Inside CTOx with Paul Benson (Final).m4a Wed, Feb 18, 2026 0:00 - Paul Benson with the fractional role, that word no is okay to say. No, that doesn't make sense for me to do that right now or for the organization itself to do that right now. You might need to think about that. You haven't seen the whole picture. Let's talk about that. And I can get into conversations and engage with them to help them explore things they might not have thought about. 0:33 - Donna Welcome to Inside CTOx Podcast. I'm Donna, Head of Membership and Partnership, and today we're stepping Inside the minds of some of the most innovative tech leaders out there. This isn't just a podcast. It's a place where CTO journeys come alive, where stories of struggles, breakthroughs, and growth We're here to unpack the experiences of real CTOs navigating through our CTOx accelerator and membership program. So sit back, tune in, let's get into the story. Welcome to another episode of Inside CTOx. Today we are so blessed to have the wonderful Paul Benson. Paul once saved a company 12k a year just by rethinking Then he led a 750,000 EMR overhaul that finished early, under budget and paid for itself. Very impressive. But for years he stuck to the W2 script until he didn't. When Paul finally went independent, things just clicked. He has his first client from a past healthcare organisation and then Then he found CTOx and shifted from tech lead to strategic advisor. Using our framework, he closed his first full-time CTOx agreement, rebuilt his brand, and is now aiming to 5X his income by 2026. And he's not looking for the next job. He's building the next chapter. This is just the beginning. I'm so excited. Welcome Paul. So pleased you you you're with us today. You you spent years as I mentioned there as a W2. What was the push that just broke that pattern and was like I'm gonna bet on myself? 2:36 - Paul Benson I had gotten released from another company that I was the director of IT services and they were restructuring their organization. And so they walked in one morning and said, well, we're gonna, we're gonna let you go. And I was like, oh man, geez. And the first thing I did was panic. I started sending out LinkedIn messages and resumes and actually, I got accepted for a job as an IT manager in Alaska. 3:22 - Donna Alaska, wow. 3:24 - Paul Benson Yeah, and I live in Tennessee, so. 3:28 - Donna That's a big shift. A little different. 3:34 - Paul Benson I got, they asked me to come and I was just pondering that and thinking about that and something in my spirit just said, you have been working like this all your life and you want to get freedom and be free and be able to come and go and move as you like and not be So you can either go do this W-2, or you can start to consult. And that's kind of what happened. I just chose to start consulting. I called the company. I said, hey, I'm sorry I'm not coming. Matter of fact, I'm actually working right now to try to get them as a client. 4:24 - Donna Good turnaround. 4:25 - Paul Benson They fit perfectly in my wheelhouse. And I just started down that road. And a year and a half into the consult, I happened to be, I can't even remember where it was. But somehow or another, I came across the CTOx information. And I was like, that's a smart idea. And so I clicked the button and I ended up with Lior and, you know, he's a convincing fellow. 5:06 - Donna To say the least. 5:09 - Paul Benson So, um, I took a couple of days to kind of ponder that and I decided, yeah, let's do that. And so I signed up and got started. Started to work with the tools and things like that. And that helped me transition the current client that I had from a straight IT consult, hands-on, deep hands-on, to a fractional role now. And we're actually getting ready they're working on their side of my contract, the CTOx contract I sent them. 6:00 - Donna We love templates. 6:02 - Paul Benson Yeah, for the master service agreement. And they're about to sign that and we're going to be in an agreement for a full year with me tapering off my time on site throughout the next six months, and hopefully by the six months, if they follow the plan that I've, using the tools CTOx gave me, I've developed a plan for them, and I have a full plan out for the next year, and with action items, and what they have to do, and what small things I've gotta do, and what vendors gotta come to the table, And changing the whole, they actually had an IT department originally, and they got rid of the whole IT department. And are now looking to be a completely outsourced thing, which is a lot different than they're used to. So their change is not easy. And so they're having to make this shift. Them through that shift along with, you know, using the information I've gotten at the CTOx meetings and talking to some of the other CTOXers. I've been able to, as a matter of fact, just yesterday I got a good idea from one of the guys in our cohort and I was like, okay, and I applied that and I've made some change just in the last 24 hours using the information that I was able Yeah, that's great. 