In this new episode of the Mastering CS podcast, Irina Cismas, Custify’s Head of Marketing, sits down with Glenn Debattista, COO at BetStarters.
Glenn shares how a sportsbook trading background shaped his leadership style, what it takes to scale a B2B organization, how he hires for attitude over ego, and why community and trust ultimately power growth.
Let’s dive into Glenn’s path and the lessons he’s learned along the way.
What You’ll Learn
- How a trading & risk-management mindset translates to CS leadership
- Building and scaling lean, high-performing B2B teams
- Balancing customer partnership with realistic timelines (and saying “no”)
- Common scale-up challenges and how to mitigate them
- Practical advice for stepping into senior CS/COO roles in iGaming
Key insights and takeaways for CSMs & CS leaders
Trader mindset → better leadership.
Glenn’s foundation in trading and risk management still informs how he builds teams, aligns functions, and makes decisions under pressure.
Hire for humility and learning, not ego.
He avoids “primadonnas.” Curiosity, openness to learn, and team fit beat pure skill if the attitude isn’t right.
Scale is a puzzle, not a sprint.
Growth requires placing the right people in the right roles at the right time—accepting that some pieces won’t fit, and that’s ok.
AI is already an ally.
Teams need to adapt and use AI to improve efficiency; being AI-ready is now a hiring advantage.
Operational backbone matters.
In a B2B setup, account managers act as the client’s voice, translating needs into tickets (e.g., Jira) and bridging customers with technical teams.
Podcast transcript
Irina (0:02)
Mastering CS and Digital Insights, the podcast where we deep dive into the world of customer success with industry leaders. I’m your host, Irina Cismas, and today’s guest is Glenn Dybakista, CEO at Betstarters. Glenn, welcome.
Thanks for joining us.
Glenn (0:19)
Thank you, Irina, for inviting me. It’s a pleasure to be on this podcast with you.
Early Career and the iGaming Journey
Irina (0:24)
How did you first land in iGaming and what kept you hooked?
Glenn (0:29)
Oh, that was a very long time ago, and it was over 20 years ago, so we’re talking about ancient history here. Yeah, well, basically, the story of iGaming about over 20 years ago. There was this idea to bring iGaming to Malta, and it brought with it lots of new roles and jobs in this industry, especially in Malta, so it was something quite new and fascinating at the same time.
It also brought with it lots of new opportunities for us, and me, myself, I used to enjoy betting a bit, and I love sports, so joining an iGaming company, as I always like to say, was a match made in heaven. In fact, my first role was that of a trader in the sportsbook where we used to, you know, create odds and make sure no risk managed the company’s bets that come through from the customers, and it was interesting because, we get to speak and talk about sports all day long during work, whereas before in a normal job, maybe that would be frowned upon.
Lessons from Trading and Leadership Growth
Irina (1:46)
You mentioned training for one of your first roles, and I know that you’ve changed a lot along your career in those 20 years that you are mentioning. Any role that still shapes how you see things today?
Glenn (2:06)
Absolutely. I’m still at heart, still a trader, I believe, because I’m always, especially with meds., was always my favorite subject at school, so the probabilities and managing risk has always been a part of me, no matter what roles I did after that. In fact, I spent 15 years, you know, working in training departments, and over the past five years, I moved on more specifically on product, and then eventually as an operations CEO role. I believe that was a normal transition, and that in fact helped me, the fact that I knew also what granular aspects of the trading department, it helped me better align with different departments and helped me build teams, because obviously in the trade departments, I managed to move up forward as well in the different roles that were available over there.
So yes, I do strongly believe that the trading aspect and the risk management aspect did help a lot in shaping my present and also future.
Irina (3:18)
And if you apply the same question, but when it comes to leadership, which move changed you the most as a leader?
Glenn (3:30)
Well, inside the trade department, as I said, I spent 15 years there, so I would say, you know, I managed to climb up the steps over the years. In fact, in my first role, I became a team leader of the traders, and that’s where sort of I started realizing, okay, I have a knack for this thing. So I really enjoyed being there, planning, building teams, and shaping up the department accordingly.
So that definitely helped me also in this role of eventually of CEO, because before that, obviously, I was also in different roles like head of and managing roles, and so on and so forth. I strongly believe that the shift that started basically by me having more responsibility and having more influence in the department I was in.
