Matt Wilson, Co-Founder & CEO at Jack and Jill, on AI Career Agents, Talent Density, and Building the Next Network-Effect Marketplace

0:00Hello and welcome back to Riding Unicorns. We're delighted to have Matt Wilson from Jack and Jill on the show today. Now, Matt was last on the show in September 2022, talking about Omnipresent, which has since been acquired by Deal. So huge congratulations on that, Matt. And today, you're back as the founder of what is arguably one of the hottest venture-backed companies in Europe right now, Jack and Jill. You've raised over 20 million to bring conversational AI to the job hunting world, backed by the great fund of EpiPen. episode one, and also our friends at Creandum who know a thing or two about building generational companies.

0:37Omnipresent was obviously about helping people hire the best people globally. Jack and Jill is about helping people find the right job in the right place. So let's start with that. What is it about helping people get closer to their dream job that has kind of linked the two and gives you that fire inside to keep going and solving these problems?

0:59Matt Wilson:Yeah, I think what we do for work is really underrated and we spend such a small amount of time on it. And I think that's true as individuals. How much time have you really spent thinking about your career, exploring the options that are available to you, mapping it out? When it does come to making a change, we often will jump at the thing that we'll talk to a few people on our network, we'll apply to a few roles and we'll go for the best of the first 10 of the conversations that we have. And even when we're choosing our first job, we do it and choosing our career, the kind of path that we set ourselves down, we do it in such a careless way.

1:41And I think as companies, I've hired

1:46Matt Wilson:hundreds of people, I think we can be guilty of it on the company side as well. And arguably the most important thing that we do as leaders is hiring people into our teams. And again, I think we could do so much better. We could be so much more thoughtful about how we go about finding the best possible people for those jobs. And so I think, you know, you think about as a person, what are the things that are important to you? It's your health, it's your financial well-being, it's your relationships, and it's your job. And your job massively impacts your financial well-being and so you know as a mission to help people get you know whether it was get the best job in the world for them by by building global employment infrastructure or whether it's by identifying what they're great at what they want to do and then helping match them with the best the best company match out there for them i think that's a huge mission that like i love and i loved building that at omnipresent i love building that here but also on the other side with helping companies get build like incredible teams of great people and identify who the best people are in the world for them to hire.

2:46Matt Wilson:It's the same underlying mission behind both companies. Matt, tell us a bit about what Jack and Jill actually is. How does it work? Yeah, it's a great question. So we build two things at Jack and Jill for two different audiences. So we built Jack, and Jack is an AI agent. He'll explain what he does. So he helps people figure out what they want in their career, learns about who they are, and then helps them make that next step in their career. So what does that actually mean in practice? It means that he chats to people either over a text interface or over a 15 minute voice call, reads through your CV, resume, your LinkedIn page, and builds a picture of who you are and what you're looking for.

3:25Matt Wilson:He then goes, okay, I'm going to look at every job on the market, continuously in the background as you're running your busy life, or if you're actively looking for a role, I'm going to monitor the market and see what's out there and i'm gonna see whenever an interesting role gets posted on the internet i'm gonna send it straight through to you he's there to help with career coaching he's there to help with interview prep you can do mock interviews with with him and we're just adding more and more functionality to say whatever somebody could want as they're figuring out who they are what they want out of their career and identifying and then making that next step a reality we're building in as functionality into jack and over time he builds up this really deep understanding of who you are and and what you're looking for that then powers that and makes that more and more powerful as as he builds context on you.

4:10Matt Wilson:On the flip side, we're building Jill. And Jill is the equivalent, but for companies. So Jill spends time getting to know companies, will ask questions if you're hiring for a certain role. You could share a job description or you could just share a brief overview. And then again, over voice or over text, you can talk about who it is that you're hiring for, what you're looking for in that person. And then Jill is getting to work, helping make that a reality. And she then works together with Jack to connect you up with this, you know, we've now got over 100 ,000 people that have signed up and have spoken to Jack.

4:42Matt Wilson:So Jack's got this big network of people he is building this rich context on. Jill on the other side is working with thousands of companies, building a rich context on what they're looking for. And then like the most highly scaled, highly networked recruitment agency, they kind of bring together the best candidate match to the best company and facilitate direct introductions. So Jill kind of works like this, you know, hyperscale recruitment agency. it's wild and everyone listening to this should 100 try out jack and jill because it's amazing amazing product and a mind-blowing experience particularly for anyone who hasn't tried speaking to voice ai yet but even if you have the nuance of the discussion will will surprise you um and that's certainly been the feedback from from early users on both sides of the marketplace so definitely try it out but Matt how do you or how did you think about bootstrapping this marketplace like there's a cold start problem where did you start cranking the handle?

