Speaker 0 | 00:07.119

Welcome back, everyone, to Dissecting Popular IT Nerds. I’m your host, Doug Kameen, and today I’m talking with David Ramsey, who is CIO at STG Logistics. Welcome to the show, David.

Speaker 1 | 00:17.845

Hey, Doug. Great to be here. How are you?

Speaker 0 | 00:20.266

I am doing fantastic. How about you?

Speaker 1 | 00:22.527

Doing good. Happy start of the week here. And I don’t know where you’re at, but we’re just south of Cleveland and we’ve got… Snow coming more and more all day.

Speaker 0 | 00:33.582

Yeah. So I’m in upstate New York, so I think we’re probably not too far apart, maybe five or six hours apart. But has it been like the winter without winter where you are, too?

Speaker 1 | 00:45.073

Yeah. I mean, we’ve been mid to high 60s in the last 10 days, and then yesterday, boom. We’re snow, sleet, everything else to remind us it’s March. So, yeah, all good.

Speaker 0 | 00:57.184

Yeah, I’m a skier with my kids and stuff like that. And this has been okay because the ski places have the ability to make snow. But overall, it’s been a pretty dismal ski season. And just no wind. I don’t know. Do you participate in any sports like that or anything?

Speaker 1 | 01:12.608

Yeah, we ski. I mean, our little hill here in Cleveland was not even able to open this year. Right. So that’s Boston Mills here in Cleveland, owned by Vail Ski Company with zero days of skiable.

Speaker 0 | 01:27.140

uh time this year so climate change whatever else is going on i i don’t know if i’d want to own mid-size midwestern ski resorts right now so i i don’t yeah i was seeing like news reports further further west like in the in the well i mean you’re in the midwest too but like the the deep midwest if you will like minnesota and stuff like that like like they they were having just no snow all the ice stuff is not you know, the, like the ice fishing and all those things, like none of it happened across like most of the Northern U S. It did not.

Speaker 1 | 01:57.272

No, I, my, my daughter goes to university, Minnesota. So she lives in Minneapolis and warmest, um, I think it’s a warmest winter on record, uh, in the last 50 plus years that there’s no ice on lakes, rivers, anything. So, I mean, for, I mean, that’s even North of there. I wouldn’t want to be in the snowmobile business as well. Right. So,

Speaker 0 | 02:19.170

yeah.

Speaker 1 | 02:20.010

Yeah.

Speaker 0 | 02:20.711

It’s wild. So anyways, we’re on a leadership podcast. Maybe we should talk about IT leadership.

Speaker 1 | 02:25.713

Absolutely.

Speaker 0 | 02:27.113

So you’re currently the chief information officer at SDG Logistics. Let’s just start and say, can you tell us a little bit about what it is you do and what SDG does to start?

Speaker 1 | 02:37.676

Sure. I’ll start with SDG. SDG Logistics, there’s a history here. There’s a legacy company called St. George. logistics and trucking company so that’s where the s the t and the g come from um and we have two private equity backers um and we’ve we’ve done a number of acquisitions and the largest one was we we we carved out um about a two billion dollar piece of xpo logistics um year and a half ago um and we’ve put this this mousetrap together um we do lots of dredge a lot of rail um you trucking as well but um there there’s a method to the madness here um i i was brought in by a few folks that i know at oak tree capital um over the over the years to kind of help uh pull everything together um you know that we’ve got some folks that uh you know have grown up at a three four hundred million dollar uh 3pl company and we’ve got other people that were part of this monstrous business unit inside of XPO. So you’ve got people that have, you know, coming out of $16 billion publicly traded and $200-300 million privately held. And we’re bringing these cultures together. And I’ve been here since June and really, you know, doing what I love to do, which is really building a leadership team, an IT leadership team. that is capable of really bringing the company together and really refining that mousetrap and all of those go-to-market things that we all have with all of these combinations of and there’s about 14 acquisitions inside of STG and then we have that big big piece of XPO and really trying trying to bring it all together and building out a leadership team. and product and technology roadmap for us for the next three years. So it’s exactly what I like to do. I like to learn a new industry every three to four years. And I do mean learn a brand new industry every three to four years. And it’s always the challenge of learning a new industry, learning a new business, bringing cultures together and trying to, you know, right size the leadership team to be able to to be to be able to really have an impact.

