Inside CTOx with Jon Benedict (Final).m4a Mon, Feb 23, 2026 0:00 - Jon Benedict You know, when it comes to technology, I think what happens the most is, you know, they're bombarded, CEOs, CFOs, just bombarded by all of these vendors with the latest, greatest tools. And, you know, a couple of clients that I've worked with in particular, they have all the latest, greatest technology, but their teams were not doing such a great job setting it up, configuring it, rolling it out. So they're quite literally throwing money out the window on the greatest technology. 0:32 - 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 growths unfold. 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 joined by Jon Benedict, a powerhouse fractional CISO, CIO, and CTO, who's helped over a two dozen organizations navigate cybersecurity, digital transformation, From hospitals to digital health startups, Jon's leadership has driven multi-million dollar revenue growth, bulletproof compliance and resilient operations. Since joining CTOx, he's landed his first client within the first month and is now co-leading a consortium with fellow members to transform small to mid-sized hospitals. And he's not just delivering results, he's redefining what tech leadership looks like at the edge of innovation. Welcome, Jon. 1:56 - Jon Benedict Thank you for having me. It's a pleasure to be here. 1:59 - Donna So thank you for joining us. So let's rewind a little bit back to when you first decided to go fractional. What was the move that pushed you over that edge, so to speak? 2:14 - Jon Benedict Sure. Well, what I found is there is a value proposition there for the smaller to medium-sized health systems that really needed not just a CIO, but a CISO as well as a CTO. And many of them could barely afford one. And so as I started learning about, you know, fractional and realizing with these smaller organizations that quite often the CIO is wearing all three of those hats, it just seemed like a right time in the market and a natural fit. And it really has been a blessing to me because I love wearing all three hats. 2:47 - Donna So talk to me. Mentioned this and I think everybody I've spoken to, it seems to have a different definition. So how do you define those three roles and how do they differ from like a small to like medium sized company to like a larger company? 3:04 - Jon Benedict Sure. So obviously your CIO is, you know, over all information, all technology, all security, all everything. And then as you grow and you need somebody who can focus day to day on your security, you pull in your CISO. And then quite often as you grow a little bit more, so, you know, your smaller companies up to about 20 million, probably just the CIO. Once they get to, you know, 25 million and above, they start looking at buttoning up their security, adding a CISO. And then usually somewhere around that 50 million mark and above, they start going, okay, we really need a dedicated person to handle our technology strategy because the three roles grow as the, as the organization grows into something that just becomes way more than one person can handle. 3:50 - Donna Now, you had that first client in that first month. Was that a CTO role, a CISO role? So tell us a little bit about that role and tell us about that journey of like signing that first client is just like, it's such a buzz, right? 4:06 - Jon Benedict Absolutely. So actually this is one that I attribute a hundred percent to the CTOx team. I was working as a fractional CISO. For the organization. And I was about to basically tell them I'm going off and doing my own thing and I'm going to have to say goodbye and wish you guys the best. And Marisa had the idea to pitch them on doing fractional CTO work instead of the CISO. And when I approached them with that, they said, yeah, I don't think CTO, but would you consider a fractional CIO role? And the conversation went from there and it just turned into be one of those where I was about to walk away from a client and turned out to just be the greatest thing that's happened. 4:51 - Donna Isn't that so funny how like we think we're going down one path and then I've heard this from so many members, then something happens. It's something someone says, whether it's Leora or Marisa or even sometimes like another member and it totally changes your trajectory. Like it's it's incredible. 5:06 - Jon Benedict 100%. 5:07 - Donna Yeah, so What is something that you consistently find yourself educating those small to mid-size business leaders about when it comes to technology? 5:22 - Jon Benedict You know, when it comes to technology, I think what happens the most is, you know, they're bombarded. CEOs, CFOs are just bombarded by all of these vendors with the latest, greatest tools. And, you know, a couple of clients that I've worked with in particular, They have all the latest, greatest technology, but their teams were not doing such a great job setting it up, configuring it, rolling it out. So they're quite literally throwing money out the window on the greatest technology. It's almost like buying a sports car, but never pulling it out of the garage, just leaving it in the driveway and washing it and waxing it. So they just get bombarded with, oh, you need an AI tool for this. You need a security tool for this. We ought to magically do this for you. We ought to magically do that for you." And they just, they start going down this road of thinking they've got to buy everything and buying a tool that's going to fix it. When at the end of the