Scaling and Building the Right Team
Irina (4:31)
Let’s speak about the Betstarters setup and about your current team. How is your current team set up?
Glenn (4:42)
“We’re actually in an interesting phase right now. We’re in the phase where we’re scaling up. So obviously, that means more resources are needed in the company.
It’s like a jigsaw puzzle, where basically you need to find the right people for the right roles for the right tasks. And so you need to fit them all in one good jigsaw puzzle. There will be some pieces that might not fit properly. And there might be some pieces which, slide in really nicely into the whole organizational chart. “
In fact, right now, I would say that we’re in a lean, right, structure, but it’s also strong. It has a strong basis. And on top of it, we’re building on with these roles. We’re always on the lookout, in fact. So if anyone wants to join the starters, just one click away from applying with us.
Irina (5:40)
What roles are you trying to fill in as they speak?
Glenn (5:44)
Well, we have different roles. And to be fair, the roles, we look at the people. I like to, in fact, when I interview people, I like to look not only at their skills, but especially at their attitude, at the way, they might fit within the company, because it’s like in a football team you might have the best footballer in the world, and you might sign him, but if he does not fit in the team, it could be just more destructive than actually helpful for the team. So we need to find the right people with the right attitude and the right mindset.
Irina (6:27)
Speaking about your process, hiring process, what’s one trait that you don’t compromise over in the recruitment process? What’s the most important? Is it the attitude towards the job, the implications? What are you searching for?
Glenn (6:48)
Yes, well, I’m definitely not searching for primadonnas or people who think that they never, that they know everything and just want to keep on, think they just basically reached the top, and so on and so forth. I feel that even us, anyone in this industry who has a lot of experience and knowledge, I mean, you never stop learning. And this is such a fast-paced industry that you need to be very humble and always willing to learn, even from people who might not be in a lower position than yourself.
Of course, I mean, you can’t know everything, you cannot expect to know everything, and you need to be willing to learn more. So definitely the trait I’m always looking for is people who are open to learn and willing to accept the fact that they don’t know everything.
Technology, Operations, and Customer Relationships
Irina (8:43)
I’m curious, you mentioned earlier that one of the things that you are trying to do as we speak, one of the challenges and opportunities in the same time is scaling the team and trying to fill in the puzzle or fill in the blanks and you are recruiting or searching for the right people at the right time with the right attitude and the right skill set. Is hiring the only way you are thinking of overcoming this challenge or does technology play a role in the scaling process?
Glenn (9:25)
Technology, I think, over the past two years has been playing a huge role, especially with AI. I know where you are going with that. I knew that, right?
“So, yes, AI has become extremely important ally in, I think, every situation. Every company and it’s very important for management but also for the employees themselves to learn how to deal with it, and survive with it and adapt to it because it’s obviously, it’s still in its infancy and this infancy stage is still a very, very powerful tool to have. “
So, having the right people is important and part of having the right people is people who actually are able to adapt themselves to be able to help the company by also using these tools and not just their experience and knowledge.
Building Trust and Long-Term Partnerships
Irina (14:16)
As a CEO, how do you balance the operational part of things and the customers? How do you try to, how do you serve equally best words operational and customers?
Glenn (14:31)
Yeah, balance. Balance is a very important aspect, right? I mean, you build trust, you need to build trust with the client. They need to trust you, they need to know that you’re not there once you sign the contract with them you just disappear. You need to be there present for them. You need to build sort of, helping yourself with networking or having a good relationship with them, with making sure that they feel like, that they are partners and not clients.
That’s an important thing because some, maybe some companies, they might treat clients just as clients, as a number. Whereas, at the end of the day, they are your partners because their success means your success. So, it is very important, it is imperative that they feel that they have your trust, that they can trust you back and that they, that you can rely on each other.
Challenges, Failures, and Lessons Learned
Irina (19:48)
We always talk about the good sides when it comes to our customers, but now I want to ask about an experiment that didn’t go as planned or a decision or something that you agreed with a customer and didn’t go as expected. And how did you turn it around or what happened? What was the outcome of it?
Glenn (20:15)
Well, this obviously happens in every company I’ve worked for, obviously. There’s always, I mean, there is no, like, 100% one size fits all that works for everyone. So, you need to learn to adapt accordingly.
