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Podcast Episode 17: You donā€™t get the corner officeā€¦You TAKE it: Brittā€™s Leadership Journey in iGaming

Mar 05, 2025

In this episode of iGaming Leader, Leo sits down with Britt Boeskov, an experienced executive in iGaming and digital transformation. 

Britt shares her journey from starting as a management trainee to becoming a C-level leader in a fast-paced and highly regulated industry. The conversation explores career progression, leadership challenges, the power of building strong professional relationships, and the impact of AI and personalization in the gaming industry. Offering valuable insights, Britt provides actionable advice for professionals looking to step up in their careers and lead with confidence.

Guest Bio

With 20 years of experience in the i-gaming industry, Britt is a board member and advisor who specialises in strategy, customer experience, and digital transformation. 

After a long C-level run with Kindred Group, she now serves on the boards of Better Collective, Mindway AI, GAMING1 Group, MAG Interactive and Racecourse Media Group; and provides tailored support through 4see Advice.

Key Topics Discussed

02:00 – Britt’s journey to C-level executive

04:40 – Transitioning to an established industry leader

07:00 – Stepping into leadership: Taking ownership and leading with confidence

09:50 – Sometimes you just have to take the corner office

11:20 – You don’t have to do it all yourself

16:00 – The importance of delegation and trusting your team

21:20 – Finding purpose in leadership and the role of responsible gaming

24:50 – The evolution of player engagement and the role of AI in gaming

29:30 – Britt’s advice for leveling up your career

Memorable Quotes

"You don't get the corner office. You take the corner office."
"High performers balance humility and curiosity with ambition and persistence."
"The one lasting thing you build in this industry is your relationships—hold on to them."

Important Links

 

Full Transcript 

 

Click to Expand Full Transcript

 

Leo Judkins: Brit. I am so glad that you're here on the iGaming Leader. 

I've been wanting to talk to you after having been recommended to get you on the podcast. I'm really excited to have you here and talk about your really long history in iGaming and the progress that you've made.

But before we even start, let me just say welcome to the iGaming Leader.

Britt Boeskov: Thank you so much, Leo. I'm really glad to be here and thank you for contacting me. It's great to have an opportunity to discuss with you.

Leo Judkins: [00:02:00] Back in 2005. You started in business development and management trainee position. I saw it on LinkedIn. And then you move all the way up to chief experience officer in that whole journey, Brit, what was some of the biggest highlights that you've had?

Britt Boeskov: First of all, I have to say one highlight was to even find the iGaming industry. I mean, I was, I was meant to go, more in the direction of academic research at Copenhagen business school. 

That was the plan, but I thought it would be nice to get some work experience and struggle to find a place where I would be allowed to use any kind of leadership theories of management theories, in practice, because I didn't have any experience. 

And this management trainee position came up. I actually thought it was an unpaid internship. And I called up the guys at Unibet on that basis going like, I might be able to do that, but I can't do it for a whole year because I can't afford that. And they were like, no, no, this is a job.

[00:03:00] This is a job where you get paid. To move to London and support the management team of this up and coming company, in the iGaming business. I was like, wow, this is amazing. 

That happened exactly at the time where Unibet's Danish country manager had been arrested by the police in Denmark because there were obviously concerns or disputes around what the law was at the time. And Unibet was very forefront about believing in the European free trade agreements

And obviously went full marketing in Denmark with the brand. So there were some skirmishes there. And I had, that was one of my first questions, to talk to the chief legal officer. And the CFO of Unibet at that time, we had a lovely discussion about, you know, risks and differences of opinion around regulatory things.

And little did I know that was something I was going to deal with. but I started out as a management trainee and it was a highlight to join a company that experienced epic growth. 

[00:04:00] Because to grow that fast and not just financial growth, but just like the mental maturity that first, Tony Johansson was He told me this in the interview.

He's like, you might not know this industry, but you'll never get a chance to be on a roller coaster like this. This is. So much fun. And the growth is going to sustain all your needs for personal growth and development as well. And I was, it was a good sell.

Leo Judkins: I love it. That is amazing. And it's, it's, it's so true, isn't it? It's such a highly volatile industry. And in that ride with Unibet later on Kindred, like how did you, yeah, what, what was some, what's, what's some of your proudest moments there?

