Inside CTOx with Benjamin Sanders (Final).m4a
Wed, Nov 12, 2025

0:00 - Benjamin Sanders
That didn't mean I can't do it, or I didn't know how to do it. It actually really just meant I didn't want to do it. But now if I was going to do this again as a party of one, it was on me and it wasn't going to be on anybody else.

0:12 - Donna
Welcome to Inside CTOx podcast. I'm Dana, 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. We're stories of struggles, breakthroughs, and growths unfold. We're here to unpack the experiences of real CTOx navigating through our CTOx accelerator and membership program. So sit back, tune in, let's get into the story. On today's show, we are joined by Benjamin Sanders, a dynamic entrepreneur who knows how to build and scale agencies. Benjamin sold his first agency to IPG back in in 2017 and is now leading a thriving fractional agency that's on track to hit 1 million ARR in just its second year. But beyond the impressive numbers, Benjamin's proudest accomplishment is stewarding a happy, healthy life with his wife and three kids. We're diving into his journey, lessons in leadership, and what it really takes to balance big business with family life. Welcome, Benjamin.

1:29 - Benjamin Sanders
Thank you. Pleasure to be here.

1:30 - Donna
Pleasure to have you. So you joined CTOx at the end, the very, very end of last year. If we can think back to the very, very start, what was the catalyst that made you realize, you know what, I got to get on board with this CTOx.

1:53 - Benjamin Sanders
So it's it was actually opportune timing more than anything else. I actually believe it or not joined in April 2014. I was like one of the first three or four people that joined and I knew that I was going to do something. I had like kind of semi-retired after selling an agency and I only use that a little tongue-in-cheek, but I took some time off like a couple of years. I got to take a break and I had never gotten to take a break since the day I started. Working when I was like 12 flipping burgers. So I had an unexpected and super pleasantly surprised third kid who's now at six birthday was yesterday. And my math didn't math anymore. I knew I had to do something. And I knew that corporate America was not my path. I had tried again. I went back to higher ed for a couple of years and ran emerging technology for a big university in Manhattan. But, you know, taking direction from others versus providing it was never really my forte. It just didn't work for me as a person, as a thought leader. So I was thinking about doing consulting work, and I did a little bit of research. I saw fractional as a word had kind of become a big deal. Earlier that year, it really sort of exploded. I was meeting not just fractional CFOs, but like fractional everybody, the entire C-suite was fractional at this point. And then a CTO came up, I think it was actually on, and I got out a little bit further and started asking some questions. And it turned out Lior was in Manhattan the next day, and I met him for breakfast. You know, very quick, like, hey, let's just come talk about this. And by the end of breakfast, I was in the car driving home, called my wife, and I said, you know what, like, this is what I'm doing, I got it. And I never really looked So I was paid and in within a couple of days of that and started attending the sessions. What I was hoping to get out of it and what I actually get out about it have a big overlap, but we're a little bit different. What I was hoping to get out of it was I spent my entire career in the agency business. The one that I sold was actually the last of many that I had been involved in, and even was the CTO for some of the top five agencies in the world, BBDO, when they first spun off their interactive like all the way back in the late 90s after the internet first became a thing. This is always what I've done. But in those roles, I had a full marketing department, I had a full sales department, I had a full operations team, you know, HR, every infrastructure you could need, which made it really easy for me to focus on the technology, focus on the team building and the architectures and go in and close sales. You know, I really enjoyed selling to big companies and, you know, important CEOs of big companies all over the world. But I never had to do top of funnel or any of that marketing, I had whole teams of people to do it. That didn't mean I can't do it, or I didn't know how to do it. It actually really just meant I didn't want to do it. But now I was going to do this again, as a party of one, it was on me, and it wasn't going to be on anybody else. So when I was really looking at this, it's like, okay, let's really understand how people who've been doing fractional for quite some time or doing it effectively, which has to include that, that's what I was hoping to get out of it. What I actually got out of it was all of that for sure, but also a community that's second to none. You know, it's really easy as a CTO or like a higher level technical leader to tell yourself that you're the smartest technical guy in the room, but it's also the only place to spend your time. There really isn't a lot of collaboration in that universe. And now, you I think you guys are well over 200 members or whatever it is, and they're great people. I knew early on that Lior was actively cultivating for a particular kind of person, good people, not just capable people, and that's really coming out. Some of my favorite people that I talk to every week are people that I talk to on Slack or through CTOx community meets. So even when my six months was done and finished, I was like, I think I got what I needed to, let's say in a digital marketing capacity, but that's easy for me. I'd been doing it for 25 years before that, but there was no way I was going to let go of that community. And I still don't have any aspirations to do that. So, you know, I'm still here doing this and I'm still joining the zooms and the links and all that kind of fun stuff.