Speaker 0 | 05:12.114

So nice. So I’m going to I’m going to. Yeah. Kind of. zero right in on that because I think that for the listeners of the podcast, one of the things that’s really going to be interesting to hear from you, I mean, you’re working in really, these are big companies. This isn’t 100 employees or 200 employees. I mean, you’re talking about thousands of employees. You’ve got large IT staffs. You’re integrating together a lot of different organizations, different entities. So in your I think what I want to ask you is when you’re integrating these teams together, how are you what things are you looking for in the leaders that you’re there? Because you’re really leading leaders in an organization of this size in a lot of ways. I’m feeling. So what are you looking for in those people and how do you bring them together? What do you do to get them to work together? And what things do you maybe even toss aside when you’re like, nope, that’s not going to work?

Speaker 1 | 06:09.078

I think, you know, for me, having done this. a few times in my career, meaning new guy, new ideas, but you’ve got to be able to pull along some folks from all these different cultures inside of, especially companies that are made up of two, three, four acquisitions, trying to find the right balance of the team where I’ve got fair representation from these different companies or business units and finding some talent. there that is committed and very openly committed to building a single, a single team that runs the enterprise. Um, and, and, and sometimes it takes, you know, putting myself out on the, out on the, the plank, so to speak, and helping people along or calming them down a bit and say, you know, we’re going to do this together over the next two years. So I don’t expect perfection, but along the way. When I can help, I’m going to help you. Just get the people’s nerves down a little bit. Get them in a safe and comfortable spot, so to speak. Make sure we have representation from all the… For us, it’s really a tale of two cultures coming together right now. Make sure the representation is there. But then also, some people that know me, we… We… I’ve got people we’ve been traveling around together for the last 20 years together. So I’ve got a number of folks and we call it, you know, basically David’s traveling circus, right? Whether if we need an infrastructure person, we know where to go. CISO, we know where to go. Or, you know, someone to help with strategy governance and things like that. We know where to go. So I try and balance leadership from those pieces of the culture with folks that I’ve worked with for. 10 to 20 years, right? And pulling them really together to say, you know, we need to build a shop that isn’t just a siloed business unit by business unit by business unit. And we’re repeating everything, you know, horizontally, meaning infrastructure, cloud, ERP and everything else that we need some people to take broader leadership across the enterprise. And that’s what I’m smack dab in the middle of right now. with STJ.

Speaker 2 | 08:39.688

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Speaker 0 | 11:00.776

You touched on something there. And I’ve been in a similar situation where I’ve been asked to come into an IT organization that, you know, maybe it had a challenge, whatever the challenge may be, whether or not it’s well run or not. It’s just, you know, there’s a challenge. We’re merging together this thing. We’re growing. These things have come. And a lot of times, like I’ve had people that follow me from an organization, one organization to the next two. And, you know, so I’m actually I’m kind of excited that you mentioned that because that is a strategy in a certain way where you’re not reinventing the wheel of the. people at the same time you know like you you bring in a known quantity and you’ve got folks that you know you can draw down on talent and maintaining that that network of other leaders that you know that you can reach out to and be like hey you know hey hey john or hey jane uh let’s you know there’s this new opportunity but it’s going to be a challenge it’s really going to present with us this this awesome like like just something just interesting you know you mentioned you like to move around go from industry to industry

