Matt Wilson, Co-Founder and CEO of Jack & Jill: BREAKING: Jack and Jill raised $40m Series A

0:00Hello, welcome back to Scaling Europe show. I'm Sam Johnson. Today, we've got Matt Wilson back on the show for the second time, co-founder of Jack and Jill, an amazing company. Welcome back, Matt. How are you doing?

0:09Matt Wilson:Yeah, very good. We're having a lot of fun over here. Good to be back. For those who don't know, can you give a quick introduction into Jack and Jill and what you guys have built? Yeah. So I think, you know, the best way to think about what we do is to think about, you know, what are the most important things in our lives? It's our health, it's our personal relationships, and the next is our work. And if you think about the process by which people have found work and workers found people, it's just insanely inefficient for something that's so, so important in our lives and in our companies. You think about it from a person's perspective, the last time you found a job, you know, it was maybe whatever happened to pop up on LinkedIn that day that you were scrolling or at the end of a long kind of brutal search process.

0:56Matt Wilson:or maybe it was through a recruiter or a search firm where you spoke to a recruiter and they were managing two or three clients and they sold you on the one of those two or three that happened to be the best fit. Or maybe it was through your network and if you're lucky enough to have a network, maybe it covers some tiny fraction of the universe of what's out there. And the kind of problem with all of these ways that we've found one of the most important things in our lives is just they cover this kind of tiny fraction of the universe. And for the first time in history, it's now possible to have an agent, to tell an agent, here's who I am.

1:38Matt Wilson:Here's what I've done. Here's what I want out of work. And then put that agent to work, covering the entire universe of what's possible. And that agent is called Jack. And Jack today is working for about 350 ,000 people around the world, primarily in London. San Francisco and New York. And the same thing has been true for companies as well. And as companies think about hiring, and we've built the analog agent to Jack for companies, which is Jill. And Jill works by learning what companies want, and then going out and helping them identify the best people on the market for them. And Jill is working with thousands of companies today to help them find incredible people to join their teams.

2:22Matt Wilson:And Jack and Jill come together to facilitate take these incredible warm introductions at a scale that's never been possible before. Amazing. And you guys are absolutely crushing it. You've got some very exciting news to announce. That's right. Yeah. So we're announcing today that we've raised a$40 million Series A to continue to build Jack and Jill to be the best possible products for their respective customers in the world and to continue their expansion across Europe and the US. Amazing. Can you touch a bit more on the round, maybe who's backing you this time around and kind of maybe what unlocked it?

2:53Because it hasn't been a particularly long time since you were 20 million rounded by Creandum, I think at the end of last year. So yeah, we'd love to hear a bit more.

3:00Matt Wilson:Yeah, that's right. So the rounds led by Airstream Capital and in participation with Creandum, who led the previous round, Madrona and a whole bunch of other fantastic funds and angels. And, you know, I think fundamentally when we started the business just in March last year, so we're less than 18 months old as a company. And since then, as you say, we raised a$20 million seed round late last year. Since that seed round, the growth has been, we've grown about 40x in terms of revenue. And since the seed round, we've landed in San Francisco, we've landed in New York. And just broadly, the thesis is kind of coming true and playing out as we thought it would.

3:46Matt Wilson:both the consumer user base and the business user base for Jack and Joel respectively are both growing very, very quickly. And we continue to be really optimistic about the midterm future, but also the possibility of building something truly again changing over the long run. It's amazing. And so the expansions into New York and San Francisco must have gone well. Can you touch a bit about that? Because especially here in Europe, everybody's always thinking about landing and expanding across the US in a successful manner. How did that process go for you and the team? Yeah, so we launched in San Francisco at the start of 2026.

4:21Matt Wilson:And San Francisco is now, has been growing faster than London was at the same time. Amazing. Indexed by launch dates. And New York is following the same trajectory, although it's only a couple of months in. And I think, you know, with going international, I think you either want to do it early in your life as a company, where it just becomes the default operating model of the company from day one almost, that you are multi-market, that you are operating with teams in different time zones, teams in different offices, and that it's just part of your DNA in terms of how you operate. And for us, it was really important.

