Upvest CTO About Scaling Tech Teams and Mastering Organizational Culture

In this episode, Philipp Deutscher speaks with Juha Ristolainen, CTO of Upvest, about building scalable tech teams, nurturing a dynamic organizational culture, and embracing transparent leadership. Juha shares practical experiences from Upvest's growth journey, including strategies to empower engineers, handle rapid scaling without compromising quality, and maintain clear communication even during critical situations. He emphasizes the importance of aligning evolving organizational culture with core values, promoting diverse perspectives, and leveraging transparency to build trust. The conversation also touches on his personal leadership evolution, effective mentoring, and the pivotal role of strategic vision for tech leaders. 

This episode is essential listening for anyone interested in leadership strategies, cultural growth, and sustainable scaling within technology-driven organizations.

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Transcript

Philipp Deutscher (00:02)
Okay. Yeah, you were speaking about the company culture and how you, and I like the fact that you were saying about, it's not, you should not focus on cultural fit, but on cultural ad because everyone brings something new and unique and different to the table. And that might also enrich the company culture. But what specifically do you consider the most essential elements for fostering such a strong organizational culture?

keep this, so what are the elements that are the most important to you?

Juha Ristolainen (00:36)
Yeah, so again, like I said, everybody brings something new to the culture when they join. culture will change over time and it's nothing to be afraid of as long as it's anchored in the values and the things that you value as a company. So like I said, we have four core values that are on the outcome and tell the story and all these kind of things. So as long as you can align with our values, then it should be fine. So

Like you've heard about brilliant jerks and these kind of things like, wouldn't hire a brilliant jerk if they can't work with the team and align with the values we have, like make it easy for others. So, so that's the basis of it, but company culture will evolve over time and everybody will contribute their part into it.

Philipp Deutscher (01:27)
Interesting, same thing happened again.

Juha Ristolainen (01:31)
I think it may be because now it's uploading in the background, my browser says 85 % uploading.

Philipp Deutscher (01:38)
85 % only, But maybe it's only...

On the client side now and on the server everything is going well. I think we should just continue. If you see a correlation between this and the uploading, then...

Juha Ristolainen (01:52)
Yeah.

Yeah, all right.

Philipp Deutscher (02:03)
We can

continue. Now I need to pick up from the last thing, because also the last two sentences that you said, I were not able to fully understand because of the scrambled voice. Can you repeat them? Can you repeat the answer? Or should I ask the question again?

Juha Ristolainen (02:23)
Okay, fuck.

Yeah, maybe.

Philipp Deutscher (02:29)
Now you're not audible at all. Why?

Juha Ristolainen (02:33)
Okay, testing, testing.

Philipp Deutscher (02:37)
but I see your speaking indicator, so something is totally off.

Juha Ristolainen (02:40)
Yeah,

I can hear you quite well, yes.

Philipp Deutscher (02:58)
Can you say something again?

Juha Ristolainen (02:59)
testing.

Testing, testing, testing.

Philipp Deutscher (03:12)
Okay, now you're back. Maybe those were, was just on my side. I don't know.

Let's try again.

Yeah, so what do you consider the most essential elements for fostering a strong organizational culture, especially when you say you're not only looking for cultural fit, but also you're looking for a cultural add. So if they bring something new to the table.

Juha Ristolainen (03:42)
Yeah, I I think that's good term because everybody who joins an organization brings something in there and the company culture will evolve over time. I think what's important is then that as long as you can align with the company values, like we have four core values on the outcome and tell the story and such, as long as you can align with those, then it should be fine. But yes, you shouldn't be afraid of the company culture evolving like that happens in all places.

I think it's on us as leaders to lead by example and show the way and point out when people exhibit their company values and also hold them accountable when they do not. So making sure that we foster the right behaviors inside the organization.

Philipp Deutscher (04:31)
And how do you address like hassle or communication breakdowns, especially in critical high pressure situations while you're growing fast or something critical is going on, especially during periods of this rapid growth?

