Will AI Kill White-Collar Jobs? | Matthew Wilson, Jack&Jill CEO

27:33You get to see people send us a message and say, I just spoke to Jack for half an hour about my career. And I cried after the call because it's the first time that I've ever felt that I can talk to somebody and have, you know, some, even if they, I mean, they know it's an AI, right? Yeah. But I felt listened to, I felt heard, and I felt I could express myself and talk about this stuff for the first time in my life and that is remarkable um that and and you know when we started i think there was a question of will people do this with an ai and it was so immediately apparent when we launched that people will have these conversations and more with an ai and they will open up and even more to to the ai what was interesting i played with jack this morning i've used jill obviously from a probably i thought preparation for the interview play with jack and um although i think my team were a bit worried overhearing me sort of talk about a new job and salary expectations but um they were it's the first time i really used ai audio yeah um you know i've just been typing away and and so on and it is amazing how kind of you know lifelike it is and you feel like you're having it's a totally different experience than i mean if you had to sit down and type for you know an hour about what your dream job was, it would be pretty hard work to do that.

29:00And you'd probably end up with something that was pretty incomplete. If you could have a conversation with somebody for an hour about that, and they would interview and they'd ask probing questions and they would listen and then reflect it back to you in a different way, it would be a joyous experience to go through that conversation. And you're doing the same thing. You're putting information down in words, But it's a totally, totally different experience. People open up in a totally different way. One of the insights we had when we launched last year. Anyway, to go back to your question, which was, what did I do in between leaving Omri President and starting Jack and Jill?

29:39I went through this period of introspection and I then decided I wanted to start something new. the things I wanted out of it, I loved what we did at Omnipresent, which was if we hadn't built what we built, people wouldn't have gotten jobs that they got. And I think it's easy to think about recruitment, think about HR, and it sounds, I think the natural reaction is it sounds kind of inconsequential, but it's not. It is the most consequential thing that you can do to, you know, for somebody, maybe, you know, behind their health and their relationships, what we do for work, what we do for, you know, whether that's because, you know, you're somebody like me who work is like a major part of your life and why you love being, you know, you love doing what you do for work and it's a major part of your fulfillment, whether it's a nine to five that's providing you with the financial ability to live the rest of your life.

30:40Like that, it is so, so important. And with Omnipresent, we'd been enabling people in Ghana to get a job for a great US tech company, paying them three times what the local rate would have been. And that person's life was like totally transformed by what we built. And on the flip side, this American company has got an amazing employee that is then transforming their business. Yeah. And I think, you know, both those two things were so magical when we felt like those, when we could see day to day, you know, we might be dealing, at Omnipresent we were dealing with, you know, payroll and labor laws and taxes, but actually what we were doing was enabling somebody to change their life and a company to change how they worked.

31:21And so I loved that. I thought, you know, is there a way that I can get that, you know, address that same underlying mission?

31:32And so I was exploring ideas around that space. I was exploring a lot of other ideas as well. But, yeah, it was probably a year from first thinking about, is there a better way? You know, we've got this amazing new technology with AI and it's pretty nascent at the time. It's still nascent now. It's still developing. But, like, what would a much better version of recruitment look like? What would a much better version of helping people navigate through their careers look like? And it was a year of thinking about that, you know, interspersed with other things and other projects. But it took kind of a year from that initial thought to then starting the company a year later.

32:16And one of the things that strikes me that you're going to get real access with so much of this is understanding the skills of the future. What people actually need to bring. And that is changing so rapidly with AI as well, obviously. But what do you think are the skills that people should be learning in their kind of teenage, early 20s? Yeah, I think there is right now, there is the difference between somebody who can utilize these tools really, really well and somebody who, you know, barely touches them or uses it as a kind of souped up search engine. and we think about our team and how we work, I think there is like a 10x difference in productivity that you can get from being right at the cutting edge of using these tools to not touching them.

33:08So I think there is like a real opportunity for young people in particular to say, maybe you're not going and working at a cutting edge AI company, but you're going to go and work inside of a small business somewhere

33:24and yes, you're inexperienced. Yes, you've not got other skills that other people have developed over 20 years in their career, but you actually can be at the frontier of what's possible and you need to do that thoughtfully. You can't just be, you know, it is possible to just generate a load of slop and make a whole, you know, actually be less productive using these tools than you would be otherwise and be a real pain in the ass to work with if you're just throwing everything into a model and not thinking about the output and not taking ownership of what it spits back out. But you can be much more productive.