4:57Matt Wilson:We think winning in what we see as kind of key taste-making markets, winning in the US as being fundamental to our long-term success as a business and our ability to win globally. So we thought it was really important to get out there and put our stake in the ground and push on those markets. And that's been a combination of action done from London, from our London HQ, as well as building out the office on the ground there in San Francisco and spending a whole bunch of time out there. What was your thinking or strategy in getting those users, right? Because you need to get people on the platform.

5:34You've now got 250 ,000. When you're going to a new city or ecosystem, what is the marketing or overall strategy of getting those first 1 ,000, 10 ,000 people on the platform?

5:45Matt Wilson:Yeah. So I think, you know, first of all, marketing is built on a foundational product. So we've got a kind of marketplace product where we've got companies on one side with Jill and professionals on one side with Jack. How do you build some density into that marketplace so that you can get over this cold start problem? you know if you think we we have a marketplace we also have standalone products so jack works brilliantly well um regardless of jill at understanding who you are and we've added a whole bunch of functionality to jack since we last spoke so jack is scouring every public job listing in the world and identifying them regardless of whether we've got a direct relationship with that that company or not so jack is kind of continuously monitoring every day is that something interesting that's coming to the market for for you so you don't have to be browsing job boards.

6:34Matt Wilson:And you're identified exactly when that dream job appears. Jack is supporting with career coaching, with salary benchmarking, with interview preparation and mock interviews, and kind of a full cycle service that you get from this agent for free throughout whatever stage of your job search that you're at. So we thought about how do we build this product so it works well in isolation of the marketplace, market that, get a user base for that, get that growing through lots of word of mouth, as well as layering on very targeted advertising channels to build density into the candidate pool and then bringing in the company side and scaling that up once we've got the density of candidates.

7:14Matt Wilson:So the consumer side kind of led the B2B side by maybe six weeks. Got it. Okay. Can you touch on maybe some success stories? Can you share some of that real use cases of people that have either found a role through Jack or Jill? the company side? Yeah. Yeah. I mean, there's thousands of people, so it's hard to pick a couple, but maybe one that I think is incredibly cool and interesting. It's a bit different than our typically use case of placing somebody in a full-time job, but we work with a number of accelerators and incubators, helping them find potential founders for their programs. So we work with Entrepreneurs First and Annala, and they work with Jill in order to identify people in Jack's network that they think could be amazing founders to join that program.

8:00That is so interesting.

8:02Matt Wilson:And we had, there was two guys that spoke to Jack. They did an online phone call with an AI agent. And in those phone calls, told Jack that they were interested in getting a job, but also interested in maybe founding something. And you fast forward a couple of months, they've been, Jill working for one of the accelerators identified these people, put them in touch with the accelerator, they've been accepted onto the accelerator. They then co-founded a company together, which is now funded, and that company is actually now using Jill to hire its first employees. No way. So it's a crazy story of this matchmaking done by these agents that definitely feels like we are living in the future.

8:50That's amazing. What a full circle moment. Yeah. That's amazing. Can we touch a bit on our Airstream Capital, you know, leading the round. Phenomenal investors in the age of AI, absolutely crushing it. I think, what, Nathan's largest solo GP in the world, maybe? Like, absolutely crushing it. What gave him the conviction? And how do you feel about getting him on the cap table? What kind of, what do you think it says about the success of the business?

9:13Matt Wilson:Yeah, I mean, Nathan is an incredibly impressive guy, as you say. He's the largest, runs the largest solo GP fund in Europe. I think importantly for us, the pace of change in AI at the moment is so quick. And everything has been built on a foundation of products and engineering, in our opinion. So all of your marketing, all of your sales, all you've got a market motion, that's built on a foundation of having the best products on the market. And having the best product on the market is not something that you stand still on today. We've re-platformed both agents probably every quarter since we started the business.

9:50Matt Wilson:They're totally rebuilt, torn down, and built again. And you have to do that in order to remain having the best product on the market. We consistently ask ourselves, if we're founding the business today, what would we build and how would we build it? And we should probably go and do that because if we don't, somebody else will and we'll be disrupted. And so when we think about that, that can't just be in a team. I think that also needs to be at the board level and also needs to be at the table. There needs to be a deep understanding of the technology and of the fundamental importance of what's going on with AI and being really plugged into not hearing about it three to six months later and living three to six months in the past, but being there on the cutting edge.

