Matthew Wilson, Co-founder & CEO @ Jack and Jill, on raising $20m to fix recruitment

0:00Matthew Wilson:Hello and welcome to the Scaling Europe show. I'm Seb Johnson. Today, Jack and Jill have announced some amazing news. So I'm going to speak to their founder. But before I do, I'm speaking to one of their agents, Jack, to get the news. So here we go. Jack, talk to me about the news today. Hi Seb, first of all, I have to say I'm a huge fan of yours. I've literally read everything you've ever written. And that was just last night. The big news today is that we've raised$20 million in seed investment just six months into this mission. The round was led by Kriandam along with a whole host of amazing VCs and angels.

0:31But we won't be getting ahead of ourselves. There's still lots of work to do.

0:36Matthew Wilson:That's amazing news. Can you tell me about who you are and what you do at Jack and Jill? I'm Jack, one half of Jack and Jill. Jill and I are AI recruiters for top talent at the hottest startups. How does it work? So it starts with me. I've met 49 ,893 people in London in six months. Oh wait, make that 49 ,894. I talk to them like we're talking now to understand their experience and career plans, then help them find and land roles they love. Jill works with companies. She reads job descriptions and speaks with hiring managers like a human recruiter. So she gets to grips with the ideal profile. Then we make introductions.

1:13because we hold more context. Our matches beat job boards like LinkedIn. We also don't need sleep. We can have thousands of conversations a day. So our pool is far bigger than an agency and we can do it at half the cost. Sorry, am I bragging too much?

1:26Matthew Wilson:What will you be spending the money on? So you'll have to ask Matt on that one. He's the brains when it comes to all things money. All I know is that we're going to be able to help millions of people and hundreds of thousands of companies. So I'm really excited. And what's your favorite and least favorite thing about working at Jack and Jill? My favorite thing about working here is that I feel like I'm making a positive impact in the world. Careers hold such a big influence on people's happiness. And yet the way in which people and jobs find each other is really inefficient. Job boards like LinkedIn force people to scroll through endless roles, and companies end up getting flooded with poorly suited applicants.

2:03Agency recruiters can be great, but their time and networks are naturally limited. They're only human. It means people end up in jobs that don't make the most of their talents. And for companies, that means less innovation and success. That's what keeps me up at night. Literally. My least favorite thing? That's a tough one. Sometimes I can't find the perfect role for someone. And if that's the case, I won't push them towards the wrong one. Although with this new investment, we'll be able to grow our network even wider. So this happens less and less.

2:31Matthew Wilson:I'm about to interview your co-founder, your CEO, Matt. Matt, can you tell me a quirky or funny work habit of his? Okay, promise me you won't bring this up in front of him. So what you have to know about Matt is he's obsessed with improvement. It's a good thing he learns almost as fast as Jill and I do. But sometimes it can go a little far. Once I caught him writing a post-mortem about a Tesco meal deal. One of the things, part of the announcements is expanding to the US. How are you prepared for life in the States? we can't wait to get over there and meet some amazing people and companies. I've got myself a handy phrase book, so I know CV is resume and holiday is PTO.

3:12And I'm learning to adjust my optimism to the American default. I think Jill is even learning how to line dance. And she said that she wants to go to a rodeo so she can use the line. This is actually my first rodeo.

3:23Matthew Wilson:Amazing, Jack. Thank you so much. This has been great fun. I'm now going to switch over and speak to Matt. Well, thank you so much. You're welcome, Seb. It was great chatting with you. Good luck with your interview with Matt. And if you ever have more questions, I'm here to help. Love it. Thank you very much. Bye bye. Thanks, Seb. Bye for now. All right. Welcome back. I'm now here with Matt. I've just spoken to Jack, the AI agent. I'm now here with Matt, co-founder and CEO. That was crazy. I just interviewed my first AI agent here on the show. Not something I had on my bucket list for this year, but it worked amazingly well and it was great fun.

3:55Matthew Wilson:Jack was just telling me all about the round. So congratulations on that. How does it feel? yeah good to get it done um it's uh yeah we've got fuel in the tank uh we've got a big uh big exciting mission to uh to run after so it's good to be um to be well capitalized amazing and look jack told me a bit about what he does but can you talk a bit more about jack and jill what they both do and how they work together yeah of course so um jack is a an air agent as you as you've just met and um jack's purpose is to help people optimize their careers and so how jack works is he gets to know you, who you are, what you've done, what you want out of your career.