6:23 - Donna
We're happy to have you. You, you're, you're a great asset to the, to the program for sure. Um, you mentioned marketing and I know a lot of the the CTOx come in and that's really where their challenge is. For you, what was the biggest challenge you faced in your first six months?

6:41 - Benjamin Sanders
So figuring out where to start is always the hard part, right? Like we're deep thinkers by nature as CTOx and it's very easy to go in one of two directions. You can get analysis paralysis, which is pretty common, like just trying to figure it all out in your head or on paper or in whatever note app you're using. To really architect your system in your head for how you want to do your digital marketing. Or even worse, you start playing with toys, which, you know, all of us techies really like playing with toys. So like dabbling with every tool and system that claims to do this low-code, no-code, AI-driven, whatever you want to call it, that can do all of your digital marketing for you, super simple. And then in that process, you're going to get marketed immediately with like 50 different agencies that claim they're going to do it. That cost an arm and a leg. But don't always deliver exactly what they say they're going to do. And you'd get stuck. And you know, it happened to me too. I started doing this in April last year. And I probably spent six months doing that, both trying to figure out what to do, trying to put together tools and systems to do it and trying to like really architect my entire digital marketing funnel top to bottom. And then I had this moment later in the year, this probably was around November 2024, where I realized, and I knew this, but I reminded myself that the doing part is a lot more important than the planning part. Because if you just put one foot in front of the other and actually do things, you'll figure it out. But if you get caught up in the loop of just trial and error and testing and playing, that becomes very self-defeating. So as an example, we have weekly peer accountability groups. And I spend a lot of time on those phone calls talking to my particular peer group, which progressively grows. It's quite a few people at this point. And it's always the same thing. One foot in front of the other. The doing is more important. I could build an entire CRM, and I could worry about that. Or I could spend weeks architecting my perfect LinkedIn outreach messaging. And I could spend a couple of weeks, or I could take a notepad and I could just write something down. And the notepad can be my CRM, you know, here's what's active, here's what's pending prospects, hot leads, dead leads, you know, follow up timelines, and just do it, like just actually get started. And it turned out also, like the messaging that I have is not super customized, but it's very specific to me, right? It's like, here's who I am, here's what I do. That's it, like, let's just be friends, let's connect. And I don't ask for anything on those calls. And then the follow ups, if they do connect, it's okay, here's a little bit more about what I do. Let's talk about that. If there's any way that I can help you with anything you need, like let's talk, here's a link, super simple call to action. And that's been incredibly effective. Like once I turned on that, my business went from one client to about 11 clients in the span of six months. And it's like, okay, now we have a whole different set problems, which is how the hell do you manage at the same time. So I've gotten into the second phase of, you know, a well known agency problem where you take on all the good work that you want to be doing. And then you build out the middle layers and, you know, the team that can help you on that without getting buried in 80 hour work weeks. So I spent a lot of time figuring that part out right now. But the model works. And you know, the the biggest value proposition in having done CDOX, at least for me, was it was an activator. It was an accelerant, right? It's not telling me things specific to me because I come from digital advertising that I might not have known, but the synthesis and the progression of it is all there. The people that you can collaborate and discuss these things if you get stuck or just, hey, what do you think about this kind of stuff is all there. And it went from zero to a hundred. And I got to figure, did this the other way, you know, I'd probably in my best case, maybe be half where I am right now, because I would have spent a lot more time doing what I'm prone to do, which is just dabbling and playing with cool things that I like playing with. But this is very, very optically business focused. It's all profit driven. So that that works.