Juha Ristolainen (04:48)
Yeah, so I mean we have quite an open communication culture anyway. teams and people talk to people from other parts of their organization and departments whenever they need for their work. So that happens quite well normally anyway. But then there are times when there's a critical project or a response to something. For example, we had a few more incidents than usual in January, for example, and we had this incident task force that we...

we set up, bringing all the right people around the table and really looking at where we are and setting up an action plan. So sometimes you have to go up the flagpole and then coming down the flagpole somewhere else. So you should put people in direct communication that need to be direct

Philipp Deutscher (05:36)
And those incidents were a consequence of high growth situations or?

Juha Ristolainen (05:41)
Well, I mean, we've been building for four years and obviously we've had to take some conscious compromises on certain things and we made some design decisions with the information we had two years ago, for example. We had a few cases where we some limits being reached now that we are getting much, much more volume and traffic on the platform and those started to cause incidents and we just had to.

start addressing those a bit more vigorously. But the good thing about these kind of distributed systems is that they are quite elastic. So it doesn't really break. It starts to slow down and then you have time to react. But yes, you have to...

Those are actually the interesting decisions you have to take as leaders sometimes. You can't always build the ideal solution, to be able to bring these to clients that need it in the next few quarters, we have to first do it in this MVP style, then we have to take note of what we need to come back and change a few quarters later. So those kind of things are now...

part of the normal work. It's not fully 100 % building new stuff anymore. It's also about keeping the lights on and addressing some of those earlier design decisions.

Philipp Deutscher (07:01)
And you mentioned

the core values of the company, but you only named two of them. What are the others?

Juha Ristolainen (07:07)
Yeah, so here we may need to break. We are actually in the process of changing one of them. Let me find the actual page because we have it written out so nicely.

Philipp Deutscher (07:16)
worries.

Juha Ristolainen (07:42)
Sorry.

Just a moment.

Okay, now I'm back. yeah, it's, so we have four core values. Number one is learn and grow. Obviously, when we started, we didn't know too much about the industry like we had to learn or as we were building. Team first is the second one. Number three is own the outcome. We don't believe in micromanagement and people need to step up and own their outcome and then tell the story. those four core values have been there.

for a few years now already. They weren't there from the beginning, but at some point we had to stop and start to think about what do we actually value as we grow the company. And those four have served us quite well. But there are sub points to each one of them. And especially the team first, we have one that says make it easy for others. So that's actually what quite a core sub value that we have. So not just.

taking something and throwing it across the over the fence to the other department and expect them to know what to do but make it easy for them.

Philipp Deutscher (09:08)
You said something

very interesting and very inspiring because you said the culture changes over time and that's okay as long as it's still in line with the company values. And yes, while it sounds so obvious, I think that many people do not take care about it. That it's okay for the company culture to change as long as it is still part of the deal. It can still be just another variation.

of the values and the DNA of the company.

Juha Ristolainen (09:41)
Yeah, yeah, exactly.

Philipp Deutscher (09:43)
Very well. How critical is transparency to you, especially in maintaining trust within your teams in communication? And how do you implement transparency in your way of leadership and how you deal with your teams and your direct leads?

Juha Ristolainen (10:04)
Yeah, so personally to me it's super important. Obviously as a member of the executive management there are things that you can't always tell people about certain things and also when we're going up the enterprise ladder getting bigger and bigger clients those are quite delicate topics so we can't always talk about them openly so we use code names for the customers to prevent leaks and...

all these kind of things because it could be disastrous for the client relationship if things leak out ahead of time. So some things, yeah, you can't share really to all of your team members, but my direct reports, have a really unfiltered access to me and the way I think and I delegate a lot to them. And then actually I try to get them to come up with a solution and decision without me needing to tell them that. So that's sort of my style.

So they get an update from me from what we discussed in the executive management. yeah, to me, it's the basis of the relationship. it will work any other way.

Philipp Deutscher (11:16)
Yeah, to me as well,

but some people might say there is also a downside of being too transparent. Did you ever face a situation where you retrospectively would say, okay, maybe it would have been better if I would not have shared this information or if I would have to be more sensitive in this regard?