day, it's people in process with the technology and having that really smart roadmap. You know, with most of my clients, what I find when you go in, you start seeing duplicate purchases. They've got tools that do the same exact thing. And neither of them are configured very well. And so as you start going through this and going through the tools that, you know, CTOx team Lior's provided, they're just fantastic. It organizes you, you go through each and every technology. When you identify exactly what it does, you start seeing very quickly, sometimes they're paying for three and four tools that largely do the same thing in like one feature here or one feature there. Yeah. They're being bombarded by salespeople all the time, trying to sell them software, trying to sell them services. And what they really need is somebody to come in and help them synergize all of it into a strategy to harness your existing tech stack. And the one thing I preach the most is we're not going to buy any new tools for 90 days. Let's figure out everything that you have. Let's figure out everything that it should be doing. Let's maximize the tech stack. That you own today than most new tools. 7:36 - Donna That's solid advice. I feel you're right. You're right with the sales. Like I've seen these sales calls and they're so convincing that this one single tool or product is just going to radically change their world and the ROI is going to be fantastic. But you know, a lot of the times they just don't know really what they're buying. So they really, they need someone like you. Like a technology specialist to come in and offer that advice and that support. Yeah. 8:08 - Jon Benedict 100%. 8:09 - Donna So Jon, when should a company bring in a CTO? 8:13 - Jon Benedict In my view, as early as they can, especially if you're open to the fractional market. And the reason I say that is, you get all the expertise of people like myself, you get our 20, 25 years of experience at a fraction of the the price, right? Hence the word fractional. So you don't have that 250 plus a year salary and benefits and everything else. And you can flex people in and out. And what's really good about fractional CTOs is we will also flex in expertise kind of like the consortium I'm leading. We've got three of us in there and each of us have different specialties. And so one of them's really good with technology. I'm really good with security. And not to say that I'm not good with the others, but we leverage the expertise of one another and we flex in and out to bring 30, 40, 50 years of experience in at way less than you're paying for a full-time resource. And the reason I say this is 15, 20 years ago, technology was something we lived with. Now, every single business, even landscape that run their business off of their smartphones, every single business is dependent upon some sort of email, some sort of document repository, you know, billing and all kinds of software as a service that's out there. So getting your arms around the technology as early as possible will save you so much aggravation and security remediations and exposures down the road. 9:48 - Donna Absolutely. I think there's sometimes we think of CTOs as only being in software companies or only being in like technical companies. But one thing Lior likes to talk about a lot, the CTO at Google is very different to a CTO at a landscaping company or something like that. It's a very different level of CTO. So tell us like, when we look at those smaller CTOs, smaller companies, what are things that CTOs can bring to those smaller companies? Particularly for those CTOs that are thinking, you know, maybe I've only had a CTO role for a little bit, or maybe I've led a lot of teams. Yes, I can't be the CTO at Google. But what can I bring to those smaller companies? 10:33 - Jon Benedict Sure. And I'll use the example of my industry, health care. So I specialize in working with smaller community hospitals, critical access hospitals, 250 beds or less. And where I see the greatest opportunity there, every hospital has an electronic record system. All of those health record systems have to promote interoperability. And that alone, just the technology of making sure you've got a health information exchange and a patient portal and e-prescribe, all of those things alone are just beyond what one person can handle. And so getting somebody in to make sure that all of your systems are running, they're integrating, they're up, you know, because healthcare is different than any other organization. In banking, you can go to zero trust architecture like that, and you can block anything unknown by default. In healthcare, you better not. You better make sure you understand the clinical workflows, because if you don't know what it is and you're blocking something, that might be a patient in the middle of a procedure, you know, in the OR. And so bringing in that CTO at a smaller organization, you know, you might think you need to be, you know, 100 million dollar a year company, but making all of those pieces work and making sure your integrations are not only functioning, but secure and HIPAA compliant. Those are all the things that we do on the smaller side of healthcare, where we bring tremendous value to just support that CIO that's in the full-time role and take that technology roadmap off of their plate, get everything in order for them and hand it back to them. 12:12 - Donna Oh, exactly. And you mentioned earlier the, what we call the triple threat advantage, the consortium of you and some other members. Tell us the story. How did that come about? 