Careers in the Cloud E34: Daniil Saiko: Lessons in Military and Martial Arts for Business Success

Joining Maurizio on this episode is Daniil Saiko! FinTech Product Manager and Director of Product Management & API at Kyriba. 

We explore his unorthodox journey into the tech industry - From his early days in martial arts to an impressive career in tech and product management. 

Daniil shares how his experiences in judo, karate, wrestling, and Brazilian Jiu-Jitsu shaped his professional path. How military training influenced his leadership and resilience, and applying those combat sports principles to overcome challenges in the tech industry. 

This conversation is perfect for anyone seeking personal and professional growth.

Watch the episode below on YouTube:

Topics covered:

1.  Daniil's Martial Arts Journey

2. Brazilian Jiu Jitsu Training

3. Founding Startups and Learning to Code

4. Journey into FinTech: From Pre-Sales to Product Management

5. The most important skills for Product Management

6. Impact of Combat Sports on Career

7. Emotional Intelligence & Self-awareness Learned in Combat Sports

8. Military Training and Career Lessons

9. Applying Military Skills to Overcome Challenges in Tech and Management

10. Interpersonal & Management Skills from Martial Arts and Military Training

11. The qualities looked for in candidates when hiring in Product Management 

Transcript:

Please note, that this transcript is automated and may have errors.

Daniil Saiko trained in a variety of martial arts and received military training. He is fluent in Russian and Ukrainian, and his last name sounds like it came straight out of a movie. One might think he would have been hired by the CIA or another agency, yet he ended up in the tech industry.

Daniil, welcome to the show.

Hey, good to see you, man.

What an intro! I just came up with that now, but no one else is going to know this. We knew each other from way back as kids, so it's real cool to have you here today and talk a bit about your journey through martial arts, combat sports, and training in the Army. We'll discuss how that's translated into your career in tech, how it's helped you, and what it's done. We'll share that with the viewers watching—the whole three of them out there.

Happy to be here. Yeah, the last time I saw you was maybe 16 or 17 years ago. We’ve seen each other in person a couple of times and had a few calls here and there, but definitely since we were kids doing karate together.

On that note, let’s catch everyone else up. What combat sports or martial arts have you done to date?

I started with judo back in Ukraine, training in Kyiv. I had a funny judo schedule: Monday, Wednesday, Friday was my special time for judo, and Tuesday and Thursday I did ballroom dancing. It was very opposite training, but in case I got my ass kicked too much, I could stick to the dance floor. Then, I moved to Canada and started training karate with you for four years. I got my black belt there. In high school, I wrestled for one year, paused, and then wrestled again in university at a much more serious level for two years until injuries from training caught up with me. After university, I trained in jiu jitsu, about seven years worth cumulatively, considering breaks due to Covid and moving for work.

In wrestling, what weight did you wrestle at?

In high school, I was at 77 kilos. In university, I fluctuated around 90 kilos.

Did you cut a lot of weight every time you wrestled or were you fighting at your natural weight?

You always have to cut weight in wrestling. It's unfortunate because it's clearly unhealthy. I don’t think wrestling is the healthiest option due to the many injuries and the toll it takes on the body. There are career options like the Olympics or pro wrestling, but it's tough on the body long-term. For example, I dislocated my shoulder from wrestling.

And you still train today, right? What are you currently training in?

Yes, Brazilian jiu jitsu. I plan to continue as long as I can, hopefully even when I'm old. I train in both Gi and No-Gi, preferring Gi for its slower pace and tactical nature due to more grips, which I find more cognitively challenging.

Some older, more experienced guys say that the Gi helps slow down younger, more energetic opponents, preventing injuries.

Absolutely. I once rolled with an eighth-degree black belt, an older, partially blind, broken man who had been a black belt for 43 years. His technique was so good that even though I'm a pretty strong person, I felt like a baby in his arms.

How much do you weigh?

About 240-250 pounds, depending on the week.

How often do you train now?

I usually train 3 to 4 times a week, sometimes more or less, and try to train when I travel. This year, I've trained in Miami, Warsaw, and Paris, in addition to my normal gym. It's an amazing experience meeting people in other gyms.

