Inside CTOx with Tony Winter (Final).m4a
Wed, Feb 18, 2026

0:00 - Tony Winter
And he introduced me to CTOx and that was one of the best things that could have happened. I actually had another referral from somebody else as well in my network when I was kind of discussing this. And that's brought it about. And you know, when you start off as a new business, you really have no idea what you're doing.

0:21 - Donna
Welcome to Inside the CTOx Podcast. I'm Dana, Head of Membership and Partnership, and today we're stepping Inside 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 Inside Today's guest is Tony, a seasoned tech executive with over 20 years leading global transformations across SaaS, manufacturing, and supply chain sectors. From earning a US patent for service-oriented architecture to becoming a CTO who empowers teams to do their best work, Tony's career is a masterclass in both innovation and leadership. Since joining CTOx, he's experienced a powerful shift, bringing a little bit of that mindset to every client call and engagement. So whether you're thinking about going fractional or scaling your impact, Tony brings clarity and conviction to help you get there. Let's get into it. Welcome, Tony.

1:43 - Tony Winter
Thank you. Thank you, Diana. Pleasure to be here.

1:46 - Donna
Happy to have you. So let's start right back at the beginning. What was the moment that pushed you to say, I am ready for CTOx?

1:57 - Tony Winter
So yeah, that was quite a journey because I'd spent many years in kind of corporate world and the last 13 as CTO and wonderful experience and great company and great, you know, leave time, exit time when I come out from there. And I'd had a few months to kind of contemplate where I was going in the future. And I was literally thinking, oh, I'll probably just go back another CTO, look for another company. But I wanted to get a lot of exposure for other companies, other businesses. I'm very passionate about founder-led businesses and startups and early stage businesses and seeing and helping them scale. I experienced that a lot through my past life and thought, well, what better way? I've got so much experience here. What better way than Potentially to look at being a fractional CTO and expanding that side. And ironically, I decided to create my business. I kind of set my profile on LinkedIn. And one of the people from CTOx reached out to me trying to sell me CTO services, which I thought was quite ironic. Yeah, he's got some good lead generation going on here. So I turned the tables and said, hey, can we have a call? I'd love to learn more about this space. And he introduced me to CTOx. And that was one of the best things that could have happened. I actually had another referral from somebody else as well in my network when I was kind of discussing this. And that's brought it about. And when you start off as a new business, you really have no idea what you're doing. And this is a good opportunity to kind of just accelerate that process. If I had known back then what I know now, I would have been hunting around for something like this, but I wasn't at the time. So I think I'll go out on my own and make all this stuff as we go along.

3:51 - Donna
That's funny. It's surprising how many times we hear that story that it just kind of fell out of the sky just at that right moment in time. Call it the universe, call it whatever spirituality you believe in, but like sometimes the timing is just like so perfect.

4:09 - Tony Winter
And I really believe like, you know, 70% make your future and leave it up to chance and see what chance throws your way as well. And this is definitely the right time and just the right place, right time.

4:20 - Donna
That's it. Now, you mentioned before, you've had a huge career. So tell us a little bit, you earned that US patent in leading global transformations, if I'm getting that right. Like walk us through that journey and like how that's impacted you now.

