Tony Jamous & Hadi Moussa at Oyster HR on leadership transition, CEO succession and unlocking global talent

0:00Hello and welcome back to Riding Unicorns. Today we're joined by Tony Jamous and Hadi Moussa from Oyster. Now, some of our listeners may remember that Tony was on the show in January 2023, introducing Oyster back then, but it was already a standout company in the future of workspace with a mission to open up global talent. Since then, a lot has happened. Tony has stepped aside as CEO and Hadi is the new CEO. And so we're delighted to have them both on to talk a little bit about that leadership transition, what's happened to the business since and where it's going from here. So welcome, both of you.

0:37Thank you so much for joining us. Tony, obviously you're back and we'd love to start with just a quick refresher on Oyster, what has happened since you were last on the show and yeah, just get a quick update on the success of the business. Thank you, James, for having me again. And delighted to be here and talk to you about Oyster. So a quick refresher. So Oyster is a global employment platform. We are a mission-driven company on a mission to make planet Earth actually become one employment market. And we do that by providing an employment platform that removes all the barriers in front of companies to employ anyone anywhere.

1:26So I started this business in late 2019. And it's been an amazing ride going through the pandemic, supporting this move to remote work and the changes that happened in the labor market. And last time we spoke in January 2023, we just closed actually our Series C, became a unicorn. And since then, many things have happened. We raised our Series D. And as you mentioned, James as well, I actually moved to become an executive chairman, welcoming Hedy as our new CEO. And how did you guys know that it was the right time to make that switch? I mean, Tony, from your perspective? It was evident to me that this company has become too large for me to be able to scale it going forward.

2:23I knew I was the right person to get it to its current state. However, I've been receiving feedback through my team, 360 feedback, that they're looking for a different kind of leader. A leader who was able to scale Oyster to his next level, who not only can design a vision and a strategy, but also executed at scale. So I came to the board in January 2025 with an opportunity. I told them, look, guys, we have the opportunity to make Oyster more successful than anybody has ever imagined. And the key change we need to make is to bring in a new CEO who is better fit for this next stage. Luckily, I had a supportive board and they listened.

3:12And that has started in nine months, actually, search process that led us to, after interviewing more than 45 executives, to be able to be fortunate to find Hady. That's super interesting. And Hady, how did you come across the opportunity? Yeah, thank you for having me. So I think, look, I came across the need for Oyster, I would say, way before I actually had learned about Oyster itself. So I worked at a number of tech marketplaces before that were looking to expand and in many cases looking to expand internationally. and the likes of Facebook, Airbnb, Coursera as well. And in many cases, we saw that challenge of wanting to expand internationally but not having the infrastructure to do so and not having the ability to hire people in some other markets in a way that's simple with a good experience that's easy to manage.

4:07So I've always kind of seen the need for the service itself. And then when the team reached out and started to have conversations with Tony and the rest of the board. I think what resonated the most was the mission itself. What maybe Tony had talked about in the previous podcast is the genesis of the idea for Oyster, what kind of the mission is and how it helps hire talent for companies, right? And hire that talent anywhere. And for me, kind of personally, I grew up in Lebanon similar to Tony. I had to leave, you know, to in search of opportunity. So when I heard about the mission of the company itself, it really deeply resonated.

4:49It felt very personal. It felt like something I really wanted to do. So between the mission, between kind of seeing the need from customers for this service, then of course, you know, spending time with the team, learning more about the culture, the way that the company operates, the size of the opportunity that's still ahead of us right now. I think it's kind of all of these things combined that made it sound like a really exciting opportunity. to jump and kind of really come and work with Tony on Oyster. Yeah, great. So it sounds like it emerged as a great fit for both of you. What was the process of sort of preparing Hattie for the role?

5:31What were the key things that needed to happen to kind of bring Hattie up to speed? A lot of things needed to happen, I think, before I started and then many things after as well. So before I started, I actually spent, you know, some time with Tony. We had quite a few, you know, sessions to better understand, obviously, the mission, the long-term vision for the company, the, you know, the trajectory, the story so far, understand more about how, about the team, how they operate. And I spent time with the team as well. Before I start, we, you know, spent some time thinking through the plan for this year, for example, like starting at the beginning of the year.