7:45 - Donna That's great. So we've gone from employee to hands-on consultant to fractional executive C-suite advisor. So like, how has that changed? Like day to day, how has that changed for you? 8:08 - Paul Benson It has changed because now I don't have to You know, being hands on, you're engaged and you're talking and you're doing and you're all this stuff. And with the fractional role, you're backing your hands out of it. And you're basically saying, Mr. Client, you need to do this. And here are the top things you're going to need. And, you know, if we need to get you some staffing augmentation, we can do that. And that'll help you get through this pitch. Right now rebuilding their network. So they're doing a full swap out of their network. And I was like, I'm not climbing up to put APs up. 8:56 - Donna Not my job. 8:59 - Paul Benson But I can, I can, I can direct it. I can make sure that it gets done properly. We can, I can work with the network engineer to make sure that the network is working I can do help do the testing because that's just quick stuff. Yeah, but I'm not changing out a piece for you. And so it's it's helped the organization understand because they had a full IT team. And now they have none. And they look at me and I'm going. I won't be passing out Adobe licenses. And so I've helped them actually develop the internal team that will oversee all their IT or technology related issues. And I basically am working with that team to try to help them understand the things they've got to think about when their phone systems do for renewal next year. So I'm helping them think about what they got to think about, and whether they get one application or three in order to handle it, and how much does it integrate with their EMR, and et cetera. So there's a lot of little things where I'm now doing more advisory role, just talking about, here, think about this. Think about that. And so I'm writing and documenting a lot more. My emails are not, oh, by the way, your laptop is ready to go now. 10:42 - Donna It's much more using what you've learned over these many, many years in the industry. And I'm being that decision maker, being that strategic lead. And as you say, taking your hands off the keyboard and saying what you get access to is my brain. 11:00 - Paul Benson Oh, that's great. So they're turning the corner. They're making the adjustments. And I think in about four to five months, I will be completely hands off. 11:19 - Paul Benson That's fantastic. 11:21 - Paul Benson The rate that they're paying me changes. 11:25 - Donna Well, this is the other thing about C2X. Of time again, people come to us with proposals and say, Hey, I think my value is this. And time and time again, Lior is like, No, you're wrong. It's much higher. And every time he's done that, bar none, they have signed for the higher price. So really, like just teaching you to, to like know your value, and then how to show it because it's just one thing knowing it, but like, how do I actually demonstrate that to somebody else can be quite tough, can be quite the challenge. 12:00 - Paul Benson And that actually happened for me here in this, in this particular, with this particular client, it, they, they were paying me, uh, by the hour and had me down real low on the hours. I was like, no, you're no, we're not doing that anymore. And that's, as I, and that's when the transition changed and it's a $15,000 a month. 12:23 - Donna So let me ask you this, there's a big shift here, but thinking back to kind of what you'd learned before, what's your approach now when a client is stuck in this old school thinking, like the overspending on the printer supplies. 12:44 - Paul Benson So how do you approach that now with a client and has that changed over the I approach their need to change by simply going out and finding information about whatever it is we're trying to change, present that to the C-suite and be like, look, you can continue to make your spin be over here, or we can do something and maybe reduce what we're doing by applying these particular things and principles. So you pay less, get better service. Because at the end of the day, it's not about the company's technology. It's really about the people that they serve. If they can't use the technology to serve the people, then you've got to fix the technology. But at the end of the day, your thoughts should always be about who it is on the ends. Maybe since I work in the healthcare space, that is my focus. I want the person coming through the door to have a desire to come back. And it's not me because the provider couldn't enter the information right, or the nurse couldn't do X, Y, Z. It's because the technology worked, so the patient had the ability to come in, to be seen, be checked in the front, be seen, and get out and have a wonderful experience. Because technology could be the best in the world, but if the process is in the middle... And I work with the customer sometimes on those issues too, those soft skills things. That they don't consider because, you know, most cases they've been, you know, they've got a variety of generations working in their environment. And I just, this is the way I've been doing it for the last 20 years. 