4:36 - Tony Winter
Sure, sure. So I was actually based out of Ireland. I started work for a company We do manufacturing software and supply chain software. And the business is probably like 40, 50 years old now. But back then they were stuck in the world of where they'd built a very early stage software, ERP, manufacturing-based software. And that was stuck on old technology and they couldn't modernize it. And I was recently, I'd moved over to Ireland, living just outside of Limerick, a beautiful place. Over when my first daughter was born as well. Then from that, in that company, we were trying to re-engineer this old product in effect. We worked out it's going to take a long time to go and do that. Through some past experience that I had, I had an idea that I was trying at home. I remember distinctively sitting at home, experimenting with code, trying to do something where we didn't have to rewrite everything, where we could maybe put a facade on the top. And this has never really been done in the industry at that time. Now it's common practice, but kind of wrapping the old technology. And one day I was out for lunch with the head of the office and happened to be just mentioning, hey, I have an idea where we might be able to do this without rewriting all the code and maybe delivering something in months instead of years. And kind of turned around and said, well, what do you need? And I got a proof of concept Got a small team, a lot of graduates in on there, and we all jumped in. It was like a startup environment, built out a prototype, which worked. I guess suddenly flown over to the US here to head office, met the president of the company, started building out the architecture. I remember in the days when the internet was still young, we had to go to bookshops, those old things, and bought several books on Java and servers. And so on, and literally built out this solution. And we took a solution that went from being able to build a browser-based application on our product, which would have taken years, into something that started delivering about 80% coverage on the application in about six months. So it was a massive journey. And at the time, I thought, everybody must be doing this sort of thing. But it wasn't the case. One of the folks in the company said, hey, you should patent this for the company. I started down that journey and thought, you know, typical imposter syndrome feeling. Oh, I couldn't have had an idea that nobody else had. But it was. We actually got the patent all the way through. Very proud to say it's been cited many times for anybody who's doing any kind of wrapper technology. It's usually cited in there because some of the early stages of putting a virtual interface. They also give us APIs across us a product. It wasn't until my next project that we actually retired that technology. It did take many years to kind of re-engineer a big ERP solution. But it was a great journey and a big lesson in both teamwork, that kind of startup and excited environment. So a belief in yourself that there are ideas, every one of us has something that's unique, and unique ideas and bringing those to the table.

8:02 - Donna
Yeah, wow. And what a jerk, like physically and emotionally, what a jerk. So talk to us a little bit about from the UK, moving to Ireland, then into US, how has CTO life changed from UK to Ireland, US? Is it the same? How different is it?

8:24 - Tony Winter
I'd say it's always different. Actually, CTO life is different all the time. Anyway, and it's kind of one of the most undefined roles. So I think, you know, for me, when I first became CTO, I was like looking at books thinking, oh my God, what's a CTO do? And then I gave up pretty quickly on that because it was just make it what you want. And there's lots of different flavors, whether you're an outward facing, internal engineering focus. I would say what I've always stood by is what are the goals of the business? And if I can always tie into what the goals of the business are with what we're doing, and always moving that needle forward, that's, that's driven success. And I think that's what, you know, kept me both in the role and kept me competitive in that time, you've got to change with the times. But I would say, I was fortunate to experience across a number of different countries. I lived in Shanghai for a while. You know, a little bit the time in Australia. So we had lots of experience to kind of work globally with different teams. And I love that experience. It's, you know, you realize, there's so much talent in the world. And it's great. You get on the call. First thing in the morning, you're talking over with Europe. And at the end of the day, you're talking with Asia or, you know, folks in Australia or something. And yeah, and then folks in in the middle of the night, somewhere in the day.

9:58 - Donna
Yeah, it's truly, truly global. And you know, we see that a lot with the community, you know, we've got people from from all over the world. And those people that are traveling all over and have clients from all over. So I do think it is one of the most diverse areas that you can work in, because you just you're going to see so many different people, which is just it keeps it interesting.

10:20 - Tony Winter
It does. And some of my clients are in Europe now as well. So I've got US and Europe and I enjoy that diversity.

10:26 - Donna
There you go. Now, you've mentioned startups quite a bit. What are, I mean, tell us the pros and cons of startup world versus global corporate world.

10:39 - Tony Winter
It's really, it's really funny because startups want to be the big players and want to be in that big corporate world. And the big players want to be like startups. So what I've done is is position myself in both of those worlds. When I was choosing my niche within C2X, I actually chose two different areas. One was kind of supporting private equity, and that's on the large players and kind of, you know, in that more financial, well-structured, everybody's got technical debt, doesn't matter where you are. But usually, you know, large companies, bigger technical debt, bigger re-engineering, and typically might be moving slower. They find it hard to get that innovation and that startup minds to reinvent themselves. So bringing that support to that side with the private equity and almost like that startup thinking. Then on the flip side, working with working with founders in those early stage, you find that they're incredibly dynamic. Because time is so scarce for them. You know that they've got to, they've got to do everything as efficiently as possible. So they usually have the best tools. They've got the and, you know, things that save them a lot of time, they're being very efficient, very fiscally aware. And then that close connection with what they're building and customer close customer tie. And so what they're looking at as they scale is more of, okay, how do we scale with predictability? How do we how do we as we get people coming on board? How do we how do we manage them and build an organization around it? And then is any founder and getting investment? Investment can be a double edged sword. Very exciting, but now you're introducing a board and that board wants confidence in how you're building out the business. And that's where bring a lot of value to help those founders with getting confidence in the team. You know, usually there might be an existing team that's in place, it's very talented, but just hasn't had the experience. And what I think all of us that who are part of TTOx bring to of the table is we've been there and done it, that experience, those people to, to build off of the shoulders of experience. And, and at the end of the day, we're just helping lots of people. It's wonderful. Actually, that's the biggest, most satisfying thing I'd say is how you're seeing great products. I'm a very product oriented person. So seeing great products, software space, coming to life and, and helping people get there quicker and more efficiently and so on.