When traveling, it's like a mini competition because you're the new guy, and everyone wants to test you. Coaches often pair you with their best to see how you fare, which is complementary. It means they see you as a good challenge for their students.

It's a great way to gauge abilities in different places. For example, I trained in Barcelona, Vancouver, and even Waterloo. It’s a cool experience.

Now, let's talk about your career progression. How has your combat sport and martial arts training impacted your career?

I’m in product management now. I got into it in an interesting way. Before my current job, I attempted a few startups with some friends after university. We tried a couple of things, and while they didn’t work out, the experience was invaluable. I had some programming knowledge from high school and university, but I had to learn more on my own, spending 60-80 hours a week learning Python, JavaScript, and SQL. Initially, I hired people, but soon realized I could save money and do it myself. Although I shouldn't be writing serious code, I'm good at prototyping.

I can get something out very quickly. It's hodgepodge. It's. But it will work. Right. That's the thing. And for POC, especially if we're being in product. Yeah, I think that's going to sell something. Right. It's like will this concept work? Right. Optimizing. That's a whole different story. Making it production grade. That's an even bigger story. But make sure something works. Right.

So I did that for a few years. It didn't work out. Had to get a real job, and at the same time, I did a finance degree. I was getting my CFA at the time, so I kind of found myself in a unique position. I knew I was pretty technical on the technology front. I was pretty technical on the finance front, doing the CFA charter. You learn a lot of very in-depth things about a variety of different financial products.

So I ended up finding myself in a foreign exchange company. They were just starting up their technology function, selling technology products to customers. I joined in a unique place where they were just rolling out their API product for foreign exchange, and I joined as a pre-sale. So I could talk about APIs and the foreign exchange a little bit. There's obviously better people at both—traders who do FX and engineers—but you know, talking about both to customers was a really cool job.

We had customers like cruise ships. You're creating these payment systems for environments with very bad internet, essentially, where most of your API calls will fail. So how do you make a payment where you have a failure rate of over 50%? Making sure the payment goes through. I worked with a lot of different companies, you know, with payroll, with banks, with all over the place.

Over time, that pre-sales role, as I grew in the role, I ended up caring about API. It was like nobody cared about it a lot. I was like, hey, this is important to me. So I kind of grew into product management very quickly, but my title and my official role was pre-sales for a very long time. And then once I got promoted to Director of Product, I finally got the product title. But I was kind of a product manager and a pre-sales leader for a while already. It just grew organically because it was something I was really passionate about. I really cared about that product and was just taking on responsibility to support that product.

The pre-sale skills I gained translated well into the product side. One of the most important skills for product management is talking to customers. In pre-sales, that's all you do. For that role, it was very complimentary because I almost didn't have to do research. I was constantly talking and listening to customers, getting feedback, and taking it back.

Pre-sales gives you a very good rounded set of skills. You know the product, you can demo it, you know the value proposition, and at the same time, you've talked to the customers. I think you're very well-rounded. I'm obviously biased because I came from there. In my current company, where I'm Director of Product and lead banking API product as well as marketplace product, some of the really good people I enjoy working with are a lot of the pre-sales leaders and just pre-sales guys. They understand a much bigger scope about the technical components of the product, the functional components, and how to position it and present the value.

You got a marketable story and you market your story pretty well. Where has your training impacted your career progression the most? So we'll start with your combat sport martial arts training.

I think the biggest impact has been on my interpersonal skills. Combat sports are very individual. You're not on a football team; it's you against the other guy and your coach in the corner. It's a scary thing. I've competed in other sports, like swimming. If you lose in swimming, so what? You’re off by a half-second, a second, whatever. It doesn’t hurt.

In jiu-jitsu or wrestling, you go out, and the guy on the other side might be your buddy, but once you start the match, he’s out to get you. The amount of adrenaline you get is intense. I've been hurt in competitions, and it's a complex set of emotions to handle. Even in class, someone is essentially attacking you, trying to choke you, trying to throw you. It’s a scary thing.

But that emotional toll and the need to go through those emotions help build interpersonal skills. You learn to be conscious of who you’re rolling with. It’s not just about size; someone half your size might be a black belt in judo. You have to be emotionally cognizant of who the other person is. Maybe they’re having a bad day, and that’s why they’re spazzy. Maybe they’ve had trauma. You learn to adjust and match their energy.