6:09it was important for me to provide input into the plan to kind of be fully bought into the plan that we are trying to execute so it involved a lot of you know time with the team to understand the company the industry the business what's working what's not working as well and then since i joined it's about two and a half months now i would say the main focus initially is that kind of listening and learning right spending a lot of time with the team the broader team spending a lot of time with customers, time with partners to again kind of get a better sense of what are the things that work really well today that have helped us kind of get to the point that we are at today but what are also some of the challenges and what are the longer term opportunity and that's been really the key focus of the first months to two months to get up to speed and then start to think about the longer term plan and the longer term strategy for Oyster.

7:04And Tony how do you think Think about the sort of difference between you two, where, you know, Hady's got sort of a skill set that is complementary to what you have and different and does allow scaling through the next stages of growth. Yeah. So, Hector, one thing is clear that Hady is the leader who deals with the day-to-day management of the business. There's no doubt about this. It's very clear delineation of responsibilities. And my role is about being one link between the board and the company, is to be an advisor to Hattie and a team, and one guardian of the mission and the culture of the company.

7:54But everything else is in the responsibility of Hattie. and what's the what specifically um what are the skill sets of a of the skills of a ceo of a billion dollar business that weren't working for you as a as a ceo and a founder of the early you know during those early phases what was it that you needed to bring someone in to handle yeah so as businesses grow at that level they become more complex they become about leading in differently, about delivering more operational rhythm, more discipline, fine-tune execution. And that's not my experience, right? I built businesses in the past that leads to$100 million of revenue.

8:48And I came to realize that while I'm able to learn this, as the major shareholder of the company, I would not want to take that risk. I knew that I could hire people that are specialized in taking us to the next level. So it became a question of conflict of interest. How I can change myself, change my role to unlock the full potential of the company and not myself be in the way to limit the growth and the success of the company. Okay. And Hadi, a couple of months in, what are the low-hanging fruit, do you think? What's the mess that Tony's left that you're now able to clear up? I think, look, in a way, it's going back to what Tony said.

9:38He was the right person to really drive the first stage for Oyster, to get it to where it is today, to kind of build the foundation that we have today. I think in terms of low-hanging fruits, it's some of the things that you need to bring in as kind of the first CEO after a founder is to kind of really build that structure, that operating cadence, that ability to really track how things are performing, where things are off track, how do you put kind of the corrective action in place to just bring more of that structure into the company. I think that immediately unlocks a higher level of execution in a way.

10:14So I would say that's kind of one key area. The second one is to provide clear direction and clear focus, right? Because, and I have worked kind of in companies before also where, you know, founders were the CEOs or where founder transitions have happened. And the amazing thing that they bring is that ability to think longer term, to have ideas all the time. And I think what I see as my role now is to actually kind of narrow the focus down to what do we want to be as a company over the next three years? What is it that we want to focus on, but equally, what are the things we want to stop doing or not do anymore?

10:50And that for me is kind of, again, a key area where, you know, if you provide that level of focus, you also improve the execution on those specific areas. And that's how you drive kind of the next stage for the company. And I think, you know, as the company has grown as well, it's to think about, you know, the structure, the team, do you have a high performing organization? and then making that transition to a high performing organization also is a critical part of where I see my focus over the next few months. Yeah, and there's, I think, a great Steve Jobs quote, which doesn't make sense to hire smart people and tell them what to do.

11:28We hire smart people to get them to tell us what to do. But that's easier said than done, Tony, when the company is your baby, you were the founder. So how have you found that? You obviously started by saying, I'm still here to advise when I'm in the exec chairman role. But what is it like when someone comes in and has new ideas that maybe challenge the status quo? Look, it was hard, I mean, to let go, right, the baby. But the baby has grown. Now she's approaching adulthood. So she doesn't need me in the same way she needed me before. So it's about having that awareness of rethinking my role and how I want to serve the organization in a way that maximizes its potential.

12:17And it wasn't an easy process for me. It was a process of rethinking who I am, right? I'm not the CEO anymore. And be in full acceptance of this new reality to allow something more powerful and more beautiful to emerge. and just in terms of um as a company i mean obviously it sounds like it was the right decision tony for you and obviously used there's still a lot of belief that there's a big blue ocean to still go after but someone might say you know was it a decision between this or selling the company and you know why is it that you didn't want to just like sell the business because presumably you could.