And sometimes, yes, things might not go the right way. So, you need to make sure that you are always prepared for any eventuality. And I think that is the only and best way to deal with failure, right? You need to be prepared for any eventuality. Sometimes there’s something that, unexpected might happen. And in that case, you take it in stride and you use it as a teaching for future lessons, even ourselves, I believe.
I mean, this is something I always tell everyone. I mean, if someone never made a mistake, they’re not going to learn anything from life or from these roles in iGaming or any other role in the industry. And I believe that all the people who are making C level or made it, at the top of their career, they all failed eventually, more than once.
So, you cannot really, I mean, that’s the only way how you can learn and improve yourself. Same things for companies. And like ourselves, once we see that a failure occurs, of course, we’re going to be, we’re going to learn and understand what we did wrong, do the introspective, and then take it in stride and learn as much as possible out of this situation.
Networking, Community, and Personal Branding
Irina (21:58)
You’ve been involved in projects like building communities and you’ve developed iGaming professionals, MIG. What did you learn from those type of projects and how did they impact you? What does it take to build a community?
Glenn (22:16)
Yes. Well, first of all, I believe that in this industry, especially networking is one of the most important aspects in the sense that, either going to conferences or LinkedIn, which is a great tool, it’s very important to be active in these scenarios.
Why? Because it’s all about personal branding. Once, improve your personal branding, then this will spread on even to your company.
What I mean is that, for example, a lot of times, people know me from my personal branding, but thanks to that, they will know the company I work for and what we do and that will generate also leads for our company in order to get more clients.
I believe that, networking is a big, big, big value. So, I wanted to create also these communities on purpose so that we can all become closer and, having a close-knit industry, especially here in Malta, which is a big, huge hub for the gaming industry, and this way,we can all help each other out. It’s so easy, nowadays, if someone comes to ask me, I’m looking for someone or a company who does this, it’s easy to sort of, yes, I know this person, I know this company, so let me introduce him. It’s part of being a community and helping each other out.
The Future of Customer Success and Leadership Advice
Irina (23:58)
What do you think will be the biggest shift in the way we serve customers?
Glenn (24:06)
Oh, well, as I think we touched it before, and it’s definitely going to be AI. AI is the present and the future. It’s becoming so important for, even just daily things, right, not just for work, but especially for work.
It’s going to be a huge, huge platform on which to build future businesses and improve efficiency, operations. In fact, I believe it’s similar to the trend in the 70s, the early 80s, you know, when computers came into play. And back then, people, first of all, were afraid that they would be replaced by computers, but in reality, people just needed to adapt and learn how to use them to be able to help themselves work better and be better, employees and better reach the goals that they have set for themselves and for their own company.
Irina (25:10)
What’s your advice for someone stepping into a senior CS or COO role in iGaming?
Glenn (25:21)
I meet a lot of people in this industry and even lots of people from high-level of roles and a few of them just love their voice, the sound of their voice. So they like to talk a lot and they like to make sure that people hear them. And I think that’s not the ideal way you can step into such a role.
I believe that, best thing to do is actually listen to what others have to tell you, let it soak in, let it soak in, let people tell you what through their experiences and then you throw your own conclusions and then you are able to speak better and tell others what you’ve learned and what you’ve heard about these things. It’s again, it’s all about balance, make sure that you listen to what people say, that obviously you tell them, you give always your opinions and build networks, make sure that your relationship with clients and employees is always good enough, that you can actually work internally and externally with these people and improve your personal branding from the beginning.
Irina (26:53)
I want to end this episode with one key takeaway for our listeners.
Glenn (27:02)
Right, iGaming, about iGaming. So a lot of people think that iGaming, all the fancy titles and tech that is available, it’s all about that, but in reality, it’s all about people and this is why I believe strongly in networking. Success is generated by the people that you meet along the way, by building your trust, make sure that people know more about you and trust you in the way that you work and the way you interact with them, the way that show that you actually can help out either from your experience or from your knowledge.
And I believe, that once people earn your trust and vice versa, then everything else will fall into its place.
Irina (28:00)
Thank you so much, Glenn, for sharing your insights with us today and a big thank you to all our listeners. Until next time, stay safe and keep mastering customer success.
Glenn (28:11)
Thank you, Irina. See you soon.
