second it doesn't work, guess who gets the phone call. So we're always in that it's working.

3:34

Well when you don't think about it, nobody notices it and it's invisible, right? Yeah, yeah, yeah. It's so interesting. Software to power hardware. I love learning about like all different types of software because you never think about all of these nuances like what you just said and like now I'll probably be paying more attention to that that you made me aware to it.

3:39

But absolutely. When you walk through the airport, all of those screens that you see with advertising going on, like we're most likely behind some of that as well. But yeah, it's sort of like your everyday experiences. Just look around for like we were just talking to one of our customers and they work with all the telecommunications companies and they think about the first responders and all of the two way radios that are used for first responders, those actually have very small screens and they have software and apps being pushed to those what you would think are just really standard devices, but just the technology behind that is so much more sophisticated and the ability to connect over 5G like we are touching, you know, all the telecoms without even again sort of them knowing it. And if we can help first responders make it a crisper phone call, then you talk about a really good customer experience. It's like how do you make sure your first responders are always at the ready through the hardware devices that they use.

3:58

Yeah, that's like critical. Critical. So that's great. So you guys like you vast over many different industries and spaces.

4:55

That's right.

5:02

That's really cool. I'm so excited to have you on Bill. And like you said, he's part of our private community at Exit 5. Our CMO Council clearly has impressive experience, many years leading marketing teams, long enough to have probably seen multiple waves of change. Maybe not like what we're seeing with AI, maybe. But what I really appreciate about your perspective and what you said to me when I asked you to join the podcast was how grounded and, like, honest your response was when it came to AI. And we are all. We are all learning this together. And I think that that's actually really what makes, you know, your approach so effective. Because I think almost no one feels like they've cracked the code here. Even the big players feel like they're winging it. You know, I certainly do, and I'm not a big player, but even the folks that I follow are feeling that. That I would consider power users in the space. So I think that that's. It's a really. It's a really great approach to this. Tell me a little bit about that. Like, how is that approach helping your team?

5:03

Absolutely. Maybe I'll start with this, because this even happened after you and I first spoke about this. So I sort of doubled down on I don't know what I don't know, and that's okay. And I've taken an approach. Started a year ago, but really trying to double down this year on, like, the growth mindset and just being overly curious and being okay with not having the answer to everything. And, like, that just starts with, like, being more comfortable with yourself as a human to be, like, I don't have to be perfect, and that's okay. But what I do need to do is recognize my opportunity to learn from others. And I believe that AI just like when the Internet was born. And yes, you were correct. And, you know, I've been through that. Like, oh, now I'm in the working world and there's this thing called the Internet changed.

6:05

Everybody works, Right?

6:52

That's right. And I just had kind of started in the working world coming into this, saying, hey, how are we going to adapt to this? I was living actually in San Francisco, so sort of was at the forefront of how do we think about putting this into our business model and how do we move from brick and mortar to everything's going to be E commerce? And now here we are again. Right. And what is that? 20, 25 years later? And it's that same inflection point moment. And I recall distinctly, you know, some of my roommates in San Francisco, we were all like, this is the next big thing. And we have to embrace it. And we were all like looking around at each other like, where do we start? Where's the book? Where's the playbook? Right? Nobody has it. And so here we are again. But you hundred x kind of I feel like the impact of AI to just the Internet. And for me this is where I come back to the double down of I literally wrote a like a detailed sort of like, what's my biggest gap for the year that I want to solve either personally or professionally. And this one ties specifically to both. Where I basically just said I'm going to embrace AI and I'm going to try to do it in both of my worlds in a way that it can be useful to me, but it doesn't determine sort of like how I live my day. And what I mean by that is like, I want it to be my co pilot, truly, and I want to learn from it and I want it to know me. But I also am like, it's important to me to keep the human element. And the curiosity is sort of like the where does AI do really well and where does it not do well? And let's not just over rotate towards everything has to be AI. And that's the mindset that I've not just tried for myself, but I've literally sort of shared that with my team to say, I think you all are ahead of me because I think a lot of my team embraced it faster than I did. And I'm like, how can you actually turn the tables and be the coach back to me? Let's sort of eliminate the hierarchy of the org and this is everybody's opportunity, not just in marketing, but in the entire company to really think about how they're going to think about their career progression. And we are just trying to embrace that growth and curiosity mindset and we want to empower the entire company. But for me, marketing team to be okay with curiosity, growth and failure as long as we're learning and sharing those learnings in real time.

