Skip to content
402- From Selling to CIOs to Becoming One w/Karl Weber

Doug Camin & Karl Weber

402- From Selling to CIOs to Becoming One w/Karl Weber

THE IT LEADERSHIP PODCAST
EPISODE 402

402- From Selling to CIOs to Becoming One w/Karl Weber

20
1 X
20
00:00 | 00:00

Karl Weber

ON THIS EPISODE

Karl Weber has a rare perspective. He spent 30 years on the vendor side selling technology, then crossed over to become CIO at Rolfson Oil, a 500-employee fuel transportation company delivering 30 million gallons monthly to oil fields. What he discovered will change how you think about IT leadership.

Karl inherited a mess: four or five overlapping tools with no strategy. His sales background taught him something most CIOs miss: "I had a lot of success trying not to sell the CIO. I wanted to sell to the person that had the business problem." The budget and pain sit with business unit leaders, not IT.

We get into his one-question decision filter (does this impact revenue?), why AI investments will face a reckoning in 18 months, and the Gap pitch that won a 100,000-employee deal because his team wore their clothes.

The payoff? A framework for becoming the strategic advisor executives actually want at the table, not the afterthought they call when decisions are already made.

Show Notes

Episode Show Notes

Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.

[[00:00:00]] Introduction — Karl Weber, CIO at Rolfson Oil

[[00:02:15]] First Computer Story — IBM AT clone with green screen

[[00:04:30]] College Registration System — Building in FoxPro for thousands

[[00:07:45]] Sales Career Path — From technical to top salesperson

[[00:10:20]] Crossing to CIO Role — Adult in the room needed

[[00:13:10]] Technology Chaos — Four tools doing same thing

[[00:15:45]] Rolfson Oil Spinoff — 30 million gallons monthly delivery

[[00:18:30]] Strategic Advisor Challenge — Seat at the table problem

[[00:21:00]] AI Hype Reality Check — What did we get for our money?

[[00:24:15]] Enable vs Replace — AI for capability expansion

[[00:27:30]] Selling to Business Pain — Not the CIO approach

[[00:30:45]] The Gap Pitch Story — Wearing their clothes to win

[[00:35:20]] Executive Understanding — Article and buddy syndrome

[[00:38:10]] Twin Brother Stories — Conference infiltration pranks

[[00:41:00]] Future Predictions — AI investment reckoning coming

[[00:43:30]] Leadership Advice — Know your business like other leaders

[[00:46:15]] Decision Framework — What problem are we solving?

[[00:48:00]] Closing Thoughts — Strategic consultant not afterthought

KEY TAKEAWAYS

One decision filter: does this impact revenue or not?
Sell to the business problem owner, not the CIO
Ask 'why' before 'how' to uncover real needs
402- From Selling to CIOs to Becoming One w/Karl Weber

TRANSCRIPT

Doug Camin: So, Karl, I'm Doug Camin. I'm one of the co-hosts of the You've Heard It podcast. Welcome to the podcast. And thank you for joining us this morning.

Karl Weber: Sure. Glad to be here.

Doug Camin: And so Carl, we've got the title here, vendor sales to CIO. Your background is not coming up through the IT chain. Recently you've been in the IT space. So tell us a little bit about your history and how you got to.

Karl Weber: Now, I've been in the technology space my whole career, but from the other side. And this probably leads to one of the questions that people typically like to come around to, I thought was sort of the bottom of your list, which is tell us about your first computer, which is probably a really good starting point for me. So I went to college in the mid late eighties, even worse. And I was in business school trying to figure out what I'm going to do, I'm going to get a business degree and then I have no clue what I'm going to do. And the school of business that I was at pulled a small group of students aside and said, here's a personal computer, and you get to use this while you're in school. And if you graduate, you get to keep it. If you don't graduate, you got to give it back. Now, this wasn't any computer. This was a clone. IBM eight with two floppy drives. No hard drive and a green screen monitor. And it was an introduction to, okay, here you go. And one of the first classes I took sort of related to that was a business applications class. And here's applications that run on a personal computer and how to use them for business. And I immediately was very interested in how can I take technology and use it to solve a business problem. And that's really sort of been my...