33:57And I think for young people, it's a real opportunity to go into businesses that are not really at the cutting edge of this stuff and go, wow, we've hired this 20-year-old. And yes, they've got some development areas here, but it'd be like kind of going back and being able to use computers where nobody in the office could use computers. And it's like, wow, that's actually a really unique skill set that you can bring to a business. So I think there is, you know, it's hard to know, you know, which hard skills are going to be done by the models in the future, which hard skills are not going to be done well by the models in the future.

34:33But just being close and being curious and pushing the boundaries of what's possible, I think you can take yourself quite quickly up into the top 5 % of people. So I think that is available to anybody. I've been using this phrase a little bit over the last couple of months of like the career catapult, right? So career ladder may have completely broken, but actually the career catapult exists where you can, as you say, go into the top 5 % of. And it's a proper quantum leap opportunity for people in their early 20s. Like in some ways, the job market, graduate market has never been harder at that age.

35:10But actually, there is also the amazing opportunity. I think we do see this a bit in the labor market in tech at the moment. is you do have a bit of a bifurcation. So you've got certain people and certain roles that are just in the most demand ever. I mean, the most extreme version of this is, you know, AI researchers, you know, being paid, you know, tens, a hundred million dollars a year, while at the same time you've got people having a harder time than ever to break in. And as you said earlier, that's not just at the entry level. It's also people that are mid-career and what they're doing and the way that their work is changing, is shifting around them.

35:59And I think there is going to be a lot of disruption over the next couple of years. The skills that are needed and the jobs that exist in five years' time, I think, are going to look different to they are today. I think it's going to happen quite a lot across white-collar work. And part of our mission is to say, in that world, if there is going to be a lot of change, we need a better way to help people navigate through that change, to help people say, what's actually happening?

36:38I've been doing this job for 20 years, and parts of it are not done by me anymore. Parts of it are going away. How do I navigate through and how do I manage that? And our career services are definitely not set up for that, for helping people navigate through that. I think AI and tools like Jack can provide so much value to people that are going through this transition. I think there's going to be a lot of people going through this transition. And likewise for companies, the skill sets and the types of roles that people need today, the companies need today compared to what they're going to need in a few years' time are going to be different.

37:10So they're going to need to change their workforce and figure out who they need to bring in to help them stay competitive. So they're also going to need better ways of helping to navigate around this as well. And I think AI has got a big role to play there as well. Daria from Anthropic says that 50 % of white collar roles might go in the next five years. Where do you sort of stand on that? I think go is maybe, is not necessarily the right word. I think change. I think there's going to be huge change. And I think if you look at the role of a software engineer today, being a software engineer in summer of 2026 compared to in winter of 2025, 2026, compared to summer last year, compared to winter previously, compared to some of the year before, it's like unrecognizable.

38:11The job is completely different.

38:17And the skill set and what you've needed to navigate through has been really tumultuous for a lot of people. And some people don't like that change. Some people love the new way of working and some people don't. My brother is a software engineer, and he is not enjoying the change that's happening. He loved how, you know, the hands-on craft of coding. And he doesn't like that that's now been taken away. And that's no longer a core part of the job. Other people love the leverage that you get through being able to delegate parts of this work out to an AI and operate at a high level of abstraction.

38:56So I think, you know, what's happened in that space, I think, is going to happen in lots of other spaces. There isn't a demand for fewer software engineers today. No. But the job has changed drastically in the last few years. And I think we're going to see a similar dynamic. And those that can adapt and change with the times are going to come out stronger. And those that can't are going to have to figure out what they do in a world where the underlying technology has changed so much. So do you think the Jevons paradox will continue to exist when it comes to this? I think so. I think it does depend on the role.

39:37I think if you look at software engineering, I think there's kind of infinite demand for more software. If the cost goes down, okay, well, everybody can have a fully bespoke CRM now in a way that they couldn't previously. Or you can now migrate off that old piece of software that you've got onto something new. or you can build automated processes to run parts of your business or you can do all these things. There is just this kind of, as the cost goes down, there is latent demand that surfaces for software engineering and that's definitely been the kind of cases that's played out over the last couple of years.

40:16Is that true for all services? Is there lots of latent demand for legal services? There's probably some. Is there infinite? But if legal services were 100 times cheaper, would there be this latent demand for 1 ,000 times more legal services or would there only be a 10x? And I think it's hard to know because you don't know what use cases would emerge as something kind of gets cheaper and cheaper. This is my fear with it, by the way, is that we end up in like an absolute bureaucratic nightmare with like the legal side and regulation and so on. Like one of the best books I've read that's actually sat behind you is the Charlie Colner is this working book.