10:32Matt Wilson:And Nathan is, for those that know, has been plugged into the veins of what's going on in AI for the last 10 years prior to LLMs and continues to be investing but also researching or broadcasting his media out on really what is going on and what is the cutting edge. So having somebody like that on the cap table, on the board, is a huge value add to us as a company. I mean, the man lives on the cutting edge and has done. He lives and breathes this more than any other investor that I know. I always want to talk about the recent announcement that you made for your engineers. You've increased your minimum compensation package for engineers towards£360 ,000.

11:22That's right. And I think this is even a large increase. I think, was it nine months ago you announced it was$240 ,000?

11:30Matt Wilson:That's right. So now you've grown it even more. It's now one of the most competitive salaries in London for engineers. Why have you done this? Yeah, I think what we see every day in the office working with the best engineers, some of the best product engineers in the world and the team, and what we see in the market with our own products on both working and representing through Jack some of the best engineers on the planet as well as working with some of the most exciting companies on the planet hiring amazing engineers is just the disproportionate value that can be brought by the upper echelons of product engineers.

12:13Matt Wilson:You think about the job of engineering, it's changed so much over the last couple of years from there needing to be a team of people collaborating across product design, QA, DevOps to be able to ship product to say, okay, we can now collapse loads and loads of that into one person. They can move way quicker because they've not got all the coordination overheads of working with a team. What used to take weeks can now take hours. And instead of working with a team of people, these people are now managing swarms of agents underneath them to be able to ship and get work done. And that means that any one individual can just be orders of magnitude more productive than they were a few years ago.

12:55Matt Wilson:And as such, the best people are levered hugely by this technology and are able to ship so much more and are able to be so much more valuable to us as a company, but also to the market more broadly. and if you combine that with the types of products that we're building you know we run with with jack and jill the largest agentic social network in the world um there's no other company out there that's got this many agents persistent waking up every day representing their users and interacting with each other we're really at the bleeding edge of what's possible so combine the kind of productivity gains that you've gone through how engineering's changed with how far we are at the bleeding edge and how important it is for us to be continually pushing the boundaries of what's possible.

13:39Matt Wilson:The number of people that can do that job is just incredibly, incredibly small. And then for us, it also acts as a forcing function. It forces us to make sure that we are living out what we say as we want to build the most talented company in Europe. And if we don't feel amazing about paying top dollar for the staff that we bring in, particularly the engineering staff that we bring in then you know there's something wrong and we're not we're not um at that at that bar and how do you i guess balance people who are coming for the highest salaries with also wanting to solve the mission you know there's been this sort of meme on social media about anthropic and the interview process asking like you know if the stock went to zero would you still work for us as do you feel like there's a tension between paying too much and getting people who are just in it for the money or do you yeah how do you balance that with getting people who are also interested in the mission of the company and building something impactful i think you have to treat the interview process and getting to know people as a as a full package um but um you know everybody's got different financial circumstances in their life and um i thought we we've got people that will take you know a 30 cash 70 equity with as part of that we've got people that will take five percent equity 95 cash so we see a full spectrum It depends entirely on individual circumstances.

14:59Matt Wilson:And we think we should not be paternalistic about that. We should, you know, if we wanted to raise more money, we could raise more money. If we wanted to raise less money and give away more equity, we could do that. So I think, you know, we kind of want to push this tradeoff onto the employees and have them manage their own personal financial circumstances rather than have that be, you know, opinionated from the company side as to what they should be.

15:24Matt Wilson:and then I think it also comes into the types of people that you hire and what they've done before. You know, we hire, two thirds of our team are ex-founders. So you're not getting people that are incredibly mercenary. You're getting people that want to be part of something huge, want to be part of something of a winning team and want to be part of a massive mission in, you know, changing the world for better, which is the kind of core of how we think about Jack and Jill. And the people that you're targeting must be, as you say, the very best of the best. There are increasing number of American companies that are expanding, particularly into London.

15:59We've seen it with OpenAR and Anthropic and a bunch of US companies coming in. And some of these salaries are£600 ,000 that Anthropic is paying. Have you seen, you know, you sit in this place where you've got, I imagine, access to amazing data. Are you seeing that have a knock-on impact on the rest of the salaries. Has that played a role in you increasing the salaries in your own company?