6:54

Oh gosh, there's so many points to that where I'm like, oh, I want to come back to that. Oh, I want to come back to that. So I'm going to see if I could remember all of them because that's exactly what I think is needed right now. Where a lot of people are seeing, you know, some AI power users on their team, but they're not really sure, you know, where to start or even to find their own people in the company that are already doing these things. And a lot of the Times, I think as leaders, we think, okay, we need to outsource. We need to go find some AI ops person and GTM engineer. But most likely the folks that are experimenting with AI are probably already on your team, so have them surface that in some way and pitch some ideas to you on things that they're doing. That's helping to kind of eliminate some of that manual boring stuff. I think that that's where AI can excel, where it keeps us in the thinking SC and the strategy seat, but it's taking away all the grunt work of building an internal deck or building a deck or analyzing a spreadsheet for two hours. Right. Where we still get the output that we want as long as the quality is there without having to do that execution work. But I loved your early on point where you're drawing the comparison between the Internet coming out existing and that essentially eliminated all of the books that I used to use or my dad's encyclopedia collection. That is how I did my homework growing up. Yeah. So it was probably. Do you see comparison? Because this is as big of an event as that, if not bigger. Right. Like, there hasn't been anything like the Internet since AI. When you think back to that time, like, was it similar in that it had to. Because what I, what I'm seeing as being a big issue with just like adoption and confusion. It's not even just about how many tools there are, because there are so many. It's overwhelming. It's. It's. It's kind of advancing at such a rapid pace, but it's more of the behavior. It's how we worked this way this long, and now we just have to immediately just work this other way. But how, you know, how AI, depending on the tool or the workflow, it's different for each person.

9:21

That's right. That's right. And maybe the way that I would sort of approach that, and I 100% agree with you, like, this is the exact inflection point, moment and feeling that most people had in the mid-90s. And it was those that were courageous enough to say, I don't know this, I don't understand it, but I'm not going to shy away from it and I'm going to fail and learn and fail fast, hopefully, and just try it in different ways. And that, I think is maybe the biggest takeaway for our company is it was almost like we were ready ahead of our board meeting, when we knew some of our board members were going to be like, what are you doing with AI? And so as an Executive leadership team. We actually got together and we said, said, we need to get ahead of this first because we need to help guide the rest of the company on, like, what is the right approach and do we have a policy around this and how do we kind of put guardrails without putting too much constraint around that? So I really give a credit to our CEO and our leadership team to step up and say, let's not shy away from this. And I think our biggest learning win was we did assign sort of like one of our ELT members. We called it the czar, but we intentionally said, yes, you sort of are the collector of, like, how are each of the departments thinking about using AI and like, what's the best use case or tools? But we didn't say, like, that single person had to run our AI approach or project. We basically said, each functional leader has to think for themselves, but we have to continue to meet collectively so that we don't go build our strategy around AI and silos. So we. So we said sort of it's like the leadership team, we want to bring in other people who are AI forward. And we did. But we're like, it starts with us, and we have to show that we're embracing it. Otherwise the rest of the company just either they won't, or they'll go do it rogue. And like, that's the worst thing that can happen is like, we want people to embrace it and use it and feel comfortable bringing their supplemental, you know, copilot with them because it is an absolutely game. It's an absolute game changer in terms of a, you know, tooling and how you can do your work, like you said. And for the folks who are still afraid or just don't know how, the answer is like, just jump in. Just take that first step, right? Don't think about the end product. Just take the first step. And it's surprising how many people, myself included, weren't ready to, like, just take that first step. Because I was like, oh, I want to know everything before I go. And like, that's that same way with the Internet. You're like, you. You'll never. You'll never catch up to the Internet. So, like, just get in there and like, you know, figure it out day by day.

11:31

That's so true and such a good point because a lot of the times I think we think about our own department and silos and like, well, let me just solve this for even just marketing. But then you don't think about, you know, well, you do. You have to at the level that your organization is, is doing, zoom out even further with, okay, but how is this going to work across sales and product and customer success and everything else? And, and then what are the tools that we need to connect the pieces to? Do we need a rev ops person? Do we have an internal person that could do some of this? Is this where. How do we. So that is. It's actually really interesting to hear how you guys have rolled that out and thought about that piece first and then going into your own individual respective departments and thinking about, like, okay, so what makes the most sense for us. But I think there's so many good points there. And I think that's why even just with when I launched this newsletter that's like AI focused for marketers, I tried to be as tactical and specific as possible. Because with any, like, anything that you're learning, even like a software, it all feels very abstract until you, like you said, just get in there and actually do it and see the outcome. But I think there's also, like you said, there's this fear. And it's interesting because it's different depending on who you talk to. But for me, this wasn't as big of an issue, but I still wanted to find tools that were protective and like, proprietary. So what's interesting is with the fear around, I think there's fear around, like, security, data misuse and folks thinking, like, if I put this in here, am I going to lose my job? Is just like, not even worth, you know, putting, like, doing this. So they just don't do anything and then also like, mistrust because, you know, we know that these, these AIs can lie to us, they can hallucinate. So once that trust is broken, I think it's harder to like, trust. So I think as a leadership team, you're saying, you know, hey, here's some guardrails and like, we understand that these things can happen, but folks don't feel like, wow, well, am I responsible for the outcome of what, whatever the downfall is. Because I trusted this AI and it wasn't correct. Right. So, yeah, that can be scary.