12:23 - Jon Benedict Sure. Well, three of us, two of us on boarded the same week. And, you know, we wound up, you know, forming a friendship there and we met another guy who'd been here a few months ahead of us and all three of us were in healthcare and we all three did slightly different things in healthcare and as I got first client, I started seeing, I'm like, okay, the problems that this hospital is having, every smaller hospital is having some flavor of that. And from just an expertise perspective, I felt like reaching out to those other two guys and going, hey, I got an idea here. You know, you're really good at this. I'm really good at that. And you really love to do this. And, you know, I was raised, you know, with the idea that, you know, it just turned out to be, you know, three guys that all three of us have, you know, very similar overlapping. And now we can cast a wider net because each of us have slightly different niche. So we're going after all three of our niches. And we're bringing, you know, a very standardized approach to come in, do a workshop, get them their their strategic roadmap, and then make the decision between, you know, basically, advisory or and then going forward. And so it's just been really exciting to find a group of people that think alike, we've all met with very similar clients. And I'll say this, when I came to CTOx, I found myself really struggling to brand myself. I didn't know how to market myself. I know how to deliver the services, I've been doing that for 25 years. I was so completely lost in how to communicate communicate my value to clients other than once you get on a call and then you start talking to go, wow, he really knows this stuff. But how do you get to that call? And I found the same thing in those other two guys. They're the same thing. They're going, I don't know how to do this. And so what I found is that you've really you've transformed my approach and not just, you know, developing a clear brand, but a compelling message and really that systematic approach to attracting the ideal clients. Building those relationships, that's the easy part. But what I'll say is the coaching didn't just teach me how to do all those things. It really taught me how to be a more successful entrepreneur and really how to look for those opportunities where, hey, if we combine together, no different than an acquisition. You buy a company to do a certain thing. Well, bring in a guy that he can do something better than I can. And having that humility to say, there's somebody I know that can do this better. And if we can figure out how to work together, we got something. And that's what we do. 15:06 - Donna That's great. You really have the fractional dream team. 15:08 - Jon Benedict I believe we do. 15:12 - Donna So I think it's fantastic that you kind of put together this membership because, you know, entrepreneurship, that's not, you know, let's just be real about it. It can be a lonely, a lonely journey. So like, how important is it to have that wider, like, you know, community of people around you? 15:30 - Jon Benedict I will say that was the most valuable, unexpected benefit. Like I joined CTOx hoping to learn how to market and sell, right? That's the part I don't know how to do. I was hoping to meet some really cool people, but I'll tell you the concern I had, I was really concerned that it was just going to be a dog-eat-dog world and we're all just getting thrown in the same bowl and we're all competing against each other and racing after the same clients. And I found that it is so polar opposite of that. None of us have the same exact niche. None of us. All of us are leveraging one another. We're learning from one another. Hey, have you tried this tool? You know, heck, if you go down the road of AI tools, oh, you got to use perplexity. It's the best. Oh, you got to use core. Oh, you got to use chat GPT and really going through all of those different things. And, you know, now leveraging that network of people, it's just been fantastic. 16:25 - Donna Yeah, it's one thing that comes up over and over again, like this is one of the strongest communities that the people have been involved in and it's not competitive. You know, everybody kind of assumes, oh, we're going to come in, we're all going to be fighting for the same clients and it's just not like that. Everybody's super supportive, they're just rooting for each other. Like, yeah, it's a really, really positive environment. 16:49 - Jon Benedict Yeah, it is. I can't stress that enough. That was, I think my, the two biggest concerns I had were, are all we going to do is bombard people on LinkedIn? And are we just getting thrown in a pool with a bunch of people that are going to be, you know, fighting each other, you know, okay, throw another shark in the water. Great. It's just not like that. It's, it's one of the most collaborative and supportive environments. And, you know, I tell people all the time, as, as we look at things, I'm like, look, I'm part of a group of 150 CTOs that I can call any of them, about any time and I can get another opinion and I can bring in expertise and you know when you can stand in front of a client and confidently say that it really sets us apart. 17:34 - Donna It really does, it really does. So what is the next 12 months look like for Jon and his dream team? 17:43 - Jon Benedict So we are pulling together our one-pagers and we've got all of that and we've pulled together our workshop and we have everything ready to to go and we're going to start reaching out to clients literally this week. 17:54 - Donna And I'm trying to pause. 