Britt Boeskov: There was so many, I mean, from seeing the Univet logo go up at the Danish national stadium, that was about 12 years after the said incident with the country manager being arrested, that journey into legitimacy. From being like an outcast pioneer challenger brand to becoming an insider, part of society, part of the dialogue in society. 

[00:05:00] I think that journey has given me many proud moments because it's necessary to move that way. It's also given me gray hairs, frankly. It's really a lot to adapt to, to all those markets. But another proud moment for me, I think was when I realized that I wanted to step into leadership. I had a situation where I was a team leader of a small team of five people and my manager had to move back to his native country very quickly and left within days.

And I was asked to look after the other departments of this rather large organization. And I didn't know what to do because how do you assert yourself as a very young woman, when the other five or so managers were guys in their mid forties. 

 And I sort of edged closer to my boss's office and ended up  sort of. Sitting a little bit outside, a little bit inside, trying to do a few meetings there. And my colleague, Mattia Stets, who is now the CEO at, Rush Street Interactive, he said to me, like, you don't get the corner office. You take the corner office. And so after a few weeks, I just walked in there and sat down at the chair.

And, sure enough, , by just. Taking that on and telling, our CEO, like, you know, I see this as things are not working. I need to get this running. Give me the keys, please. And, and he said, yes. And that was my entry into, to the world of, leading people and having a greater responsibility in the company.

Leo Judkins: Leading up to the moment, what did that look like and how did you feel? Because I can totally imagine, you've got it in your head, right? You're going to say this thing of, all right, I see this opportunity and I want to step up. But there's all these thoughts racing through it.

So take me to that moment, please.

Britt Boeskov: [00:07:00] I don't think I felt conflicted about it. I saw some actual problems that needed to get solved and, and people that needed to feel assured and needed guidance, and I just felt that that was a very practical thing to do. 

And it was a bit the same way I got involved in a lot of other things, but sort of seeing that this isn't working, you know, our tech team isn't working or the business development isn't working and just getting involved.

I didn't feel anything other than a sense of duty towards solving the problems. And, also, of course, a sense of gratitude that I had colleagues who would definitely support me. I knew that. That was a great precondition. I knew I had a network of peers that would support me and, and guide me.

Leo Judkins: Such an important thing, right? Your environment really dictates your like your whole trajectory is such an important, important piece of it. And you mentioned it when we spoke before as well. And you were talking about how important it is, you know, to have a bit of luck, to have the right timing, to have the right people.

[00:08:00] And this is, Although I completely agree that that is true, I also often feel that it takes, takes some of the shine away from high achievers, like you said, you know, who have progressed and have sustained performance and have gone through the challenges that were needed to, to get to where you are.

Right. So how do you feel about that? Talk, tell me a little bit more about that, 

Britt Boeskov: Timing is very important. Of course, there are some conditions that I continue to see in people who have sustained performance and it's very often, it's about balancing things. 

So on the one side, I see high performers being extremely humble, curious, interested in other people, showing lots of empathy and sort of soft skills.

And on the other side, I also see high performance, you know, being ambitious. Being hungry, being stubborn, qualities that are not always described as positive ones, but it's when the two of them can sit together, that people can continue to, to sustain performance. If they have too much of one or the other, I think it becomes difficult.

[00:09:00] So, I think in my personal development, it's not one or the other, but it's a combination of those factors. And then timing. It is really important. It's not always that something opens up for you in that company where you are. 

And, that's always why I also say to people that, you know, you need to forge your own way and. 

Maybe your right path is to go out and start your own company or work for someone else, just because a company is really good, like Kindred Group was an amazing place to, to grow up as a leader, but it didn't mean that it was right for everyone. And so you got to respect that and not feel tied down just to a brand.

Leo Judkins: Yeah. And that, that makes so much sense. But sometimes you just gotta take the corner office. Right? That's what you gotta do,

Britt Boeskov: I would say then, once I did that, I also realized what came with that. And that was, you know, like jumping into the abyss.

[00:10:00] I felt like I was in the very, very deep waters. And just two days after I actually did this and felt very proud of myself, one of the managers who would report to me quit and went to an editor and asked a range of people to go with him. 