13:10 - Donna
Yeah, they really value that experience. And I think that's the one thing I always encourage the members to be like, yeah, don't be afraid to show your experience on that, on those initial kind of like that marketing and sales and outreach. What was the thing that surprised you the most when you started to do that marketing and sales? Because it's different when you're selling yourself versus being as part of a company, you're selling a product or a service or like something else. Like, what really surprised you in that journey?

13:42 - Tony Winter
Yeah, well, it's funny, because in my past life, I would say, oh, yeah, I was like a salesperson, because I was always brought into the deals with the executive team, the kind of long stage closing, and thought, yeah, sales, that's easy. Oh, my God, sales. If there's any one shock for everybody, it's lead generation and sales. And everybody, even we have a great community of marketers as well, professional marketers. And I've met personally with a number of them. And even they find this lead generation and the kind of closing the most challenging part of the job. So it is. It's getting that sales mindset. It's building the closing techniques. It's having a glass of water at hand, which Donna recommended to me. When you get to those awkward moments, you need to ask a challenging question. Have a glass of water while you wait for the response. So always having those things at hand. But I think then really truly understanding your value, who are you really servicing? And I think for me was really digging into what's that passion, what is the driver of, as I said, founder-led businesses in the software space. That's really what drove me. And it's almost like a mission. And I think that passion then starts to come through as you're in conversations and so on. And then it takes time, you know, building up connections.

15:15 - Donna
It does. I think everybody's surprised about how long it takes. It's not a kind of quick pill. You just flip a switch and it just happens. But when it happens, it's so amazing. And it's amazing.

15:32 - Tony Winter
I mean, one of the things is obviously leverage your existing network of people. So one thing with that is great catching up with people I haven't spoke to in years sometimes. But it is amazing how the most bizarre connections, you know, I could go through every customer that I that I have. And the connection was not linear at all. It wasn't kind of a, you know, the yes, there was the odd cold outreach, but the strange, this person knew this person and just so happened that something that you said in the call triggered something and then somebody connected you. And then a few months later, that's follow-up comes through. It's just so, you know, it's all about people. I think that's the most important thing and establish that connection. Um, and then, and just have fun meeting up with people.

16:20 - Donna
It's a great, great excuse to reach out to people and be, be human. You know, we've all used AI and we're all big fans of AI and that, but, but you know, my one advice is always like, just be human, have a real conversation with another human. And you'd be surprised where that leads to.

16:38 - Tony Winter
Just even on life or just in general, I mean, the number of people I've spoken to, and because I've spoken to a past colleague from past lives, they've all said, wow, I need to catch up with that person. And you kind of all of a sudden, you're becoming the glue of and it's not a one time pass as well. We kind of keep regular connections between all the a lot of opportunities.

16:59 - Donna
And it's funny because we, you know, there are certain, there are certain do's and don'ts with, with sales and marketing. There are very much do's and don'ts and there are certain, um, tactics. So the one you mentioned was the drink water. So we're trying to do a price drop or an awkward question and we need to maintain that silence. And the easy thing is just to grab a glass of water. Um, but what are the other things that you've, you've learned that really kind of was like, wow, I've never heard that before. I've never heard that positioned in such a way. That's helped you either on the marketing or on the serve side.