Juha Ristolainen (11:35)
Yeah, I I think as long as you are clear on the expectations, I mean, I've gone through the learning with my directs as well that sometimes in the earlier parts, I forgot to tell that, okay, well, this is information just for this group. So please don't pass it on. And then there were things that were discussed outside the group as well. And then like sometimes in the absence of information, rumors and gossip start to...

to fill in the void. I always tell people that if you hear something that seems weird or you're not sure of just being me on Slack directly, I can always give you the straight answer on what or whatever I can to avoid any misinterpretations. But yeah, that's a learning I had earlier on this that you have to be specific because normally in my weekly with my directs, we discuss everything quite openly. And sometimes I have to remember to say that, okay, well, this information is now just for this group.

because it might be something about an upcoming business decision or something else that isn't ready yet for company-wide consumption, but it's important that they know. So it's just about...

Philipp Deutscher (12:45)
And the direct reports

and the direct reports you are having. So those are mostly people you helped growing into this position or where it's mostly people that you hired and they were joining the company for, especially for this role.

Juha Ristolainen (12:58)
It's both. when I went from five to 50 engineers, that's when we started the tribe structure. And so I hired my heads of engineering, but some of them actually have grown from a tech lead manager to a head of a now director. So it's a mixture of both.

Philipp Deutscher (13:19)
Okay, and do they need to have some critical skills that you believe would help them to become better leaders? So how do you select someone climbing up the ladder and becoming a director at some point?

Juha Ristolainen (13:35)
Well, mean, my group is also quite eclectic, so everybody has their own strengths and weaknesses and working on their growth plans is interesting and rewarding. So, but I think it's ultimately about owning the outcome, delivering results and making sure that you bring the people along. Like I think as a leader, it's super important always to set the context on like sometimes even if you have to decide on something.

Not everybody always agrees, so you have to be able to disagree and comment. as long as you give the why and the context why this decision was made this way, I think you can bring people along. So it's about realizing that, OK, we're here to drive business outcomes. facilitating for that and forgetting your ego and any of your personal preferences on technologies or solutions. think that's quite key. Also, communication skills are super critical.

I can't. Most IT projects that fail, don't fail on technology, they fail on people and communication.

Philipp Deutscher (14:29)
Yes.

Couldn't agree more.

mean, but you also you were talking a bit about your direct report. So this is this group of people. How do you see them? Is this like a very diverse group of people or is it more more homogeneous and more aligned to your way of thinking? How do you set this up? I mean, I'm also asking because in the last episode I was talking to the former CTO of TeamViewer Mike Eiseler. He was my former boss. I was part of his management team many years ago.

And he also came up with the idea and said, like, he liked the fact that his management team was kind of, was very diverse in their approaches and their way of thinking, which I found very difficult at that time because it felt like we were never able to come to a conclusion because we were so diverse and had so many different opinions.

Long story, but the thing is like, how are you handling it? Is it like more diverse or more homogenous?

Juha Ristolainen (15:35)
Yeah, yeah.

Yeah, I mean, if you look at it from a demographic perspective, I think it's quite homogeneous. So, I mean, we're in an intersection of financial services and technology. So it is not that diverse from a demographics point of view. I think from a diversity of thought point of view, have people who think differently. Some are more long-term thinkers, some are more pragmatic and tactical inter-orientation, some are more theoretical. And then...

Some have really strong opinions. there's been quite a lot of discussions, sometimes heated discussions in there, but ultimately if they can't come to a conclusion, then you are there to be the tiebreaker and remind them on what is important. But yeah, I think it's important to me. might actually a good topic for my one-to-ones with them is that how do they see that sparks flying sometimes around topics.

not being able to convince people of your argument over another argument. But I think it's always good that we get varied points of view across before then coming to a solution and decision.

Philipp Deutscher (16:52)
And when you apply like practical leadership in your daily work, when you talk to your direct reports, when you talk to engineering teams, do you also realize that there are some myths about leadership in general? And if so, what kind of myths do you see, like things that people believe which are part of leadership and later on in practice they turn out to be totally different?