14:13

Yeah. And maybe I can comment just a little bit further because we did take it one step further than just saying, you know, each functional leader has to figure it out. Part of our committee around AI included our IT leader and our people team leader, because we wanted there to be an official policy such that you have a reference document as an employee to be like sort of what is inbounds and what is out of bounds. And then that has to be kept up because things are changing daily. You know, tools come out that you're like, I haven't tried that.

16:27

Right.

16:58

And more people are bringing them into the org. So we did define a very clear process for folks to say it's never going to be perfect. But if you can sort of follow these steps of if, you know, if you want to introduce a new tool, here's how you would bring it to either your manager or specifically to our IT team who also runs security for us. And there's. So there's a little bit of a vetting process. It's not like the full wild west.

16:58

That's great.

17:24

Yeah. But at the same time we're like, we kept sending the message of if you find something that you think is going to be game changing for our company, don't shy away from it. Don't make your own determination around security or compliance. Like we have people that can help you with that. So we kind of encourage them to say go pilot it if you can, without ingesting any proprietary company tech information into the tool. Like just play around with it. A lot of these tools out there, right, have like your, you know, five, your seven day or 30 day free trials. Like without giving away the IP, you can just get sort of a feel for like what could this thing do? And then we're like, bring it to us and if you think it can be valuable, like we will evaluate it at a committee level and we promise to be fast around like the decisioning around something.

17:25

Yes.

18:16

Because we know it has to sort of move at the speed of business.

18:17

I love that. I love that. I was actually reading about how Google's doing this internally and they did something like it's very similar to that and then they just made it more public where they're trying to basically find like the people in their company who are like the AI rock stars, the people that are doing this and they're like, but, but they want to hear about it. And I love what you guys did where you, you made them feel very comfortable with that experimentation. And just like, here's some guard guidelines, here's how to do it, you know, without leaking that, that info, but see if it can eliminate some of that work. So they did like a shark tank kind of style where someone could bring a tool and like pitch it and they just, no decks or anything, they just show the tool. You know, they share their screen, they walk through like, hey, this is how. This is eliminating two hours. I don't have to actually put this deck together anymore. I give it the prompt, it spits out a deck in 10 minutes and I go and work on something else. So what was interesting too is they, they push for folks to pitch like the boring AIs, like the, you know, the, the ones that are going to not like the flashy like, oh my God, this is like the one that's doing predictive analy, but it's more of like what's actually taking your, like doing the work you hate. Which for me was just living in spreadsheets when I just, I know the data that I need. I've got my report from the CRM and I'm like, I just want to get that output. But do I want to spend two hours in Excel, you know, doing, you know, pivot tables? No. So that's, those are like the instances for me that I'm like, I don't enjoy that aspect of. But this is a very big part of my job and I need that output and I know the questions that I need to ask to get that information. I know the data that I need to give it. But as it goes and works on my spreadsheet for two hours or you know, 30 minutes, I can go work on strategy or something else. So those boring things that really eliminate the manual work, I think are a great place to start.

18:19

Yeah, maybe if I could just add to that. Because I've been thinking about this in real time as how I kind of roll this out to my team is it's like a maturity model where we're like, we're all at phase zero or phase one, which is exactly that of like, how do you think about that repeatable process oriented work product that you have to do every day? And to me, AI phase one is about productivity gains and being intentional about efficiency. And that's how folks are measuring it, which is like, how many hours did I get back in my day? Right. And to me, the holy grail of sort of when I think about my team being successful, it's the ones that go, yep, I've already figured out how to do phase one and now I'm into phase two of what's the impact type of work that can be given to AI? Like you were saying, it's like, how do you have it be truly your copilot to be like, what insights can I get from my customer data? What is, you know, how is it that machine learning can actually assist my decision making processes?

20:14

Yes.