41:05And it's basically the opposite of Jimmy's jobs, right? He goes and interviews 80 people about their jobs today. Came out about two years ago. And it's fascinating about just how much of people's jobs doesn't really matter. And it's just partly health and safety culture. Not even gone mad, right? But there's a great example of it with a construction site worker who is like, I basically cannot have a conversation on site without having to then go and put it in an email afterwards. And that's because technology and email has allowed that to happen. And so it is one of the things I worry about is that humans are very good at creating work for one another.

41:39I think that's true. I think you also see the opposite happening with AI. You know, we think about when we're hiring and building our team, you know what would have been needed a team of people you know if you think about building um a new feature as part of as part of our product previously you would have had you know a product manager that would go out talk to customers think about what needs to be done write up a spec that would then get handed off to a designer who would take that take that set of requirements think about how to how that should be designed and then they'd work then that would get handed off to an engineer who would build this.

42:17And then that would get tested off to somebody in a quality assurance role. And that whole process, because it had these handover points, because you needed to meet and do a scoping meeting, and then you needed to meet and do a team retrospective of how we were communicating with each other, and you needed to have, everybody needed to get coffee with each other once a week to make sure the relationships were kind of staying strong. and actually now that's like one person can do all of that work. Yeah. And it requires a different type of person, but that person can go from idea to executed, to tested, designed, within the space of like half an hour, what would have taken two weeks, three weeks, with loads of overhead and kind of like nonsense, you know, human fluff that needed to be done.

43:09And the AIs don't need that. The agents don't need to have these handover points and have these back and forth. So if you can collapse down work into a single person's head that would have taken multiple people previously, you don't just get the cost advantage to that. You also get this massive unlock of the coordination fluff that takes place when you've got people and they need to collaborate together. Completely. Let's talk a little bit about building Jack and Jill from a team's perspective and so on. how many people are you now we're just over 20 people now just over 20 people right um because you have hired for roles publicly with you know pretty large salaries it's the end time i've seen over sort of 200 grand advertised on a salary anywhere i think um which is a i'd be interested in your thoughts on advertising that publicly um but just why you're hiring that way yeah i mean to answer the first question, why would we advertise that we pay people really well?

44:11I think it's a kind of no-brainer thing to do. We're trying to get the word out there about what we do and attract amazing people to come and work for us. So I think part of why we do that is to attract the attention of amazing people. And if we didn't tell, I mean, I think more broadly, companies should be transparent about their compensation. But particularly for us, if we're going to compensate people really well, it would be crazy to not talk about that. In terms of like why, you know, our kind of talent philosophy and how we've built the company, I think there's a few things that come into play.

44:48So, you know, one is we've hired a lot of ex-founders and ex-entrepreneurs. So about two thirds of our team have founded a company. And, you know, why have we done that? I think we're trying to do something new, and there's a lot of surface area. We've got an agent in Jill for companies, and we need to build that, service those customers, go out and market to and find customers. So we've got this B2B part of the business. We've got a consumer product in Jack that we've got to build. We've got to do support for hundreds of thousands of users. We've got to then market that product. And the way that you market a consumer product is very different than the way that you market a B2B product.

45:38And we're 15 months in, and we're doing this in London, in San Francisco, and New York. So we're now across three markets. And in order to do all of those things, there's zero to one activities across all of those different products, parts of the business, markets. and we value very highly the ability of people to, you know, not do a narrow job but take an abstract job, go and figure out how to launch us in San Francisco, go and figure out how to, you know, make the product better in this way and then to be really resourceful about thinking about the right way to do that. So we've hired a lot of people that are very entrepreneurial and that know how to do these more kind of complete tasks rather than doing something narrow.

46:34We then have a premium. We place a premium on the effectiveness of the people that we work with. If you think, we use AI a lot in how we work. And one way that you can think about AI is it gives leverage to the people. and so if you think if you know one of our software engineers is working with a team of coding agents that person is kind of like eight times more productive if they're working with eight agents than they would have been previously so getting a person that's really really good you know somebody that was maybe twice as good as you could get and twice as productive better judgment than what somebody was before.

47:17You actually get 16x improvement on the output from that person. And you get another benefit, which is if you then have, instead of two people, you have one person, you decrease the amount of overhead in the company, you decrease the amount of communication that needs to be done. So you can keep the team smaller. And anybody that's been in a small team versus in a big team or in a small company versus a big company knows just how different it is and how oftentimes you get a team of 100 people that is only 20 % more productive than a team of 10 people. So I think you get this massive diminishing...