Juha Ristolainen (17:20)
Yeah, I don't know about myths, but to me, good leadership is boring leadership. Like you're well prepared for things in advance and you don't always have to be firefighting. it's this myth about a great leader who comes in and saves the day because of a disaster, but you could have probably avoided the disaster by planning ahead a bit better and all these kind of things. So this

firefighter who starts the fire gets all the credit. that's a bit of a sort of a bias in the industry that people who make a lot of noise and tend to be seen as getting things done much more than actually when things are going smoothly and running smoothly. That's actually a sign of good leadership and you having been prepared. So I think that's one of my sort of things. I don't know if it's a myth, but

I subscribe to this boring leadership.

Philipp Deutscher (18:21)
Okay. Do you have some personal apprentices, so to say? So people you feel like they could be very good leaders, they could be high potentials you would like to support them on their path for becoming, I don't know, director, tech lead, whatever. Yeah, you have such people that you, so protegees, so to say, people that you help more than others?

Juha Ristolainen (18:48)
Not so much inside the company. Obviously, I want to grow all of my people and they are all, even the ones that I hired as head of, all of them promoted to directors already. Some of them have gone up two levels all the way to director. So growing people and that's really a lifeline of a company is growing your people and it's always way less risky to promote from within than hire an external leader.

So I like to do it that way. But there are obviously certain people in the company who if you see that they're not the most outspoken or championing themselves. I try to always remember to hold out for the little guy as well. Somebody who doesn't make noise, but this is a good contributor. not to forget about them.

I used to do more mentoring. In the early parts of my career I was mentoring foreign exchange students trying to integrate to finish work life as well. Those were actually always super rewarding jobs but I haven't had a mentee for a while now.

Philipp Deutscher (20:04)
Okay, and is there a way for you how to measure the success of leadership initiatives? I mean, or are you mentoring someone? How do you measure the success? Is this even possible?

Juha Ristolainen (20:18)
So currently I measure success on how my directs achieve outcomes and we achieve our business outcomes. But we do have an L &D manager in the company. We have learning and development paths that engineers can take part in and also trying to identify future leaders and all these kind of things. I think it is critical to grow our people.

I mean, we talk about talent density and bringing in barraisers, but also not forgetting about the people you've already brought in.

Philipp Deutscher (20:56)
Did you ever have a

situation where someone was knocking at your door and telling you, well, you, I also want to become a CTO. Can you tell me how?

Juha Ristolainen (21:04)
Not so much lately, but earlier in my career when I was mentoring people at Consultancy a bit, I had one developer who said that, when I grow up, I want to be like you. But then I was still just transitioning from a senior. I see really good at what I'm doing to leading people. But again, that was where most people in that part of their career, have.

some false assumptions on what the CTO role is. And actually, I think the best thing you can do to them is lay out what the role is actually about. And if you are really a technologist and passionate about doing things with technology, CTO role might not be the right one for you. You actually have to be a pizza business.

Philipp Deutscher (21:55)
And what false assumptions did you see?

Juha Ristolainen (22:00)
Well, most of the senior engineers or engineers in their career, they say that, I want to be a CTO. What they're thinking about is basically like this Alpha geek who designs the whole architecture and calls all the shots on technology and everything. No, that would be a really bad CTO. It's about empowering and enabling your teams and setting objectives and guardrails for them and letting them do those decisions.

Philipp Deutscher (22:28)
Yeah, right. mean, it's, it's you said it and I also saying this very often, like CTO is a business function, right? So of course, if you're, if you're having a tech background, that might help. And I would also say the best CTOs definitely have a tech background and started as engineers. But there are also CTOs out there who never coded by themselves. And some of them are also good CTOs. So it's not like you can only become a CTO when you were like a brilliant engineer.

Juha Ristolainen (22:56)
Yeah, I mean, I think it helps in the way where, especially if you're building an organization from scratch, when they know that you've done the job and it's easier for you to gain their trust because they know that you have experience and you've gone through what they are going through. But it's not an absolute must have and you can be an effective CTO without having that background. Obviously then you have to figure out your ways of how to talk with engineers on their level as well.