5:44Matt Wilson:So I think you can you can look at the business as a marketplace where we're bringing together job seekers on one side and candidates on one side and companies that are hiring on the other side I think the other way to look at it is two independent products so Jack actually works brilliantly well regardless of the jobs that jill is bringing to him that's like a bonus on top so we think about how do we make jack work well as an independent product so jack has access to all the incentives scrape all the public job listings and runs in the background monitoring what's getting posted for you regardless of you know what jill's doing and the state of the marketplace dynamic on that on that side of things he's also offering interview coaching cv and resume coaching and we think about what value can we add in what we call kind of single player mode on both sides of the marketplace that we're able to distribute those products, get them out in front of as many people as possible and then over time start to bring both sides of that marketplace together.

6:37Yeah, it's awesome. And I think it's an amazing use of AI and obviously you did manage to solve some of that cold start problem by just making a great product that then just recommended the jobs that were already out there. And then now obviously Jill is starting to sort of bring a sort of custom experience around that. And I wanted to reflect a little bit on the last time you were on, because it's amazing to have this context across a couple of businesses. And you talked about leadership first hiring and how you, once you felt you had something, you quickly assembled like an Avengers style team of leaders that could really take control of their own departments and allow you to scale incredibly quickly.

7:23Have you done the same this time around? And why is that so important as a venture-backed business to pull that team together and create that real momentum by knowing that you've got top operators leading their departments?

7:41Matt Wilson:It's funny because we actually have taken a slightly different approach this time around. And I think obviously we're an AI first product, but we're also we were founded in march of 2025 so we're you know kind of founded in as an ai native company as well and i think as you think about the org structure and the talent i think that's the way that you build has changed compared to the way that you'd have built a few years ago and we've been quite intentional about not um i think you know the at omnipresent the approach to building the org was okay we've got this really strong product market fit covid was this huge accelerant and we needed to run really quickly so let's divide up the the org into you know almost kind of parallel streams hire strong leaders in place to let them build out their functions and then we can we can run this kind of multi-track approach to uh to building up the organ and operating quickly and lots of advantages to doing to working like that but actually with ai and with the way that we want to build the company this time around, I think we want me and Sarah, my co-founder, we want to stay much closer to the action and keep a much flatter org and a much leaner org.

8:54Matt Wilson:I think the things that I really want to do differently this time around is keep the talent bar super high. I think as AI is levering up everybody's productivity, the most productive, the best people can be 10x more productive than the next best person. So if you can do that, you can get a smaller team that doesn't need as much management overhead. It doesn't need this parallelization in order to scale headcount. You can keep a lean team. You can keep much closer to the action. And then you can kind of have the power of a 200, 300 person org, but with 20 or 30 people without all the kind of comms overhead and the complexity.

9:32Matt Wilson:And then the misalignments that you get as you build out a more siloed and fragmented org. so and you have have been quite public about the fact that you want to be a company that pays over over and above the odds for talent so does that link into that kind of like talent density strategy where you'd rather sort of almost like overpay but make sure you're getting the top top person um rather than sort of trying to sort of balance and worry too much about hiring too many people I think we would prefer to have a team of 20 people that are absolutely brilliant and world class that are 10x more productive than they were two years ago because they're using AI in their day to day work and pay them 50 % more than market rate than have a team that's 10x the size that's costing 10x as much and comes with all of the kind of communication overheads.

10:29Matt Wilson:I think you get much more bang for your buck in doing that. And I think, you know, there's a whole bunch of other advantages to really well compensating your team. Obviously, you attract great people. You can pull great people in. But it also acts as a forcing function. You know, if somebody's not at that bar, it's pretty painful at the end of the month when you're running payroll to be paying somebody. So it acts as a forcing function on you to go like, okay, you know, do we really buy into this philosophy that people can be 10x more productive? are we seeing the 10x productivity and if we're not well then then that's a painful thing that we're kind of having to uh having to to wrestle with on a month-by-month basis so it helps us kind of police the police the talent bar as well that's really interesting um yeah because uh i think that they might be a misconception that maybe you would um you wouldn't people wouldn't be hungry anymore or something if they're onto a higher salary but actually they're not locked into some crazy long contract it's not like a footballer who like plays well in their contract season gets whacked onto 400 grand a year and then just drops off and then but they've signed a four-year deal you are sort of almost like constantly reviewing them because you're like they're expensive now and you know they've got to deliver i mean yeah i mean i i think it's probably not it's the sounds that that sounds a bit transactional you think about it like that but we also it's also comes down to the people that you hire and you know the the people like we more than half of our team i think 60 66 percent of our team two-thirds of us are ex-founders You know, these aren't people that are, you know, going to phone it in.

