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378- Stop Losing Executives w/Bill Dillmeier · You've Been Heard

• 0:09
  Speaker A: So welcome everyone. Back to dissecting popular IT nerds. You had a little preview there. We're talking with Bill Mir Dillmeier. What's really cool today, guys, is we can even role play this a little bit. We're speaking with a cfo. We're speaking with a cfo, someone that you should have a close relationship with. Any cto, cto, cio, IT director, person looking to climb up the, the corporate ladder in IT needs to have a relationship with the C cfo. So we're just going to play, let's just role play this for a second. I'm going to just pretend I'm, I don't know, IT director and. Hey, Bill, I'm Phil. I, we have, we haven't had a chance to meet yet. I'm, you know, I just started, you know, a month ago and just kind of just going around getting, getting ready to meet everybody and you know, I don't know if you had a few minutes to talk, but would love to just chat with you for a few minutes, right? This is what we should do. What do you think?
• 0:58
  Speaker B: No, I, I love it. I love these types of conversations. One of my favorite roles is playing the role of a finance business partner. So at any given moment I actually have five different bosses. Head of sales, head of marketing, head of product, head of engineering. And I actually enjoy sitting with each one of those incredible leaders who have so much domain knowledge and hearing what's going on in their business. And I'll play the role of internal consultant, external consultant, and at times I'll give you filtered and unfilter altered advice on how to move forward within your org. So these are actually some of my favorite things where we can talk about some of the challenges you're facing and how we can partner to be able to move forward.
• 1:40
  Speaker A: So let's just say I took over a new role. New in the role. It we meet, I come to you, I say, Bill, I just, I gotta know from the perspective of it. I mean obviously the old lies out or whatever it is. There's been a changing of the guards when it comes to IT or technology leadership, just in general with, with what you've known over the years, what's what. Or here, better yet, how about this? As the CFO of the business, I just want to know like what keeps you up at night? What's your biggest problem, frustration or concern in your job right now? Forget technology. I just want you to forget my job completely. I just want to know what keeps you up at night.
• 2:20
  Speaker B: No, it's a great question. So for me, honestly, it's multifaceted. It's everything from the quality of the leads to the effectiveness of my sales team. But really, it starts with the product. Have I solved product market fit or as I like to say, I like to start with another P, which is problem market fit. Are you actually delivering a solution that solves a problem? And how can I go ahead and partner with an IT organization to be able to go ahead and solve that problem and make sure that they're properly sourced?
• 2:55
  Speaker A: So you're not just worried about EBITDA and like cost of goods and, I don't know, operating costs and all this type of stuff as a, as a CFO or. I mean, I'm thinking I'm playing cfo, you're playing CFO right now. So I'm just curious.
• 3:08
  Speaker B: No, I will tell you that I am not the typical cfo. I'm not the guy that's going to look in the rearview mirror and tell you what happened last month. I'm actually more of an operator. And I'll tell you what's actually going to happen over the next 36 months as all of these pieces come together so very keenly concerned about revenue and cost. But if I don't have the right product at the right time and the right marketing engine to be able to target the right customers that want my product, I'm really just going in circles and I'm not going to get there.
• 3:38
  Speaker A: Cool. So, I mean, as is IT guy, if I could make any dream come true for you, I mean, what would it be? Would it. Would it mean solving how to find better quality leads? Would it be some sort of analytics around sales? I mean, would it be research and development, using AI to find better problems to solve? I mean, if I could do anything as a support technology person to help drive the business, what would it be?
• 4:07
  Speaker B: Oh, that's. I like that framing. So I would say externally, let's make sure that we're aligned from end to end on developing a product that we can bring to market, that customers want, that we can monetize and that it solves a real problem. And internally, I would always appreciate support on the analytics side. Like, let's talk about a data lake. Let's talk about building an analytics platform to allow me to see customer behaviors, whether I'm using something like Appendo or how am I going ahead and measuring time on site for users and making sure that the UX is incredibly useful to our end user. That's the one thing that I always sort of bristle at is like, great idea, but like super choppy ux.
• 5:01
  Speaker A: Yes, yes. The single pane of glass that we hear so often. Ladies and gentlemen, IT leaders. Before we move ahead, the this podcast is not just a stream, it's a stage. And if you are an IT leader with something to say, we want to hear it. Join us live, interact with the host and guest, and if you've got the insight and courage to step up, we promote you to the mic. Apply now@popularitnerds.com waitlist if you have what it takes, join our growing network of over 160 senior IT leaders, where real voices shape real conversations. If there was a favorite department that you had, this stays within this room. Right? Right. If there was a favorite department that you have, is IT Sales, marketing, operations, it. What is it?
• 5:52
  Speaker B: You know, I've been fortunate and you.
• 5:53
  Speaker A: Just be frank and brutally honest here.
• 5:56
  Speaker B: Brutally honest. I'm going to give you probably the shocker answer. It's honestly, it's the sales team.
• 6:01
  Speaker A: Because I don't. That's not shocking to me. That's like, I was going to guess that you would say that. Why is that?
• 6:06
  Speaker B: Because there's usually like a tension between finance and sales. And, you know, sales team always thinks that finance is going say no. Whereas I actually want to work with sales leaders. I tell them I want to make you the richest person in the company, but it's going to come at a degree of efficient growth. I'm not going to go ahead and buy my revenue. And again, what I look at is if I'm going to pay you, say, 300,000 in total compensation between your base and your commission, well, I want a minimum of five times that number as your quota.