14:55 - Donna We've all heard that. 14:58 - Paul Benson That's not necessarily the way you ought to be doing it. And so the technology has advanced so greatly. I mean, helping the organizations transition out of that stuff into the new items that can make things faster and better for the customer. That's where we want to be. 15:23 - Donna And what would you say is the biggest mistake in tech for healthcare organizations? Is it that lack of transformation and updating? Or is there something else, particularly in the healthcare space? That's a challenge. 15:38 - Paul Benson What I've seen is they're stuck doing it the way they've been doing it. The applications are coming along, the EMRs are really developing, and if there was ever a case to have AI in medical, you'd want to make sure that it was the EMR providing because it puts the legal onus on the MR provider or vendor versus you trying to do some stuff in-house. I have a whole conversation I can have with groups about that. But the biggest part, I think, is just dealing with the individuals changing how they do things. The applications are now easier, able to talk to each other. So if I'm XYZ provider at XYZ place, and I need to send an information note because the patient is actually in Alaska having surgery, and I need to send that information, it's digital transfer. It's not picking up things and scanning it. And then faxing it over. That stuff, those days are gone. 17:02 - Donna Too slow. Too slow. Too slow nowadays. 17:07 - Paul Benson You know, you got to depend on people to touch the paper and it's just, it's one of the biggest things that I've, I mean, I'm experiencing even now trying to get them to understand that you just use the digital transfer. Most everybody has now has an address. It was required by HRSA, the main medical organization in the United States, it was required by them to have this ready. So the EMR vendors have supplied and it's just people making the transition to do it, to use it. That's the big part. The vendors do upgrades once or twice a And what I've also seen is the clients don't necessarily spend the time training or learning the new stuff. So they're still trying to find workarounds for the old stuff when the workarounds have been fixed and all they have to do is enter the data. 18:17 - Donna Yeah, these are like soft skills. Like that's so interesting because we think of technologists as and the CTOs have been like hard technology people just knowing every single possible technology Inside eye. But actually what I'm hearing is going, actually the soft skills are possibly the same or even more important because all the technology in the world doesn't help you if nobody's going to use it. So like what ratio would you give that like the importance of those soft skills versus just pure technical knowledge? 18:55 - Paul Benson I'd say it's 70-30. I mean, the soft skills is what will help the people use the technology. Help them get in the mindset of using the technology. Many times, you know, I found when I'm working with IT teams and I found that that, you know, there are two basically kind of teams. There's the kind of teams that are kind of like crazy like me and always want the new, latest, greatest, make it go faster, sleeker, easier, better. And then you have the other team that basically makes sure that the water and the water tap turns on just nice and make sure that the computer boots up and, oh, look, there it goes. And they're satisfied. And in healthcare, because it evolves so much, I mean, it's evolving daily. If you don't, you know, help the organization move in those directions, they'll be stuck. And they'll be doing, you know, they'll be sending out faxes on a hotline that's not managed by anybody anymore. And could potentially get cut off because the AT&T tech is out there going, la la la. 20:31 - Donna It's, it's, it's, it's incredible. And yeah, having like bringing people along and, and yeah, it being able to explain the technology and talk to it and, and understand it from their perspective. Like this is here to help you, even though we know you didn't get into the healthcare industry to work with technology. That was not the goal of joining. I want to do tons of paperwork and use four different technology systems every single day. That was not the goal when you joined healthcare. So, yeah. 21:03 - Paul Benson You didn't go to school a million years to become a doctor. 21:08 - Donna To do anything. Other than help people. 21:14 - Paul Benson The unfortunate thing is that they have to use the tool. 21:22 - Donna It's required for the billing. 21:24 - Paul Benson It's required for insurance companies to validate the information. It's required by the Fed. 21:31 - Donna It's a necessity now. There's no getting around it. But the easier we can make it for people, then the better and that's for sure a role that the fractional CTO plays. So Paul, you said in your own words, you quoted this at me before, you want to 5X your business in 2026. That's incredible. I love the ambition. I'm excited to see you, but let me ask you straight, what's the plan to get there? What are we doing? 