Speaker 1 | 12:02.598

I do think that balance though, of balancing, you know, bringing people along for the ride. You know, anybody that I’ve been working with for the last 15, 20 years started new somewhere, right? So finding people who want to be along for the ride to maybe they’re someone who is a director of IT in a business unit. And we, you know, we have, hey, you know, really your skill set is more engineering. What, what? how would you like to run the app dev team across the enterprise, right? Well, geez, you know, I’ve never done that. Don’t worry. We got your back. Let’s figure out how to do that. And getting people to pull themselves out of that, either acquisition mode or a legacy piece, or in our case, a very large chunk from a public company and take on, you know, ownership across all of our different products and business units is really important. And to… do that and to make make an impact in that first year you’re probably going to need to infuse a little bit of um a little bit of energy from the past right in terms of i i just i don’t have time to recreate the wheel here when it comes time to you know how do i build a it governance model it executive council without over engineering it but i need some some folks that that you know know how to do that and are you know closet financial people that can roll up budgets and know the difference between capitalization, expense, cloud, on-prem, you know, how do we shift models, things like that. So I try, probably not always successfully, but try and really balance making sure we’ve got, you know, we’re lifting some people up that maybe it’s probably not the happiest day of their life, you know, meeting a new boss, you know, so to speak. And how do we get over that quickly? But then how do we accelerate folks and our impact on the company within that first year, right? Because you only get one chance to be the new person, right? You get six months in, you’re starting to inherit. You know how this goes, especially in our line of work. It’s not fair, but it is what it is. I think anybody listening to this podcast is probably a reason why you listen to podcasts like this, because I personally believe CIO. gigs, CTO gigs, Southrop Cesar’s in there these days, right? These are some of the hardest jobs in the world, in my opinion. They’re not only because they’re just not fair, are they? Right? You have to put so much on your back and, you know, basically roll rocks up the hill for a living humbly, right? And there’s no, maybe 30 years from now, this role will be… will be easier to understand or business folks will take more ownership on that digital so to speak end. But I’ve been at this for 25 years as a CIO and it is the most unfair role within a corporate America. And once you accept that and once you kind of let it sink in, then how do you how do you humbly start pushing rocks up the hill? building roadmaps, building strategies, and really starting to underpin how the company runs. And could we, you know, everybody wants to hit a home run with technology. How do we get to that point of large-scale investments? And that requires a ton of trust. In our case, this is where it’s challenging for us, right? It’s private equity owned. We have a huge chunk of a former publicly traded company. We have a really profitable, smaller piece from the past. But these cultures are massively different, right? And how do you build a team that can, and knowing full well it’s a private equity world, right? These guys want to hold these things for three to four years, add value. and potentially exit down the road, it does take a team that’s kind of been there, done that before. And a lot of these thoughts or emotions or feelings have nothing to do with technology, do they? It’s just how do you get these groups to start working as one and then over time adding value? And that’s really what I like to do. It’s not easy because it requires you to… man, be the new person every three to four years.

Speaker 0 | 17:03.698

All the time, right?

Speaker 1 | 17:04.719

All the time, right? And you know how much energy it takes to be the new person, right? One-on-ones, trips, get to know you, dinners, lunches, everything else, nonstop, back-to-back, Zooms or Teams calls in the middle of this hybrid world. And I wouldn’t want to do anything else. So that’s… That’s… That’s kind of where we’re at right now.

Speaker 0 | 17:31.106

Now, you know, two comments and then another question here. First comment is IT folks with finance knowledge and backgrounds are understanding of finance underrated skill. One hundred percent. Like, you know, and, you know, when you come to like tech, when you come to tech, like tech is not always. I like to tell folks, you know, particularly other leadership when they come in, they’re like, oh, how can we solve this? And I’m like, tech may not be the solution to your problem. Like my job is to know when tech is the solution to your problem, not to make tech the solution to every problem. And and that’s that, you know, that’s a that’s a tough one to get across to a lot of leadership who are used to just being like, you know, please fix this problem right now and do something, you know, like, can you write a can you write a program for this? Can you do this thing or whatever the case may be? And, you know, that’s it’s really challenging when you’re you’re working at these breakneck paces. And. And so there’s a lot I can just hear. Yeah, I can mentally envision this, like the weight, if you will, that comes down to solve the problem rapidly. And then a lot of people are like, David, solve it with tech, right? Problem solved. Moving on. You know, we’ll come back to him later. And you’re like, whoa, whoa, whoa, wait a minute.