• 6:43
  Speaker A: I just got done having this conversation today. I said I was saying to somebody, and I've said it a long time, and I think other people have said, and I think Zig Ziglar said it a long time ago, if you can just learn to sell, you will never have to worry about money ever again in your life. And I said, but. Because I was like, honestly, like, if you come to me and you tell me, yes, I will sell and grow your company, then I'm willing to pay you whatever it is. As long as the multiple that, that I get paid from you, selling, growing, my company is more than what I pay you, like anyone. I will pay you $20,000 a month, base salary, 240,000 a year, plus commission. On top of that, if you bring in $1 million a year, or whatever it is that one of the numbers that you come up with. So, and that's why the sales department, I was like oh, the comp chan the comp plan again this year. But I would, I would think that you would say sales because nothing happens until someone makes a sale. And, and sales is kind of like the big driver of everything, which is the hunch that this is my, this is my assumption with technology leaders and if they can learn to do this, I think, and there's the sales guy, Trinity Solar, trying to sell me solar. Literally it's getting spammed as we speak. I think CTOs, CIOs with the aspect of AI along with technology are sitting in a very interesting position where they could both be sales and marketing and do better or be a very, very significant driver. Sales and marketing from the position in the seat that they sit in. But they're not used to doing that and they might be afraid to have a number attached to them. But I also think it's a big opportunity for a technology leader to say please attach a number to me, attach a number to my results, give me an mbo, give me a management by whatever business objectives, put something on me and pay me more if I hit that number. But I think a lot of guys are afraid to do that.
• 8:53
  Speaker B: I, I, I agree. I mean especially now with the emergence of it. I mean, I think it's only a matter of time before you start to see unicorn companies that have like three people because they've either vive coated their way to success or they've been able to unlock some degree of secret sauce to be able to go ahead and create that magic with just a very minor amount of internal staffing. And yeah, as an IT leader, I think this day you have to be willing to put yourself in the forefront and be a vocal member of the leadership team and say this is where we need to go. It is moving at an exponential rate aided by the use of AI. And how do I get there in the quickest and most expedient fashion. And yeah, I would love to be able to partner with IT leader that is an amazing technologist, but maybe just needs a little bit of help with putting the numbers together because let's, let's talk about that.
• 9:52
  Speaker A: So what would the advice be to some of the numbers that I've seen, whether they're accurate or not, is that 93% of C level technology leaders still think their team is the help desk guys.
• 10:11
  Speaker B: That's unfortunate and shocking.
• 10:14
  Speaker A: They're still saying this is just A common, I mean like if I go to my listeners and I say if this every time I have this conversation, hey look, here's what's going on. It is very lonely at the top. The reason why it is lonely at the top is because you have to explain technology to people that don't understand technology. You have to use sports metaphors, you have to use football metaphors to explain very complicated things. If you start saying BGP and, and you know, start talking in nat port forwarding and IP addresses and things like this, people are going to glaze over. They get really, really bored and they just want to see, hey, where we at before? How much money are we making now and how is this going to help us make more money and what's the, you know, what's the cost of this going to be and how long is it going to take and how quickly can you roll it out? They don't hear all this other stuff. They don't care that you're a Zero Trust certified. I've literally had in groups, like high level, level people say, yeah, we, in the company meeting, we, we announced that we were now Zero Trust certified. Like, do you have any idea how hard that is? It's very, very, very difficult. And everyone was like, cool, all right, next, you know, so there's this, there's this kind of gap between, it is very lonely at the top because nobody understands your world except you and you in this. So there's kind of like this, I don't know, all kinds of fires that you need to put on a daily basis. You're completely overloaded with an ERP upgrade that needs to be done faster, better, shorter time span. And then once it's done, it's really not done, but everyone says it's done and checks off the box. So you don't get the money for the, the bolt ons and the APIs and all the other stuff that you need to do and you don't get the buy in from the rest of the end users for the training because all this stuff takes time. Maybe there's, then you, then there's two other mergers and acquisitions and now we need to merge all them into this new CRM. And it's just like it's constant nightmare and really just pouring lemon on paper cuts and whatever. So there's that aspect of I being very lonely at the top and then they can't really express that frustration through what they say. It's our team below us because I need my team doing their best job. I can't have them focusing on constantly getting fired or I can't have them living in fear to do their job. My team. So they're not saying my team is the CEO, the cfo, the VP of sales, the VP of marketing. That's not their team, but that really is their team. If they have the letter C in front of a T and an O, that's their team. But they're still saying their team is the help desk team. So if 93% of those people are still in that mindset, then I am asking you, what do they need to do? What are some of the tricks of the trade? You, you open up, give us the. Give us what you got to. That we can just give some real good, juicy stuff to people. Like, you said it at the beginning. You know, I want more quality leads. I want effective sales. I want a problem that the mark can fix. How, what, what is something that these IT leaders can come in. They're just like, hey, guys, don't tell them that we're Zero Trust certified. No one gives a crap. Let's go in and tell them like, hey, we found a way to uncover 20% more leads that are like 120% more qualified than the ones. Whatever. I don't know.
• 13:29
  Speaker B: So there's, there's two things that come to mind. One of them involves sort of a Japanese leadership principle called Gemba, which means go to where the work happens. And so I would actually look for people in my engineering team, in my IT department to go and shadow a salesperson, shadow a mark, a marketing person, understand what a day in the life is, understand how the sales team is actually describing our underlying technology? Does that match with what they think they're building? Does that align to, you know, the current Sprint? Does that align to how customers are augering in on specific functionality that they think is most important? That, you know, an engineer may think as simply trivial. And inversely, one of the things that I've actually seen work really well in organizations is have the IT team, like everyone always talks about, like, Python this or Java that, or, you know, AI agent. Why not actually have the IT team go ahead and host a class on, you know, say you want to be a Python developer. And actually I did that at one of my portfolio companies. And I had everyone from like the person sitting at the front desk greeting customers to, you know, finance people, salespeople saying, hey, I need to understand about PY because it's on the tip of the tongue of everybody that I talk to and I need to understand, you Know what is agentic? What is chain of thought reasoning? You know, how do I become much more knowledgeable about the IT space? So there's definitely grave hunger on both sides of the deck.
