This weeks episode we’re sitting down with Oleg Simonov. Oleg Simonov is CTO at Dots, a T2 Interactive mobile game studio, where he is focusing on scaling technology capabilities. Oleg is passionate about enabling organizations to do things bigger, faster and better – modernize, scale up, operate with high performance, break into markets, maintain customer trust through quality. Prior to gaming, Oleg worked on real time financial systems and direct to consumer platforms.

Oleg’s Top 5 Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week. Take a listen to the episode to learn more about the thoughts behind these tips –

  1. Drive Change
  2. Be A Human
  3. Culture Is Key
  4. Invest In Improvement
  5. Get A Coach

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript

Ryan: Hello, and welcome to this week’s episode of the full stack leader podcast. This week, I’m here with Oleg Simonov, he’s the CTO of dots, an amazing mobile gaming company who ironically has one of my favorite games in their portfolio. I’m really excited to have you here this week. Oleg welcome, 

Oleg: Ryan.

Thank you for having me. It’s great to be. 

Ryan: Yeah, of course. It’s my pleasure. I’m really excited to hear how you ended up getting to the position of CTO at a company like dots the path that takes you there deep into the casual gaming environment, but also really the amount of data that’s happening across mobile.

Maybe you can give us a little perspective of the early parts of your career that led you here. 

Oleg: I had a curious past gaming. , I didn’t play a lot of games growing up, but fell in love with programming at age of 12 and became a lifelong engineer. I loved building new things. The first half of my career focused on productizing, next generation technology and building new products for financial and direct to consumer companies.

I switched to gaming six years ago because of the freedom for creativity and innovation. It offers in both technology application and product design. In addition to innovation, I help companies accelerate business growth and build high performance technology teams. I hold an undergraduate degree in computer science from Stony Brook university and an MBA from Columbia business school.

And I also did uh, theater and ballroom dancing for about 10 years. And I love traveling to discover different cultures and try different Cuis. 

Ryan: very cool. Yeah. It’s really interesting. You’ve got a, an MBA from Columbia. You also do ballroom dancing travel. Like it’s just a really great combination of things.

That’s a that’s amazing. One of the things that I know about you is that Earlier part of your career was in the financial industry. And maybe we can talk a little bit about that, but what I’m really interested in is the similarities and that are between the financial and the gaming worlds and hearing a little bit about that.

Oleg: Believe it or not gaming and financial systems are actually quite similar. Both are rules based environments where actors compete using available resources and sophisticated strategies. I often joke that New York stock exchange is probably the most amazing gaming platform in the world. Gaming also borrows heavily from e-commerce around user acquisition, over personalization bonding pricing, and otherization strategies.

Games are really eCommerce platforms for digital goods and services and similar to many modern businesses. Technology success criteria in gaming about delivering high quality, reliable, and user experience, enabling actionable insight about customer behavior and personalizing products accurately and quickly to the user’s needs.

Ryan: Yeah, that makes sense. I, because I’ve worked in and around both industries over the course of time, I kind of know the relationship you’re talking about. Cause there is a lot of data transfer between them. And I know you worked in that financial part at the New York stock exchange at one point how did the NYSC like experience give you some perspective on fitting together, large scale projects?

Oleg: Program managing pillar at neuropsych change was a wonderful learning experience. Technology projects truly succeed only if they are aligned with the needs and opportunities in the various business functions, such as product and operations. And increasingly also in compliance sales legal. New York stock exchange taught me how to engage with various non-technical stakeholders.

Bring them into the conversation about the system delivery and give them a voice to shape the technical end result in a way that offers them the best chances of success in the marketplace. When this happens, technology truly becomes a business multiplier.


Ryan: That’s a really good perspective on it. So how. Well, is it helpful to have project management and architecture experience together? Like, it’s a, it’s an interesting bifurcation of the two and to, and they’re very important roles, but they live in different spots within the development process.

As you’re growing into the CTO role, how important was it actually having both of. 

Oleg: Most definitely helpful CTOs are measured on being able to deliver on unpredictable timeline systems that work technical architecture experience gives you the ability to identify design parents that feed the problem and anticipate technical risks that may not be immediately obvious.

It enables you to ask questions that help engineers develop new insight. And consider blind spots. For instance, I learned a lot about data gap detection and recovery patterns at New York stock exchange, something that is also critical for building high confidence, analytics, pipelines, experience, executing programs teaches you how to communicate effectively throughout the project.

Aligned resources and stakeholders manage risks and dependencies, being able to hit your dates with quality, built confidence in your team. So, yes, knowing how to execute well is very helpful, but I found the hard way. It is not only thing required for success as a CTO. You also need to build systems that move business KPIs and cost aligned with company revenues.