22:07 - Paul Benson Well, I'm going to be calling Donna almost every day to review my marketing information that I'm sending out. I will be calling Lior quite regularly. Lior, okay, I got a proposal here. Now, please look over this thing and make sure that I get... And Marissa, I'm running into this roadblock. These people are acting just kind of... How do I overcome? And after I've gotten taken the advice from you all, I'm fairly certain that I exercise that information and put it to good use. I fully suspect to do actually more than 5X, but 5X is a decent target. 22:59 - Donna Conservatively 5X. 23:00 - Paul Benson I still have to build some infrastructure in behind that. I believe it's doable. I believe it's very doable. 23:09 - Donna So what's your approach now, given everything you've learned to like marketing, to getting out there and getting those, those clients. I know that's something that a lot of people struggle with. Um, so talk us through kind of like what your approach before, and then like, what's the approach now, knowing everything that you know, to get to that minimum finance. 23:32 - Paul Benson Well, my approach before was, God, I hope somebody calls me. 23:37 - Donna Hope is not a strategy. 23:40 - Paul Benson Let me just put another LinkedIn picture up and maybe they'll recognize the fact that I made a change on my LinkedIn. But through the meetings and the sessions that we've had, with NCTOX, I've learned how to use some tools and to really get after the marketing thing. My LinkedIn page is being updated now three, four times a week. I'm posting questions and things like that and even posting stuff about me so people can learn who I am. I'm not Paul Benson the smart guy. Paul Benson, the smart guy with a personality. I'm I'm human. And we can get together and relate. CTOx has taught me so much, broadened my horizons and helped me think. Not just about getting through today, but what is what's out there? How can I how can I reach out? And you guys have given me a variety variety of tools and I'm just executing. I'm simply executing. I've hired a little intern. I've taught her some of the, given her access to some of the CTOx stuff so she can see and she's learning and she's developing. My CRM is, what was a CRM before? It was a spreadsheet. Now I have CRM, and she's building cold email campaigns, and she's got like five or six already ready to go. And I'm just going, huh? 25:34 - Donna She's doing a great job. 25:38 - Paul Benson I've used, I've done, I've listened, I've learned, and now I'm executing. The things that you all have taught. And I fully believe 5X is doable. 26:00 - Donna Oh, I've no doubt. I've no doubt with you because you have a bias to action. And I think that's the one thing it's difficult for us to teach you. We can give you the tools. We can give you the templates. We can give you the outreach script. We can give you the step-by-step guide. But if you don't have that bias, is to action, nothing we can do. 26:22 - Paul Benson And it was real difficult for me initially because I was on site with my hands so deep in stuff. And I'd be missing meetings and can't get home too tired to listen to the recordings. And I was like, I've got to do this. And I found a way to do it. And one of the biggest things that would tell anybody starting out new is, if you're going to do it, do it. And be consistent doing it. If it's, you can handle four emails a day, do that. Challenge yourself, maybe after a couple of weeks, see if you can do eight. And multiply and just keep trying. 27:12 - Donna Keep building. 27:15 - Paul Benson I mean, I've heard all kinds of people get gigs like that. And that's great. In my situation, it hasn't been like that. But I've been consistent. And my LinkedIn profile has grown now. And my website is now ready. And I've redesigned it based on all the things that, that CTOx said to do. And here we go. 27:50 - Donna Here we go. So here we go. I think that's, that's great advice. Just start off small and build and the consistency rather than I'm going to do two hours of work today and then nothing for like a week that, you know, an extra four emails a day, we could all fit in four emails a day easily. We could all fit in one LinkedIn didn't post a week consistently. Like we can all do that. Like you say, just do it. You just need to take the action and just do it. 28:20 - Paul Benson I've talked to several people that say, I just, I'm just too busy and blah, blah, blah. And you know, I've got to feed my kids and I, I get it. But you, you, you also have to, you've invested in this program. You, you need to take the steps to, to keep moving. And it doesn't take a whole bunch. If you have the right, and it hits the right place at the right time, you could literally triple your income. Oh yeah. And all you did was I sent out four emails this week and that's what happened. 