• 15:15
  Speaker A: Just made me think of like, you could host a class on how to sell to me and you buy. I hate you. It's like, you know, there's this constant, there's this old, you've got to be destroyed. But I think there's this old, I don't know that IT and sales don't get along, but we need to merge the two. I think is where the, with where the winning is really going to happen. Go to where the work happens.
• 15:39
  Speaker B: Yes.
• 15:40
  Speaker A: Okay, so we're gonna shadow a salesperson, we're gonna host a class on Python chain of thought. We're gonna give people some of the technical terms that we use that no one really knows in order to help them in their own sales world.
• 15:52
  Speaker B: Exactly. I mean, that's where you can create the greatest degree of cross cultural integration. I mean, one of the projects that I, you know, often think back about is, you know, I look at it from at times, you know, the number line, and I'm like, why is my AWS cost going up faster than my customer growth? Why is this number feeling like it's exponential month on month? So I literally spent three weeks with my DevOps guy. Every morning we would sit and review our AWS nightly charges and he's like.
• 16:25
  Speaker A: Oh, well, hey, look, we just turned that up because we needed to test this and we're going to run a new idea and we're just having fun. I mean, come on.
• 16:32
  Speaker B: It was a combination of that, but it was like, oh, why do we have dev servers running on the weekend when there's nobody in the office? Why are we not purging logs? Why are we, you know, turning on services that do this or that when that's not part of a core? And honestly, in three weeks we drove that number down 20% just because we.
• 16:53
  Speaker A: Started turning off stuff so much. One of the things that our backend program does is just AWS cost containment because it just gets so out of control. People charge for that. We don't even charge for it, but people charge like some like 3% or something like that for AWS cost containment because it can get so. Get so wild. Then there's, then there's Azure and Google Cloud probably also that the why is Iot the department of no stereotypically the department of no no, meaning they get a no to every time they go ask for something from budget, what are they doing wrong?
• 17:30
  Speaker B: Seneca, I've been super fortunate. All of my startups have been SaaS technology focused.
• 17:35
  Speaker A: Like I where is the department of yes?
• 17:37
  Speaker B: I was more apt to say yes. And I came at it from there's actually some really good benchmarking data that's out there. So there's a company called like KeyBank Capital Markets or KCM and every year for the past 13 years they've been publishing a study and what it shows is what's the percentage of revenue that goes to sales and marketing and ops as you continue to grow? What should that percentage be? I use that as a litmus test to say am I actually giving my team enough money? Am I going ahead and empowering them? And I've actually been in situations where I've knowingly overdriven that percentage because one of my clients we actually had an on prem solution and a public cloud. So my sales team was constantly context switching to find, you know, I'm going to try to sell to T Mobile or Tesla. I'm like, yeah, they're going to laugh in your face if you try to say public cloud. So how do I continue to have two dev teams that are trying to go ahead and create market share? And so for me, I knowingly overspent. And it was a board of directors recurring theme every quarter of why are you overspending? But that's actually how I think about empowering teams and I honestly feel bad when they become the department of no because as a technology team your job is to continue to unlock that next feature. You know, every four to six weeks on a Sprint.
• 19:18
  Speaker A: That's a whole nother agile show. It just is. It's a whole nother. It's like a whole nother hole or great awesome hole, we can go down rabbit hole. What was it KeyBank? What was the percentage of revenue that goes to it? What was the.
• 19:30
  Speaker B: It's the survey's KeyBank Capital Markets. You can totally find it on just Google it. They publish fresh versions every October. But I'll tell you, every investor, vc, private equity company, they will actually have that in their pocket. And my board would always come ready with those numbers and they would think that they were at times trying to give us the gotcha. But I'm like, we had already done our homework and we're like, you know, we're delivering this, we're delivering that. We're owning a quadrant, we're building a quadrant and in order to get there we're going to have to double down on our IT spend and you know, a lot of it comes down to having the right IT leader who can understand the technology, talk about the roadmap, but also understand at least some of the cost drivers of what it's going to take.
• 20:26
  Speaker A: So this is my argument all the time that then let's just say I don't know and my communications might take up 2% typically on a P and L or something like that. I don't really know what it is. I'm assuming it's a low number. So the, the yet it's such a, it affects so much. Like if your communications are down, like what. How are you communicating? Right. It's like such a big. So what happens if we raise it a percentage, two or two points? How does that affect business growth? Do you have any correlating numbers or have you seen, have you, have you yourself seen or have use cases of where I spent more money on it? I got return.
• 21:06
  Speaker B: Oh yeah, completely. Yeah. So one of the things that we were doing was the, one of my clients, they originally architected the product in a vertical manner and we were actually switching it to horizontal and putting in microservices and containers. But in order to get there, I mean we had to knowingly overspend. But as soon as we were able to get to a, you know, market ready horizontal architecture, we saw a tremendous uptick because it made it easier for our end customers to continue to do updates because we were using Docker and containers. And it allowed us to be much more efficient and it made them as an IT organization realize that it wasn't nearly as much overhead for us to go ahead and deliver the product.
• 21:57
  Speaker A: And is this kind of a step two steps backwards or one step backward to take two steps forward type of thing?
• 22:02
  Speaker B: 100%. 100%. And by doing microservices we were actually able to increase the speed of the product, the reliability of the product. And along the way we also had ISO certification, you know, SOC 2 part 2 certification and agile certification taking place.
• 22:26
  Speaker A: Awesome.
• 22:28
  Speaker B: So that's one of the ways and for us, you know, we're kind of touching on the notion of agile and sprints by this actually also allowed us to go ahead and put out features in a much more targeted and focused manner. Or you know, the other thing that people always sort of take a deep breath on is tech debt. You know, it's a great way to go ahead and clean up very targeted areas of tech debt to be able to go ahead and continue to make your product more efficient.