11:07 - Donna
Yeah, absolutely. Thank you. Thank you for that. That's amazing. So looking back at your journey, what surprised you the most about your personal growth? So we've talked a little bit about the business. Personally, what's been the biggest surprise?

11:23 - Benjamin Sanders
That's a fun one for me. I always grew up, as many engineers do, identifying as more of an introverted personality. And in my younger years, that probably had a lot of truth to it. Turns out that's not true at all anymore. Can go hippie and say sex. You know, it turned out that's not true at all. I actually really do like going out there and hustling. And like, that's really flipped the script. And it's really pushed a degree of like self, not self centered, centered centeredness, and confidence in what I'm doing, how I'm offering it and proposing it. And, you know, at a very quick inflection point after the first couple of clients are under your belt, like, there are accounts that I really do want to work with, because I like what they're doing. But I'm not beholden to any of those to be able to feed my family or, you know, I'm, I'm in the beaches in South Turkey right now. And none of that has a dependency on whether anybody said yes or no anymore. So then again, that reinforces, obviously, the messaging is right, you know, I'm selling the right thing at the right time for the right people. I really enjoy that a lot of people that I deal with, it turns out I like my clients. They're nice people. That's a big one. I took that straight out of the CTOx playbook. Like, I don't want to work for people I don't like, I learned that lesson on my very first account when you guys passed one over. And a month in, I met a very different person than the one that I signed up. It's a famous CTOx story as they go.

12:56 - Donna
Yeah, it happens. It happens. That's great. Thank you. Thank you for that. So thinking about relationships, and that's a very big part of CTOx, we all like to build these relationships. Through your CTOx journey, what's one relationship in particular that stands out for you?

13:17 - Benjamin Sanders
So it'd be really easy for me to focus on the relationships to Lior and Marisa and yourself and the other leadership team at CTOx. You guys are some of my favorite people, even though we don't talk with weekly cadence that we previously had, because everybody got really busy as this has succeeded. But it's also succeeded. So my other favorites are probably the peer accountability team, Paul and Andrew and some of the other people that I talk to on a regular basis. It's been really very deeply satisfying to me to be able to share the way in which I pushed this forward. Because as we were talking about, some people are much more prone to overthinking thinking their problems. And my approach across the board has always been elegant simplicity in the way you approach your work. You know, like, let's find what works, do that, it doesn't have to be overly complicated. And after many, many conversations, you know, in some cases, we're talking about people who are like ready to pull the plug and go back to corporate America, and instead have moved in the direction of six months later, like a pretty thriving practice unto themselves. I love helping people, I always did. It's a great vehicle for it. And I know you guys know this, but I get to enjoy some of that myself.

14:37 - Donna
Oh, that's so nice. So nice to hear that. How important is accountability and the peer progress group within the journey of C2X?

14:50 - Benjamin Sanders
So I think for the vast majority of the people that I've met in that program, it's pretty critical. To do in my opinion. Now, I also say that where I don't find it a must-have in like, I'm not going to get up and do the work that I'm going to do personally with or without it, because I've always been incredibly self-directed. Like, I was just built that way. But most people really do benefit, and even I do really benefit from weekly check-ins. I can make some commitments really at the end of the day to myself and then make sure that I live up to those.

15:28 - Donna
Good, accountability is one thing that I really push for in CTOx because we can't run your company for you. You really got to go out and as you say, you just got to do it step by step. If you could share one piece of advice that you learned through your participation in the Accelerator but that you'll carry forward forward forever?