Combat sports teach you emotional intelligence. It helps you deal with fear, ego, and complex emotions, making you more self-aware and better at understanding others. This translates to the workplace, dealing with colleagues, bosses, and clients, especially in international assignments or different cultures. It really helps with emotional intelligence.

What about your military training?

Sure, here is the transcript formatted into paragraphs without changing the actual words:

---

Same question. But just instead of respect to combat sports, let's talk what you went through in the military. How does that impacted your career progression?

I think military, you know, I've learned a lot and I attribute it a lot to my military career.

You're a corporal?

Yes. Yes.

Um, Infantry?

Uh, yes. Infantry. But I had a bit of a unique assignment in the infantry. Um, I was in the reconnaissance, so it's almost very much opposite of what traditional infantry is perceived to be, and kind of what it does, because in the when you're reconnaissance, you operate in small man teams and you're completely unsupervised. You're just given a task and like, we'll see you in a few days, do whatever you need to do. So there's a very you know, if you're an infantry, you're everything is very regulated. There's a lot of rules. You have to, you know, it's. What people think when they think military. Exactly right. Recon is exactly opposite of that. It's like, okay, well, just check in every 12 hours so you're alive and don't miss the check in. And it's usually a code word and that's it. You know, like.

So are you deployed?

I never deployed uh, I did a lot of training in Canada. Um, I went to, like, Nunavut. I've been all over Canada, but I've never deployed outside of Canada.

Wow. And so it's, uh, with respect to that, then. I mean, not like like we said, perhaps not what people like civilians was. When I say people right would think when they think military, right. When someone goes through military training, perhaps a bit of a different, uh, experience between recon and traditional infantry, I guess. But what did you take from that, and how do you think that's kind of helped you progress to where you are today, if at all?

I think one of the most applicable things, and I think a lot of people can apply this, and I've been trying to coach some of my my team members on this. One important skill is there is something that was called commander's intent.

What's that?

And essentially what you're trained, especially in recon and not even before recon. It was an airborne operations. They just done differently than normal infantry operations because of potentially high casualty rate. Um, you're trying to think of understanding what your boss needs to do and his his boss's intention. And what that creates is that you really and you're not trying to go out and do your boss's job. You just need to understand when he's telling you to do something, like why you're kind of getting the bigger picture, and then you need to understand your boss's boss, because in the military, there's potentially, you know, casualty and your boss might. So you need to really be dynamic about, um, kind of leadership a bit there. So what that is very applicable to the corporate world is and this applies to everybody, you can be an analyst, you can be a manager, you can be a director. It's like, what is my boss's boss is trying to achieve with this. Right. You're given a task. Well why? What is the bigger picture? And you're not trying to do something different. You're still trying to do what your you're being assigned to do, let's say a project or a task or whatever, but you're really trying to understand and cover it off. Maybe you're given instructions, and those instructions missed a key step because you just know, because your day to day, you know. Good example. Uh, on my team would be somebody somebody specializes in maybe security. Maybe they're specializing in specific technology. Right? I'm not a deep down expert. I want them to understand my scope and what we're trying to accomplish commercially. And then on the product side, but hopefully I give them enough context that that person understands. Maybe, hey, they see something else that's applicable that has a second order effect, right? So when instead of just telling people you have to do X, Y, and Z, I hope that they're able to think about, well, what about A and B and C? They're actually related to x, y and Z. Right. And that's kind of what commander's intent is is, is I'm trying to understand the bigger picture and then thinking what I'm doing, is this going to really accomplish that?

Okay, so that's a bit of a curveball for me because that's the but it's good because the next question I was asking was a bit assumptive on my part because again, civilian never trained in the military, right? My, my perception. Maybe it's because I've seen too many movies, or maybe it's just what I think, right? It's when you're told to do something, you do it. You don't ask questions and and you execute. Right. And that's what I think a lot of people perhaps I don't have data to back that up, but that's what I would think would, would expect from someone who has had their their military training.