Doug Camin: Was it Visicalc? Did you use Visicalc?

Karl Weber: I used Supercalc.

Doug Camin: Supercalc. Yeah.

Karl Weber: Which goes back even further. Yeah. That was precursor to Lotus one, two, three and all the rest of that. So but I learned that and there were some other things that then I got involved in. There was a business on campus that I helped run where we took our summer facilities in the summer and rented them out to different groups and camps and different things. And a group came in and they needed an advanced registration process for a couple thousand people coming in from all over the world, and we built that at the same time. I was taking a lot of my electives ended up being technology related. So database design courses, it took a class in FoxPro and built out an advanced registration platform, which is basically just a database with some business logic behind it for tracking. So people could register in advance. Of course, there was no web portal. Do it. They fill out a form, email it to us, and we would enter the information in the database. But we then had a database of every single person coming. We knew where they were staying, their activities, all the rest of that stuff. And we took through this advanced registration process. We were able to save hours and hours for every single person that was showing up to register, we knew exactly where they were. We sent them a letter in advance and say, go to this dorm. Here's your ticket for this. Here's how you're doing this. It was really very good. And that all sort of came out because we had this business problem and I was taking this class, used the class to do the project to build the tool. And I sort of said, hey, this software thing is really sort of cool. And I ended up there, never wanted to program, didn't want to be a coder. But how do I use software? How do I use technology, what business problem am I solving? And then you start to get down to, well, if I can solve it, what does the problem cost us? What's it worth to solve it and go from there? And then I ended up in sales. So I ended up on the technical side. I did training and then I went into a sales engineer role, working in my first software company. And then I figured out I'm doing all the work as the technical guy, and the sales guy is making all the money. So I migrated into sales, became the top sales guy in that company. But it's always been this methodology around what's the business problem? How can I solve it? What's it worth? Which then leads to the value and all the rest of that. So, I've worked in sales for thirty years and about a year and a half ago, sort of trying to figure out what I was going to do next, and was talking to some people that I'd become friends with. I'd done some consulting for some of their businesses, and they owned a holding company in the Dallas area. I was in Colorado at the time, and I'm talking to the CEO, and he says, I need an adult in the room. I need somebody to come in that I can trust, that understands technology from a business standpoint and can come in and help run the business. I don't need you to come in and code anything or do any of that. We just need someone to come in. And what I inherited was a situation where people had made a lot of individual decisions about solving a single problem without a cohesive strategy. So you ended up with two or three or four or five pieces of technology to all sort of do the same thing. And so I came in and I said, all right, let's clean this up. What's our strategy? And looking at it, where do we have risk and where do we have risk to the business? Let's eliminate the risk. Where are we paying for things we don't need to pay for? So how do we streamline things and reduce costs? And then what's the overarching strategy for the business and how do we invest in that and impact that going forward? So, and then, last fall, the owners decided to spin off their largest entity, which was Ralston Oil. And I went with that. And I'm the CIO now for Ralston Oil. So, we're a fuel transportation company, mainly in the oil field. We deliver about thirty million gallons of bulk fuel every single month to the oil field. We have a fleet of vehicles that go out, go to refinery, pick up the fuel, drive two to three hours in the middle of nowhere, deliver it to a frac or a production site, and then turn around and do that over and over again. And then we have a bunch of corresponding businesses around that, that support that business. So, we're probably a bigger company than people realize, about five hundred employees, but we go through quite a bit of product every single month, and there's a lot of technology that then supports that.

Doug Camin: Awesome. So for those just joining us, I'm talking with Karl Weber, the CIO of Ralston Oil. Carl, just give us some of his background on where he how he came up in the background, the sales history, and you made that jump. So you started in sales, as you mentioned, but technology has always been a passion and always been where you've lived. What in the company that you're in now, you mentioned it just spun off recently, and what kind of challenges have you encountered or were the biggest hurdles that you had to overcome in standing up an independent entity from the IT perspective?