29:03 - Donna Sometimes it is just that. It's that combination of, yeah, I just took this one action and that one action, it's like you go to one networking event and you meet one person and that person is the person that turns into a client. And it was just the moment of, I'm going to push myself out the door and go to that, that networking rather than sitting at home and watching Netflix. 29:24 - Paul Benson Yeah, I can tell you, I, I, you, you, because of CTOx, I've done a lot of stepping out. I actually did a, a Nashville Entrepreneurial Center pitch, three-minute. The IT guy who likes to be behind the computer, quietly doing things, standing up in front of 150 people, giving a three-minute pitch. 29:55 - Donna That's fantastic. I hope you got it recorded. We'd want to watch that. I did. There you go. 29:59 - Paul Benson I did, and I'm actually getting ready to rerecord it and put it on as a marketing tool. So yeah, I'm taking the things that CTOx has taught me and I'm just applying it. 30:14 - Donna Yeah, that's the only part of it we can't do. Paul, thank you so much for sharing your journey and opening it up. It's been so, so fantastic. So now we have our Final segment. We're going to do a little special. Paul doesn't know anything about this, but take a deep breath. I'm going to ask chat GPT live right here, right now for a thought provoking timely question, completely generated on the spot. And Paul, you got to answer it. Are you up for the challenge? All right, let's go. Let's bring up my chat GPT. Here we go. I'm going to prompt it with, hello ChachiBT. We love a bit of spontaneity. So we thought who better to challenge us than AI? What question would you like to ask fractional CTO Paul at this exact moment in time? Oh boy. This is a good one. 31:22 - Paul Benson This is a good one for you. 31:23 - Donna This is a good one for you. Chachi Petee would like to know, what's one thing you now do as a fractional CTO that would probably get you fired in a traditional full-time role? 31:42 - Paul Benson Say no. 31:45 - Donna Tell us more. 31:48 - Paul Benson There are times when an organization, like if you're a W2 employee and your boss comes to you and says, hey, Mr. So-and-so, or Paul, could you do blah, blah, blah. You're like, yeah, sure, yeah. I'll go do that. With the fractional role, that word no is OK to say. No, that doesn't make sense for me to do that right now or for the organization itself to do that right now. You might need to think about that. You haven't seen. The whole picture, let's talk about that. And I can get into conversations and engage with them to help them explore things they might not have thought about, which a lot of times what happens is, you know, they get hit by the the client gets hit by the great salesperson who lays them out and they buy the shiny new thing. 32:53 - Paul Benson When in reality, all they had to do was go over there and fix the old small thing, change it a little bit, and save themselves 30 grand. 33:10 - Paul Benson But they don't know that because they didn't think about that. 33:13 - Paul Benson They just got caught up with the shiny salesperson with the shiny toy. 33:20 - Donna They're just doing what they're told as opposed to... 33:23 - Paul Benson Kind of happening with AI and the medical industry and how they're trying to respond to that. 33:32 - Paul Benson And many times CEOs need to be said no to because you're going to expose the organization in ways that you don't want. 33:41 - Paul Benson And your compliance have their head spinning over. 33:50 - Paul Benson And Lord knows if it gets out, then the other people are coming wanting big money. 34:01 - Donna More of a serious problem then. 34:02 - Paul Benson Yeah, absolutely. 34:05 - Donna Say no, I love that. 34:06 - Donna Paul, I love that. 34:07 - Paul Benson Say no. 34:08 - Donna Yeah, that is such an important part because you're there to make a decision. 34:14 - Donna What do we do? 34:15 - Donna What do we don't? 34:15 - Donna You're there to lead. 34:17 - Donna And I think that coming, you know, as a, as a, a CTO, um, is so much more powerful than, than just having the yes, yes, sir. 34:28 - Donna Yes, sir. 34:29 - Donna Yes, sir. 34:36 - Donna I love that. 34:37 - Donna Paul, that is fantastic. 34:39 - Donna Thank you so much. 34:39 - Paul Benson That was a really, I appreciate you. 34:42 - Paul Benson I've always, and I appreciate everything CTOx does. 34:46 - Paul Benson Let them know that. 34:48 - Donna We will. 34:49 - Donna Thank you so much. 34:50 - Donna Join us again next time. 34:51 - Donna Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. 35:00 - Donna To our listeners, thanks for tuning in to Insight CTOx. 35:03 - Donna Don't forget to follow us on social media, tag us, and share your favorite insights from the episode. 35:09 - Donna We love hearing your feedback. 35:10 - Donna Make sure to subscribe and check in again for our next episode, where we'll continue to explore the stories behind the tech leaders shaping the future. 35:18 - Donna Until next time.