13:06There's lots of revenue and clients, et cetera. So was that a part of the decision? Did you have to think about that as an option or was that never really on the cards because of what you see as the potential? It wasn't really on the cards because for a number of reasons. Number one is I've already exited a unicorn before, right? So I'm not chasing a short-term financial return. I started this company to reverse brain frame, to reduce wealth inequality. That's why we are a B Corp. We are a benefit corporation. We are a mission-driven company on the core. So the question is, what needs to happen to maximize its impact?

13:47What needs to happen for Oyster to be the largest impact work tech company in the world? That is the guiding principle. That is a North Star. and to get there there are going to be a number of steps and one of these major steps is to shift how I relate to the company to unlock its potential and by I have absolute faith by being truly and honestly focused on the mission to provide more equal world through equality of work I have absolute conviction that Oyster will become the largest impact work tech company in the world. And Hadi, how do you feel as a CEO? Like we tend to have founders on this podcast, right?

14:41And I'm very intrigued and I'm sure our audiences as well to understand whether you feel like a founder, whether you have the founder mindset, what drives you? Like, is it the financial outcome? Is it process optimization? Or is it that same mission as Tony? I think absolutely the same mission. I think if you are not driven by the mission, then it's very hard to kind of operate, right? It's very hard to have the drive also to drive a business like this. So, you know, there is no doubt that it is the mission. You have to feel like a founder at this stage. we are not a large company yet right we are still going through that scale-up phase there is a lot more that we can do to kind of james's earlier point there is a significant opportunity ahead of us and you have to operate with that mindset we're not at a point where we're looking to optimize and exit and sell the business right so we are at the stage of defining where do we go from here where do we double down where is the opportunity and i think that's the mindset that you need to have coming in at you know a company like this one but that only works if you like the mission itself deeply resonates if you want to create you know the multi-billion impact business that tony is is talking about and that kind of is the main driver for me personally and the reason why i took this job in the first place yeah and haddie maybe could you could give us a bit more detail about some of the skills and lessons you've learned from working at the likes of deliveroo and Airbnb and Coursera, these amazing, very large tech companies that have maybe gone on that further step of the journey and what you think you'll sort of bring to Oyster to help them do the same.

16:28Yeah, absolutely. And I think, as you mentioned, I've been at a few of these companies as they were going through the scale up phase. I think what kind of changes over time is, you know, how can you bring again, that level of focus? And how can you bring more structure Right. Again, you don't want to create a structure that kind of suffocates the company, but you want to create enough structure for the company to be able to scale. Because going from, you know, as you know, from zero to one, one to ten is different than going from ten to a hundred. And the biggest differences come from, you know, what team do you need in place?

17:06What talent do you need to have in place? But also how you run the company. right and you know in my case personally what i've seen work really well is you have to you know put the right structure with the right people give them a clear direction and empower those people right when you're scale you're at the scale of the company that we are when you're at the scale of companies you know like airbnb and deliveroo and they're looking to go through that scale up phase that's the critical piece right and for it to work you have again to put the structure in place where you are really able to provide clear direction, clear metrics, and then have the, you know, structure in place where you are able to track and review and adjust.

17:51But that kind of clarity of what outcomes you're trying to achieve, whether you are on track to achieve them, and what you need to do, you know, to pivot or to make changes or take action, that I think is what kind of changes fundamentally. The other big piece is, and every single company going through that phase has had to deal with, is how do you manage the complexity, right? So it's, you know, when you're a small team, everyone works closely together, everyone knows everyone else, and then it's a lot easier to make decisions and, you know, have things move very fast. When you start to reach the size of a company, 150, 200, in our case, you know, closer to 500 people, then the level of complexity has increased exponentially.

18:35And for that to really operate, you have to think about what's my operating model? How do I make sure I have clear decision-making, that people are empowered to make decisions and move quickly, that you still have a growth mindset where people can learn, iterate very quickly. These are, I think, some of the things that start to really slow down a company at the stage that we are at right now. And you have to unblock that complexity for a company to be successful, to go to that next phase. So it's really that combination of clarity of the direction, the ability to look at how well we are executing, where we need to make changes, and removing that complexity that comes from a company scaling up and growing the size of the team.