15:55 - Benjamin Sanders
I really, I can't say that it's a single concise soundbite that I could share. But there's a concept really is a CTOx philosophy. And I'm going to go with that instead, right? So fundamentally, this is an investment in yourself. It's very easy. People are very tuned by the world that we live in these days, to spend money on all kinds of things. You can buy a car, you can buy a house, you can buy a toy, you can buy a laptop, like, the list is endless. And it comes at you, you don't even have to go find it. But sometimes it almost feels like an alien concept to take a similar amount of time, money, and making sure that you have everything that you need to be the best version of yourself. And more than that, this is a CTO thing. Otherwise, I really did find and do find that the entire program is set up to help people become the best versions of themselves. This is just one particular expression of it. But once you figure out how to do that, you can apply it anywhere. You can apply it to your life. You can apply it to your relationships with your wife and your kids. You can apply it to anything.

17:07 - Donna
Very true. Very true. Good advice. I like that. And where do you see yourself in 12 months, 12 months from now, thanks to your experience here at C2X?

17:21 - Benjamin Sanders
So 12 months out, I definitely will be doing exactly what I'm doing now, but with a much deeper bench. So my time commitment right now is kind of at the upper end of what I'd like it to be, because hiring people and training people to do very particular things for particular clients is itself more work. So I'm in the more work phase of more work. A year from now, expect this business will be twice the size that it is right now. I expect I'll have twice as many people working within my organization as I do right now. And then hopefully my time commitment will go back down a little bit. Now, I would also say, four years out, that might still be true. You know, I'm really aiming this as a model that'll like theoretically double every year, and I have no reason that it couldn't. You know, the goal is to put absolutely everything that I have into this right now, because when I'm done, I plan on being done, you know, once and for all. And like, I had that exit once before, it's a good feeling. But life, circumstance and all that kind of stuff. You know, it really ate that, took it all. You know, it's like, I had a previous marriage and an older kid that I really had to get out of a situation that for him personally needed to evolve. So I put all of it into that. You know, like the common theme there is I tend to put all of it into anything that I do, but you know, five years out, I'd like to exit and like go buy a place on the beach and just hang out with my family. Like that sounds pretty good to me.

18:58 - Donna
Just chill out on the beach. I love it. I love it. That's an awesome.

19:02 - Benjamin Sanders
We'll see how much chill we get there. We'll find something.

19:08 - Donna
Just start another startup.

19:11 - Benjamin Sanders
You know, every time I say I'm not going to go back into the agency business, I've done this like five times. I always end up back in the agency. There's something very satisfying about it. My wife asks sometimes, like, how do you multitask like that? You know, just context switch between so many different kinds of work. Because also very unique, I think, amongst the CTOx journey, you know, you, you guys advocate, and I think this is partly a marketing and just simplicity of understanding what you're trying to do, going into a very granular niche. And I went the exact opposite direction of that after all these years as an agency guys, like, I can't go niche, but I can go big. So I've got, you know, 11 different clients right now in 11 different verticals. It's just that was that was for me, one or two of them actually double up in like ad tech and advertising. And that kind of makes sense, because I've done a lot of that. I can't imagine doing it differently.

20:07 - Donna
What works for you. This is what it's all about. It's figuring out, like taking our framework and then applying it to you. It's not cookie cutter. Everybody's got to find their own journey, which is so interesting to see all the multiple different journeys in the CTOx across the program.

20:25 - Benjamin Sanders
Yeah, that's actually one of the things I really loved about that program is that when you figure it out, you really can make it bespoke to you.

20:35 - Donna
And now for our Final segment, Benjamin doesn't know anything about this. I haven't told anybody. We're going to do something a bit special. I'm going to ask Chatupiti live right here for a thought provoking timely question, completely generated on the spot. And you have to answer it.

20:59 - Benjamin Sanders
That's fine. Here we go.