So, I was stuck and I was, I was scared there because I thought, you know, What if I've gone beyond my post and now I'm ruining things and, and it's going to be a really bad thing for the company and, oh my God. 

But I was very fortunate that not only did I have good peers, I had contact with one of the board members at Unibet who also supported various processes in the business and he said, Oh, this sounds bad. Let's go and fix it together. 

And so we went on a mission to fix this department and find a new person. Just having someone who was more senior, who didn't tell me what to do, but who was there to reflect and support was something that, helped me immensely.

[00:11:00] And I would always say to people, don't shy away from getting help.

Look for people who've done the stuff that you are getting into and see if they can give you some advice.

Leo Judkins: Yeah. That's such great advice because you don't have to do it all yourself. We often feel that we have to, right? That we have to figure it out, or that we even have to have the answers already. Which is just not true. 

Tell me a little bit about how you felt in that moment when that manager quits and took other people away, like I'm sure emotionally that must've been so difficult for you for, for a period of 

Britt Boeskov: Question yourself and say, Oh, I probably went ahead of myself and, ahead of my rank and I probably don't have the skills to do this. So

there's definitely the whole imposter syndrome in, in very real time. And also watching the teams who are then suffering from that lack of clarity and them sitting there going like, well, what are we going to do?

[00:12:00] There's no one here. in charge. On the one hand feeling the concern, but also the, still the, the sense of duty to say, okay, This is my thing. I need to do something about it. 

And I think that was,Leo Judkinsthat was at the end. You just need to have that little extra wish for fixing the problem and making that more important than your concerns and your worries and your insecurities.

Leo Judkins: Yeah, that makes a lot of sense. What happens to a lot of people in those type of situations, though, because of that sense of loyalty and ambition and curiosity and empathy, like you said, which really underlines high performance for a lot of people, is that they almost also forgo their own well being, right?

They start compromising on their own personal life just to make sure that they get things back in order. that happened to you? And if so, how did that show up for you?

Britt Boeskov: Not really. I don't know. I'm a fairly balanced person and I know that I need to look after myself, but, but there have been, you know, times of worry and times of concern. 

[00:13:00] And I think the kind of energy that eats at you, doesn't have to do with the real problem, but the fact that you define the problem as so existential and so, you know, terrible.

And the truth is that most of the work we do, no one's going to die if we make a mistake. And that's very different from other people's jobs. , but you can hurt people if you make mistakes. And so of course you need to take a judgment and you do that better if you've had a good night's sleep and some fresh air. 

So I try to get that in no matter what. I think I've managed most of the time. I've been more pressured at other times in my career, for example, when my kids were very small. And I would say, especially if you're in a situation in your life where you can't sleep,

Someone's keeping you up all night, that really impairs your, your sort of resilience. But definitely, remembering to, to take time out for yourself is important.

Leo Judkins: [00:14:00] Yeah. As a parent myself, I'm also super curious how you did it. Like what, what were some of the things that really helped you maintain that balance through those early years with kids, right? When they keep you up, but also just being present at home when stress from work is maybe still on your mind, like how did you deal with some of those things?

Britt Boeskov: We lived in London at the time and the UK compared to Scandinavia, there's a whole different paradigm for what you can do. Like, for example, it's okay to have a nanny, 

which was. In Denmark, it's like, no, you're a bad person. 

So glad I lived in the UK because that did allow me to professionally outsource some caregiver parts that were really important to my kids. The people who supported them and I came home fairly late. 

That's just the truth. And I traveled as well while they were very young. So I'm certainly not getting the gold star mom thing. But I, I think I felt there was enough of a balance and enough of an acceptable situation for everyone that I was very happy with that. But what I was able to do early in my career was to establish a leadership paradigm that had to do with empowering other people.

[00:15:00] And that helps a lot. And it doesn't matter what level you're at. If you're a team leader or a CEO, I think the moment you believe that the people who work with you are for you. can handle stuff. You can, you can breathe in a totally different way.

If you believe you always have to be on top of everything and always have to ask questions and that everything's probably going to fall to pieces, then you get no peace of mind.