12:00Matt Wilson:You know, we've got people that want to win. They want to build a global category leading business. And there are other options of companies that they could go and work at. They could go and start their own businesses. Like we want to take comp off the table for those people as a reason to come and work with us and say, look, we're going to look after you really well. You're going to work really hard here. we're working harder than I've ever worked in my life here and everybody is pushing really hard and you know that it's not you know you come in and you're well looked after you're pampered as you come in and you work really really fucking hard and for that we're going to compensate you well and we're going to compensate you as well as you could um you know as well as you get doing anything else and uh and we're going to kind of you know assemble assemble the avengers here and uh and and I think you know previously I was thinking about doing that at a leadership team level I I think here it's like how we've got a bunch of people that are ex-CTOs now as engineers, ex-CROs that are ICs in the go-to-market team.

12:58Matt Wilson:How do we pull these people down and let them be kind of closer to the action, but still get in the people that are going to be world-class? I think the other huge benefit to paying these huge salaries is the brand awareness. It's caused a stir on LinkedIn. it paints you guys as a world-class team just by virtue of paying huge salaries there's a sort of implicit assumption that you would only pay that for the very best people in the market and thus like in a market in a space where I think this is about king making there aren't going to be that many winners probably there might be a small number but you have to be a lot of this is to do with outside perception.

13:42And so you get those benefits as well.

13:47Matt Wilson:Yeah, I think, I mean, I would also say that we're not paying, I think you're making it sound like we're paying like crazy, crazy money. Like we are paying, we based the team in London. If we were in San Francisco, our salaries would be like median or below market, right? So we're building a global category leading business and we've chosen to build the business in London and we think there's a talent advantage to being in London because there's people here are just as good and by paying what we pay for the average person in San Francisco we're getting the top 0.1 percent of people here in London so that is it's not like we're throwing money away we're paying what it takes to get the people in that are going to build a global category leading business and we want to do that with the headquarters of the business here in London you also talked about about king making and about the kind of category creation and it's interesting i think going through another cycle of uh of we think there's a that there's a category to be created with what we're doing and i think you get one winner in most categories that dominates the value that gets taken and you know there's a network effect behind what we're doing it's even more true where there's a network effect and i think in the early days of category creation you're at the speed to get the flywheel of having like a brilliant team attracting great people bringing them in getting them working really well together to build great better products than what the competition's got going to market more effectively than than they do which is again is kind of fed by the quality of the product and the quality of the team that then feeds the kind of capital injections that come that then feeds that flywheel more so i think the uh i think a lot about how do we in the early days of a company get that flywheel spinning faster and faster and it's not just about the public perception but all of those things feed each other and matt the dream is of course a super fast growing entirely self-sustaining marketplace where where you're growing without any input of course you'll need a team you'll need uh there's operational complexity to it but how do you measure whether you've hit sort of escape velocity like what's the metric that tells you you've hit that point?

16:03Matt Wilson:I mean, I think with what we're doing, there's a lot of different metrics that we look at. I don't think we can necessarily boil it down to one. I think that the North Star metric that we use as a business is looking at the number of candidates and the number of Jack users that we're getting into interviews with our customers on the Jill side of things. And then obviously measuring that that then converts to hires at a good rate. but that to us is the north star metric that we track and we'll slice that by geo, by segment, by sub-segment, by role and try and understand the marketplace dynamics from that perspective but that for us is the true measure of are we getting great people to work with Jack?

16:42Matt Wilson:Are we getting great companies to work with Jill? Are we getting the overlap? Are we getting the roles onto Jill that the users of Jack are wanting and vice versa? so that for us is the kind of is the measure of the marketplace liquidity and the marketplace health and that's the number that we we've been kind of growing 100 % month over month on that on that metric for the last few months so that's that for us is the sign that we're that we're doing the right things on both products and both go to markets and what what have you found to be the most efficient growth tactic or channel for each side of the marketplace like on both sides it's building a great product and driving word of mouth like that is the by far the most effective and efficient growth channel and um that comes down to building value for users and trying to do that with with great user experience and matt you know you've made it when um other companies start calling their business sort of like yours so yesterday i was pitched the jack and jill of insert different verticals.

17:46So you've officially made it. At what point did you put a name on the product? I remember us talking before it had a name. And it's such a great name for the business because it just encapsulates this two-sided product marketplace. So when did you come up with that? Who came up with that? Who can take the credit for kind of nailing it on that side?