For example, many of my recent initiatives focus on improving user retention and. Through tighter integration of customer analytics into products and a look for opportunities to shift fixed costs into variable costs, both in the delivery and operating teams, as well as in the infrastructure, we also live in a highly regulated world.

Be that data, privacy, security, or industry regulations. This regulation should inform how we put systems together to avoid operating costs, certification delays, or being in the news for the wrong reasons. For instance, we minimize any private data. We collect and isolate it from the operational data using minimized IDs and minimize data is much easier, cheaper, and safer to handle.

Technology can also accelerate or slow down product development, a perfect buck, free release, but six months in development that only delivers a small test idea to market is not very useful. We need to be able to balance the product that energy needs with a desire to build every system perfectly. I often use Jeff be’s approach to help decide how much engineering should go into a feature.

If this is a two way door that you can exit later, that is you will have a chance to harden the feature before use volume scale up. It’s likely okay to do it quickly and help business experiment and tune it before committing a lot of engineering behind it. This technology powers or informs every aspect of modern.

And although delivering on time and with quality remains very important among our CTO has to be fluid and key business success metrics in drivers. 

Ryan: Well, maybe tell me a little bit about that. Because how do you transform business goals, KPIs, things like that into actually becoming an engineering led organization.

Like how does that.

Oleg: It is another great question. How do we help business maximize the return on the massive investment they made in the engineering talent and how do we best educate them about what engineers need to thrive? Business, expect us to inform them about the technical visibility and costs of the ideas and vision.

They also expect us to educate them about the new product and services the literacy knowledge could enable or how it could enhance the existing services in new ways. That differentiates, for instance, we should advise our business partners that it could be a waste of time and money to try building a certain predictive machine learning model.

If they include custom behavior that is not full observable. The model training data and resulting models will be incomplete. On the other hand, latest technologies such as AR. While unlikely to drive a standalone product at this moment could create complimentary user experience with real differentiation potential in the near.

Technology organization is a bit like an aircraft carrier. It takes nine to 12 months to turn, to develop expertise in new technology, to productize it, to understand how to operate it. So it is important to create a company and culture that gives voice to engineers to communicate about technology driven opportunities and looks 12 to 18 months into the.

I’ve used both tech, SOS and hackathons, inclusive to business, product teams to help nurture such a culture and integrate engineering input into the product conversation.

Ryan: Yeah, that makes a lot of sense. But how do you work with your engineers to come up with ideas? How do you actually inspire them? Pull creativity out of them? Cuz I know when you’re engineering led, that’s a big part of. 

Oleg: We want our engineers to be problem solvers and feel a strong connection with an on an ownership of the games we make.

So it is critical as we allow time in space for them to come up with ideas and work on them. It is built into O S D C draft product specs, routinely previewed with engineers and QA and adjusted based on the. Product and engineering regularly discuss technical data opportunities and jointly agree what to tackle on development side.

We expect every engineer to own creating his or her design specs, drive those through reviews and then own the delivery to production. So it’s a very bottom up culture that explicitly places the expectation for tion with engineers and we of course run hackathons. About every six months to foster out of the box, thinking a left field ideas.

We encourage teams and cross functional participation so that the front end engineers can pair up with backend an artist or data engineer. We love when folks engage in fun and creative activities outside the immediate team or respons. 

Ryan: That makes sense for a gaming company. I love that. Cuz just even experiencing your products, it feels like that is what it should be like.

Right. To create them. And hearing like the level of kind of bottom up responsibility you put on the engineers, it brings up the question of like, how do you. How do you best hire the most quality engineer that can fit into your system? 

Oleg: That’s a $10 million question as this is how much, right?

Yeah. Engineers cost this days. But providing you do have the budget, how can you be sure that this very smart, an experienced developer will do great on your team? Because if it’s not, then it’s a waste of $10 million. As I am manager, I started out by overemphasizing technical and analytical skills.

I was not aware of the critical role communication, empathy, intellectual agility, growth mindset. Play in building great systems and product solutions with every step up in my career, I had to adjust my hiring approach. What really helped me to clarify and tie it all together was a book by Jeff smart, who I met for hiring.

It made me realize that we hire people for a concrete mission. And the first step toward a successful hire is to get in sync with your team about what the real mission for that role. Such clarity and drives understanding of the key behavioral attributes and concrete problem solving experiences. We can then look for in the candidate during the interview process, then the candidates with the right abilities and the track record solving the right problems.

End up coming to the top.