So I was in a very fortunate situation to have C level roles with competent, highly competent And, lovely, senior managers who reported to me. And not only were they able to manage their own areas, they were also enabled to contribute to the company's development

beyond their own department. And that, that meant everything for me to get them to that point. 

Leo Judkins: [00:16:00] A big part of that is also you trusting your team. Right. That's kind of what you highlighted there earlier, which is one of the mistakes. So many people, I'm going to say more than half of the leaders and managers make, which is they become their own bottlenecks, right?

Because they can do it faster or better. And then they become the crutch to the tip team doesn't solve things, but you've decided that you're going to trust your team. Of course, there were good people there, but you decided to, to give that trust away and almost, and, and then also show up for them in, in cases where perhaps that didn't go the right way.

So. So did you learn that early on? How did that how did that form itself? That kind of leadership style?

Britt Boeskov: You can only learn that by doing right.

And I had some lovely people reporting to me, also people who were more senior and older than me. but one of the first people I recruited from outside the company to work in a senior position for me was, Daniel Esla, whobecame head of Poker at the time. 

[00:17:00] And when I interviewed him, I asked him, what do you want to do five years from now? You know, the classic. And he said, I would like to have it. I was a CEO at the time, for the company and, and I thought that was great. 

And I was like, that's really great. I'm, I'm absolutely sure you can make it. And I'm also fairly sure that I can find something else to do. So, let's work towards that. And I think that became a starting shot for me to start sharing a lot of stuff with my direct reports

that didn't just have to do with their business, but has to do with the, why, why did we decide on the budget like that? Why did we not go into that market? 

Why did we decide on a strategy that held back on bonuses here and there? Why did we go for this regulatory regime, but not that one? Stuff that maybe wasn't central to their job, but it made them able to grow into people who could handle the business and who could handle their peer group in a completely different way.

[00:18:00] And so if I've done one good thing, I've given a lot of information to people and trusted them with the, with the bigger picture. And that started early on because I saw that. Quite a few of them would at some point move into sea level.

And I think about three or four of the people who reported to me eventually did move into sea level and therefore needed that information and that frame of mind, and I was just happy to have that. It helped me so much.

Leo Judkins: Yeah, that's amazing. It's such a big part. You mentioned it, when we spoke before as well, where you talked about that, just being able to give the why and, and, and, or also understanding your why in, whatever role you're in and understanding your purpose and having purpose in your role is really important.

So, Tell me a little bit more about that Brit. Where did that first show up for you? And, and how did, when did you realize that that was such an important part of, of feeling, you know, being motivated and engaged in your role?

Britt Boeskov:[00:19:00] I think it happened when, especially around the time where Unibet Group changed to Kindred Group, because, for a long time, the why was so we can become bigger, so we

can become faster, so I can get a new job and, and, and, you know, have more insights and more opportunities. So the questions were very, growth oriented.

But then around the time where there was a very serious debate in our core markets about the social license for a gambling company, like why should there even be gambling? Is it, does it do anything good? 

The purpose started to seep in and we got a really good head of communications who really challenged us as a leadership team to talk about these things. And, and I could feel that. 

[00:20:00] From talking about financial targets. We started talking about what the group wanted to be in the world. And, and that was, that was a great process. it of course came down to defining an actual purpose. and it also came down to. Getting people more involved in being honest about some of the backlashes that gambling has.

And that of course  led to Kindred's investment in all sorts of, responsible gambling measures and in a debate, a dialogue with lots of people around this, even people who really did not like gambling. Kindred or Unibet, and that's a really helpful thing to debate with people who are in your opposition. 

So that, that sense of purpose and that sense of finding your way in the world was really something I was happy to contribute to,

Leo Judkins: [00:21:00] Yeah, it makes it such a game changer. I think even with delegation and with leadership, right? We often talk about it in our program. We talk about almost as an inverse pyramid, but we talk about why, what and how, you know, for delegation. 

And I think it's one of these big pieces that Often people just miss, you know, if you don't talk about the why, if you don't help people identify the purpose of what they're doing and how they're actually contributing to the bigger whole of either the business or just what the world in general, it just becomes a salaried role, right?

Britt Boeskov: It also becomes a drag on people's emotional resources because they feel like they're fighting against Some unknown. 