19:20And at the beginning of this conversation, Tony, you mentioned you'd received 360 feedback, and that's a super healthy thing for management to be receiving to receive as well as give feedback. But I'm kind of fascinated by the sort of mastery of giving feedback. And Hadi, I mean, I think a big part of the CEO's job is, you know, yes, there's the stuff you're talking about. And there's this sort of setting the vision and making sure that the decisions are being made in the right way. But the optimizing of humans within an organization is so key and creating a feedback loop for those people so that they improve is so important.

19:59And I wonder, like, how you have sought to master giving feedback to employees so that they can do the best job for themselves, but also for the company? Yeah, it's a very good question. And it's one kind of that relates to what I mentioned in terms of building that high performing team. And I think now, again, you get to the point where you have to be able to provide that very clear feedback. And, you know, that happens obviously in, you know, two simple ways, right? providing feedback when you see something on the spot and being willing to have that conversation. And I think the second piece is to be much more structured in the way that you give feedback.

20:39But you can only do that if you set clear expectations. And I think the key is setting those clear expectations. What do you expect from a person to achieve? And then have an objective conversation in terms of what they have been able to achieve, what you've observed in terms of how they have done it. And, you know, those conversations can be uncomfortable, but I think you need to like really learn kind of that skill because it's really critical for you to be able to scale a company at this point. And there is a concept that I talk to the team a lot about here, which is, you know, we have a great culture at Oyster.

21:14You know, people are, you have, you need to have a high level of trust to be able to operate the way that we operate, which is a fully remote distributed company. But that trust sometimes can translate into, oh, well, we need to be nice to each other. And I think that's where you have to manage and you have to manage a change where it's trust is really important. Absolutely. Care is super important. But what care actually means is that ability to give the difficult feedback. If you care about someone, you need to tell them what's working and what's not working. And I think that is a transition that we are having to make right now and to be able to build kind of a high performing team because i think again when you're smaller things work in a slightly different way when you are bigger you need to be able to provide that clear feedback in terms of how someone is performing and then where are some of the gaps and how do they continue to develop those gaps and that's one of the key focus areas i would say kind of for me right now as again we want to build a the highest performing team in this industry Yeah, there's a dynamic in venture and startups at the moment where the age of AI founders is much younger than in prior generations of startups because these people are AI native and there are lots of reasons for it.

22:31But the maturity that comes with age manifests in large part in ability to give feedback and not being a people pleaser. what would you say to your 25 year old self in this sort of in this area what advice would you have given i would say be a lot more vulnerable because that's kind of the first step to build the type of relationship where you are able to give and receive feedback but that's very hard to accept when you are still very young right and you think you're top of the world and you know you are great at what you do. But that for me is kind of the critical first step for you to be able, again, to give and receive that feedback.

23:16That would be the key thing. And, you know, especially people that are, you know, starting, maybe starting up, starting a new company, think about, you know, some of the gaps that you might have today, right? And be open about those and have those conversations, because that's the only way you are able to bring the right people and get the right type of advice for you to fill those gaps and ultimately be successful. And if you combine being AI native, having that energy that a founder has, being really excited about something with filling the gaps in terms of experience, then for me, that's the recipe for success at that age.

23:52Yeah, super, super interesting. And I just want to flip slightly to asking Tony about the process again. sorry I'm coming back a little bit but I wanted to ask about sort of you obviously ran a process and you had a number of candidates that you spoke to why did you not go with an internal hire was there anyone that could have been considered that maybe you had to sort of manage that their expectations that they weren't going to jump into that vacuum being left by you what are the advantages of having fresh eyes and experience other businesses to bring that fresh energy. Can you just talk us through that kind of complexity as well?

24:33Because it's not just about finding the right person. It's also about managing the existing team who are also there and bringing someone else in. Yes, James. So the process actually started two years before this transition, really. And I asked myself the question is what needs to happen from a team configuration standpoint to allow a new leader to come in. So I've done a reorganization a year before actually the transition has happened to make that configuration work. And I already brought in new people and made some changes. And I also wanted to make that transition at the right time, which mean that I wanted 2025 to have very positive results before making that transition.

25:23So the timing was really important. I wanted to hand over the role to the new CEO from a place of strength. So that's why we spent 12 to 18 months before preparing the organization for that change. And also the interview process was very revealing, right? We interviewed 45 candidates. Through that process, we were able to mirror of what this organization needed. And that process was very structured. A number of interviews, of course, with the board and the search committee, but also with a rigorous case study that allowed us to rate the candidate on a number of dimensions. And I'm very happy to say that Heidi had won 100 % of the votes of the board.