Speaker 1 | 18:45.733

No, I’ve learned, you know, over the years, it’s not all just tech. It’s funny you mentioned that about finance skills. Fortunately or unfortunately, I had the pleasure of working for a CFO for eight, nine years. So I was on the CFO staff, right? With the controller, head of planning, treasurer, the guy running Sarbanes-Oxley, this, that, and the other. And whether I loved it or not, I guess when I reflect on it, that’s how I really became a pocket finance person, right? you know how to capitalize things what is depreciation why does a fixed asset and depreciation block you from moving to the cloud right how do you get out of these these cycles of you know capitalizing everything but i want to move to the cloud in which is pure expense um i really think you for younger IT leaders, even at a manager level, knowing how to run a P&L, read a P&L, understand your depreciation, how big is that fixed? How big is that asset, right? When people say, oh, just capitalize that work, right? At some point, that hairball is growing larger and larger by the day. So I really feel like the ability to be an extremely competent financial person kind of disguised as the nerd down in the nerdery there’s some pretty pretty good skills to have meaning i don’t know how you would fund anything cool without knowing how to kind of how to put that business case together how to sell it how to shop it how to socialize it um how do you go from i’m fortunate enough to work for our ceo um how do you go from a decent conversation there to selling it to CFOs, COOs, and then showing up at the next board meeting with the big lump in your throat. I don’t care how old you get when it’s a $5, $10, $20 million project. Everybody’s staring at you and saying to themselves, like, okay, here we go. You’re taking a big risk here.

Speaker 0 | 21:06.612

Follow the line.

Speaker 1 | 21:07.693

And what I meant by maybe in 30 years, the management team and the boards will understand it’s not just a single person that’s putting those chips out onto the table and it’s not a gamble it’s the full company right and i think that’s what that’s what gets a lot that’s what probably keeps a lot of cios up at night is that is the fact that you feel like you’re the only one taking the risk the company takes takes the rewards when they’re there And, you know, punishes the punishes the response of, you know, that go live didn’t go great or something extended out, went over budget, things like that. But there’s always there’s always there’s always someone like you and I willing to kind of push those chips on the table and say, I’ve been around long enough. I see what the problems are and I’m willing to kind of take a deep breath and and stand by that. The fact that we need to make these investments. And, uh. I have no problem doing that. It just takes a lot out of you, right? And that’s where those scars come from is learning a business, understanding a business, taking a deep breath, taking a step back, but then kind of getting to the point of, these are probably the three bets that we probably should be making over the next two to three years. There is that moment as a CIO where you feel the weight of the world on your shoulders and you feel like, okay, you’re the only one right you know as i always say you there’s not many people or roles that are like this where you feel like you’re taking that gamble or risk with your own career your life your your your kids may love the new town you live in and you’re already making the big gamble on your new technology project and um life life doesn’t go perfectly right and um but sometimes the biggest risk

Speaker 0 | 23:07.132

you take with your career is not taking one right so yeah and then sometimes it’s really hard absolutely yeah i’m i’m going it’s you know for me it’s you know i guess personal story time flip the tables here for a second but uh you know so like i’m doing that in my current role where we are where you know where i work for a non-profit uh a human services nonprofit in the rochester new york area and one of the where we grew a lot you know we were about 500 employees and about 40 40 50 million dollars in revenue and we’re but we grew doubled in size over the last you know 10 uh seven years or so and as a consequence like a lot of our systems were were outdated they were built for you know a smaller version of our company yeah so we are in the process of of going through a comprehensive project to build out an enterprise architecture model that architecture against what you know our our our needs and you know solicit the feedback and everything else to push through doing new erp and and crms and you know workforce management and human capital management systems and stuff like that realistically like wholesale out the business’s back end of uh software operations and like that’s a yeah it’s a big deal to have to stand up in front of somebody and be like you know go to the ceo go to the rest of the board that’s out there and say like hey guess what we’re gonna go spend you know this is probably going to be a couple million dollars worth of of investment over the course of, you know, 18, 24, 36 months. And, you know, That’s if it doesn’t go well, it’s there’s only one person they’re going to look at to say that it didn’t go particularly well, you know, in spite of what might happen.

Speaker 1 | 24:44.020

In spite of people believing that this role has changed over the years, I think it feels almost exactly the same. Meaning you feel a massive sense of accountability that you are putting yourself, your career on the line to do something big. And I know full well, if you just sit there in the comfort zone for two to three years, you’ll probably be labeled the CIO who just didn’t know what to do or they weren’t visionary enough, right? You’ve heard it all before and inevitably that cycle kind of collapses on top of yourself, right? So you have, I think that’s what’s addicting about the role is that you know you… You have to push the rock up the hill while making progress at the same time. There’s not many jobs like that, right? I mean, there’s days where, I mean, I have a lot of good friends that are CFOs. But you know what? Rarely are they asked every two and a half years to put your neck out on the chopping block and to move forward, right?