21:23

Less so about the like, it's almost Phase one is going to become table stakes at some point in time and the expectation is sort of already there from some forward thinking boards of like we expect the ELT to be all over the efficiency gains. Now it's the what are you learning in with augmented, you know, brain power and capacity with you as a co pilot that allows you to sort of see where the market is headed and what are you doing about that as humans to take advantage of the ability to get those insights out of machines faster. And I haven't found a lot of companies who are there yet, but I think that's where we're all going in that phase two and at some point in time I think then we'll be like the phase three and the phase four which is like how are software companies building that right into their product and there's some that are already there today or they're getting there faster which is like how do you have that copilot sitting right on your desktop in a way that you're just interfacing with it and getting those insights without having to sort of go off into your own GPT and think about it as a separate workflow? It's like, no, it has to be just in your daily rhythm of work. And to me that's the phase three that I'm looking forward to.

21:24

Yeah, no, I love how you explain that in different phases because it start to get complex when you think about toolage and behavior change with humans and adoption and then learning tools on their own to help them with their own day to day work. But I think you're right in that, that first phase I was reading about this where you know, you've got for an example, a product marketer who's using AI to using NotebookLM for an example. I know a lot of product marketers love this tool because they can, you know, use call transcripts and upload so many sources. Sales, you know, sales call transcript, use that to create content or battle cards or give them information. Things that would have taken them weeks to do are taking them hours to do. But what I'm finding is that, you know, they may just be a more tech forward person and they tried these different tools and they've realized, oh my gosh, I can get the output I need in hours. Which is, you know, if you were doing this before the tool and after the tool, it's kind of a mind blowing experience. But a product marketer told me that her boss is now asking like, how do I scale that across the rest of the team? Because they're working at two to three times the rate and capacity of what? I guess a human without AI is working in that way, just from a workflow perspective.

22:37

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23:59

And I would just say to that it speaks to exactly where we started. Which is if I think that I should be the leader that comes in and has all the answers, I know I've gotten it wrong. Which is let the folks on my team who are more AI forward than me lead this in a way that it allows them to feel valued and validated that they have a real meaningful contribution to the company. But it also gives them a clear path to say you actually are impacting the trajectory of this business in a way that not only will they become, as an example, smarter marketer, but I look at it as this is your inherent professional development happening in real time. So rather than the traditional like let's Work with the people, team on like a 6 to 12 month professional development program and we should send you to a conference. It's like, nope, nope, nope. It doesn't work like that anymore. Like, let's let anybody at any level in the organization leapfrog leveraging AI to be like, they can make such impactful decisions and produce such impactful outcome that I think it really is about, like restructuring the organization. And like the change management, like you talked about, like, this is a change management moment of maybe this gets rid of the hierarchy of the workforce. It feels like there still needs to be a little bit of structure. But I don't like thinking about this in the context of like, well, you're at this level and so you get this level of tooling. Like, I want to empower people to be like, how did I stitch all of the processes cross functionally together in a way that it breaks down the silos? And I think that's going to come from people who are in the tools every day going, oh, I didn't realize that if I integrated it with this other tool or it's, you know, already assimilated with our CRM. Like you said, like, we're gonna, we're actually gonna be able to empower people outside of marketing to help us find market insights. That would be amazing if an engineer came to us and said, hey, I think there's something here and there's a market here. Because I'm watching this happen in the way in which we're trying to create more of that visibility through the AI tooling.

25:37

Yeah.

27:55

And it, it was interesting because I was, I was reading this, it was like a report or maybe an article that just came out from Google where they were talking about like how with AI, it's just, it's advancing at such a warp speed that like humans, we tend to adopt things more like logarithmically. So like, well, there'll be a big burst of interest and then you'll start to feel like there's a plateau or flattening. But the gap feels so wide because it's like the AI is advancing the AI even more due to the nature of AI. So like, the gap keeps growing wider and wider. So it's like it's less even about. I think it started with the tooling, but it's like less about what tools. It's more of like the adoption piece. Right? The behavior change piece. Because you could find the best tools for your business for every single person, every department to use. But if we don't Fix the behavior change thing. We're not thinking about that. Then we're going to just be kind of observing from the outside going, well, what do we now what? Because that's why I love your approach, which is just bring it forward and more experimental and not afraid to fail and just being more courageous and actually bring forward a prompt that didn't work or bring forward Even with the AIs you're experimenting. I was terrible with some of these tools when I first started using them. I'm like, oh, is this that good, really? But then I actually tried different things and I started, you know, and I like, I got better every time I did the tool. So even sharing those failures and having that culture, it's really a culture change too.

27:55

I think with this, it absolutely is. If I can use a perfect example of that. I was fortunate enough to meet a gentleman who was the former AI strategist for Amazon.

29:29

Okay.