18:07Matt Wilson:Yeah, it was Cyrus and me early on. We'd spent about a month with the product with a different name. And it was always a bit of a placeholder name. And it was funny. I mean, you know, this was like month one of the company or maybe month zero of the company. I'd come home from working with Saras every day. Shannon, my wife, would ask if we'd changed the name of the company. I actually hated the first name of the company. She said it's a terrible name. Like, the company's not going to work unless she fixed the name. And as I say, like, it's fine. Like, we'll solve that problem in like, you know, once things start to work, we'll solve that problem.

18:44Matt Wilson:It's not the rate limiting problem in the business at the moment. We haven't got a product. We haven't got any customers. Like, that's a problem for later. Eventually, I decided I'd spend a weekend and have a bit of a think about it. And we realized through a lot of the customer discovery we were doing that a big part of the issue that both candidates and companies had when they were working with recruitment agencies was that they felt that there wasn't incentive alignment where you have a third party that is being paid commission and being paid on a successful hire being made and that leads to funky behaviors where they will be overselling candidates to companies, overselling companies to candidates and trying to get a bum in a seat rather than trying to find the best thing for that candidate, the best possible person for that company.

19:36Matt Wilson:And we realized actually the right way to build this product that we were building was with two independent agents that were optimizing 100 % for their own customer. So Jack to work in the best interests of the candidate, Jill to work in the best interests of the company. So once we realized that, we wanted to anthropomorphize them. They have personalities in how they act. I think it's a very vulnerable thing talking about your career and talking about what you want. and you often get people at really difficult times in their lives when they are going through a career transition. And so we wanted to anthropomorphize them and make them feel friendly and make them have some character.

20:13Matt Wilson:So then it came down to thinking about what would be a great, you know, kind of name for this pair of characters and pair of agents that we wanted to build. And, yeah, and Jack and Jill was the, we had a few different options. Jack and Jill was the one that we felt was right. yeah I'm expecting to be pitched by Starsky and Hutch AI Butch and Cassidy AI now so you've probably created a trend I love this concept of anthropomorphizing the the product because I think in in AI but voice AI in particular you know I'm actually an angel investor in Bordy and we've had the founder on on the Riding Unicorns podcast as well but there's this difficult thing to overcome where speaking to an AI can be on paper a really great experience, but you miss the sort of human touch.

21:05And I think naturally people place more value on a content and a conversation from a human because they fundamentally care about other humans, whereas an AI somehow feels more disposable, even if the content coming from it is potentially better. So how do you create an experience that feels really, really special and customized and tailored where the customer feels like they matter to the AI?

21:36Matt Wilson:Yeah, I think I would slightly disagree with what you said about having a conversation with an AI versus with a human. I think it feels different for people having a conversation with an AI versus with a human, but it's not better or worse. It's just different. Like there are, and you don't want to pretend that the AI is a human either. I think that is like creepy and weird and gets into all sorts of issues around trust. I think it's important that you're always clear and upfront. Hey, this is an AI that you're talking to. But what we found is that people, when you make sure that the AI is working in the best interest of the person, people are much more likely to be open with the AI than they are with another human.

22:20Matt Wilson:You're talking about your career. there's lots of awkward topics you know how much money do you make how much money do you want to make especially as british you know people are not great at talking about these these these topics what's your ambition what do you love doing what do you not love doing what was the day that you like really enjoyed recently at work or is the day that you didn't really enjoy at work like if you're talking to another human there's this social pressure and there's social you know you've got this conversation and you feel like you're being judged by another person you know and with an ai you can really relax you could actually i can just like tell it what i want and what I've done and what I like and what I don't like.

22:52Matt Wilson:And I don't feel like I'm being judged. And that allows people to be much more open and be much more honest and do that with less stress. And for the most part, it's even worse with careers conversations because if you're talking to a recruiter, you're also being judged at the same time. It's not just you're being judged because there's this way that you're talking to another person. You're being judged because you're being evaluated. Are you good enough for this role? Are you the right fit for me to put forwards to my client? and so you're playing this kind of game all the time um so for us it's been around how do we build the ai that there's lots of engineering work that goes into the conversation design into the voice interaction to the latency into the tone um and tons of products and engineering thought that goes behind that but fundamentally it's around how do we make this thing useful and feel like it's working for me rather than feel like it's something that's judging me yeah and just to flame that a little bit I mean I've tested out the product and I completely found that I felt like I could be much more direct with the AI and even to the point of just going yeah can we move on to the next question like just like get me through the process a bit quicker or I don't really want to answer that or actually you're an AI and you need this data to give me that so I'm just going to be really direct and honest so it's kind of a refreshing experience as well and obviously the AI is very polite and calm.