17:35 - Tony Winter
And I'd actually say, I'd say there's not any, just one thing, but I, I'm a very visual person. So for me, I, in now, in every kind of engagement, every part of this working life, I've got mini CTOx team on my shoulder in different forms, but it's helpful on the sales side, or Leora in the original deal or thinking about delegating down through to Keely on the social side, and Donna on the sorry, Marissa on the on the well being side. So I think when I came into this, like with all past jobs or new experiences, you come in with certainly I had imposter syndrome. I mean, you think, Oh, how could I possibly be doing all of this? And the scene like so much to kind of learn as well. One of the things that you realize you bring so much value. I remember, for instance, speaking to Lior and saying, I don't feel like I know enough about startups, new systems, building out new products. Because I've always been in the transformation in the large scale product space. And the one thing he said to me was, well, you know, that large scale product, it was something new that you designed. And came out, he said, that's no different than what early stage companies are doing. And I thought, yeah, what am I thinking? This is obvious. So some of those really obvious things that are just in front of you, but the support from the team has been amazing. I do feel like I've got mini versions of everybody sat on my shoulder in every kind of part of the life here. I think it's a phenomenal program.

19:19 - Donna
Thank you for that. And it takes a village. It's not just one, you know, not Lior on his own. He's amazing and the clarity he brings is fantastic. But when you bring the whole team together, all the experts that we bring in and everybody has their little thing that they are particular and expert at. And then there's the community. Like what we've learned back from the members has been just like phenomenal. Is there somebody in the community that you've particularly kind of built a special relationship or has sort of impacted you in a certain way?

19:53 - Tony Winter
Yeah, there's quite a few, actually. Again, I've kind of, this feels, first of all, the transparency and openness within the community of CTOs. I mean, we talk about everything, even down to how you're feeling and it's that resonance. So I would have never believed in kind of this work environment that you'd be so open with people. And that's obviously a great fostering of the kind of ground rules, let's say, that everybody brings to the table. But a number of folks, like Benjamin was the person who brought me in to begin with, and he has been a periodic coach for different things throughout. So it's amazing how available folks are. Bob as well has helped out a lot. And then we have a peer group. You know, this is one of the things I loved is kind of having these peer groups where you have a small small group of you who are all starting at the same time, and then helping keep each other accountable. That's one of the hardest things I think, as an entrepreneur, kind of when you're starting up your own businesses, how do you keep the motivation for yourself going? How do you commit to somebody? You know, you don't have a boss? Well, I do have my wife, but who's the, you know, the boss that's keeping you on task? And that's yourself. Are you accountable to others? Peer groups have been great. The insight in on there, the education, the things that we share, we're all in the same boat together. So the community has been incredible. And even with customers, I say, hey, I'm part of a 250, 300 person CTO group. I can ask any question of that group, and somebody somewhere has probably been there, done it, or knows somebody. That's the power of what we bring to the table. And it's an incredible asset. I used to shy away from things. I think, oh, I shouldn't tell people I'm part of a group. Strange mindset, but You know, sales thing, it's, I mean, one of my clients explicitly said, we're really interested because you're connected. We need that connection because we need to find the best knowledge out there. And if you can facilitate that, that's fantastic.

22:14 - Donna
It's amazing. And when you look at, you know, the community, the backgrounds that they have, as you say, like if you need help in any system, any tool, like anything, somebody, one of the closing in on 300 and I, one of them will have had experience in it. A lot of people will have an opinion and are willing to share it. But I think the one thing that's there that's stands out time and time again is the positivity. There's no competition. As you say, like there's openness. You know, people are just being honest with each other and everybody's rooting for each other. Everybody's supporting each other. And you don't often find that, unfortunately, in these types of communities.

22:55 - Tony Winter
It is totally, I mean, I've been part of lots of different things and some great communities, but this is unique for that openness and just making yourself want to be better. Not through force or anything, You just you get a passion for wanting to be better doing things in smarter ways and it changes you definitely know over this last year the mindset change of How you just think about things? I know it if I if I went back into regular CTO job I will be so much better through everything that I've done in the last several months than ever before It's always a good sign that you're learning something new. Anyway, that's it. It's very satisfying Every day is a school day, especially here at the CTOx.

23:39 - Donna
So, so looking ahead, six months from now, we get on another podcast. Tell me, tell me what that looks like, What does success look like 12 months from now?