17:56 - Jon Benedict Yeah. And, you know, leverage, leverage our own networks of, of other CIOs and CTOs, because almost all of us, everybody in my group, we've all been CIOs. We've all been CTOs for other organizations and we have a large network. So we're going to, we're going to reach out and see who we can help because this problem universal in terms of smaller hospitals have smaller budgets, but they have the same cybersecurity and technology needs. They need to have a functioning EHR. It needs to promote, it needs to align with HIPAA. It needs to align with promoting interoperability standards. None of that changes, even physicians groups. So, you know, a cardiology group, you know, a radiology group with, you know, 20, 30, 50 doctors, that's also in our area of expertise because they have the same thing. They have to do the same things and they have to be the same. So over the next 12 months, we're hoping to reach out to all of our ideal clients and get a few signed up and really start replicating the model that we've started with the client I'm working with now. In my first 60 days here, not only have we made a lot of progress, but we've saved them over a half a million doll software subscriptions t tools doing the same thing we can't promise that to it everywhere that I've w duplicate tools, they've g for things. And you know, savings and align that to a powerful message and I' and hitting it with these guys. 19:44 - Donna Yeah, I have no doubt. Knowing the three of you guys, I have no doubt you're going to be super successful. I'm excited to see. I'm only excited to see how successful it can be because I have no doubt that success is in your path. Thank you, Jon. Nye. Nye for my special segment. You don't know anything about this. This is my little surprise segment at the end. We're going to do something a bit special. I'm going to ask Chat GPT live right here, right now for a thought provoking timely question generated completely on the spot. 20:23 - Donna And Jon, you got to answer it. 20:25 - Donna Are you game? 20:27 - Jon Benedict Hot seat. 20:28 - Jon Benedict Love it. 20:30 - Jon Benedict I can only say the one, so let's do it. 20:35 - Donna MyChatGPT, and I'm gonna get on the microphone. 20:40 - Donna Hello, ChatGPT. 20:40 - Jon Benedict Can I have MyChatGPT answer your ChatGPT? 20:46 - Donna No, this is a challenge for you, and it can only be MyChatGPT. 20:50 - Donna No cheating, no cheating. 20:52 - Donna Hello, ChatGPT. 20:53 - Donna We love a bit of spontaneity, so we thought, who better to challenge us than AI? 20:58 - Donna What question would you like to ask FractionalCTO Jon at this exact moment in time. 21:07 - Donna Okay. 21:09 - Donna It's thinking, it's thinking. 21:11 - Donna I must be coming up with a really good one for you. 21:16 - Donna Okay. 21:19 - Donna All right. 21:23 - Jon Benedict I should write this down. 21:24 - Jon Benedict Let's go. 21:24 - Donna This is a good one for you, Jon. 21:28 - Donna So Jon, Chat GPT would like to know, are fractional CTOs just a stopgap for companies who are too scared or too cheap to invest in a real tech leadership? 21:45 - Donna Check it in Sassy today. 21:47 - Jon Benedict Yeah, I'll take that one. 21:50 - Jon Benedict That's an easy one. 21:51 - Jon Benedict Absolutely not. 21:53 - Jon Benedict You know, to me, I look at it as if And if I'm going to spend my money, if I can go get three experts or two experts and not have to have to pay full salary, full benefits, retirement, all of that stuff that you pay C-level executives, I'm going to do that every day of the week and twice on Sunday. 22:16 - Jon Benedict So, you know, the best clients that I think are out there are the ones that once we get them delivered through the Engage model, We identify their strategic roadmap, help them drive that to completion. 22:29 - Jon Benedict Then we move to the advise model where we stay in there and we meet with them every couple of weeks and make sure that they're staying on point. 22:38 - Jon Benedict And as all these new vendors come in, making sure that we're not making purchases that don't make sense. 22:44 - Jon Benedict So I would say the smarter businesses are leveraging fractionals, not because they're cheap, not because they can't it because why not spend your money somewhere else if you can bring in fractional expertise to do this. 22:58 - Jon Benedict And you know, there's so many of us out there that we love, you know, I love doing the fractional part because I love working with multiple clients. 23:05 - Jon Benedict I love the challenge of always fixing something or always improving something. 23:10 - Jon Benedict So I would say take that money and put it into sales and marketing rather than hiring a full time seats. 23:18 - Jon Benedict That's just me. 23:20 - Donna Solid advice, solid advice. 23:23 - Donna So thank you, Jon. 23:25 - Donna Really, really appreciate your time with us today, sharing your journey and your insights. 23:30 - Donna And join us next time on Inside CTOx. 23:33 - Donna Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. 23:41 - Donna To our listeners, thanks for tuning in to Inside CTOx. 23:45 - Donna Don't forget to follow us on social media tag us and share your favorite insights from the episode. 23:50 - Donna We love hearing your feedback. 23:52 - 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. 24:00 - Donna Until next time.