• 22:57
  Speaker A: So talk about that for a second because one of the biggest complaints that we've had for years is got all these old silos. And that's part of tech debt, I guess. I don't know. Unless it's still not paid off and we're completely beyond the silo. But maybe it comes a lot like what's the. How do we eliminate that? Or how do we get that off our back?
• 23:19
  Speaker B: I mean, for me, within, if I kind of look at, Let me take a step back and take a look at the business as a customer. You want it lighter, you want something new, you want new functionality, you want to feel like you've bought an evolving product. But if I'm doing a Sprint or a defined set of work and it's all tech debt, I'm not delivering value to my customer. So how do you go ahead and balance some degree of cleanup with new features, new reports, new functionality? So I mean, if you have it and I feel like it's almost like a necessary evil when I'm a big fan of the innovator's dilemma where I'm going to go ahead and test and fail and fail fast and recycle. But that creates stuff in the background. But you have to be ready to go ahead and acknowledge that that's part of the game. So for me, if you can tell me I'm going to deliver at least 50% new functionality and 50% cleanup, that's a win. But if you tell me it's a 90% cleanup and a 10% functionality, I'm going to be like, ooh, like you're.
• 24:27
  Speaker A: Making me feel better about some of my wasted spend. So let me ask you this though. How much money should one feel guilty for? There's money spent on technology. I don't want to say pipe dreams, but how often do projects are just like, oh, let's just crap that. Let's just scrap that one up as a failure. It wasn't a good addition, it wasn't a good add on. Move on, screw it, move on.
• 24:57
  Speaker B: Yeah, that's part of the learning process. And you have to have a culture that does not place a lot of blame when things like that happen. So I'm going to say it's going to happen. You know, I'd go up to like 15, 20% because you have to acknowledge that there's an agree of experimentation that takes place. And okay, you just want to see.
• 25:19
  Speaker A: What my percentage was. I have a lot of me personally, and we're just a podcast, okay. With like 13 people. But you Wouldn't think that we're a podcast with like a production team and you know, like wasted spend on this and that and oh, gosh on when it comes to the website and integrations and stuff. And it's just. All right now, but we have huge, massive secret coming up and it's going to be a big unveiling. It's. I can't wait for it. Let me just see what we have. For percentage of just pure waste, I would say it's in. Oh, it's not 10%. I would say it's more like 8%. What do you think? 8% waste?
• 25:56
  Speaker B: That's. I mean, that's incredibly efficient. I mean, I'm a big fan of innovation and you know, sometimes you have to break things to go ahead and get through that innovation curve and you have to be ready to go ahead and test.
• 26:10
  Speaker A: Angel funders and venture capitalists understand all this. You being a CFO and a fan of this, I just want to make sure that I'm like, hey guys, listen to Bill. He's the CFO and he's a fan of, of innovation. And we gotta test, we gotta test. But we're not. We don't want to waste Amazon. We don't want to. We do want to be efficient on the Amazon AWS spend.
• 26:33
  Speaker B: Correct. I think VC stupid waste. Understand that it's an evolution. It's a cycle. And angel investors, depending on their level sophistication. I mean, most of them, you know, could simply be safe holders waiting to convert into real equity. So you could be, you know, cap table adjacent and waiting for something big. And I think it's having the right temperament as an investor. But definitely the VCs that I've worked with totally know that that's part of, of the game. You're going to miss a release window, you're going to have some type of, you know, error or fault that's, you know, under. That's not predictable right now. I mean, having a bad, you know, set of it waste using like 8, 10%. I mean, think about it this way. Say you put out a crappy marketing message that goes nowhere. You know, how many customers have you just lost? Because that first impression is the only impression that you're going to get. So that's a great question.
• 27:38
  Speaker A: I mean that you asked yourself. I need to hear the answer to that. What is the problem with the crappy marketing message? Oh. Cause marketing is like, I would say marketing. I would say sales. Sales has to deliver every single day, every single month. Sales must deliver You've got A players, B players and C players and the D players and the C players get pipped and move off, move money. And those are the guys that you see rotate through the industry. And then you've got your A players, which every company's got one or two that are fighting for the top. You've got all your B players that are just really happy driving Mercedes around every day, making their money. They're okay, mean, whatever, they got to do it every single month. Marketing, they've got to hit one out of the park once or twice a year. I would say 85 to 90% of their stuff flops. Is that true or no? Would you say that's a true statement or no? How often does marketing hit something out of the park where the sales guys are just like, dude, marketing, freaking A, thank you so much. Like, you actually made this easy on me.
• 28:36
  Speaker B: If you're a salesperson, you're going to put that number probably at, you know, maybe two out of ten. You know, if you're a marketer, you're going to think that, you know, eight out of 10 are winners.
• 28:46
  Speaker A: So need sales.
• 28:49
  Speaker B: It's all about the perception. But if you think about it, if a consumer needs to be touched with seven different ways and seven different message formats.
• 28:57
  Speaker A: Yes.
• 28:58
  Speaker B: Like, you have to get that message to resonate. And, you know, maybe I don't want to hear about your next webinar. Maybe I don't want, you know, the recurring blog post is starting to feel like spam.
• 29:10
  Speaker A: So, okay, so let's give some information to, to IT guys. They could run with. What do they want to hear? What is a good marketing strategy because.