Karl Weber: So I think the transition was actually coming in because I'd had about a year in the position as the CIO for the larger holding company, and the company was spun off. Ralston accounted for about eighty to eighty-five percent of our revenue. So it was a bulk of the operations that we did were based around that business. So and I had been pretty intimately involved in those for a year. So I'd come in, I'd learn the business, very familiar with the technology and so it really made a lot of sense for me to make that transition. I think the opportunity has been, and this is probably a challenge I see in a lot of organizations is this technology is sort of seen as the afterthought. Okay, we're going to go do this now. Let's go figure it out. Go talk to technology and tell them what we want to do. And I think the CIO really needs to be seen as a strategic advisor to business. And that needs to be included and has a seat at the table when business decisions are being made, because technology can impact that and oftentimes make that transition more difficult, or in some cases easier if you've done the right thing. So in the twelve months I was in this sort of larger CIO role, it was trying to determine what is our strategy, what are the longer term things that we want to do. Do we have the platforms in place to allow us to scale and grow the business? And in the type of world that we're in, there's a lot of mergers and acquisition activity. If you don't have the right tools, process, people in place, acquisitions can be really, really painful. And so there was always sort of a thought around, okay, as we go do these acquisitions or sell off companies, do we have technology in place that allows us to more easily do that? It's never easy, but it shouldn't be a stumbling block.

Doug Camin: So I'm thinking about you have this perspective where you're coming in. You spent many years not in the CIO seat. So what do you think CIOs like obvious things, or maybe not so obvious things that CIOs commonly get? Like, what's the most common impediment stumbling block? Like, darn it, I wish they would get that. Or I wish maybe I should get that or whatever the case may be.

Karl Weber: Yeah, I think the challenge is that the big one is AI. Everyone's coming at it now. It's like, okay, what's our AI strategy? What are we doing for AI? How many people are we going to replace? I think you always come back to what's the business problem we're solving? And is it worth solving? Because in some cases, what? The way we're doing it today, the cost to do it, the disruption to the business. Maybe we don't do that now. Maybe it's not a we'll never do it. But it may be, strategically we got ten things we want to do and we have ability to do four of them, which are the four that we're going to do. Yeah, so yeah, I think that there's that perspective of, instead of this rush to go do the most current version of technology, AI is a great example, what's the problem we're solving and how are we going to leverage that?

Doug Camin: Yeah. One of the things that when it comes to the AI stuff, I think there's a concern that in certain instances, especially heavy workload, is you got to be careful about what you're replacing. The dollars may make sense today, but in the future they may not, like you could get three years from now. They're like, oh, by the way, we're done underpricing this, you now have to pay full freight. And next thing you know that three hundred and fifty thousand dollars service is like six hundred or six fifty six, seventy five that you're actually spending one hundred, two hundred and fifty thousand dollars more than if you had retained your people in your process and try to augment them slowly and steadily.

Karl Weber: So I think the way that people need to look at it is instead of replacing, what are we enabling that we can't do now? And I think AI is great if you got good data. If you don't have good or clean data, you're going to end up with garbage in, garbage out thing. But, I think what are we able to do with AI that we can't do or that we just can't throw more people at it or more systems? That's the to me, the real advantage, allowing somebody maybe you're not replacing somebody or allowing them to do their job a little better, a little easier, and then technology needs to be an enabler. It needs to allow us to enable cheaper ways of doing things, or even better. Are there new revenue streams that can be generated from that or a competitive differentiator in how you do your business?

Doug Camin: Yeah I agree. I am cautious from experience that people have a tendency to headlong rush into it for a lot of businesses. There's a lot of like, we must do this or we'll get left behind. And I'm like, I don't know that you'll actually get left behind in most businesses if you just take a deliberate approach, unless the core of your business is to actually use the cutting edge to get ahead. It can be challenging to operationalize those tools in an effective way that actually produces return in a reasonable fashion and in a reasonable time frame for you.

Karl Weber: Yep.

Doug Camin: So, Carl, thinking more about some of the things this background in sales, I'd love to kind of plum that out a little bit more. Sure. Just bring out some of the observations and things that you've seen. I know you shared about AI from sitting in the sales side of the house, for so many years at various companies. What things did you think that the CIOs that you worked with through those years, where did they encounter challenges? What do you wish they had done differently or seen differently or understood from your perspective in those places?