I mean, the entire time I've been working, the companies I've worked for have been growing and there has been growing pain, meaning that there's been change, there's been limited resources.

[00:22:00] There's been priorities that couldn't be met. There's been stress about timelines and deadlines. And if people don't see the wider picture, those become the thing that. It just eats up everyone's time and resources and you've got to be careful with that.

Leo Judkins: Yep. Makes a lot of sense. when we spoke before, you mentioned, You were talking about perception and, you're talking about how, you know, you moving from kind of the sea level to now more advisory roles and non executive roles. You talked about perception there. Can you tell me a little bit more about what inspired that move?

Kind of moving into where you are today? and perhaps some of the challenges that you faced with that.

Britt Boeskov: Absolutely. Yeah, I would say it has been one of my big challenges because, I'm very, I'm sort of personally very wedded to the present and I like things to just continue and I'm like, Oh, I have a big job. That's what I have to do. and I would say everything about working for Kindred Group was wonderful in terms of the credibility and the sort of ease of connecting with people.

[00:23:00] And, you know, everyone knew where you were from and, and all of that. So this break to being sort of just a, A person who does work for various groups instead is, it's very, very different from an identity basis. And I would say it didn't come as an inspiration. 

It came like more of a life work balance car crash and, and and as it does for most people, like it's, it's, it's really, you know, a nicely managed process, but I had moved back to Denmark, gotten a new full time job.

I was very excited. And then, my, my time commitment to my family suddenly rose, cause I have elderly parents and young kids and the setup is totally different in Denmark. And I was like, what am I doing? I cannot make this work out. I have to quit. And it was not a fantastic experience.

[00:24:00] And I would say, I was worried that I would sort of burn a lot of bridges, but I do everything I can to not do that. And, and I think that's worked. and then of course the board roles came in on the side. 

And I started wondering, is that something I can do a full time instead? So I fairly quickly built up my portfolio of five companies that I, where I serve on the board, one of which I am now the chair of a small company from all who's called midway.

Very exciting one in the responsible gambling space. so I'm very pleased to be able to contribute in this completely different way, which is much more from a helicopter perspective. I don't get to do my operational stuff that I love. I don't get to have staff, which I sometimes miss. 

[00:25:00] But in return, I get to contribute to the growth and transformation of those companies, while also having some space for my family life. And, right now that's a great balance, but it is a trade off. And, I sometimes wake up thinking I'm a bit like a 65 year old man, should that's, that's kind of my work life. but, I hope that I can contribute in a, in a good way that helps each of these companies and, and continue to learn myself. And so far, so good.

Leo Judkins: I love what you guys are doing with MindWay. It's amazing. 

I had a question from one of the people in our mastermind, Jordan Erasmus. He's the CEO of Retention Studio. And he asked, with your experience in strategy, customer experience, digital transformation, What major shifts have you seen in player engagement over the past decade?

[00:26:00] And how do you think operators should adapt to changing player expectations, particularly with the rise of AI and personalization? 

Britt Boeskov: It's a really good question. It changes all the time. I would say my work with customer experience is most visual on my CV from the three years that I was, but it started a long time before with the net promoter score, that was actually a fantastic tool to find out if people would recommend you. And a lot of people in gambling, discarded that saying, Oh, no one wants to recommend gambling anyway.

So we can't use that instead of saying, hang on, we're working for an industry. No one wants to recommend it, maybe we need to do something about it. So I think that journey of actually working with the customer's experience and asking them, what is it you want and what is it you want now and differentiating that it will never stop.

[00:27:00] And I've seen big changes from. gambling being online gambling, being extremely niche and something that people did to outwit the operators. I mean, it was a sport in 2004 and five in Denmark to try and outdo the casinos on bonuses, right? It was a sport too. 

Then win in poker and get sent to Las Vegas to play a big tournament. There was like, there was an opposition from sports bettors, you know, hated, you hated your bookie because they were the bad ones and you were the good one. You knew more than them. So the tension between customers and, and operators was very significant. And to move that into a situation where you have trust and wellbeing and, and, and, and entertainment as the main. parameters has been a really big shift. 