29:40

And he actually went out on his own and he's now started a company that is basically a training company for AI specifically. And he wants to do it mostly at the executive level to get people to kind of embrace it. But his insight was, I'm starting with the CEO paired with the chief human resources officer. Right, Chief people officer. Because it's a change management meets human issue that we're dealing with here. And he viewed it, and I view it the same way, which is it's an amazing way to elevate the chief people officer and tie that person to technology, but keeping the human element, because again, it's not that one leader does it for the whole company, but if the chief people officer is the one that kind of bring, you know, kind of is leading and rallying the company together, it almost ensures that you keep the people element to this. And it's not about the tooling, it's about the change management and how people interface with the tools. But from that, human stays not just in the loop, but really top of mind for how does this shape your culture? So to me, that was the biggest insight. And what I learned, because I've done a lot of marketing in the HR space is the age old adage is like, HR leaders never have a seat at the table. And I'm like, wow, this is their inflection point, point, moment to actually get the seat of the table. So the CPOs that are out there, you know, embracing AI, they actually can elevate their career and they can be tip of the spear around technology. Which is like kind of ironic that it's like it took this level of technology to actually elevate the chief people officer in the company.

29:41

I love that. Thank you for sharing that because I think that this is so helpful to a lot of folks who aren't really even sure how to, as a leader themselves approach this, but also with the other executive members on the team and how they should all be working together. But I think that is so smart to start from the top and not just think about this from a tooling perspective. That's one scenario, but it has to start from the culture and the behavior perspective. So that's great. Yeah, I love it. Anything else you want to hit on with AI and your team? I feel like we got some good stuff there. I think that's going to be a lot of what you said I think is going to be just absolutely critical to a lot of, you know, CMOs and marketing leaders all just trying to figure this out right now.

31:28

Yeah. The only other thing I'll add, and maybe this just kind of gets into the other element of just who I am as a human around mentoring and mentorship and what's really important to me. And I'm also very biased. I'll just say it up front. I have two kids in college right now, so I've been living through what does it look like to have your high school age students embracing AI, AKA oh, you're, you're using it to do your homework. Let's have a conversation about that. Right?

32:14

Yeah.

32:43

So that's the fun part of it as a parent, but more so I think now as they're into college and the mentorship I've been doing is more with MBA students at the University of Washington. And that to me has been really eye opening to come in and be able to guest lecture.

32:43

Yes.

32:59

Because those students are already 10x ahead of me and I know that coming into a lecture. So I'm like, how am I going to lecture them? And their questions are definitely more oriented around AI and the mentorship that I'm trying to do with them, I think. And the teaching that I'm doing is not just about the curiosity and the embracing, but I'm trying to pitch it more as a. Not to be sort of anti institution, but as the person paying two private school college bills every quarter or semester. I'm like, is this the way of the world? You know, because it's gotten a little outrageous and so maybe if I can be that contrarian a little bit, it's like, you know, embracing AI while you're in school. Is your leg up to Entrepreneurship. And you know, that I think is the most interesting thing about being in higher ed today, and especially an MBA program.

33:00

Love that.

33:57

I'm hopeful that, like, more people will come out saying, I'm in the me economy now and how do I leverage these AI tools to actually put together a product, Product being them and what's their personal brand? And that's a lot of the mentorship I do is like, what's your personal brand and what's your distinct value that you bring to an organization? And maybe you go work for a large corporation. But I think a lot of folks are kind of like coming out of the, in this next generation. They're like, like, I don't necessarily want to go that path and I have a really interesting idea and now I have the tooling behind me where I don't necessarily need, you know, 10 engineers to go build something. So this is, this is the fun of like, it's going to change the sort of the perspective of like, what are my job possibilities? And I try and I, what I'm trying to push is like, everybody is talking. They always play the fear angle of like, oh, it's going to take your job. AI is going to take your job. Hell no. Right? You could, you could have made the same case for the Internet. Right? And so exactly.

33:57

Just going to change your job potentially.

34:59

It'S just going to change. So just, just think about the, what's the change aspect where you take control of your future as an entrepreneur and 10X and disrupt A, you know, a traditional industry that is ripe for disruption. So it's fun.