• 29:18
  Speaker B: It keeps constantly changing through the magic of AI. I think your marketing strategy is first and foremost, know who your ICP is, who that ideal customer profile, and then really continue to hone in on them. Like the one thing I always say is, where do my customers eat? Where do my customers consume information? I need to be in that medium. I can't be spraying on LinkedIn hoping that a CTO is going to read my stuff. I'm like, I have to go to something like a trade publication, a really highly vetted organization. I need to listen to podcasts that go ahead and meet my needs and give me something insightful and actionable and that's really where that message becomes delivered. The marketing strategy that used to be incredibly popular, it still works to some degree is this notion of account based marketing, or abm, where I'll send you as a CTO and your first Five lieutenants, all roughly a contoured message looking for a champion. Trying to go ahead and find out who's going to open my mail and then from there use that as a wedge to go ahead and get them to continue to advocate for your product and then ultimately work cross company. That's really how an effective message can happen, is every product and process needs a champion.
• 30:47
  Speaker A: Yeah, that's the old LinkedIn sales navigator approach. Like connect with five people in the company. They, you know, get in with one to get in somewhere. I mean, it just sounds. Obviously there's multiple ways to do that and touch points.
• 31:01
  Speaker B: Yes.
• 31:03
  Speaker A: What can. Where have you seen the technology department really hit home runs? Do you have any use cases or examples? Oh, yeah. Really hit some home runs.
• 31:11
  Speaker B: Honestly, I think it partnering with a strong comms group to go ahead and talk about a case study. So let's talk about how our technology was used to go ahead and move the needle from X to Y. Whether that be marketing funnel conversions, whether that be efficiency within an organization that a company was able to have a major unlock by using our technology to go ahead and, you know, make a difference in the world. Like, I just saw an amazing statistic that, like, I think it was Norway. They've actually saved like 200,000 hours a year by going all in on it and running a lot of processes in the background. So the government itself is becoming much more efficient in how they go ahead and think about how they want to position themselves, how they want to go ahead and process information. So that, for me, is a great case study to see what were the building blocks? What challenges did you face? What challenges did you overcome?
• 32:22
  Speaker A: Where would you even begin that going tech, technology, all in? Someone had the idea or someone sparked that. There was a curiosity like, how could we, how could we. I don't know. This is me throwing it out there because is it even possible? I would say in some areas it is. How could we eliminate 25% of our sales force and leverage AI to increase sales?
• 32:49
  Speaker B: Yeah, exactly. I mean, it's all going to start with sort of a white paper and a thesis statement. And I mean, you know, to like, where you begin.
• 32:58
  Speaker A: Like, where do we begin with that?
• 32:59
  Speaker B: Where do you begin? I. I think it's going to start with a really bold idea. So right now I've been amazed at. And I'm gonna say in your theme of making sales more efficient, there's a number of really cool tools that are out there to go ahead and make you a better salesperson.
• 33:16
  Speaker A: So you go fire Away.
• 33:19
  Speaker B: Yeah. And for me it's like there's one where there's an avatar and you do your sales pitch and you can actually sort of set it like you're at a carnival, like low, medium, hard, and like it'll be everything from like, hey Phil, nice shirt. Like that's what you're going to wear to this meet to, you know, talking about the cadence that you're doing and it'll actually give you kind of a score on how you can be more effective as a salesperson. There's other ones where it's looking for sentiment to be like, this person likes to have communication delivered this way. So say I was to go out and use AI and start looking at websites. What can I gather about Phil? How's the what, what way does Phil communicate externally so I can go ahead and build a message internally that will appeal to him the most. Is he an authoritarian guy? Is he a team player? Does he need permission from someone? So there's tools like that that will actually go ahead and better tailor the message. And if you can get better tailored messaging, you can actually push up your sales win rate. So right now I usually give teams one in three on a win rate basis. So that means I need three times as much pipeline coverage to go ahead and hit my target.
• 34:45
  Speaker A: That's how I was. So if you've got a hundred leads, 33 are closing.
• 34:50
  Speaker B: Yeah, that they all have to be in the right.
• 34:53
  Speaker A: They gotta be qualified, they've gotta be in, They've gotta hit the four or five star lead status. They've gotta be in a place to buy out of contract, whatever all these different things are, I'm assuming.
• 35:04
  Speaker B: And they have to be ready to spend the right amount of money. It's like, I can have 33 good leads, but I'm like, if you're not hitting my average contract value, like it's not gonna work.
• 35:14
  Speaker A: Some of these AI tools and stuff. You have any, any suggestions for us?
• 35:19
  Speaker B: Oh, gosh, there's.
• 35:20
  Speaker A: I like the, I like the research and personality on the individual person. Because we all know there's like the four different buyer types. There's like the, the last minute buyer. There's the like engineering guy that needs to know every detail of everything. There's the, you know, all this different, you know, whatever the psychology around that. You got any, any good AI tools for that?
• 35:38
  Speaker B: I, I mean, I, I feel like there's like so many names that are out there. Like there's not really one that comes to mind because they're all not 100%. Like they have an MVP, but they're not like fully bulletproof yet. So I don't really have any one given name. I was actually talking to a guy in Florida who's building one, and he just released, but he's not ready for primetime yet. And I would be doing him a disservice if I told him that I'll get totally ready.
• 36:10
  Speaker A: So we got sales and avatar. We got AI research and personality. I'm trying to think of some different things that even CTOs, IT directors, VPs of IT could do. They could even use that little avatar thing for selling to the CEO. I've got to go ask for the new CRM upgrade bolt on. How do I do that? No. Oh yeah, keep going.
• 36:30
  Speaker B: Oh, no. Actually, one of the things that I was actually doing some work for a really innovative company here in Washington, and we were looking at, you know, Fortune 500, Fortune 1000 companies. Like the average life of a CTO, I was shocked is like 24 months. And because there's so much pressure on them to continue to deliver in the face of AI. And if you're doing a huge modernization project, it might take 26, 36 months, but your lifetime is really on average closer to 24.
• 37:10
  Speaker A: Here's what we've noticed from the podcast. After 360 episodes and using AI to analyze transcripts and different things like that, we've got our own little data lake. I guess a lot of times ctos are the heroes. When they come in and they fix broken or they fix a problem, or they forklift some silos, or they make something happen that everyone's really paranoid and pissed off about, they make the mistake of thinking they've got tenure after that.