Philipp Deutscher (23:20)
Absolutely.

And is there a counterintuitive piece of advice you would give someone aspiring to become a CTO? Something they would not expect?

Juha Ristolainen (23:37)
No, like I said, I don't think it's counterintuitive, yeah, think the higher up you go, have to really have business skills and people skills. That's the more important part and the technology skills.

Philipp Deutscher (23:51)
And in general, what personal qualities differentiates like a great CTO from a merely good one?

Juha Ristolainen (24:00)
Well, mean, obviously you have to know your stuff, I think having the strategic eye out, but also realizing that the practicality is on the ground. So you have to be able to know what kind of comprises to take and what brings you the most value for now and then doesn't sink you in five years as well. So you have to always walk that tightrope between.

long-term and short-term delivering of value. So it doesn't make sense if you always keep taking the short-term decision and then in five years time you have to scrap everything you've done and start over again. I think having that long-term vision and being able to effectively communicate that to your stakeholders and peers, it's super important.

Philipp Deutscher (24:50)
True. And are there any other common pitfalls so those emerging tech leaders should be wary of when transitioning from the individual role to executive?

Juha Ristolainen (25:03)
Yeah, I think in general, this is a good rule for leaders, this over-communicate, because especially in a growing organization, there's always new people joining, so they haven't heard you say the things that you've said to other people many times. And even if it's things you think that it's too much and I'm preaching always, over-communicate, that's one of the keys. And especially over-communicate to your stakeholders and make sure they know where things are.

going on and what's happening and all this kind of.

Philipp Deutscher (25:36)
Yeah, true. mean, as you said before, as a CTO, you need to be boring, right? And over communicating the same stuff again and again. that it's also it's it might be boring for some people, but it's still essential. So as you said, new people are joining the company all the time and they never heard what what you told like six months ago.

Juha Ristolainen (25:56)
Yeah, exactly.

Philipp Deutscher (25:58)
If you could go back in time, what one piece of advice would you give your younger self before becoming a CTO? Or would you say do everything as you did perfect?

Juha Ristolainen (26:14)
Yeah, I think usually when you're younger people tend to be bit more cocky. know I was like just out of uni, you think you know everything. And I was also quite opinionated and things like that. So and also like utilize your strengths and also use the tools available to you. So for example, coaching is a super helpful tool. So if you have access to having a coach or

somebody to spar with, those are super useful tools when you're going up your leadership journey. So we've had an executive coach, for example, facilitate in our management team for a while, not anymore, but last year. Those prove really useful. So use the tools available to you and then like don't think that you know everything yourself.

Philipp Deutscher (27:09)
Very well. And last question for today. Do you have like a saying or like a motivational quote which is very important to you because it defines who you are, it reminds yourself about what's important? Anything in your life that is defining the way you are?

Juha Ristolainen (27:32)
Yeah, again, I think it comes back to my Nordic background and the values there. it's, well, probably no bullshit. Like I don't tolerate bullshit. And actually, when I took my first job in the UK outside of the Finnish consultancy, was, thank God I was in a leadership role so I could get away with it. But like cutting through the

Talking around in circles proved to be quite effective and actually served me really well. Faking and doing things for appearances, that's like I'm allergic to that kind of stuff. So no bullshit, it served me well for the whole of my career.

Philipp Deutscher (28:20)
Yeah, and I assume all your employees know that, right? So whenever they are talking to you, no bullshit.

Juha Ristolainen (28:25)
Yeah,

we have this practice where we write this, read me so people who join the company can read about what makes me think and how to interact with me. So it's hopefully useful for people who work with me.

Philipp Deutscher (28:41)
It's like a manual, right? A manual for human interaction with the CTO. Very well, I like that. liked it. Juha, it was great talking to you. Thanks for the great conversation we had today. Thanks for following my invitation. Yeah, thanks and talk to you soon.

Juha Ristolainen (28:42)
Yes.

Yes.

Alright, thank you and it was a pleasure. Bye bye.

Philipp Deutscher (29:04)
Thank you. Bye bye.