47:55Speaking to a man who worked in government for three years. Yeah, you get these massive diminishing returns to productivity as you build out a bigger team. So we place a lot of premium on how do we get the best possible people into our team so we can keep it as small as possible, but as productive as possible. and with that we think it's really important if we do that that we then compensate at the top or above the top end of market so we can get the best possible people and attract them into the business and those people could go and found a company they could go and raise millions of dollars for their business they could go and work for a big American frontier lab how do we attract those people?

48:38we need to have a whole package as an employer but part of that is definitely the cash and the equity compensation that we give to people. But does it not get to the rub of Jack and Jill a little bit in terms of the broader argument we were talking about at the beginning of the conversation about what's happening in the job market, right? As if the companies can start and scale with much smaller teams, which is undoubtedly true. Doesn't that get to the problem of the sort of, you know, total addressable size of the market for Jack and Jill more broadly about where people go higher. Well, maybe.

49:11I think, you know, if there's a fixed number of companies solving a fixed number of problems in the world, then that would be true. I don't think that's true. I think there's a lot of problems in the world that nobody's working on that could be solved. I think if you could have, you know, the same number of people working at twice the number of companies working on twice the number of problems, that would be fantastic, right? Yeah, totally. No, I think it's a fair point on that. And what have you learned already about launching in San Francisco and New York and London? Like just comparing those cultures to us.

49:47I see on your LinkedIn profile that you list yourself as San Francisco based. Yeah, I mean, I've spent, I probably spent 50-50 time in the US and in the UK this year. So I've been spending a lot of time out in the States, getting the market up and running. and I think we work in the tech industry in London, which is closer to the Silicon Valley culture than it is maybe to the rest of the UK culture, actually, in a way. You've got a lot of the companies that we'll work with or that we'll be spending time with, whether they're customers of ours or whether they're vendors of ours, I'd say do have this kind of Silicon Valley DNA of being really ambitious, of being quite aggressive, of thinking about how the world could be a vastly different place rather than thinking in these kind of incremental terms.

50:47So I do think we have some of that in pockets here in the UK. But when I just contrast our launch in the UK last summer to our launch in San Francisco this year, I think the thing that has been more difficult in the US is just breaking through. There's so many more companies, so many more tech companies in San Francisco. It's such a noisy market. It's such a, you know, if you announce a fundraise in London, it's actually still kind of interesting that this company has raised some money. You know, we were six months old. We raised a$20 million seed round. That's pretty interesting in London. it's kind of, you know, one of 10 that day in San Francisco.

51:32So, you know, you have the, just to be able to cut through when there's so many people kind of shouting and trying to get attention in San Francisco is definitely harder than it has been in London. And doing that with a team, you know, we're big believers in the quality of the talent in London. And we think there's massive, you know, alpha and arbitrage imagine the world undervalues the quality of the technical talent in London. So we intentionally built out our core team, our engineering and product team here in London. But, you know, that obviously then comes with, you know, a network and a platform in London and connections of the team in London that we didn't have as much in the US as well.

52:19So that was also just kind of going from your home market to a new market. It comes with its own challenges. How did you go about using your – getting those first few hires? I mean, obviously, you've been a sort of entrepreneur before, so you've got quite a – but how did you do that? I mean, presumably now you use Jack and Jill Bright. Of course. But how did you put together those first few, I guess? Yeah. If I look back at the first couple of hires, there was a mix of –

52:52the first hire came in and applied I posted about what we're doing just after we'd launched in April of last year and I posted saying hey we need somebody we've got a lot to do the market's responding really well to what we're doing and we need an extra pair of hands in a generalist role and we're looking for somebody really entrepreneurial who wants to come to something super early on and we were two people and six weeks old at that point

53:22and had a whole bunch of people apply and message me, but there was one guy who messaged me. And it was actually a remarkably quick turnaround. He'd just finished, wrapped up his own startup. He tried to build something. It hadn't quite worked, and he decided to move on. And I think I posted about this on a Friday or a Thursday afternoon. He messaged me that evening. we got on a call that night he then came in i think the next day or the day after and we part of our interview process we always do a full day working with somebody um so i think it was actually on a saturday he came in and we did a full day working together and um i think he finished up at five o 'clock we wrapped up and i said um and i said look like me and sarah's my co-founder will have a chat.