35:01

I love the entrepreneurship angle and I think it's really cool that you do those. The guest lecturing. I recently got into that as well over the last few years where I've been doing like. I'm an adjunct professor at Florida International University and I love it and I was so impressed with the students I teach. I teach digital marketing and marketing analytics. And over, like when I first started teaching, really AI was just chatgpt then. This is like a couple years ago. And I was worried about, I knew that they were using it to do the work. So I did try to structure some assignments that made it, I thought almost maybe impossible to do, but at the same time just kind of like, like there was no policy around there still, I think is a hard thing to figure out at the academic level. But what I tried to do from my end is like, I wanted them to understand marketing as it is today. And I know a lot of marketing curriculums and these Are like typically seniors in their bachelor's programs aren't getting the modern take on and a lot of us like that. I've been doing marketing since I when I graduated in 2009, so 15 years. So a lot has changed in that time and I learned on the job. Right. I didn't learn in my program. Whatever I learned in my, in my bachelor's and master's is probably changed or outdated outside of just the fundamentals. I think the fundamentals of marketing are still there. We just need to use AI to amplify them. Right. Still just good marketing. But I think that. So I tried to introduce things like tooling like Lovable. I did a Lovable assignment and because I want. But I never thought about it from the entrepreneurial angle. I love that because there is a moment right now where even the way like software was built in 2017 and 2018 is very different than how software is built today. Right. And how like a lot of it's just being a builder and entrepreneur, sure you could buy code some things, but it's about. You're more like an orchestrator and you could tie different softwares together to make a software. It's just even that has changed so much. So there is never a better moment, you know, to be then go build, go be an entrepreneur and build a software. Build a. Like there is a time for that and it's, that's a smart way to think about it because I don't know if if your children's. The academics have figured out how to manage that with ChatGPT but like use it to get smarter and successful and make money versus, you know, just to do your homework.

35:16

Yeah. Well, I hope they're doing it because that's, that's what we're paying them for. We hope. But no but, but in all seriousness, I think the, the interesting point of the sort of the entrepreneurship meets the working world where we're at at Esper. And I'm going to use your example around Lovable. At Esper, we did a hackathon recently and we intentionally sort of mixed up, you know, the departments so that we would have some engineers and some marketers and some of that operations people all together. And we asked everybody to kind of come up with a business idea that would help support the company. And we actually did in our group group we did use Lovable to build an app and it ended up being an app that was more specific to capturing leads at in person events in real time and being able to distribute that information inside the company. In real time. And as a marketer, I'm like, oh, my God. And then the funniest part of the whole thing was at the end when we were just kind of doing our own, like, retrospective as a team of, like, what worked and what didn't. The thing that came out by not one of us, but three of us, we all looked at each other and we go, so who's ready to actually leave Esper and go start this business, go build this thing? Because there's a need, right? So it's like your entrepreneurship. So of course I'm like, well, I think that's Esper IP now, but, you know, put that aside for a second. But it is. It's the fun of it of like, oh, my gosh. I think we actually just built something you could use. Yeah. That we could use. Yeah, yeah.

37:44

You're literally also. This is also going to change software, right? It's going to become more commoditized because we could build our own software tools now to do that. And I know you just had a big conference, right? You had your nf.

39:13

Yeah, the National Retail Federation. So NRF in New York, deploy those.

39:23

To the sales team, and they can just record it, get it in, and boom, you've got emails going out to those.

39:28

Yeah, no, honestly, like, here we are trying to collect leads across the company going, man, if we only have this.

39:34

Tool, we could make. Yeah, yeah, I've done that on a couple things just to help our internal workflows too, where, you know, just there was this manual process of literally loading HTML for a newsletter. And I'm like. I'm like, there's no way in 2026 we're still spending hours writing HTML code. So I built a little formatter tool that we could just. There, three hours gone. Like, things that probably may exist. You could go look and buy them, but custom to you. Takes a couple hours to build. Have ChatGPT build your prompt for you, build your logic, and then, you know, go. Go build a tool for yourself. That's so cool.

39:40

I'll add just one last thing. And I think that this ties back to sort of the next generation, too. I've been thinking a lot about the distraction economy, right. With all the apps that are out there and all the node push notifications. And they say, I recently read a book. It was called the Ruthless Elimination of Hurry. Really interesting book.

40:17

Love that.

40:39

And they basically said that we now have the attention span slightly less than a goldfish.

40:40

Less now. Okay.

40:46

Less now now at 8 seconds. And so in that way. To your comment about, I'm just going to go build something in two or two hours. My advice to folks on this is like, you actually need to like, set aside dedicated time and it call it experimentation time and build it into your calendar. Because to me, that's the only way that I could actually make this work was I'm, I have to commit to this time as this isn't to, you know, go do something else. Fifteen other things. It's one or two hours a week minimum. That's experimentation. And I'm trying to encourage that with my team to say calendar block, because if you don't guess what, everything's going to be in 8 second increments and we're not going to actually get learning from it.