Karl Weber: So I had a lot of success over the years trying not to sell the CIO. Yeah, I wanted to sell to the person that had that business problem that we talked about earlier, and oftentimes it's not the CIO. The CIO oftentimes is tasked with helping solve it, or the CIO wants to come in and have an input in how it's solved. But ultimately, the person that owns that particular part of the business, whether it's an HR function or an operations function or a finance function, whatever the type of organization is, those are the people that have the real pain and oftentimes have the budget to go off and make a decision on doing something. So I always tried to come from a perspective of what are we providing that will change their world, make their life better, make them more successful in what they're doing. And then I've got to make sure I hate to use the term, but placate the CIO and make sure that the CIO feels like they're supportive of this is the investment, this is the decision we want to go with, etc. Now there's some businesses where somebody says, hey, I got a problem, Mr. CIO, go fix it. And then it's the CIO's decision. And oftentimes, people tend to have a particular perspective on what they want to do. I'll give you an example. Back about two thousand, I was working for a software company out of the Bay area. We did call center technology. Eventually the company became part of Avaya, but we had a suite of CRM applications that were vertical specific. So we had a CRM application for consumer product call centers, and Procter Gamble was a big customer, United Airlines, John Deere, some really big Sun Microsystems from really huge names in business where our customers that we're using our call center apps for a specific out-of-the-box application function. So, we got an opportunity to bid on the business for The Gap. So The Gap, Banana Republic, Old Navy, all those companies based in the Bay area and one hundred thousand plus employees, and they were going to set up an HR call center. So if you were an employee and you had a question, there was no really good way to communicate with the HR department to ask that question about benefits and enrollment. And, I'm having a baby and whatever else, what do I do? So they were going to build this call center. And so we replied to an RFP and got shortlisted. And it came down to us that the HR department liked us because we had an out of the box designed application that we could go deploy in about ninety days, whereas the other competing vendor was Remedy. Okay. And the IT department came in and said we're going to build you something in Remedy. Okay. So those were the two camps. Yeah. And so we were coming at it from the HR departments business challenge. And our experience in doing these types of call centers for other customers and very, very focused on the business side. Remedy was very focused on supporting the IT organization and enabling them to go build this thing and then own it. And so, we got called into, not headquarters in downtown San Francisco, but San Bruno by the airport as their big procurement and HR and a bunch of their business operations were down there. We get called in to do this final vendor pitch in this giant auditorium probably set about three hundred people. And we get in there and these giant plasma TVs on the wall that probably cost twenty thousand dollars. And I had told my team in advance, I said, we're going to go in and we're going to wear their uniform. I said, every one of you go to Old Navy, go to somewhere, and we're going to buy their clothes. We're going to show up wearing their clothes. So when we went in and we got to go pitch first and we went in and we pitched and I popped up, I turned on my computer. It the background was my son wearing their clothes, and I heard some people in the room saying, he's wearing our clothes. And at that point it was done. We won the business. We had a great solution for the business users, but we met them where they were talking their language and we knew their business and we ended up winning the business. So I think that's the sort of old challenge for CIOs is that you come at it from the technology perspective. But when you start to look at things from the, who's your customer? My customer is every single one of our five hundred employees and I help them do their job. It's an agreement we have with my boss, our CEO is every decision that we make is based on does this impact revenue? Is it a nice to have or does it impact revenue? If it's revenue impacting it goes to the top of the list. Can we do it first? And technology that has become a strategic part of how we run our business is we use technology to improve the business and drive new revenue where we can.

Doug Camin: I appreciate thanks for sharing that story. Putting the hat of your current hat on. Yeah. As a CIO. What ideas do you wish that the other executives would understand about modern IT?

Karl Weber: Yeah. I think that the access to information and everything else. People come at it from, "Oh, I just read this article, or I just listened to this podcast, or I've got a buddy of mine that uses this tool at their company. Why aren't we doing the same thing?" And it always comes back to, okay, what problem are we solving? And then the other thing is does the tool that we want to invest in the platform, whatever we're doing, how does it tie into the overall strategy of where we're headed as a company. And that strategy might be cost reduction. That strategy might be enabling new lines of business. Reducing the number of tools that we use, improving the life of our employees. Those are all important things in the business. So I think it's you have to help people understand that's a great tool. Here's why we use something else instead, or that's a great tool. Let's investigate it and let's consider it in relation to our overall strategy.