21:02 - Donna
Hello, ChatGPT. We love a bit of spontaneity, so we thought who better to challenge us than AI? What question would you like to ask a fractional CTO at this exact moment in time? From ChatGPT, in a world where startups can assemble entire tech stacks in hours without writing a single single line of code, what's the next big existential risk for the CTO role that no one in the boardroom is talking about?

21:41 - Benjamin Sanders
So, I don't know if nobody in the boardroom is talking about it, but I know only some of the CTOx are talking about it. So, I think of this in an analogy going all the way back to when I first got my keyboard at seven years old. I've been programming since I was seven. And I've asked myself this question a hundred times since then. If you can build anything that you want to build, what do you want to build? Now for me that answer is companies, right? It's not I want to build some SaaS platform or I want to build some app. Those all happen, but fundamentally I enjoy building businesses. Sometimes they're my businesses as a fractional, they tend to be other people's businesses. But the goal is to create, right, to test, that's our favorite metaphor. Now, as a as a fractional, I think of all of these AI tools, and I've been in AI for like nine years. So long before chat, GPT made it popular. I think of these tools as upper mid level employees. And that means that you need to communicate with them that way. It's not just Hey, chat GPT give me this SAS platform and it's going to do the whole thing for you soup to nuts because it's not but our skill sets are changing so if they can build you an entire stack with like replet or lovable or one of the other half a dozen stacks out there that do it or Claude code I mean there are so many of these it's hard to even stay abreast of them but in all of those they'll do the code they may do it effectively they may do it with some security problems that you still have to really make sure they don't, or some scalability problems, which they're getting much better at, but you still have to check. They don't really do a lot of cloud architecture at this point, other than using a couple of stacks that make it so you don't really have to do it. But again, it comes down to what do you want to do? And when you prompt them towards doing these things, you have to be incredibly detailed, but still concise. You don't want to overload a context window, and very descriptive. And the more you can communicate your ideas concisely and efficiently and effectively, the better the product you're going to get is. Sometimes you can just iterate on that, but then I'm not sure you're really being much faster at this point. So I think of the existential part of it is like the skills of a CTO change. It used to be that if you were, you know, the the old 1970s stereotypical neckbeard programmer in a basement of a building, full of refrigerated computers, you would be able to build something. Now, it's changing entirely because your ability to communicate is your value proposition. And for certain kinds of business-focused CTOx, that's always been the case. But for the much more engineering-focused CTOx, I think that's going to change pretty quickly. I think it really is going to move down to your ability to manage teams of effective AI-driven developers, You know in my case literally globally everything from West Coast, California all the way out to Sydney, Australia Like covering the entire planet 18 a day I have teams on six continents at this point that I have to talk to all the time Sometimes in the morning sometimes at night depending on where I happen to be but that's a lot of a communication challenge when you're teaching or Mentoring people and how to effectively use AI to do their work faster, but still effectively, you know velocity and quality and that same communication becomes much more critical.

25:14 - Benjamin Sanders
So it's like my entire business now is becoming voice and my ability to convey ideas to people and to machines, rather than being able to just shut myself into a room and write code for And I think that that's going to be the shift between, you know, the wannabes and the have-beens or the will-bes.

25:40 - Donna
Thank you for that.

25:41 - Donna
Yeah, it's going to be an interesting future.

25:45 - Donna
That's for sure.

25:45 - Donna
That's for sure.

25:46 - Donna
Benjamin Sanders, thank you so much for sharing your journey and your insights today.

25:51 - Donna
We really appreciate you.

25:53 - Donna
We love you here at CTOx.

25:54 - Donna
Thank you for everything you do.

25:56 - Donna
And you're such a great member.

25:58 - Donna
We really, really value your participation.

26:00 - Benjamin Sanders
It is my pleasure.

26:03 - Benjamin Sanders
Thank you much.

26:04 - Donna
Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOx, but for the broader tech community and leaders.

26:13 - Donna
To our listeners, thanks for tuning in to Inside CTOx.

26:16 - Donna
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26:22 - Donna
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26:24 - Donna
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26:31 - Donnar
Until next time.