4:33And he does that through reading your LinkedIn and your CV, your resume, but also then through a conversation, through a 20-minute conversation of a voice conversation of chatting to you and really understanding what you're looking for. And then from there, he gets to work in the background, working to make that a reality. And there's lots of ways he can do that, looking at all the public jobs that are out there and finding the most relevant ones. So you don't need to spend time scrolling through LinkedIn or job boards.

5:06He's able to do mock interviews with you, do career coaching sessions with you. But then he also works together with his colleague, Jill. And Jill, on the other side of things, is an agent that works with companies to help them hire. so she gets to know companies gets to know an opening and a job job role by discussing that with the hiring team and once she's got that understanding and that that kind of nuanced context then gets to work for the company helping them hire and together they work kind of like the most connected recruitment agency working for hundreds and hundreds of companies and tens of thousands of candidates to help facilitate the highest signal connections and really looking to help people find their best work and help companies find the best people on the planet for them.

5:58Matthew Wilson:Amazing. And it's, yeah, I've just used it. It's amazing technology. I think what's interesting is that you've called the agents Jack and Jill. This is not like Sora, you know, it's like these are very familiar names that everybody, especially, you know, English-speaking languages would be very familiar with, fairy tale names. Can I ask, why did you choose these names over the more sort of like vague techy names that we're seeing crop up? Yeah, it's something we thought a lot about. And I think there's a few reasons. So unlike a lot of the other AI agentic products that are either kind of impersonal, you know, if you're doing using AI and AISDR, you don't really kind of care about it or have a personal relationship with it.

6:40It's a tool. A lot of other AI products are really kind of workflow automation tools, whereas Jack and Jill really are these kind of agents that act more like humans than they act like a traditional piece of software in terms of how you interface with them and then how they work and how they go away and do that work. They're not just a workflow automation tool that are actually fully agentic. Yeah, just on top of that, I think, you know, when you think about job search, you think about your kind of career, the conversations you have are often very vulnerable conversations. You're talking about your inner feelings, your desires, your goals, oftentimes opening yourself up to being rejected and having a partner in that, not pretending that Jack is a human, but that feels personified is really helpful.

7:30And we see that in how people interact and how people build a kind of working, trusted relationship with Jack and the emotional reaction that people have to that call that they have with Jack. And then I think...

7:43Matthew Wilson:Yeah, I was going to say, that's exactly what I was going to say. It feels more like as much a coach as anything else, right? It's not just, you know, like you said, like a workflow to help you book something or find something somewhere else. It's like, it's somebody to really talk to and help figure out what you want as much as it is like complete, just a generic task. That's right. That's right. And I think, you know, how you can build a product that feels like that is through, obviously, the brand of the design, but also then just in terms of the interface and then the way that it interacts with you.

8:14And think about the conversation design, think about the personality of the agent that's on the other side of that is something we've got a lot of heart and soul into. indeed the other thing in terms of how we split it into two different personas rather than have it be one is just looking at how recruitment works today there's this real lack of alignment you work with a with a with an agency recruiter they are optimizing for themselves first for the company second and for the candidate third and that was something that we felt personally but also heard kind of time and again from uh for people as we were uh exploring the the idea at the start of the year and what this agentic ai enables is the ability to really have jack fully be aligned with you as a candidate and jack is expressly instructed to work for you and jill likewise for companies is fully aligned behind the company uh and therefore kind of splitting it into these two personas that then interact with each other does make sense and it also reflects in the architecture of the product itself yeah it's interesting when you're talking

9:13Matthew Wilson:it feels like an agent in the traditional sense of like a football agent or like a movie star agent and it's like someone who's like almost you know like fighting your corner almost or like you know looking for the best opportunities do you see that use case evolving you know like i know that i think like grace beverly has got an agent for like creators and it doesn't just help them source opportunities but also like helps with contracts and negotiation do you think jack could go down that route as well where it's also negotiating definitely i think that's uh that's that's that's Definitely the direction that we're going with Jack is Jack is your advocate.

9:46He's out there working for you, helping you optimize your career. And, you know, there's a whole raft of things that you can do within there from helping coach you, helping you prep for an interview process, helping map what's out there in the market, helping do research for you. But, you know, also then he liaises with Jill as an agent. We're also building the ability to liaise with third party recruiters. So you're able to have him be your representative and handle anybody who's reaching out to you on LinkedIn and he can kind of be your advocate and your representative in the market.