26:13And yeah, so this is how this is how the process went. And it was an opportunity for us to really learn about what this organization need in terms of leadership to unlock its next phase. Yeah. OK, now I'm going to jump back to sort of where we were and what I wanted to talk about next, which was the sort of future for Oyster. And we've talked a little bit about Blue Oceans and big visions and scaling the company. but we're obviously entering the world of AI and there's a lot of uncertainty for a lot of people there might be people listening to this job who listening to this episode have just lost their job or are worried about losing their job or have seen colleagues lose their job so how do you think about that as the opportunity to connect the world into a single talent marketplace when proximity might not be available to you or might not obviously be available to you and what do you think about the sort of talent marketplace with AI people talking about zero employee businesses and all these types of things what is your thinking around that as experts in the world of talent management across the world I think look it's obviously a really big question one that all companies are trying to answer at this point.

27:31I think, you know, we see risks and opportunities. There is always a risk in a way that, to your point, companies would start reducing the number of people that they hire over time because they will be powered by AI. You will be able to operate smaller companies at higher efficiency. And so that could impact the number of people that companies that we work with are looking to hire over time. However, what we think, you know, is going to happen and we start to see some signals of that is companies will want to find people who have the ai talent and that's going to be across functions right like the marketing person who knows how to use ai the sales person uh you know who uses an ai kind of lead generation and you know ai outreach and there are a number of different tools that are being developed the software developer that you know obviously is using all of the available tools as well and so we see a lot of companies that will want to start to hire those people.

28:27And again, a big role that we think we can play is help you identify and find that talent at a global level, right? And be able to distribute the opportunity of AI across the world. And I think that's where we see a very interesting opportunity for us. In addition to that, we see a lot of opportunities for us as a business, right? So we are, you know, a compliance heavy, knowledge heavy type of business. And so So the opportunity for us to use AI to better serve our customers is like 100 % there, right? In terms of how we surface information to them, in terms of the service level that we are able to provide.

29:04These are things that can be game changing because we see ourselves as a company that provide an exceptional level of experience. I think AI can help us do that while still having a human in the loop when things go wrong, especially, you know, because we deal with very sensitive relationships. relationships, employment relationships, et cetera. So that's kind of a big opportunity that, you know, we see to transform the way that we deliver the business to our customers, but also the level of efficiency that we can have in the support that we provide to customers. So it is really a big question, one that we are looking at actively, but we do think there will be this need for AI kind of native talent, similar to what we discussed earlier.

29:48and that's what we want to enable our customers to be able to hire across the globe yeah super interesting and do you see yourselves as a statement of record for hr is it you know salesforce sort of see themselves as that statement of record for for sales and then doing agent force on top of that do you kind of sort of take a similar view i mean we see specifically in global employment that's what we want to enable right so we are focused on global in, you know, employment, not providing the end-to-end HR suite. There are, you know, companies that do that. We want to focus on the vertical and that's what we have been focused on and become the best of breed in that space.

30:31And then, yes, absolutely build the agents on top that can help provide a surface the information. Again, it's a complex business. You know, there are lots of rules and regulations that our customers have to deal with that we can surface much more efficiently with AI and then do the same in terms of the level of service that we provide. But I would kind of describe it more as a vertical focus on global employment specifically. No, that makes sense. Okay, so it's been really great. We've covered lots of ground and it's been so interesting to hear about what actually happens when one of these big transitions occurs, the preparation phase, the search phase, the handover phase, etc.

31:11So thank you so much for sharing all of that. We're just going to move on to our final two questions. And I actually don't remember if we did this back when you first came on the show, Tony. But if you did, hopefully, you've got some fresh answers. But our first question, which we'd love to ask both of you, is a future unicorn prediction. So this is just another company in the market that maybe you've seen that is not yet a unicorn that you think could be and it can be as early stage or mid late stage as you want really but just another company that's doing something really cool how do you i'll go to you first okay i'm happy to go first um it might be more recency bias but i'll share my prediction i don't know if you you've seen the company cross sense which kind of was recently in in the news here what they have done is you know they've developed ai software that you can embed kind of into smart classes and it provides real-time assistance to alzheimer's and dementia patients.