24:17And, you know, so it, I think it's a great way to, yeah, get what you want as a human is to be able to actually tell the AI what you actually want. And you're not getting that kind of judgmental feeling. So just from trying it out and giving it a go, I definitely felt that I did also, my wife did walk into the room and go, who the hell are you talking to and telling all this information to? And I was like, Oh, don't worry. It's, Jack and Jill, don't worry. So yeah, no, it's very cool. And then obviously recruitment as a space is massive. There's lots of traditional recruitment agencies as well as new tech solutions kind of popping up the whole time.

24:55How do you think about sort of trying to build some defensibility and moat and kind of owning this very large space? As you said, it's kind of category creating, but obviously it's an existing category in the traditional sense. So how are you thinking about that long-term defensibility?

25:13Matt Wilson:Yeah, we think we're going to live in a world in a couple of years' time where every candidate, every person has an agent working for them that knows who they are, knows what they want, that is out there acting in their best interests, looking at what's available, helping them figure out where do I want to be two years from now? What do I need to do to get there? And is then representing them. we think every company will have agents working for them and we think that there will be one company that both these agents sit in that they will be able to communicate with each other and they'll be able to make these like extremely high signal matches because they'll be very deeply understood on both sides and you can imagine a world in which you know jill is working with 70 of the people that could be your future boss and like jack would be the best way to go and find find an opportunity and vice versa.

26:11Matt Wilson:In London, we've got a very good percentage of startup talent in London, both on the market and passively exploring things, already working with Jack. We have this huge network. It's such a big advantage to companies that come in and work with Jill that over time, we think that network compounds and you end up with one player that's dominating in the space in any given market so we think there's going to be a winner takes most kind of dynamic in the space and that's what we're building for very cool yeah I mean I think it's that thing of with a human recruiter you're only really engaging at the point of like I need a move or I need a job because you've just lost your job or whatever whereas with an AI you're kind of like well you know if it hits certain thresholds on pay or something you know so i might as well tell jack about what would like actually turn my head even though i'm not really looking to move at the moment so it actually makes the market 10 times larger doesn't it because all the best candidates are hopefully in jobs already but they would probably turn their head if the pay was good enough or the flexibility was better or whatever it might be yeah or the team was right or the mission was right or whatever was important.

27:26Matt Wilson:And like, why not spend 20 minutes getting an AI that is connected to, you know, thousands of companies on the other side and say, look, here's the bar. Here's what I want. Here's the things that I would like entertain. And then you can go back to your job. You can update it once every few months and you can have a situation change. You have a bad day at work. Okay, like maybe bring the bar down a little bit, you know, and why not set that up? And then you have that passively running in the background. And then, you know, on the other side, it's like having a recruiter that knows every single person, you know, it knows over 100 ,000 people.

28:02Matt Wilson:You know, if you're hiring for somebody right now and you had a friend that you could go and talk to that knew 100 ,000 people and what they wanted out of their career and what they were looking for, like, why wouldn't you go and call that person up as your first person you chat to when you go out to make a hire? That's what we're building. So we think the defensibility, I don't think you can build defensibility from building functionality. Like everything can be built that anybody else can be, you can build anything, anybody else can build it as well. And you can get ahead of the competition from shipping faster and having more product taste.

28:34Matt Wilson:But over time, the only defensibility comes from having this network. Yeah. Awesome. I think you might be onto something here, Matt. so talking of uh future unicorns as jack and jill obviously is on our list of future unicorn predictions but is there another company that you've come across that you think could be a future unicorn i've got i've got a couple of thoughts i think if i look at like the rawest most hungry most aggressive founders that i've come across over the last couple of years i i worked as they were going through entrepreneurs first a couple of years ago with timon and armando at a company called Strala and they are absolutely killing it.

29:16Matt Wilson:They're building AI and claims automation insurance. And they're two young guys, a German and Austrian guy, and they're out in the States now. And they are just ever since the first day I met them when they were on day zero of the company through to now where they're flying. They're just absolute machines, really young guys and maturing very quickly, like deeply thoughtful about building the team, like very mature in terms of how they think about talent and how they think about building the company for such young and kind of hungry and aggressive founders. So I'm a big fan of the founders at Strala.

29:49Matt Wilson:I think this is a bit of a later stage company, but the product that has just like completely blown me away in the last week is a product called Hex. It's a data platform. It sits on top of your database, your CRM, whatever data systems you've got. And then it has an agent that you can, you know, in Slack, You can say like at Hex, tell me what the conversion rate from this step to this step is for this segment of customers. And it will pull that, build a retention analysis cut by this. It's an unbelievably powerful platform and truly AI first in terms of how it works. And I think it's going to absolutely fly.