16:21Matt Wilson:Yeah, I wouldn't say it was as direct as seeing Anthropik coming and offering a salary that then has caused us to then change our compensation approach. But obviously we are playing in a market and we want to make sure that we're really competitive for the best people. But the best people have always had tons of options. Anybody in our team could go and move to the States and go and work for a company out in San Francisco and earn the wages that have been possible out there, which are higher than what Anthropik's been. in London, they could go and be a founder and raise millions of dollars on day zero of a company and go and plot their own path.

16:56Matt Wilson:So it's not just about the labs. It's about the whole universe of the opportunities that people have got that we've got to make sure that we're conversed with when we think about the types of people that we want to bring into the team and the type of talent that we want to bring. I think in terms of the rest of the market, there is at the moment a little bit of a bifurcation that's happening in the market where you're seeing well-funded companies, and this includes the American companies, seeing the returns to talent density and then rationally thinking, okay, if people are going to be 10 times more productive and we can be incredibly talent dense, we should be willing to pay more to attract the best people.

17:41Matt Wilson:But at the same time, you've then got, I think that's a tiny fraction of the overall labor market, a tiny fraction of what's out there. And we work on both sides of that. So we work with a lot of the American companies that are expanding into London, helping them build out their initial teams out here. And so we work with them, we benefit from them, that candidates that are working with Jack are exposed to those opportunities through working with us. But we also work with a a whole bunch of other companies across, you know, the kind of full spectrum of the economy, not just, you know, hot AI companies.

18:11Yeah, it's really interesting. Going back to the salaries that you're paying for engineers, we're in this incredible, we're seeing this incredible demand for these top tier 10X engineers, whatever that, you know, whatever they really are or look like. What's the, what's kind of the standout traits you think? You know, I know that you hire a lot of ex-founders. What is it about maybe ex-founders, all these engineers that you think really makes them phenomenal at what they do?

18:38Matt Wilson:I think it's, you know, think about the job having kind of compressed down from large elements of what a product manager would do, what designers would do, what you do with DevOps, what you do in engineering. Like the collapsing of all of those into a single person means that that person has to be excellent commercially, really deeply understand the business, be really deeply thoughtful about products, and be able to go and talk to customers and understand the customer impact of whatever they're building and be able to take something that's much more ambiguous than maybe a few years ago you'd have requirements broken down by somebody else and then handed over to an engineer.

19:20Matt Wilson:You'll say, actually, you're going to go way, way further off in the abstraction layer, and you've got to be able to work at that abstraction layer, work with customers, deal with all of the traditional elements of products, have really good design taste, be really thoughtful about that. Plus, be at the forefront of how to be an engineer that's using AI to be as productive as possible and how to be working with building AI agents and building AI-navel systems as well. So all of those three things together is just a very, very rare combination. And yeah, we tend to find that people that have been founders and have been the founding CTO that's had to go and figure something out for the first time, has had to go and work with customers, has had to be really commercial and think about building the business as well as building the product and doing the engineering work behind that, that they tend to have a really kind of strong mix of these skills across the board.

20:09Yeah, it's a real all-rounder. One final question before I let you go, Matt. You've just raised this big round. It was another big round last year. You're looking forward to the next 12 or 18 months. What have you and the business got to achieve to get you to that next stage of your journey?

20:23Matt Wilson:Yeah, I think it's a combination of doing more of what we've been doing, continuing to grow in the US, continuing to launch in new markets, continuing to build better and better products and continue to have market leading products for professionals and for companies. with also, as I was saying earlier, thinking about the markets changing, the competitive landscapes changing, the underlying possibilities of what's possible with technology is changing. How do we kind of disrupt ourselves every three to six months and think about if we were founding the business today, what would we build? So I think it's a combination of continuing to build out the team, continue to execute on the work we've been doing while making sure that we're disrupting ourselves as we're staying as relevant as ever.

21:10Amazing. Well, I look forward to catching up again, no doubt, shortly. But best of luck and congratulations.

21:16Matt Wilson:Thanks, Seb. See you later.