Speaker 0 | 25:54.334

Let’s reinvent the place.

Speaker 1 | 25:57.116

You got a monthly close. You got a quarterly close if you’re private. might be a little bit easier than being public if you’re public then you’re a little more outward facing and i and i get it it’s a tough role but these cio things are just so unscripted meaning if you sit there in the chair for three years and don’t do anything except you know maybe make the help desk run a little bit better you’ll probably be known as that guy that now they’re looking for the innovative guy right so um i would say i tend to be more towards a builder than a maintainer. So taking those risks a little bit, I’ve been doing that my whole career. But as I get older, I do ask myself, is that really fair, right? Have we not infused this technology everywhere in our lives where everybody can say, hey, we really would like to do more here and I’m not boxed into a… percent of revenue or a it cost per end user um type of discussion that we were having maybe 15 years ago so um so i’m gonna i’m gonna change this just direct into a different area of discussion here but you mentioned about you

Speaker 0 | 27:16.841

know the culture and bringing people together and and so can you maybe share with our listeners a little bit about what elements of culture do you want to build in the organizations that you build you come into these you come into these you You’re doing this every two, three, four years at this point. So each time you’re having to figure out what kind of culture you want. So you probably have a lot of experience and insight to share. So I’d love to hear more about that.

Speaker 1 | 27:41.720

You are right. And if I think about it, I do start to laugh. I have an embed, almost like firmware. I have a playbook in my head. I know really what I want to get after in those first 90 days. six months, nine months, 12 months. The biggest thing for me is if you find that you’ve kind of wandered into a brand new shop, then the problems aren’t easily, you can’t really learn. It’s impossible to learn a company, meaning it’s not open. There’s not a Teams channel or Slack channels with tickets coming in and I can start to read tickets in real time and see where the issues are. everything’s, if everything’s cordoned off and hidden, I spend a lot of my time just turning black boxes clear. Whether they’re issues or not, we need to be very upfront about, you know, our service metrics, where are the problems at? And when you said door culture, you know, how do you build that cultural world where you feel like you’re in a safe place to… run out in traffic on a Saturday, meaning in a public Slack channel and say, hey, this is blowing up on me and I need help right now. You know from probably your career, engineering teams that feel safe, like they’re in a safe place to do that. Time to resolving issues or fixing things is just second nature.

Speaker 0 | 29:25.380

They are more productive because they will collaborate to solve the problem as opposed to like trying to hide it.

Speaker 1 | 29:31.242

This is where you see some of that, you know, IT abuse creeping in, meaning, man, I tried to be open one time and, you know, the VP of fill in the blank just crushed me for being too open and too honest and said the other. So how do you create a culture where? the problems really surface themselves. And we reward that behavior more than we do hiding the problem. Meaning, you’ve heard this a hundred times, or at least this is one of mine, where it ain’t broke till it’s fixed, right? Meaning no one really knew what the issue was until someone issues that walk-off, home-run hero email that says, hey, I just fixed this problem. Number one, I didn’t even… didn’t even know it was a problem. Number two, that’s a lot of users there that were impacted. We probably could have done a better job communicating. So for me, it’s the first stop on that culture train is just developing a culture of being transparent and being comfortable enough to step out there and just say, hey, I got a problem and how do you help? And now that we’re all in this hybrid world, what are the tools? what’s the tooling that’s needed in order for a shop to function like that so um the first stop for me is just that transparency sometimes it’s a tooling issue as well right just you know i got you got nine different help desk platforms um nine different leaders trying to do things different things you know how do we consolidate so that visibility goes goes up and the trust goes up right so and and and you’ll see with your with your business you know users owners whatever you want to describe that when when they see someone being that open and transparent it tends to rub off um and we’re coming together we’re not button heads and we’re really solving problems and and and a lot of times i think with having done this yeah five five six times um that playbook of just creating uh openness and transparency It works on the business side too, because a lot of times from the business side is, you know, you get that age old thing. Like, I just have no idea what you guys are even talking about. There’s just, it’s a lot of acronyms. It’s a lot of gobbledygook. And I just, I need a translator, but I need someone who’s willing to help create a culture that it is open. And it’s okay to raise your hand and say, I got a, I got a major problem here. And I need some, you know, whether it’s talent, more. more resourcing or, you know, some investment in some new technology, it’s, it’s, it’s all, it all starts with being transparent, um, where your issues are. And if you’re not, you know, good luck to you and your funding. Right.