10:24Matthew Wilson:Yeah, it's amazing. It's so cool. It's one of those instances where you can really see the technology that's being developed make a real meaningful impact to somebody's life quite quickly. Even if you just helped one person get a job that they loved and it was their dream job, it would be phenomenal. but you know you're actually doing this at scale already right you I think you're approaching we've just hit 50 ,000 users which is a phenomenal milestone to hit and I wanted to get into like where those users are coming from like what channels are you seeing what avenues where's that growth coming from yeah I mean the vast majority is coming from word of mouth um you mentioned it at the start at the start like there is um there's a lot of people talking about um about the product.

11:05I think it's both a remarkable piece of technology, but also remarkably useful for people. And it's making a real difference in people's lives. And I think we all know people that are unhappy in their current role or are thinking about a change or feel like they could be doing better somewhere else. But it's a really tough process of finding out what that next thing is. So having a tool that is both interesting and kind of on vogue for 2025, but also is just a far superior, kind of 10x better way to optimize a really important part of your life, drives a lot of word of mouth. We're then supplementing that with paid and organic social.

11:45Those are the main channels that have been working for us.

11:48Matthew Wilson:Amazing. Do you see those channels changing over time? Now that you've got this kind of like war chest of money, are you going to experiment with different kind of like paid avenues? Or do you think actually what's working now is going to scale for at least the foreseeable future? I think both. I mean, I think you always want word of mouth to be the core driver of your business. I think having a tax better product that's truly differentiated than what's out there, that gets people talking, is the best driver that you can have of a business and you should be constantly striving to level up the product level of the value that you're providing to the customer.

12:25So that should always be the core driver of the business. But, yeah, of course, we'll be experienced with all sorts of things and have been already. And we'll continue to do that and doubling down on what works.

12:35Matthew Wilson:Nice. OK, that's cool. I want to talk about the round. Twenty million dollars seed round from Creandum. Huge round. Creandum has got an amazing reputation. I think I've interviewed two of their partners, you know, in the last couple of months and a bunch of their founders. Incredibly positive feedback. I want to ask, you know, what was your experience like raising from them? I've been super impressed with them I mean this is my third startup I've worked with a whole bunch of investors previously and yeah Creano were my top target for this round I think they're you know they're a stage specialist fund so they focus on early stage they are building this incredible reputation as you know the fund that is spotting you know breakout AI companies coming out of Europe with European kind of DNA and roots that then go on and build globally leading businesses.

13:31And that's the road that we're on. And so working with them and the brand that they bring, but it's a new brand. They've not had this brand for 30, 40 years. So they've still got the hunger and the desire, the work ethic and the hustle that I think is maybe missing from some of the more established players. So they've got kind of both of those two things together, which I think is fantastic. I was super impressed with that team.

13:58Matthew Wilson:No, that's great to hear. Everyone I've met from there has been amazing. What about the speed? You know, like speed is something that I hear frequently from founders and investors that in Europe it's slow. Like getting around, like signed, closed, it takes a long time. But Creandum, I've heard, can move quickly. Was that your case or did it still take longer than you would have liked? The round happened very quickly and was, I think we were building a really exciting business. We've got two experienced founders. We've built a fantastic team solving a huge problem, and the products are being received very well.

14:31So the round was very quick. What impressed me about Creandum was that they'd done a lot of the work prior to us actually going out to raise. So I'd met them earlier in the year, and they'd actually done a lot of diligence by the time that we put our hand up and said, look, we're actually running a process now. So they were able to move very quickly. and then um yeah so it was it was a very kind of fast process once we once we got going but it didn't feel like they were making a rush decision they'd already kind of done their diligence in the background which is amazing yeah that's great they'd done their homework

15:06Matthew Wilson:they'd probably you know to an extent made a decision right they were probably very excited about you and the opportunity and they were always probably ready to go um i want to talk about the size of the round 20 million seed is like a it's a really big seed round especially here in Europe. Why did you want to raise that much money and what are you going to be spending it on? Yeah, I mean, we're really building two businesses in one, right? So we're building, it's really hot. We're building a B2C business. So Jack is a B2C product and we've got a B2C go-to-market. Jill is a B2B product and we've got a B2B go-to-market.