23:51 - Tony Winter
Well, I'm building up a really nice community of both early stage businesses and private equity and supporting those. And it's really exciting living in both those worlds. And I think there's mutual benefit for businesses at both ends of the spectrum. So for me, it's really expanding in on that, you know, building out more repeatability and cross pollinating some of these ideas, helping businesses be more successful while protecting those businesses as well. So they don't kind of hang themselves, especially, you know, things can go south quickly if you're not careful. So making sure that things stay safe, but it's, it's really exciting from that to feel that you're, you're building out that business. And getting confidence in that side. But I think also, you know, an important arm to this one thing learned throughout all of this is it's about family, family life as well. And, you know, having that freedom. For me, I can, I can work anywhere in the world if I want to. I can take the time off. I can, you know, I've got my own freedom. I choose my own customers. I don't like who I'm working with. I don't have to work with them. So it's a very different life. Lifestyle and mindset. Yes, there's challenges, but there's personal and important, kind of personal driven goals as well. And I see both of those being realized as we go forward here.

25:13 - Donna
Oh, we've no doubt, no doubt you'll be incredibly successful. Okay, we now have our Final segment. Now, Tony doesn't know anything about this. This is a surprise on Tony. And the members have been great about sharing this with each other. So, we're going to do something a little special. I'm going to ask ChatGPT live, right here, right now, for a thought-provoking, timely question, completely generated on the spot, and Tony has to answer it. Are you game?

25:47 - Tony Winter
I am game. Oh my god, what the hell?

25:53 - Donna
Hesitation, hesitation. Alright, well let's see, we've had some real fun with this. Everything can be solved with a glass of water. Okay, so I'm gonna, I'm gonna pull up my GPT. I'm gonna say, okay. Hello, chat GPT. 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 Tony at this exact moment in time. Okay, it's thinking it's thinking. It's thinking. It's really thinking about you. Oh, okay. This is this isn't this one before. This is interesting. Okay, cool. Chatty PT would like to know, if your clients suddenly banned all buzzwords, digital transformation, AI, innovation, et cetera, how would you explain your value without using a single industry term?

27:13 - Tony Winter
So for my clients, I help founders keep their business as they scale. There we go.

27:23 - Donna
There we go.

27:25 - Tony Winter
And realize and maybe realize their own dreams as well.

27:30 - Donna
Everybody is interesting because you see that so often. I know a lot of times that's one of the things some of the members have said where they, you know, they want to work with startups have reached out to founders. But there's a fear, particularly if it's a somewhat of a technical finder. But not to the extent of you guys. And they're worried, I'm going to bring somebody in, I'm going to look dumb, they're going to come in and take over the company. So like, you know, what's what's your advice? What's your advice to CTOs who are facing that challenge? Like what should they say? Banning all buzzwords? How should they put their mind at ease for that for that finder?

28:09 - Tony Winter
For that founder, I think they bring I mean, I think for any CTO is really connect with the business and understand what is the business trying to achieve and where it is.

28:23 - Tony Winter
If it doesn't have investors, I mean, there's always some investors, but if it doesn't have professional investors, it's a bit of a different control side, but always tie in with, well, what does the business need?

28:34 - Tony Winter
And then keep it simple.

28:36 - Tony Winter
Don't talk tech.

28:38 - Tony Winter
I hate tech for tech's sake.

28:41 - Tony Winter
There's always got to be some business connection there.

28:44 - Tony Winter
So I would say to, to other CTOs, keep always keep that business mindset.

28:48 - Tony Winter
Like I said, at the beginning here, I built my whole career around understanding what the business needed, and what their strategy was, and making sure that everything that I was working on was tied to that in some way.

28:59 - Tony Winter
And every one of the bits of eating the elephant will ultimately business to grow.

29:09 - Tony Winter
No, we sold our company three and a half times its value that we got for shareholders, employees, and so on.

29:17 - Tony Winter
So it's, you know, that's the benefits of kind of thinking in those sorts of terms.

29:24 - Donna
That is solid advice.

29:26 - Donna
Well, thank you, Tony.

29:27 - Donna
Thank you for sharing your journey today, sharing all that wonderful advice.

29:32 - Donna
I hope it was really helpful for everybody listening.

29:35 - Donna
And thank you for asking our ChattyBT questions.

29:39 - Tony Winter
Yeah, no worries at all.

29:41 - Donna
See you next time on CTOx Insight.

29:43 - Donna
Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders.

29:52 - Donna
To our listeners, thanks for tuning in to Insight CTOx.

29:55 - Donna
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30:01 - Donna
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30:02 - Donna
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30:11 - Donna
Until next time.