Speaker 0 | 32:30.996

Yeah. Yeah. I’m, I’m a big, I’m personally, I’m a big fan of, I refer to it as radical transparency. I I’m sure I did not invent that word. So, but, but the, you know, the idea that, uh, I, you know, is, is the leader. I am always comfortable answering a question about like what’s going on, you know, so like there should never be a point in time when like somebody comes to us and they say like, hey, what’s happened here or even the team as well. You know, like you should be open about what is happening at any given point in time within confidentiality reasons, of course. But but to like I shouldn’t have to to to conceal the the activities of the department from somebody else in order to more effectively get our work done. And that really creates a. As long as you are open and sharing, you really build, that’s one of the key ways to build bridges with those different departments that you’re working with. Because you’re a service organization at the end of the day when you’re in IT, you’re servicing the rest of the business. I guess unless your product is the software and you’re the software development person, but for the most of us, we’re in service to something else.

Speaker 1 | 33:39.771

Absolutely. Yeah, I think that’s well said.

Speaker 0 | 33:43.846

So we talked a little bit, we talked about what you’re doing now, what, you know, the cultures that you like to see and build. But we’d love to know a little bit more about like you, you know, your history. So how did you, you know, can you walk us through kind of your professional history a little bit to understand how you got, how we got to now?

Speaker 1 | 34:03.391

Sure. I think it goes, it goes, goes back to, it goes back a ways. I think there was a really. One person in my life who took a great gamble with his own career and made a 28-year-old kid a CIO. And I was at a post-IPO of a company down in Jacksonville, Florida called PSS World Medical. Later, we sold to McKesson. But I was working for the CFO at the time, Dave Smith. This is a CFO we were just discussing to teach you all about. you know he’s a former uh like pwc partner right so very finance heavy but um but a great but a great mentor very loud loudest voice in the room great mentor things like that and i was i was i was my first role there was we were rolling out oracle financials uh back in the oracle 10-6 days for those paying attention here which is really old um we’re doing financials ap some different things um helping the company go public at the time was about 160 million. Something happened over in IT, I really wasn’t paying attention. And I ended up as the interim CIO there, which I never really aspired to do. But I spent almost 10 years there growing that business. So we grew that place from about 160 million to over 3 billion in that course of 10 years with about 125 acquisitions. All of us, I mean, we used to laugh. We used to have people tell us that your compensation is experience. You know what I mean? At my age now, I’d be like, yeah, okay, that’s funny. Let’s have another conversation. But I think back to those days, and those are some of still my best memories kind of growing up in the business world. And I probably have spent the last 15 years. chasing, looking for another culture like that because it was addicting. We were doing so many acquisitions even back then in the early 2000s, right? The technology platform really, really mattered, meaning there wasn’t anybody sitting back and saying, this is a waste of money, even back then, right? We put warehouse management systems and ERP systems in 50, 60 warehouses at a clip, 2,000 sales reps. We were doing, even at the end, almost 70% of that revenue in the early 2000s, e-commerce revenue, which if you remember that fun e-com bubble, that’s kind of all that mattered. I did that for almost 10 years. And I really wanted to find some experiences around manufacturing and international work as well. So my first run-in with an actual executive recruiter, I guess I had been sitting in a chair long enough where someone would call you. Sometimes that’s really exciting. Like, you want to talk to me about what? Like, oh my gosh.

Speaker 0 | 37:32.913

You want to speak to me?

Speaker 1 | 37:33.974

I feel special today. One thing leads to another and you get a first interview and they’re like, went really well you want to keep doing this and you know one thing leads to another you get a new role um we we moved from jacksonville florida to texas to san antonio for a crazy mid device company at the time called kci um that thing went from about 200 million to 2 billion in less than three years um the growth was crazy um and that eventually kind of i i i learned a lot It’s publicly traded again as a CIO, all that fun. Sarbanes-Oxley, good times there. But I got a lot of international experience, which I had never had before. We were a US-based company at PSS. So that was really fun for me. Trips to Amsterdam, India, all that kind of stuff. So all of that international stuff started to open up for me. Great experiences there. And along the way, like we all do, we meet different people from different companies. And we found ourselves up here just south of Cleveland at Diebold. I don’t know if you’ve ever pulled money out of a cash machine.