• 37:38
  Speaker B: Yes.
• 37:39
  Speaker A: So there's this. I. I have a seat at the executive round table now. I have my seat here. I don't realize that they've got to earn that seat every single day. And there's this kind of unfair, A lot of unfair. When you get to a certain level, let's just put it this way, when you get to a certain level in corporate America, you realize that there's a lot of truth to the, the movies out there, I guess. And you. And even if you told the story is real, sometimes they, I don't think people would even believe them. So. But technology people, CTO, CIOs, have very big trust issues. I mean, they wouldn't. There's. There's literally a term called zero trust. Right? So. So they're, they're very big on kind of like, there's a lot of trust issues going on. And so they earn their c. The executive relative, they help for Cliff, all this stuff. Everyone's like, congratulations. So awesome, right? But then, okay, you've already done that. So now it's back to a cost center again. So it before, everyone loves you when you fixed broken and you've fixed all these problems, but now when everything's working and everything's good, it's kind of, this is kind of a cost center now. Like, so you came in, you fixed this big thing, but you didn't realize that that wasn't your only job. Now your job is to now drive revenue. And then so two years later, three years later, they get the message of we're doing some restructuring and we're just, we're going a different direction. Like, you've been great. Thank you so much. Goodbye. And it's very disheartening for a lot of high level CTOs because they're like, what the hell? Like, I did all of this, like, I brought this company like from the, the, the ground from like, you know, the depths of despair and fixed everything and merged all these ERP systems and fixed everything. And now I just, like, what I don't understand. I was brought in to fix all this. I did it all and then now this. So that's what we're trying to fix here as part of the revolution on, or the, the IT evolution into whether it needs a revolution or not or a, a just more of a deep inward. Like your job is not to just keep the blinking lights on or fix broken. It's actually to drive revenue after you do fix all of those things so that you continue to earn your seat at the executive roundtable. It's not like you're tenured once you get there. Am I hitting on the right points there? Do you think that's why there's so much turnover, the 24 month turnover or what do you think it is?
• 40:08
  Speaker B: No, no, you're, you're definitely going in a really consistent conversation path that I've heard from IT leaders. And I often think of a modern IT leader. It's a team sport. So say you're doing like a modernization project and you need to call in like Deloitte or Accenture. So you're not only bringing them in to help you, but you still have, you know, a hundred plus people on payroll. You're like, okay, do I give my entire IT team to Deloitte to be able to go ahead and be like, I have a $3 million carry for my IT team jolt. You need to put these folks to work to go ahead and make sure that I get a positive day too. Because if Deloitte can help you get to that full modernization and restructure your org, like say you're doing cloud modernization, you know what's going to happen to my server and rack guys? Like do they just get fired? Do I get them retrained? Or what's now the state of like you were talking about like an ERP bolt on like is it going to continue to deliver? So I look at it in terms of de risking. That's a really popular finance term. So I come in and say Mr. IT leader, Ms. IT leader, how can I help you de risk your project to continue to get the greatest degree of return, whether that be from cost savings delivered to the business, incremental revenue delivered to the business, but at the same time, you know, help you stay within some spend parameters to be able to go ahead and continue to come back to that table the next day and be able to go ahead and earn your seat repeatedly. So it's very much of an exercise of what tools can I leverage to go ahead and make sure, like do I need ServiceNow to continue to run help desk in the background? Do I need like a Matilda if I'm doing some type of migration type of project? And how do I constantly think about being able to eliminate as much risk because it can only take a handful of sort of rogue people who don't understand deep in the bowels of your IT org to completely side step like one of your projects and you can go off the rails.
• 42:30
  Speaker A: More reason to make your team the C suite.
• 42:33
  Speaker B: But that's part of like staying earning your seat at the table and you're, you're totally bang on that. You know, it's funny even from a finance perspective, like least to have this sort of running joke. I'm only as good as my last presentation to the board of directors and the last set of financials. I'm only as good as that. And next meeting you have to raise your game, have to tell a new story, have to be able to go ahead and show that you've moved the needle. Like whether you're in finance, sales or technology. If you think about like a traditional SaaS company and whether you're doing, you know, monthly fixed price for a service or you're even trying to move to usage based pricing, if you're a salesperson and your bookings target is $2 million, $3 million for a quarter if you miss that number and you're in a SaaS business, you've effectively now just right, shifted cash flow for the entire organization. 36 months to the right. That means there's not 36 months of forecasted cash coming into the business. And that's actually going to go ahead and be the barometer to say, am I going to go ahead and invest in this IT project?
• 43:46
  Speaker A: It's pretty mind blowing for salespeople. That's pretty mind blowing for the salespeople and the technology guys. Because the salespeople, they don't think that I think salespeople pretty much think, all right, I hit quarter last month. I'm back at zero. What can you do for me this month? I think that's pretty much how salespeople think about it. I don't think they really give a crap. They want the CFO spreadsheet. I used to be in sales. I used to be a sales trainer. I was the top sales rep at every company. And the, the directors always hated when they would ask me what my forecast is for the month and I'd just say, quota. They hated that.
• 44:20
  Speaker B: Of course.
• 44:20
  Speaker A: I'm like, I'm sorry, like, pound sand. Like, I'm going to hit quota. Like, you know, they. No, we want to really know, are you going to be over? I'm like, okay, quota or 10% over? Yeah. And they hated that. But no one ever said what you just said. If they just said, Phil Howard, if you hit quota, you're going to give us this much more cash flow. If you over exceed quota, you're going to give us this much more cash flow. Yep. Then I probably would have been like, give me this much more stock option.
• 44:50
  Speaker B: Exactly.