Ryan: Yeah that’s really good. I can completely understand that, but one of the things that captured me on that was this idea that you’re kind of looking at yourself within that process. And as you’re trying to hire people or you’re bringing people on board and thinking about it what are you doing?

Within your own personal leadership to like create connection or to like, have them understand that you’re able to work with them. Are there blind spots that you have to be aware of? What’s that like for you?

Oleg: We all have blind spots and usually that what blocks us and it was a real struggle for me to start feeling uncomfortable at meeting. I don’t know. So. What engineer would want to do that? You don’t get good grades in college for saying you don’t know the. Right yet, one of the key leadership responsibilities is to effectively course correct in the face of new information circumstances.

So I now tell engineers that challenging the status quo is everyone’s responsibility. I try to model their behavior by inviting people to call out gaps in my assumptions and decisions. I give public shoutouts to people who generate new and different ideas. I feel it strengthened my management team and improved their teams in turn.

It also allowed me to scale up and tackle more strategic problems and lead larger teams. 

Ryan: That’s awesome. Yeah, that’s really good. I sometimes think about that dynamic between kind of managing from the top versus the bottom. You mentioned that a few minutes ago and kind of what you have to be able to make it successful and facilitate good communication between you know, a manager and an employee or a leader in the team.

And so I guess, like one of my questions for you is if you’re working so much from a bottom up perspective, Which is great. How do you take and accept bottom up ideas versus just setting the approach from above and kind of demanding everybody follow it. What’s your process on that? 

Oleg: We work as a team, the modern business problems are too complex for any individual to solve well.

I try to create an environment where ideas, thoughts, comments, and critique come from all parties, engineers, product artists, just create data. Folks. I do like to contribute. If I believe I can bring value of fun into the conversation, but my priority is helping the team understand the goals, understand the opportunity, understand the risks.

I want the solution to come from. 

Ryan: Yeah. That makes sense. I like the idea that you’re putting forward of just like understanding, like, and having an understanding between the two. I think a lot of CTOs kind of need to take the reigns fully and maybe don’t empower their team as much. Do you think it’s possible?

The CTO can become a bottleneck. 


That’s really scary thought you have a group of highly paid talent engineers sitting and doing nothing. You never want to be a ball neck. You want to be an accelerator. I actually work once for a CTO that insisted on making every decision himself and the team quickly learned to sit back and relax.

In one of those moments, I realized that the CTO’s job is to coach people, to develop internal frameworks for coming up with the right decision making and making intelligence tradeoffs. CTO’s personal years of experience. Certainly matter. We can anticipate longer term implications, not obvious to engineers.

We should be careful, however, to not let our experience block the autonomy productivity in growth of our. It is hard to resist the impulse to solve the difficult problems ourselves because it’s fast and sometimes better yet. I observe the leaders who coach the teams, how to fish scale much better and have happy teams than those who fish themselves.


Yep. That makes a lot of sense. What and I think when you’re thinking about those qualities that allow for that what do you think are some other ones that make or help make a great CTO? 

Oleg: That’s a tricky question, Ryan. I believe. Great. Good question. Yeah. Yeah. And I believe great CTO is a great problem solver first and different problems require different skills.

a great early stage CTO would have strength in different areas from a CTO leading a thousand people. So if you’re looking for a founder CTO to build a team and technology from scratch, you would want someone who can create structure out of chaos can operate on a true strength and dig into the code to fix things in the fly.

Mistakes cheap and raw and speed. Of the essence. If you’re looking for CTO to lead 50 to a hundred engineers, you probably have real revenue while still looking to grow aggressively. So you will also want your CTO to instill a culture of quality and operational effectiveness while organizing multiple teams for speed and agility.

So understanding team dynamics is a great skill. Technology budget is likely in millions now. So the CTO needs to think in terms of ROI, understand budget, structure, and cost manage. Also at this scale, engineers believe they can have a career in the company. That’s great, but the CTO now needs to be good at growing talent and creating meaningful career paths at the larger team sizes.

Yet technology is now part of massive organizations and the CTO needs to be great at identifying and leveraging the mini strength and capabilities of the overall enterprise. You would want multiple strong and experienced technical leaders in your organization. So the CTO needs to be able to lead and empower other leaders.

The challenge I had really defines the person best suit to lead through it. However, I found that the great CTOs I’ve had privilege to know all had a few things in. There were team players who were great at partnering and complementing. They were curious in always learning. They build a culture where people felt empowered, cared for each other.

And for the company, they were great at identifying and communicating a purpose that inspired and rally troops through ups and downs and instill confidence tore, and they were able to put it all together and deliver.