So I can I can tell you a really good movie. It's a series Band of brothers. They're actually famous scene there when the orders are given by the general to everybody. And usually, you know, general goes to the colonel, Colonel goes to major, major, you know exactly what you think. But in airborne operations, kind of similar at a much bigger scale. In recon, everybody is there for the general because you don't know who's going to land on the ground. Your captain, like your captain, everyone might be dead. So you have to know the general plan. So literally, the general was presenting the whole battle plan. So even the privates were in the room. Everybody knew. They knew the general commander's intent. And that was a D-Day operation. That's a massive, massive airborne operation. Right. So that's kind of the example of, you know, there's a famous scene where they doing that, uh, and a number of other movies, they cover that, but that's a I think it's a very important skill that you can even intern as an intern. You can do it.

Oh, man. Like that, that for for when you talk about emotional intelligence. Right. Being able to even just start because some managers, if they're a good manager, they're going to think like that in my opinion, because they're going to make sure that their team understands the scope. You understand why we're doing what we're doing. You're going to understand, even though it's perhaps above your pay grade, to know, but it's good for you to understand the scope of what's happening. Why do I need this information from you? What does that mean for my bosses? Right? When someone is new, you can explain that as an intern or even anyone joining a new job, their manager may not be that good, right? Where they're thinking, they're thinking the other side of it, where they're just saying, I'm telling you to do something, go ahead and do it. But, uh, if I think someone looks at their managers that way, where they actually actively try and understand, they may be able to sort of break that barrier, right, and open the door where maybe that manager actually is a bit more forthcoming, I would imagine, is that have you had that experience?

Exactly right. It's if you have a great manager and they'll do it for you, but you know, it's going to be taking a bit of more positive control of the situation. Right? Tell me. More. You can make it happen. You can make it happen. Right. And you make your, your, your manager's life easier that way. There's a bit of a dark side to it where I've seen in some cases, um, where people, you know, are trying to over overdo it in a way like, oh, I know what they're trying to do, so I'm going to do something else instead. Okay. You still have to do what you've been asked to do, right? I think that's the key component. And you just try to enhance it. Don't try to if I if I tell you to do a and you come in and do B, well, maybe I have a reason. I ask you and you say B is better. Like, no, maybe there is a specific reason a technical, regulatory, legal, whatever reason. Right? There's a very specific reason why I ask you to do it. But you might do a and then you say, hey, I can also do B, or I've done a partially B as a POC just to show you. Right. So I think it's key that do what you're asked to do and then just show that, you know like the other side I understand I understood the assignment. And there's this is a way how you can enhance it. But tactfully in a way where you've done some thinking, where this is how it's going to be best received by my boss.

So that's probably where the discipline comes into, because no doubt you've I'm sure you've taken a little bit of discipline from from the military. Right. A little bit, yeah. Perhaps, perhaps a little bit. Uh, being disciplined in that. Okay. You're going to do what you're what you're told to do, but you're just thinking ahead and not doing it blindly. Yeah, I would, I would say right. So between martial arts training, between military training, looking at both of those, in contrast, uh, are there similarities, are there differences in what you've taken from each of them and applied to to your work life? I do, I do think they're a bit different. I think I think martial arts is a very individual journey. Whereas we talked about really emotional intelligence where military is more of a social thing. So I picked up a lot of my social, uh, components from that. So I do think they're different. I think they're complementary in a sense. They're both. I won't say aggressive, but in a way they are. I would say that's a unifying factor, that in both cases there's somebody on the other side you're trained against that. You know they want to hurt you. Right. So I think that was the common factor that, um, I think drove a lot of kind of behavior and some of the patterns. But I do think they were definitely complementary.

Now again, this could be you could have already answered this in a given way. But I do want to go back to it, because every every martial arts gym will say, right, or, uh, they run a little bit differently. They could be right. Some of them are a bit more like, we can say culty or cliquey than others in some fashion. Right? Uh, are there any are there cases, you think where perhaps what you what people take away from their experience, whether it be in the military directly, whether it be in martial arts or combination of both, that perhaps there's, uh, a negative to what they take into their career. And an example of this would be someone becoming too much of a of a yes man. Where there, there used to perhaps obeying. Right or or just following. Perhaps following blindly. Maybe not in the military, but I've seen some gyms where the coach says this and, and, and with things outside of, uh, of training. Right. And the person just asks how high without asking any questions. Right. So like that kind of obedience, does that turn you into too much of a yes man in the office where when you have a boss who. Maybe. Does want to take a little bit of advantage right of you, you don't really realize that. You don't know how to tactfully push back. And now you're in a position where maybe you're burning out as an example, or perhaps someone who's thinking there. They come from that world where, you know, it's continuous improvement and all of that, where they're striving too much for perfection. You got to get out of POC, and this person is trying to do every little detail, you know, like in the BlackBerry movie. I don't know if you saw that he's trying to get everything perfect before he kicks it out. Before he before he sends out the prototype. Sometimes things are time sensitive. Nothing's going to be perfect. Is this a factor at all, or am I just kind of crazy in my head?