• 44:51
  Speaker A: And I won't sandbag. And I won't sandbag these two deals at the end of the month and hand them in the next day. That's very, very mine. That's very, very useful. No one's ever said that. No one's ever said that to the sales team, probably because most of the sales team is young and they have no clue about ebitda. And you have to have a whole class on just explaining EBITDA to them to begin with. So just go hit quota or you'll be pipped. Or, or you're going to be, or you'll be richer than you've ever been before. And then, you know, and then. Okay, so that's really. Okay. So teamwork. This is nothing that hasn't been said before. Teamwork, but it's, it's the nuances. Of the teamwork and the, I think having the relationship with the cfo. We, we've, we've, we've talked about this many times before on the podcast. But I guess what does that really mean and what does that look like? And kind of really understanding those numbers and how you think and I think sharing the pressures of each other, understanding the pressures of each other's job, it will create that camaraderie. Understanding that maybe you sat in with the sales guy and you're like, holy crap, I could never do this job. Your job's really, really hard. And then understanding that the CFO has to come up with a new presentation, like you just said, you're only as good last presentation. Then maybe some of us IT guys that played with technology ever since we were growing up realize, will realize all of a sudden that we're not getting paid to just play with technology anymore. We're not getting, we're not getting paid to just because we fixed printers back in the day. And the, the majority of the tech leaders right now are probably X gen people that were that person. They, they had a Commodore 64, they had an Apple IIe, they played with technology, they FE technology because they are the guy that could move the ancillary cables around and fix printer problems and issues like that. And they just didn't become an engineer and they were in engineering before and they ended up being the IT director. But there's going to be like this new breed of people and it's going to be coming very fast.
• 46:47
  Speaker B: Exactly. And, and that's where we're talking about like your, your LinkedIn post yesterday, I thought was such a great wake up call where you as a technology leader have a seat at the table. You have a voice. You need to understand how you can now significantly influence the company. Like you've heard of companies that are sales led where sales feels like they can direct traffic and tell the organization what strategic direction to go in. Now that's actually now much more the role of a technology department to say we need to invest in X, we need to go ahead and move to, you know, this LLM or we need to go ahead and bring this degree of agentic to the market to be able to go ahead and make a difference. And that's where the importance of like the partnerships that we talked about, having finance person be able to help navigate your vision. Because there's one thing that I ask every founder that I work with and I think this would even apply to every technology leader. It comes back to, you know, what are you good at? And from a founder perspective, I say, are you a sales leader? Are you a technology leader? Are you a podium speaker, an evangelist? Because I want that leader to tell me what they think they're not good at. And now you will say, then let me help you fill in the areas where you're not as proficient. And like you said, you could be that greatest Commodore 64 kid knocking out really cool stuff. But if you don't understand that bigger dynamic, you're only going to end up hitting the top of the ceiling pretty quick because you're not really looking at the long play in the business.
• 48:36
  Speaker A: Yes. And there's. I'm trying to think of how to link this to the post that you said that you liked so much yesterday. And it does link because ultimately I'm the. An expert, you know, Cisco Startup guy that was sales, that was in. A sales trainer that was in then to technology consulting after he left corporate America, Technology consulting to now, hopefully the voice of IT and all this other stuff. But this infographic from yesterday, my technology guy had to have a single source of truth from the past episodes and a whole lot of different AI engines and I don't know, what do we call it? What is the coding again? For the coders that aren't decoders. What's wrong? You said at the beginning of the call, oh, vibe coding. Vibe coding, right. There's probably like a lot of vibe coding along with. Although he hates the term vibe coding, he's like, I never want to be known as a vibe coder. Sorry, Greg. Greg Liddell, the Frenchman. So he's crazy good with AI and he completely.
• 49:38
  Speaker B: He.
• 49:38
  Speaker A: He vastly underestimates himself. Someone's probably going to recruit them and steal them from me now. But we basically have like a lot of different data dips and AI bots going through and really pulling kind of like the meat of all these episodes. And we'll do it with this episode too. And then we come up with like three infographic ideas, three carousel ideas, key quotes from the show, key moments in the show, and this whole. The new. And then basically we. We come up with some. Some infographics and then we have another team member make the infographic. And then I go through and I look at the. The title and stuff and I'm like, okay, because this. There was a different title on this one yesterday. It's the new IT Evolution means Big Disruption. I think it was that new IT Evolution means new. Like it was something else. I can't remember. But so I started Thinking I was looking at it from support function to business driver and then these things start to click and you start to see the patterns over time. But it took a technology AI guy to put all this information in front of me and then I'm able to look at it and distill it down like oh wow, that's very interesting. IT guys used to be really good at the averagely. The average good, if that makes any sense. The average good, top echelon CTO is going to speak about roi. They're going to be able to talk about return on investment. They're going to know this project has to somehow pay for itself. Right. But they're not taking the next step beyond that. And how is it actually driving business? And that's what we really, that's what I would really like to show and that's what we're all about is how do we take this technology leadership piece to the next level so that you become, how do we say, irreplaceable, highly valuable cto, cio, IT Director, VP of it. And I think with your, your advice it's yeah, sit in a big teamwork, understand it from people, sit in on the sitting on some sales meetings and everything and any other piece of that you advice that you'd like to give before we sign off here because we've been talking for an hour and I'm very, very thankful for the time that you've given us.
• 51:47
  Speaker B: No, I've really enjoyed the, the conversation as well. And it's, it's a two way street. I mean there's plenty of non technology people that are, you know, always curious like what's the buzz going on in the technology pod? Or how do, how do we think about like even just on a quick like help me understand story points, help me understand what you're picking to go ahead and roll out like what's your technology roadmap? Because if you are a series A founder, every investor is going to want to know, okay, I know you are now, but I need a good point of view on what's happening in three months, what's happening in six months, where are you going to be in a year? How is your technology path going to get you the customer unlock? So even just having a technology leader in a series of, you know, the one downs from that leader would be.