Ryan: Yeah, that’s a great overview. Really appreciate you taking the time. It’s rare to hear a CTO really synthesize it with such kind of clarity. So, we really appreciate you taking the time to share with us today and giving us some good oversight on some of the qualities that make a great CTO as well.

Some of the experiences you’ve had that have led to it. So, that’s amazing.

Break One

Ryan: I really appreciate how much joy in programming OEG exhibited at such a young age. He built on the passion for developing complex technical architecture early in his career. When he put attention on constructing robust financial systems, the foundational depth of knowledge gleamed in that space opened up a variety of other opportunities, including in the burgeoning game market.

Coming from an artistic background as well. It’s no surprise that OIG found a bridge between programming systems and the creativity of game development throughout his path. As an engineering leader, Ole has shared his insight into the successes and failures that shaped his approach to the CTO position.

He reminds us that understanding empathy, along with the desire to grow. They are often more important than building a great product and just technical skill alone.


Ryan: right. Welcome back everyone to the full stack leader podcast this week, we’re here with Olig. Simonov welcome back. Glad to have you here. And we’re excited to hear your top five 


Ryan very 

Ryan: happy to share. Awesome. So let’s jump right in. What’s tip number one that you have 

Tip One (Driving Change)

Oleg: the tip number 


Oleg: is probably. About driving change. And as liters, we are always expected to drive positive change. We are measured on the impact we make. So we often feel a great deal of pressure to improve reform things, 

Ryan: fix gaps.

Oleg: I however, had in the past made things a little bit more difficult for myself by Russian. Organizational process or assistant changes. And, as, , John Maxwell, so elegantly expressed in his 21 irrefutable laws of leadership people buy into letter first then into the lyric ideas. And by the way, thank you so much for recommending the book.

I really love it. 

Ryan: Yeah, 

Oleg: absolutely. So my advice is move slowly. Earn people’s trust before introducing changes, build trust by learning the business, the existing process, the people help people realize some of their ideas first to build Goodwill and become a part of the team. Then help the team to see the opportunities to do things differently, to do things better.

Make the team, the part of a solution, get them to contribute. Everyone likes to implement their own ideas, putting the team in the driver seat of making and driving the change results in much more durable and 

Ryan: lasting impact. Right. I love that. It, it really is about kind of that group mind share and it, and it makes a lot of sense to, to empower that.

All right. How about tip number two? What do you got? 

Tip Two (Be A Human)

Oleg: Tip number two is super simple. Be a human admit, not knowing something or not be an expert. Admit mistakes, ask for help and advice. Build relationships. We are often forced to make decisions with incomplete information. Sometimes new developments create new opportunities or change the cost benefit equation, making the regional decision, some optimal leaders who free admit mistakes or routinely seek advice and different points of views create a culture that makes it easier to course correct.

And maximize opportunities available to. Ask for, and accept it back with gratitude, ask what you can do differently to support your teams and partners. We all have blind spots. We can eliminate them only if we know about them, build relationships. It’s the most human thing we can do. As engineers, we are thought from early age to form relations with a computer precise, transactional, finite as leaders.

We need to connect emotionally with people, for them to follow us. And it’s much easier to connect with and build a relationship with a normal, imperfect human. So try being one for your team. 

Ryan: Uh, imperfection is kind of the beauty of humanity and like even bringing that to the, uh, applications that we build and the interactions that we have with, with the computers is I, I think kind of some of the sweet spot of, of being a leader, cuz that human quality in all aspects is important.

All right. How about tip number three 

Tip Three (Culture Is Key)

Oleg: for the tip number three. I’d like to share a realization I had after years of building engineering teams for 

Ryan: performance. 

Oleg: And the realization is that the team culture drives the team’s outcomes, view an organizational culture as the norms in the principles, people used to make every decisions, those micro decisions that often fly under the radar shape the marker outcomes that we observe.

By helping people realize how to make decisions best align with the desired outcomes we help. The overall organization consistently produce the outcomes we want as leaders. For instance, you want to reliably achieve high release quality because maintaining a trust with the customer is critical to any successful business show to your team.

How customers engagement, retention. Ation directly relates to the number of cut fixes and customer visible box. Help the team to discover and agree ways to minimize cut fixes, which could be shifting testing, left high units or integration, test coverage, small APRs, et cetera. There are many ways to do it.

The key is for the team to buy into the outcome and feel responsible for two minutes, I use Daniel Pinkston play for building the central pillars of culture purpose. The outcome that brings good. Mastery, the better decisions we all want to make in autonomy, letting people come up with their own solutions for achieving great 


Ryan: That’s awesome. And what about tip number four? What do you got. 