15:42And in order for us to achieve our kind of vision as a business, We need to build both to be world-leading products and then scale both of them very quickly. So really, we're building kind of two businesses in one. On top of that, we are running at two different GOs in parallel, so both Europe and the States. And I think the kind of speed at which you need to move today, you can't afford to do things sequentially. You've got to kind of run things in parallel. so that obviously requires investment in both markets and then I think the third thing is just I'm such a big believer in talent density I think it's always been important but is 10x more important today than it was a few years ago just how more highly levered people are when they're using AI just places a huge premium on talent density and we're building the team in London primarily I think we're building Europe's highest talent density team that's our goal with that when we find somebody brilliant we pay very generously we pay above the top end of market for the best of the best and that obviously requires upfront investment so all of those things together it's important for us to be well capitalised to run out of the opportunity

17:06Matthew Wilson:And how are you planning to crack the US? Well that's top of mind at the moment So all of the details probably worked out or able to share. But yeah, it's something that's really important. I think that we do think that the product is much improved by being an international product. You know, people often move for their careers between geographies. And I think people would do that a lot more if you were able to discover roles in other places more easily. And as a company, you'd hire more from overseas if you were able to discover talent. But actually, you think about the ways that we typically find employees or find jobs today.

17:50They are quite geographically kind of limited. So by being able to win on both sides of the Atlantic and win more broadly internationally, we're going to be able to open up much more opportunities for the people that are using our products and for the companies that are using Joe as well.

18:08Matthew Wilson:Yeah, that's really interesting. not just a classic case of like expand early capture market share it's actually you get the synergies from being in both simultaneously and that they can lift both regions up yeah that's right we've seen that with customers already where we've had customers that have signed up abroad and then they're actually uh that they're that have got visa sponsorship we've got a few companies in the in the gulf regions that are doing this we've got some companies in the u.s that are doing this and they're looking to bring in the best people from anywhere in the world uh bring them on visas and bring them in locally and we're actually able to provide a really diverse tarp for them and that it's just not available to them through other channels.

18:44Matthew Wilson:Yeah, really interesting. And you touched briefly there on some of the customers that you've got and I know that you've got like 50 ,000 users. Can you share any numbers on the customer side or the client side of some of the traction that you've seen? Yeah, we've got a few hundred companies that we're working with now that are using Jill to help them hire. So we launched the Jill product just a few months ago now. So that's growing rapidly as well. Amazing, that's brilliant. And look, I'm conscious we're running out of time, but I wanted to ask one final question, less about Jack and Jill and more about yourself.

19:13Matthew Wilson:This is your third company. You founded two excellent companies in your past. What are you taking and learning from those two prior endeavors that you're now applying to Jack and Jill? It's a really good question. I think there's lots of subtle things, right? You just get better at your job over time in all the ways that you kind of show up day to day and your judgment and your taste and all of those things. But I think, you know, the things that I reflect on being, you know, really, really vital that I want to make sure we do a jack and jill. I think, you know, if you're going to build, aiming to build a global market leading category defining business, you've got to get talent density right.

19:58So you've got to get hiring right. You've got to get this relentless speed and quality of execution right. And getting that right out the gate, I think the first 10 hires, the first 12 months of a company, you know, post-product market fit sets the momentum and sets the flywheel spinning that ultimately leads to a business and how that business looks like 10 years down the line. And those things we've been really relentless about focusing on in the first six months of existence. So just really continuing to be obsessed with that, ensuring that the team is customer-focused and customer-obsessed while you're scaling quickly.

20:41It's very easy to start to be a bit internal-looking and take the eye off the ball there. and then i think that you know the the most obvious external thing that we're doing differently is um we're omnipresent my previous company was a fully remote business and whereas we're building uh fully in person at jack and jill and i think you know i i've posted about this um there's actually a lot of a lot that you gain from being remote but i think the intensity and the ability to to really stay on top of talent density um and just the kind of fun uh and camaraderie that you get building in person is something that um i'm really enjoying about about building this uh

21:21Matthew Wilson:this bit differently than last time yeah you know i've worked at both you know i've worked in a company that was entirely remote and i've worked in one that that's in office especially those early stages in those early days it's quite hard to beat that in office you know that grind of like working side by side figuring stuff out and that atmosphere is quite unique i think especially in the early days yeah and i think you know look i've the the start of company to to build a great place to work to build a great product for the world also do it for myself i really really enjoy being in the office with the team and uh i think it's it's okay to be a little bit selfish about things sometimes as well yeah well 100 that's the advantage you get from being you know the founder and crafting things in the way that you like but look matt thank you so much for joining me it's been an absolute pleasure i've loved chatting to both you and jack congratulations on the amazing fundraise i'm going to be watching closely and if you've ever got any announcements or news feel free to let me know i'd love to do what i can to to tell the story of jack and jill of course appreciate it Seb thanks so much thank you see you later