Doug Camin: So let me change gears here a little bit. I think you shared a little bit of your background coming up. You went to college and the things you learned and stuff like that. But tell us a little bit about, like, were you always a technology person as a kid, were you growing up? Were you exposed to technology. Did you come to it late? Like how'd you get into being.

Karl Weber: Probably more of a late bloomer? It was, I've got a twin brother, and he was always probably more along the lines of the technology side. And he was always more of the dive in. How are we going to go do it? And I was always sort of on the business side of things. So but I always love technology and what the end result is, and that's probably the first thing. Whenever I see anything that's new, I'm like, okay, why are we what does it do? Why does it do it? And how do we then go deploy it and things like that? Yeah, I love tech. So that means you always get the calls from your friends. Okay, I got this problem. Can you help me with this? And what should I do with this? And, but probably less so technology for technology's sake, but more technology for, how can it be an enabler?

Doug Camin: Nice. Nice. So, I always ask our guests a little bit about their non tech things that you do. So, like, can you tell us a little sometimes people wouldn't expect about you?

Karl Weber: Wow, that's pretty cool. Oh, I think I mentioned this. I've got a twin brother that always ends up being very interesting. People want to hear about that stories, games. You play it on your classmates or teachers or other people, and we even still do some of that today. We're identical twins. And I will travel someplace to where people may know my brother, and they think it's me. And I walk up to them and shake their hand and say, hi, I'm not who you think I am. And, that's interesting. I was working for a software company, and we were exhibiting at a conference in Amsterdam. I wasn't there, but my team was there, and my brother was traveling from the US to South Africa, flying through Amsterdam. Happened to stop to go to this conference because he was looking at some technology related to his job. And I said, hey, you got to swing by my booth and you got to mess with the executives. So he walks in a booth, and one of my sales guys knew who he was and had met him. And so he goes up, he's talking to one of my sales guys and the VP of marketing and the division president walk up and start talking to him. And he literally had a ten minute conversation, and the VP of marketing looked at him and says, you're not Karl. Who are you? So, we've done that over the years, but that sort of stuff is fun. He's a college professor now, and I've gone in and he's had me go in and start his classes, and students walk up to me and think that I'm him and asking questions about an assignment. And I'm consulting with them, and I have no clue what I'm talking about. And then, he'll walk in the room and they're like, what's going on? It's fun. But I love travel. Travel is probably one of the coolest things that you can do is go see the world, go see other people, other cultures, try lots of different cool food. And, that's everybody should do more of it than they do.

Doug Camin: That's awesome. Yeah, So I know we talked about AI, but I'll say what's the biggest future thing or the thing that you think is going to change in the IT space here in the next

Karl Weber: Yeah, I think that, in a lot of cases, sometimes things start at the top with the board or investors come in. "Oh, what's your AI strategy and how much money do you invest in AI? And let's outspend your competition and all the rest of that." I think people are going to look at it and eighteen months from now. They're going to say, what did we get for our money? And I think that there's probably going to be a recognition that was there a realistic expectation of what AI was going to do. And you've got to have your data, your systems, everything have got to be cleaned up if you're going to leverage the tool. I mentioned the garbage in, garbage out thing. It's even more so when you're looking to do all that fast compute and lots of data and all the rest of that. If the data isn't consistent and clean, you may not necessarily end up with the result. And here's the other thing. You use AI and it may make a recommendation or a suggestion or something. You always got to counter check it. And okay. Do we think this is realistic? And is this accurate? And there needs to be some checks and balances along the way to evaluate that. So I think those organizations that came at things like you talked earlier, sort of at a managed pace rather than just, oh, we're going to go, invest one hundred million dollars on it. But what's the result? And if you can set a realistic expectation on hey, we're going to go do this. And here's what our anticipated results are going to be. And then we're going to continue to improve. Those organizations are going to be in a much better place than people went out and spent, hey, our CIO dropped one hundred million dollars in AI and we got no return for it, and he's no longer our CIO. So, I think it probably needs to be a little bit of self-preservation in trying to set a realistic expectation with executives or investors.