40:47

That the last point you said too, especially where you as a leader are giving permission to your team to do that, that needs to be said because I think that there's maybe a lot of folks who want to do that, but you know, they still have things that they have to execute on that obviously, obviously take priority, be smart about your time. But just hearing that, I think from, you know, your, your, your leader, I think will encourage folks to feel like it's okay to do that and to make time for that as part of your workday and ultimately will have payback compounding returns for you, your team, your organization. Because I also think that like just the, the exercise of learning AI and going in there, that is what, for me at least it was almost like a gateway into more AI, you know, so it's like the more you use it, the more you realize its capabilities and that you're, you get more excited about what's out there and like, you're like, oh, this is what the. Okay, I get it now. It's less abstract every time. And like the fear in the wall that you have continues to break down over time. So even just like that as a behavior change, you know, exercise.

41:31

Yeah.

42:36

And you, you. I'll just. Sorry, I have to keep building on this. This is so much fun. I'm loving this conversation. Like, so if you take it to that next level, which is you and I both being teachers, right. Or mentors, how do you know somebody really learned something? They have to say it back to you. So have them explain the tool and that's where they'll realize their own gaps of like, what do they know? What do they not know? Have people challenge them or ask questions, and then they truly become the expert either on a tool or a process because they're Invested in not just the learning of the tool, but the how is that then tying back to the change management of the business. But like, if you empower them to truly be the teacher and flip the role and be like, you know, tell me what you learned and give them that space to say and what did you fail on? And like, how are you going to change from there? That to me really is. That's the moment of they go, oh, I do feel safe.

42:37

Yeah.

43:36

Because you let me explain my failure and then let me tell you what I'm gonna do differently next.

43:37

Yes. It's such a great point you make. Cause I've said this to somebody else before where I actually too, when I'm teaching, I learn more. So like, even when I am like, all right, I really wanna give them this lovable assignment because I wanna like, I want them to be lovable. Was just out for like six months at this point now it's like the fastest growing company in history.

43:41

Yes, it is.

44:01

And I'm like, oh, what a way to get them like ahead and just for them to, to see like what is available to them. And it was when I put this assignment together, I had to do a lot more research and I learned a lot more about lovable through that experience. I'm like, so you do. When you're, when you're presenting on something, you need to feel like the expert on it and you need to become, you know, especially I want to feel like I'm really, you know, able to answer any questions to it. And I needed to learn at a deeper level myself.

44:02

Yeah.

44:29

So, yeah, and I was just so impressed by some of the, like, the things that they built marketing dashboards just to even use for like internal calls. Like you could put your metrics in. It gives you like a nice report. Some of these. I was like, oh my God, this is good. Like, I might use this. This is great. Um, but yeah, like that. That you learn by teaching in ways.

44:30

But that's right.

44:48

Yeah, I love it. I know where I'm like, so sad. I'm like, we have a few more minutes. If you have. I. I would love to just dig a little bit into if you have just a few more minutes left, like the leadership perspective and like, like, you know, me coming in as a new head of marketing in this role at exit 5 and just any new, you know, somebody becoming a VP for the first time or CMO for the first time, what is some advice that you would. Would share to those folks? Especially, I guess in this day and age but they've got all that great information from the first part of the call. But any like main piece of advice you'd give somebody in their like first 90 days or even just beyond, if.

44:49

I can take it at the leadership level, like first, first time marketing leader. I think the biggest learning that I had was I thought that the job was about being the leader of marketing. In the case of being like a part of the executive leadership team. Cmo, if you're at that level, the biggest learning I was given was that's your first team. Right. And first team is more of a military reference. Right. And there's books about that where the executive leadership team that is your number one team, then the functional team you manage is the number two team. And I didn't get that right at first. Right. I was always about like, how am I going to defend my team and how I'm going to promote marketing. And it's all about like making marketing look good. And it was like, no, is the real value as a true marketing leader is you understand the rest of the business, you build the relationships with the rest of the executive leadership team, you understand what is important to each of them and like what is the mission of the company and you build your own personal brand in a way that's like, oh, he's just not the marketing person or she's just not the marketing person. She is thinking holistically about the company and what impact we can drive for the company. And it just elevates you in the, in the company and in the eyes of the CEO or even the board that much more that they know they just hired a business leader, not a marketing leader. So that's probably number one.

45:26

That's such a good way to look at it. Because I think that, you know, a lot of folks that are promoted into this role were usually very high performing marketers and ICs and hadn't had to develop the skills at that level to you know, to be thinking about, you know, thinking like, okay, I just scale what it is that I was doing really well, but they're not really paying attention to the business aspect of it and how marketing fits into everything else and how marketing works with the CFO and the CP and the CEO. And yeah, I think that that's a great, great call out and just thing to remember that you now have multiple roles in what you're doing. Yes, scale your team, but there's a bigger picture. And to be a respected leader in marketing and to be respected by your leadership team, you know, you need to understand that and know how to deliver. But how do you learn how to. How to do that?