[00:28:00] I think it will continue, but I would say, the reduction in, attention span is probably one of the most, difficult things to grabble with, ideally you would want people to stick around, read your content, see what you have to offer, but we won't get that. 

What can we find that makes the experience integrated and, Still waiting for that perfect personalization from operators, still waiting for that flawless integration into new channels. so, I think there's lots to do.

But customers, don't ask me. That's an important message.

Leo Judkins: Yeah, I love that. I think often in gaming, we're just a little bit behind other industries. You know, we kind of need to catch up here and there. And I think that's okay. Are there any potential market shakers that you've seen that really caught your attention when it comes to those kinds of things?

Maybe personalization or AI?

Britt Boeskov:[00:29:00] It's hard to say, but I think you just need to look at the difficult ones where there's a real battle for, for people. So whether that's finance or sort of, B2C brands in general, I think that a lot of them are working hard with storytelling. 

I think, I also am a board member of a gaming studio, small mobile games and the amount of pride and, and, sort of innovation they put into making games that really. Work on people's, behavioral, psychology to keep them in there, to keep them engaged. They do so much more than we do. And, I think we could really learn from that.

Leo Judkins: Yeah. I love that. And, and, and how does that sit with, with mind way ai then Brit? like how do you see AI and personalization affecting player protection and, and, and RG in general?

Britt Boeskov: [00:30:00] I'm extremely hopeful about what AI will do for our business because I see MindWay was an early example of just how very few people can make a global product that can have a huge impact really fast. And yes, that's together with the biggest operators in partnership. 

But it's still mind blowing that you can take neuroscience or any kind of science and bottle it into an algorithm. so I have huge hopes for more bright people finding a connection, ideally between a science space, and the technology and bottling something that we need, for the industry. 

To be faster, better, and more interesting. It doesn't just have to be in the RG field, it can be anywhere, but to build the responsible gaming algorithms into everything we do is obviously next level, and we want to see that shift. to have the good effect, but it could equally be an innovation on marketing anywhere else. I'm just, I'm really excited of what, what can be done.

Leo Judkins: [00:31:00] Love it. really fantastic. I've, I've got one more last question for you, Bri, if that's okay. Um. I've been super impressed just talking to you before and then looking at your LinkedIn and then doing some research. I've been so impressed with all of the progress that you've made and, you know, the projects that you've led and, and, and your overall mindset.

And even this conversation is amazing. You're very, you're a very inspirational person. I'd love to hear from you for somebody that is maybe also, I don't know, mid to senior level and is looking to progress in their career. Doesn't just want to depend on luck and timing, but really wants to hone their skills and their behaviors.

What would be some of the best advice you could give them, to make further progress in their career?

Britt Boeskov: Yeah. I think that all the people who want to do that, they look very much at what they want to achieve. Maybe it's to launch that product. Or, get that marketing campaign out or enter that market or even, you know, start their own business or something. 

[00:32:00] And so you link your achievements to, to some, those kinds of items. And I would say, stop doing that today and realize those are all exciting projects, but no matter what you produce in that space, whether it's the best marketing campaign, best product, best software, whatever. Someone will supersede that at some point, it won't be your finite contribution and it won't be your finite result.

You won't get to hold onto that because of the growth and the innovation in the industry, you'll need to let go of that at some point and see someone else doing it even better, and that'll kill you if you don't accept that. 

[00:33:00] And then I will say the one lasting thing you will build that you can always take with you will be your relationships. with the people that you meet in this business, in this fantastically, colorful and diverse business, build those relationships. 

Also people you disagree with, because you are very likely to meet them again somewhere. And you might as well have. Brilliant working relationships with a ton of people, even those you disagree with, that will last.

And it means that when you meet them 20 years later, you give them a big bear hug and it'll be fantastic. And you'll feel like you've achieved something that you can hold on to forever. Even if the company you used to work for is no longer there. Even if. what you did has long been forgotten. 

So hold on to the relationships, and make sure you build those also with people who have tons of knowledge, and can help you with young people who are coming up through the system and, and with your peers.

Leo Judkins: Amazing. Thank you very much, Brits. It's been so fantastic talking to you and thank you for sharing, sharing all of that. It's been fantastic. Thank you.

Britt Boeskov: [00:34:00] Lovely. And thank you, Leo.

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