So I think in martial arts, I haven't seen really a downside, to be honest. Um, I think it's generally positive. If anything, you could increase your confidence and that confidence is going to let you tactfully say no to things, right? I think in the military, you know, and I'm part of a couple of veterans groups, I'm heavily involved with some of the topics. And, you know, it's, um, I think there are some downsides there where some people can be very institutionalized.

That's the word. They really, you know, think a certain ways, and especially if they've done their whole career, they might come out and they have a hard time thinking beyond their role. Right. I carried a gun. I need to be carrying a gun so I can only be a policeman, right? Or a fireman. That's kind of the two common, uh, very common reactions for people. Right. And it's fine. It's there's a lot of similar types of people, but there's other roles you can do. Right?

Um, I know one one of the captains. I know he's a behavioral scientist now, right? I know guys, one of the guys at recon school with. He's interior designer. Come on. Yeah, I try to call him up to design my new house, but, um, he hasn't responded to me. But, you know, I think I know. If you need one. Maybe. Maybe. But there's guys, you know, who go out and and explore things. But there's a lot of guys, especially who've done it. Uh, that was there. They started young, and that's the only thing they know. They kind of have a hard time leaving that. And that's what a lot of veterans groups, uh, help with that. Like, for example, I'm part of, uh, Treble Victory Group, uh, which is a veterans network, uh, on Bay Street. And, you know, they try to help people to show how you apply those skill sets, project management leadership, whatever to other sales? No, exactly. Sales managing. Get involved in that and help with that if I could. Sorry, I don't mean to cut you off, but I love that. Yeah, yeah. So yeah, there are groups and people do realize this. I'm just repeating some of the stuff that, uh, those groups kind of communicate. But I've definitely seen talking to people where they're like, you can do more than just that. That's, that's that's great. But, you know, it's it's not just carrying a gun and yelling at people. Right?

Okay. Very interesting. Does, uh, does getting humbled on the mat, right. When you're when you're sparring, when you're training, uh, do you feel it makes you a better manager? Yeah. I think going back to the emotional intelligence, right being. Yeah. Like losing and facing that adversity is is important for anybody, not just the manager I think is a as a as a father and a husband. That's important. But as a manager overall, I think it's important, right? If you always win, there's something, you know, you're not training hard enough. You're not training the right place I think. So you do need to be humbled. You do. And it does help because it's a I think a healthy part, especially in product. If you're always right, you're not taking big enough risk, right. You need to be doing something different. Um, so I think it's important for product. I could definitely see relevance. Like, you know, you need to be it's, you know, creating a hypothesis. It fails. Try something different. Right. It's kind of very similar that way. Right. In jiu jitsu, you lay a trap that fails, you lay a trap that fails. But the third thing works, right? And the third thing is like, amazing, right? Maybe you have to do five steps, right? Kind of the same thing. As long as you're progressing and you're, you know, if you think about it in jiu jitsu terms, as long as you're improving your position and you know, you could be starting in a like a equal position. But as long as your every attempt gets you closer to a really good position, that's all that matters. So I think the same thing, right.