Doug Camin: Yeah, And in the AI space in particular, it's hard right now because there's an enormous hype cycle associated with it. And like, there's a huge fear of being left behind without knowing what you're actually being left behind about. So coming to the end of our podcast interview here. Always at the end, this is the leadership podcast. We're talking about leaders. We're talking to new leaders, the leaders that are coming up. I always ask our guests about your advice to the emerging leaders that are coming up, the people coming up behind you. What advice do you have for them? Start with that.

Karl Weber: I think the CIO needs to be understood as a strategic consultant to the business. And as I said earlier, we need to be included early on in the decision process and in the strategy discussion rather than an afterthought of, hey, we decided we're doing this. Go deploy this. I think that's probably one of the biggest challenges. And I think the CIO as a leader and really you're running a business, you're hiring, you're firing, you're managing a budget, you're negotiating contracts. All these things that you do, you're a leader in the business. You may be related to technology, but a good business leader will be recognized and considered a strategic part of the organization. And I think that's the challenge. And that's what I think people need to aspire to do is, hey, we're going to go deploy this technology. Hey, we're going to go solve this problem or we're going to enable this for the overall business. And I think that's the perspective that you need to lead with and have the organization understand that you're providing is that leadership around technology and organizations that embrace technology? That's great. There's some organizations that are resistant to it, and that's probably even better angle is to come at it from, we're going to go solve this problem. By the way, here's the technology we're going to use that we're going to go do it. So I think that's the biggest challenge is know your business, know the business that you're in. Know it as well as the other leaders. Know your costs, know your competitors, know your challenges, know all of that. And that will put you in a better position to be able to be seen as a strategic leader in the organization.

Doug Camin: Awesome. Thank you. And that's advice for the people who are coming up behind you? What leadership models or what things do you live by? Like do you have any like, the quotes, the whatever, the short things you always say. What, what?

Karl Weber: Oh, man, I mentioned it already. It's what's the problem we're solving? Where's the pain? Here's the big one. Why? Somebody says, I want to go do this. Why? Or what if we don't do that? What changes or doesn't change? How does it impact you if we don't do that now? And I think that those are some of the questions that you gotta you gotta ask somebody, well, why are you looking to do this? Well, I'm doing it because of this. Okay. So maybe you don't really need what you think you need. You need something else instead. Or here's a better way to do it. Or, hey, by the way, did you know we already have that capability in a platform we have today? Let's go train your team how to do that, rather than going off and investing in something that we don't need to do. So I think oftentimes it's the why question is great. And a lot of that I think comes from my sales background. It's always answer a question with a question, it's what color does it come in? What color do you want? Those types of things.

Doug Camin: So it feels like a sales piece right there too.

Karl Weber: It is.

Doug Camin: It is the sales part come through here.

Karl Weber: Yeah. But it's diving in and trying to identify the pain. And what's the challenge and why do we need to go solve this or do this?

Doug Camin: So great. Awesome. Well, Karl, thank you so much for investing your time with us on the podcast today.

Karl Weber: Oh, no. Appreciate it. Thanks for having me. And I look forward to learning more from everybody else in the community. I'm new to the role and trying to absorb as much as I can.

Doug Camin: Awesome. All right, well, that's a wrap on today's episode of the You've Been Heard IT Leadership podcast. I'm Doug Camin and we look forward to seeing you on our next episode. Thank you.

Karl Weber: Thank you.


Doug Camin: So, Karl, I'm Doug Camin. I'm one of the co-hosts of the You've Heard It podcast. Welcome to the podcast. And thank you for joining us this morning.

Karl Weber: Sure. Glad to be here.

Doug Camin: And so Carl, we've got the title here, vendor sales to CIO. Your background is not coming up through the IT chain. Recently you've been in the IT space. So tell us a little bit about your history and how you got to.

You've Been Heard - IT Leadership Podcast logo

You’ve Been Heard

You’ve Been Heard is where IT leaders stop being sidelined and start being amplified. We’re the triple-threat platform: podcast, community and vendor-neutral advisory that elevates your voice, your value, and your influence because when IT leaders rise, so does everything else.

© 2025 You've Been Heard. All rights reserved.