Tip Four (Invest In Improvement) 

Oleg: the tip number four is invest in improving your team’s dynamics teams with great team intelligence outperform. I stumble up in the concept of, uh, team intelligence, cautions, or TQ, trying to get my direct reports to act as multipliers for one. As leaders, we only as good as our teams are TQ measures the discrepancy between the reality and the team members’ expectations for attributes such as mutual trust, shared purpose, psychological safety, information, sharing expectations for autonomy and decision making process amongst others, identifying where such discrepancies exist in fixing them.

Enables the team to engage each other at the deeper level, collaborate more, become more creative and happier. Different team missions could require different configurations of team dynamics. In gaming, we work in a high pace, rapid product innovation, massive cross functional and delivery environment.

There are a lot of decisions that need to be made quickly and. The team dynamics set up that has successful work for us is a self managed team. Whether it’s flat organization, bottom up decision, making a strong sense of ownership, initiative, and team based problem solving. This is incidentally similar to how special forces operate the missions.

And by the way, a fantastic book on role of a leader in Saia set up is, uh, extreme ownership by jock of ING and leaf.

Ryan: That’s a great book. I love it. Okay. That’s amazing. Yeah, I find like the concept oft IQ and, and putting the whole, , organization into, uh, a functioning. Organism in a way, it’s a great, it’s a great approach. And it opens up the ability to think about how the unification of everybody works, which can be really daunting sometimes.

Tip Five (Get A Coach)

Ryan: all right. Let’s jump into tip number five. What do you got? And my, 

Oleg: uh, tip number five is find a coach. Our blind spots define us. We all have them. I, for example, would routinely. Crowd out other opinions in the room for years without realizing I was doing it, it took a coach to pull my peers in direct reports for me to discover it.

It limit my effectiveness for years. As people held back better ideas and undercommunicated risks. Another blind spot. My coach helped me discover and overcome is not valuing no investing enough in building relationships. I thought I did, uh, but having a very strong focus on realizing my own vision, I did not fully appreciate other people’s needs and aspirations.

My coach reminded me for years to keep thinking about until I became better at mentors. Great. My mentors taught me incredible new things, but we probably learned as much from book or block coaches. On the other hand are trained on identifying one blind spot and helping us understand and internalize them.

Mic coach helped me see things about myself in change in ways I wouldn’t be able to other.

Ryan: Such a great final tip. And it is like thinking about how to do all of these things on a control level. We can read the books, we can understand it is okay to like take it all in ourselves, but having a little bit of guidance to actually put them into action or to think about, or to challenge us.

It, it’s a powerful thing that a coach can.

Books Section 

Ryan: All right. That’s amazing. Thank you. I was wondering, know you and I have had this conversation in the past, but I know you’re a fan of books and learning from them as as kind of an extra tip. What are some some titles that really impacted or influenced you as a leader that you’d like to share 


Oleg: Although great books brought about many key moments in my leadership career. I already mentioned who a method for hiring by George smart, which for me went a long way toward minimizing the pay, the pain of that hires. I want to add a few more boxes list. Drive by Daniel pink, which reset how I think about creating high performance environment and culture by dysfunctions of a team by Patrick , which opened my eyes to the incredibly powerful concept of team dynamics.

And resulted in multiple improvements in the contribution from my direct reports, as well as their personal happiness and satisfaction. Good strategy, best strategy by research remote that finally created clarity for me about what the latest. Jobs really should be identifying growth opportunities.

Often beyond the horizon, eliminating risks, communicating both to the organization and then empowering people to successfully reach those opportunities. This titles were real step functions in my career, and I hope they could become the same for your listen. 

Ryan: Yeah, there’s a few titles on there that I don’t know that I’m look forward to going and reading myself.

So thank you for sharing that. Well, we really appreciate you taking the time today and going through all of those amazing tips with us and sharing those book titles. It’s. Been awesome to have you here. Your feedback and your insight is invaluable and a pleasure to talking to you. 

Oleg: my absolute pleasure to chatting with you and I’m looking forward to our next conversation. 

Ryan: Oftentimes in the role of a CTO decisions come to a bottleneck. If you are a leader that’s relying too heavily on your own intuition and not on the collective inside of your team, then you can quickly paint yourself into a corner with little or no support. OIG sheds light on the intrinsic benefit of hiring better teams to keep expanding support.

He confirms for us that surrounding yourself with people you can trust to get the job done is a critical play in any leadership handbook. But especially one in a collaborative field like tech and games throughout this interview, I was reminded that CTOs truly benefit from connecting deeply with their teammates.

And when they bring a human quality to a field full of automation, everyone expands their overall team intelligence.