46:48

By.

47:44

By failing. Right. And being. Yeah. And being humble. Right. And. And. But no, I would. I mean, I think there. That you can do a good example would be like, hey, what are the metrics that the CFO and the CF CEO are using with the board and how do they think about the health of the business? So if you haven't engaged with a board member and build a relationship with a board member and build a tight relationship with your CFO and CEO to be like, what are the metrics we care most about? And make sure you have a good understanding of, like, how are they actually calculated and what are the levers to actually impact those metrics? And so you can show up talking about beyond just the traditional marketing water waterfall metrics. You can be like, hey, I noticed this about, you know, this metric, which.

47:45

Right.

48:27

Hopefully doesn't even, like, maybe it's indirect to marketing, but you go, I have a perspective on this. And like, that just immediately changes the game for you. And the, the thing I would say just sort of later in my career now is that it also opens up the door where you see a lot of, you know, folks saying, well, marketing's now rolling under the chief revenue officer. And there's a lot of, of, you know, consternation about that. And the way I look at it is like, stop being the victim. You have every opportunity to go be a CRO or a COO or even a CEO. And so that's how you. That's where you start, is like, be a steward of the business. And then your career progression doesn't necessarily have to end at cmo. You can actually go start thinking about, like, you know, do I have the capacity or do I have the interest of going broader than marketing, But I have this deep level of marketing knowledge and expertise that is just an added component to whatever I go decide to do next.

48:27

So true. Especially in this, this era where, you know, we have AI with us. I've seen some really strong CROs with marketing backgrounds who are, I think, initially going that route and then just got so deep into how, like, the revenue impact of marketing. Right. And that's where it should be, where marketing's focused on pipeline and revenue and what really matters and being able to speak in that way and at that level, but then owning that, you know, and if you have a sales background as a marketing leader, you know, you can, you can see that across, like, the spectrum. But.

49:24

Yeah, exactly.

49:58

Well, thank you Bill, this is awesome. I love this.

49:59

Yes, I agree.

50:02

Are you coming to the marketing leadership retreat?

50:03

I am. I'm super excited. And yeah, can't wait to meet other fellow marketing folks on the CMO Council. It's going to be awesome.

50:06

That's going to be awesome. I will see you there as well. I will be in Arizona. I'll be attending that. So we'll meet in person. So can't wait. Yeah. So this is great. Enjoy your weekend. Hopefully you've got some good family time planned.

50:14

Absolutely. And go Hawks. Sorry, have to say it.

50:25

Go Hawks. All right, see you, Bill. Thank you.

50:28

Thanks, Jess.

50:32

Bye.

50:32

Hey, thanks for listening to this podcast. If you like this episode. You know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. So we've built the number one private community for B2B marketers at exit 5. And you can go and check that out. Instead of leaving a rating or review, go check it out right now on our website, exit5.com. Our mission at Exit 5 is to help you grow your career in B2B marketing. And there's no better place to do that than with us at exit 5. There's nearly 5,000 members now in our community. People are in there posting every day, asking questions about things like marketing, planning ideas, inspiration, asking questions and getting feedback from your peers. Building your own network of marketers who are doing the same thing you are. So you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join. Join for seven days so you can go and check it out risk free. And then there's a small annual fee to pay if you want to become.

50:37

A member for the year.

51:34

Go check it out. Learn more exit5.com and I will see you over there in the community. Hey, it's me, Dave. Our friends over at Customer I.O. are sponsors of today's episode. They're a really cool company that helps marketers turn first party data into engaging customer experiences across email, SMS and push. And they built their platform for marketers who actually care about the craft because marketing is a craft. It takes creativity, thought and taste. Right now, everyone thinks they're magically a marketer because they have access to AI and the result is kind of painful. More robotic emails, more noise, more bleh. AI isn't magic. It's not going to fix bad strategy or write great copy for you magically. But the best teams also aren't ignoring it. They treat AI as infrastructure. When it's built the right way, it actually makes marketing feel more human, not less. And that's what customer IO is doing. Their AI handles repetitive work like setup, orchestration, and tasks that should be automated so that you can focus on what actually matters. The craft of marketing, the strategy, the creativity. This is how good marketers are using AI right now. Not to replace thinking, but to support it. If this landed with you at all, this idea about the craft of marketing, I want you to go and check out customer IO. Go. It's customer IO, exit 5. Go and check them out. Customer IO, exit 5.

51:35