• 52:44
  Speaker A: Tremendous to that missing piece actually. Because every IT leader loves to talk about their roadmap. Yes. And they also love to talk about why their roadmap's not getting funded. Well, maybe your roadmap's not getting funded because there's no customer unlock, as you say it, or no value driven customer piece that's going to drive higher quality leads more and help people solve a problem that we can monetize in the marketplace to come full circle from the beginning of the episode. Yeah, right.
• 53:18
  Speaker B: Because the one thing I always tell folks, and whether it's on a PowerPoint slide or whether it's a technology, don't build it because you think it's cool. Like I don't want to look at a PowerPoint chart. Like if you show me an org chart in a PowerPoint slide, I want to know how much these people cost or how you're restructuring this order to be more efficient. And it feels the same problem. And the same is true with technology. I'm like, don't build this, you know, funky widget because you think it's cool. Like I need to go ahead and get a full 360. Like I need my customer success team to be the ears of that customer, to be able to come back to have that conversation with product, with engineering, to say, oh, this is really an opportunity for us to go ahead and hit and unlock, you know, oh, they really want like role based security. What would that take? Or they're really finding that there's a disconnect here. Like that's the kind of stuff that I want my IT team and IT leaders to be acutely aware of and helping thinking about the business.
• 54:24
  Speaker A: I love that you said that it is not about just organizing and making more work for people. Really. Like I didn't just build a widget to show you something. Like, look at what I built last night. It's really, really cool and it's gives you this much more stuff to look at. I don't need more stuff. I just need it simplified. In fact, I think taking things away would be. I'm just in this big theme of like, how do I take things away, how do I eliminate things, how do I take things off my plate right now? And technology should be doing that. It shouldn't be making it more complicated. Sometimes it's like, hey, with this extra spreadsheet and I need you to check this column now. I'm like, no, I don't want to check an extra column, I want to uncheck an extra column. Can you take a column away? I don't want to add a column. And I think that, yeah, technology people, especially in the dawn of AI, with so many flashbang, flashy new AI products, hey, look what I did. Why did we not do this first? Other than that? So it's been an absolute pleasure having you on the show. Any final words of wisdom for the technology leaders of the world to give them hope or prosperity or an action, an action step to take today to move forward into a better, brighter future?
• 55:32
  Speaker B: I do. I'm going to, I'm going to give you one of my number one hacks. And this would be totally something that every technology leader could, I think, really grab onto and really deploy quickly is when you're telling a story to an audience, especially if you're at like the leadership table like we were talking about earlier, or even if you're talking to the team internally. Here's the trick. Tell the story backwards. Because right now we are so bombarded with slack text, you know, your phone's chirping left and right. I have no confidence when I tell you a story, Phil, that I could go once upon a time this and then once upon a time that. If I open with this is my technology roadmap for this quarter. It's going to unlock these five things, it's going to deliver this degree of value, and I'm going to use the next four slides to go ahead and show you how I'm going to go ahead and deliver that. So you've now completely flipped it to be able to go ahead and make it. I'm telling you the end of the story. I'm inviting you to tell me where I'm gonna go wrong and I'm now then going to take control of the conversation. To be able to go ahead and own the room and not be having to, you know, have people talk about, yes, what is mcp or, you know.
• 56:53
  Speaker A: Say that one more time. So we start with the end in mind. Here's what I'm gonna show you today, how we're gonna make extra 5% of the bottom line next year. And here's how we're going to do it.
• 57:01
  Speaker B: You can go that broad, you can bring it down to. We're getting ready to come into Q3 right now. So what has to true for Q3 in order for us to continue to move forward as an organization and as an IT leader. My Q3 must haves or my Q3 custom truths are this, this and this. And so that's your opening slide is you're basically telling them the outputs and then use the next two to three slides to go ahead and use that for support.
• 57:37
  Speaker A: To say, this is what I need.
• 57:39
  Speaker B: This is what I need this, or this is how I'm going to do it with my existing staff. We can deliver X if you want that. And I'm going to need some contractors or I'm going to need the opportunity to buy more AWS instance or a better Azure experience. But by starting with that front page and simply framing the conversation, you've now brought it to the forefront. And you don't have to worry that someone's not going to go on that journey with you. Like, imagine if you started with something nuanced like, you know, I want to go ahead and deploy this. Like, people are going to start to, like you said earlier in the conversation, they're going to start to fade out. They're not going to really care because it's not important to them. They don't see the big picture. I'm going to start with the punchline of the story first.
• 58:32
  Speaker A: Yes, yes, very helpful. And because that's where a lot of people go wrong. So thank you. Thank you so much. And if you have any examples or anything you want to give away too, when we produce this episode, we'll put it on the webpage and everything and anyone out there listening can, can find bill on LinkedIn. And when we produce the episode as well, his LinkedIn link will be on the profile. So I'm sure you're, I'm sure you're welcome to have anyone that's listening to the episode reach out to you and ask any questions.
• 58:59
  Speaker B: No, would love to reach out and, you know, I'll put it out there right now. You know, the, the first 10 people to message me on LinkedIn. I'll give you 30 minutes of free consulting and we can talk about anything from if you're a founder, if you're a technology led founder, you know what role finance can play. Or if you're a much more established IT leader, it's about helping you tell your story at the table to be able to go ahead and as we talked about, earn and maintain your seat.
• 59:28
  Speaker A: One of the infographics is going to have to be this PowerPoint presentation, how to sell your stuff. But we'll see, we'll see what, we'll see what the technology puts out there. Thank you so much for being on Dissecting Popularity Nerds.
• 59:39
  Speaker B: Oh, thank you so much, Phil. It's been a pleasure.