Do you see a difference in approach between. So if you if you work at all or have clients at all or just in your experience at work, you've interacted with people, other managers, for example, that do train and those who do not. And do you see a difference in their in their in their manner and how they approach different problems, how they manage people with that respect, where you can tell that this person has been humbled and this person like they're a God at work, and that's what's always in their mind, you know what I mean? That's where their head is. And you can feel that from them. It's hard for me to to say definitively because I don't think I know enough people. I think I definitely get along with the people who do train. I was at a at a conference recently speaking, and my co-speaker from Bank of America used to wrestle. Right. And we get along very well. Yeah, yeah. Um, I found out one of our one of our heads of sales, uh, he's a brown belt in jiu jitsu, and I get along with those people, so. Maybe I go. With him like we. Planned a couple of times. We just never ended up doing it because of he's running. From, you. Know, just the flights. You know. Just the flights. Didn't work out. Uh, but, you know, I think that people I do know, I do get along with, but I don't think it's a big enough sample set for me to, to definitively say, that's fair. It maybe just something it's a weird hobby we're both into. Who knows? Yeah, I know that's fair. I've seen some, um, from like some very, very senior people who are in positions where I've seen other people in those same positions have like, incredibly large egos, even with me earlier in my career. Be very, um, I got to say patient where typically like when I, when I started and making all these calls talking to people and you call someone at that senior level and you're you're still like a young guy, right? So you say the wrong thing or you approach the wrong way, might chew your ear off. Right? But there are some definitely people who were put in positions where they could have did that to me. And and they didn't. I found out later it's like, oh, this guy's a black belt in judo. Oh, this guy's trained jiu jitsu for for forever. So I don't know if that's a direct correlation, but I definitely I would agree with you that I think getting humbled on the matter, at least in another part of your life, it does make you, um, you're just you're checked. That's the only word that I can use, right? You're checked in other areas of your life because you, uh, you're constantly losing somewhere, even when you're doing well, somewhere else. Yeah, but but you're also learning from it, right?

If you're. In a. Good way, you got to lose. Right? If you're a black belt in jiu jitsu, I have so much respect because you've committed your life to. So it's a lot of hours, right? A lot of other you know, I have a black belt in karate and that was four years, right? Right. I'm seven years into Jiu-Jitsu. I'm a purple belt, right? I'm still, you know, I'm still a few years away from a black belt. Right. And and it's going to take a lot of work. Right. So it's, it's a very hard belt to get. It's a huge achievement. And I think anybody who's achieved it is like you know it's just overall the grit and the patience because it's not like you're going out and you know you're going to have some rough days, you're going to get hurt and you know, you people, some of these knee will slip and you get hit in the head. You're going to, you know, you're gonna you're going to suffer a little bit. And that's a lot of suffering over nine, ten years. So I have a respect. It means if they're applying the same grit and the same patience to their other concept of aspects of life, I think, yeah, they will be successful there too.

Mhm. And uh, last question, when you're hiring other people, we talked about some of the qualities that you've been able to gather in parts of your life and apply them to work. Uh, which one of those qualities is the most important? What do you really look for when, uh, when it comes to hiring in that respect? So I look for their, their, uh, attitude and kind of those soft skills, but really the attitude because, you know, I guess if I was maybe hiring for somebody in deep security or, or something very specific, the skill set might be really important, right? But generally, as long as you're in the general vicinity of the skills, I think if you have the right attitude, I can coach you through that. Right. But but attitude I cannot coach, no doubt. So I think I really look for the attitude and then. Two either. One, it's very hard. It's doable, but it's so hard to do right to motivate and change a person motivations there. So I really look for the attitude and they're and they're kind of the soft skills and their willingness to do things. So ideally it's a high agency person that's willing to go out and do things right. And then if you want to, if you're that kind of person, listen, I can put a training program for you no problem. And we can get you where you need to be. Assuming you have some foundation. Right? You still need to be have general foundation, but I can get you to the next level.

Yeah, that's like the best foundation, right? Like the the attitude, the initiative. Like, these are key things that, like you said, you could teach, but you probably don't want to teach that stuff. They got to come stock with the rest of it can be learned, right? Bravo.

Okay, well, hey, man, it's nice catching up with you after all these years. Your gym now. Do you want to say which one that is?

Yeah, I'm in Gracie Baja Toronto. So it's, uh, I'm on major intersection of King and Bathurst, so anybody's listening wants to come and, uh, train in mornings, evenings, they have a lunch class. We gotta open that. Um, I don't know if we have an open mat. It's, uh, I guess it's Sunday. It's more of a Sunday thing, but, uh, everybody is welcome. Uh, and, yeah, it's a great school shout out to all my training partners, uh, all the coaches, professors. It's it's a great place to train.

All right, maybe I'll swing by for an open mat if you're up for it.