Speaker 0 | 38:54.936

I know Diebold well. So I’m an audit committee chairman for a large credit union. So, you know, and I’ve done many years when I was at IT consulting. I was playing with the ATMs on the backside. So.

Speaker 1 | 39:08.294

Yeah, we can have another discussion one day about the company culture of a 155-year-old company, right? Basically, a safe manufacturer that was crazy enough to stick a laptop inside of it and put cash inside of it and push it out onto a street corner. We did a lot there, a lot of ERP work. And again, just 82 countries. Probably. this is probably some of the toughest stuff that i’ve ever done personally in my career was you know the 80 plus countries it starts to get wildly complex um regional differences um things like that so i did that for right around four years um and then you know from there on i’ve been i’ve been remote since 2000 and 2014 really um kind of doing these types you know two to three year runs as cios whether they’re interim or others um i’ve been i’ve been in the bpo space with t-tech out in denver for a little over two years for that project and then i went back in to private equity um with the background screening platform so i i kind of learned um my engineering chops all over again um and then an old friend called and i Over the last two and a half years before STG, we were at a startup called Butterfly Network, which creates the world’s smallest handheld ultrasound on a chip. Your big medical facility there in Rochester was our largest preeminent first client. So you may see a butterfly device if you unfortunately have to check into your local. big clinic that you have there in town. We did that for two and a half years. I’m going to say we again. We’ve got a little bit of a traveling circus of friends and probably I’ve got two people that we’ve done the last three to four things together. And then now we’re at STG. And that opportunity really came through some connections. from the private equity side. I’ve got someone that used to work for me way back in our PSS days, Ish Sundaram. Ish was the CIO at JetBlue for many, many years. And now he does a lot of advisory work with Oak Tree Capital. And we talked maybe once a month, we have for the last 20 years. And the opportunity to come kind of help this newly formed… And… thing together was a little bit was was an offer i couldn’t refuse so that kind of catches you up to current so um awesome a lot of a lot of different experiences a lot of different industries um things like that i mean i always get it’s kind of funny we’re doing a podcast like that this is the running joke with most of my teams is when are you going to retire because i just want to sit back and and listen to the podcasts of all the stories right so you

Speaker 0 | 42:33.930

We’ve got like 260 episodes. This is a good start, right? Yeah, that’s right. You can just add it right to the catalog.

Speaker 2 | 42:41.693

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Speaker 0 | 45:06.321

going back in history so when what got you into technology and or what was your first like technology or computer experience like what were you were you like Were you like an IBM PC person, a Commodore 64? Were you, you know, TI? I was a TI-99-4A guy. But, you know.

Speaker 1 | 45:25.328

Did you get that? So I had, we had a TI. My father was an engineer. So willing to step out there and buy, you know, brand new IBM PCs back, you know, in the days where they were, you know, XT. uh i forget those things but yeah no i i probably had a pc available to me fortunately uh since i was you know fifth grade um and for someone my age for people listening in it was a very big deal back in the day to have one sitting in your basement um but yeah that was so but the technology to me was always been something um lots of pieces of technology you don’t have to pay me to continue to do research on what’s coming next, what’s really out there. Even in my advanced age, I find myself lapping the 20-somethings on what’s really happening in the tech world. It hasn’t been something I’ve had to force myself to learn. I’ve had to learn the finance stuff, the leadership stuff, but the love of technology has really always been there for a very long time, still to this day. I can’t even…

Speaker 0 | 46:45.650

disclose what my gadget budget is in this household right so i i was you know similar similar background like i was as a kid it was just sort of assumed that i would be in the computer business you know like it was like oh doug doug knows computer things and he’ll do computer stuff and he’ll be all set because he’ll be in the tech business and like that that that solves one problem of what what what the kids are going to do in this family but it does i mean even

Speaker 1 | 47:15.570

It’s kind of like being the AV kid back in fourth, fifth, and sixth grade. It continues on to this day. Even though we just had a board meeting back in January, and someone just says, there’s going to be four or five board members that aren’t going to be able to attend. Can we just set up a mobile Zoom room at the hotel? This is completely off-site. So there I am, show up at this board meeting. Again. two backpacks full of gear like i got one i got a little owl thing you know for the 360 camera i got a 4k projector separate laptop to run the zoom room got a little mac you know a little little ipad screen to run the mobile zoom room and boom you know i’m down there at 6 30 a.m um cobbling this thing together and loving every minute of it still and everybody walks in and just you know

Speaker 0 | 48:13.374

You got the Mary Poppins bag. That’s what I refer to that internally as the Mary Poppins bag.

Speaker 1 | 48:17.175

That satisfaction of just like, oh, yeah, look at this. And it’s on hotel Wi-Fi. Can you believe that, right? So, yeah, don’t have to wander far from the love of technology at all.

Speaker 0 | 48:34.783

So we’re coming to the end here of our interview. But before we go, the one thing we… One thing I always make sure to ask is there’s well, two, there’s really two questions, I guess. One is you’ve been in this a long time. So what lessons did you learn now that you wish you would learn then? And also, what would you want to share with listeners about like being a leader in the IT space that like if you’re giving advice to somebody?

Speaker 1 | 49:01.495

Oh, man, I think the biggest thing that I’ve learned along the way in terms of IT, IT projects. Getting to the other side, ripping the bandaid off, so to speak. I know this is hard advice to take on, but the smoothest way across a gravel road is 90 miles an hour, right? So this is, from my grandfather, he used to say this, like, literally, the fastest way across a bumpy road is 90 miles an hour. And he’s wrong. Meaning, you are always going to have problems. You’re going to have problems. 10 problems every morning. Doesn’t matter what you’re doing. It’s just how can you absorb those? Did you plan well enough? But once you get moving. you better go fast, right? And this incessant desire with IT people to chunk things up into yet another phase, and I’m going from pilot to phase to this, and that adds up, right? And your time as a CIO is over after those first 24, 36 months. And if you haven’t really moved the needle too far, they’re going to… probably look for someone who can do it right now granted our profession is much like being a my wife calls this like you’re essentially like an offensive coordinator for an nfl team right sometimes it comes down to how good of a quarterback you have what kind of this is not just all the magic that you personally bring but i guess the biggest piece of advice i have is when you see the business need and you know exactly how you can solve it And if you know how to get through, how to sell it, how to fund it, how to capitalize it, how to push it to the cloud, how to do that. When you get that green light, you got to buckle in and go. And you have to have thick enough skin to keep going until it’s done, right? Because everybody’s rooting for, a lot of people are rooting for you to kind of slow down, take a break, don’t worry. Oh, you want another phase. oh you want to delay your go live by six weeks that’s smart right you know i think that’s the smart thing to do i’ve learned that like not to do things you know reckless but when once you get that momentum you will never get that back at that company right and you had better go and you’d better have enough resolve and enough gas in the tank to make it through right so then this comes back to that this is where i think the role is sometimes unfair where people are asking you to gamble with your life, right? So to speak for an ERP project or a big replatforming of your cloud product, right? It’s all on you, right? And trust me, I’ve moved three kids all over this country with all of these moves that we were talking about. And sometimes those moves aren’t the happiest times when you talk to your kids, but… When you talk to them now, though, they’re very happy they have all these crazy experiences. But I can think back and say, you know, two times where we went and did something new was because programs or projects kind of fizzled out and they just kind of ended, right? Because we just, we lost sight of having enough mental fortitude to just finish, right? If you have that opportunity to get that momentum, the funding, the board support, leadership team support, they want to see you have that leadership kind of backbone to be able to finish that thing off. Because it’s never going to be perfect. It’s never going to be easy. And do you want to be known as a CIO who actually is the one that got them off the mainframe or moved them from SAP to the cloud? If you… If you want to be that person and have that big of an impact on a company, you can’t. You got to go as fast as you can. So and that’s not it’s not fun. It’s counterintuitive to life.

Speaker 0 | 53:25.127

That’s that. That’s amazing. I’m really glad you unspooled that. And it was it was a great narrative to share. So, David, thank you so much for investing your time with us on the podcast today. And that’s a wrap on today’s episode of Dissecting Popularity Nerds. I’m Doug Kameen, and we look forward to coming to you on our next episode.