54:15He was on his way home. We decided we'd make him an offer. I called him up. He was on his way home, made him an offer, and he turned around and came back in and worked the rest of the evening with us in the office. So it was probably like three days end to end. And I think that is a superpower in terms of the ability to drive cycle time on these things. It's something we think about through our recruitment process today and getting really up and close and working with somebody. You get so much more signal than you get in an interview. So that was one. The next two... How do you find people respond to you with that?

54:44Because, I mean, Barney said something very similar to me from Clio. He's like, try and work with someone like before, and all those points around signals, so true. Like, how do people respond to that when you say, look, I want you to come in and work for a bit? Yeah, I mean, we pay people. So we pay, you know, if we bring a software engineer to come and work with us on a trial, you know, we'll pay them$1 ,000 for the day. So, you know, it's not we're getting them to come in and do free work. Like, it's very clearly we're going to pay you half of this day. like this is, you're going to come in and you actually do real work on that day as well.

55:15I think people respond really well. If I'm, you know, if I'm really ambitious and really discerning about what I'm going to do with, you know, what job I'm going to go and do, I want to see how you guys work. I want to work with you. I want to, you know, come in. I want to have dinner with the team and see who I'm going to be working with. And so we view that as not just a, like, you know, an interview should be a two-way process of us getting to know you and you getting to know us. So people, I think, see, you know, if they're going to want to come and work really intensely as part of a startup, and they've got, you know, all of these options, they are equally as discerning as we are about the places that they go and work, as we are about the people that we want to work with.

56:00So it's definitely kind of positive two-way exchange. I think if we were doing it and we weren't paying people, I think it would be a different thing if we're asking people to come in and do, you know, day of work with us um obviously people people that have got full-time jobs we've got to work around that so we'll do maybe two evenings or we'll come in on the weekend and work with and work with someone um but um yeah it's been received really well i think it's really interesting we've done it a bit with people coming for strategy days and so on um it's interesting yeah we're not obviously as software dependent as you guys um but it is it is a very interesting way of doing it yeah you get so much more signal um and um yeah one of the learnings i've had from that is you know when i'm running those i really like to work on like a real life problem with people i think you can if you make the problems artificial you're not engaged in the outcome i remember we had somebody else come in and we were doing uh we were going on a company off-site in the next day and somebody coming in for a chief of staff type type role and i hadn't built my presentation for the next day to the team for the offside.

57:05So I was like, look, let's sit down, let's talk about what I want to say tomorrow and then I want you to build the presentation I'm going to give tomorrow. And I was really engaged in that he did a good job because if he didn't do a good job, I was going to be up all night putting together the presentation and that gave me so much signal because it was like, it was, that That could have been his first day and it would have been a real project. And I was engaged in that versus it was a hypothetical assignment that we gave him that we were kind of going through the motions of asking questions and probing on.

57:44Yeah, it's really interesting. What were you talking – I mean, I was just asking you generally about how you built – The early hires. Yeah, the early hires. The other early hires we made, we made through connections we've made. So through people we knew previously. So the first software engineer we hired was somebody who, Saras, my co-founder, had actually been trying to hire for about 18 months at that point. He'd had another company previously, and he'd been pursuing this guy for 18 months of like, I want to work with you, and he'd always said no. And Saras is amazing at this, kind of relentless, and won't take no for an answer.

58:27and he, yeah, just, you know, we're working on this new thing. Come in, let's have dinner together. Let's talk about what we're doing. And that was the second hire. And then the third was, in between the two companies, I've been working, helping out with a program called Entrepreneurs First. I think you're familiar with the Entrepreneurs First program. And that's an early stage startup accelerator and Incubator where they take in people before they've got a startup, kind of throw them in a room together and shake them up and then support the teams that kind of form out of that and the ideas that form out of that into being companies.

59:09And I was, while I was in between the two companies, I was helping them out and going in and, you know, once a week meeting with the teams that were going through the program that were maybe in their, you know, their first week or their fourth week of their company and helping to kind of advise and be a thought partner to them in their companies. So the next hire we made was somebody who I had actually, he'd gone through that program. I'd been his advisor through that program. He'd not founded a company. And I then, this guy's amazing, amazing software engineer. I really want to work with him.

59:45And he was, so that was, it was going off of existing connections for those first couple of hires. Because at that point, you want to get somebody really good they kind of need to know who you are because you've not got any other proof points yeah um why would why would if he have kind of worked for a two-person company um that had you know was eight weeks old um there's nothing to believe in apart from the people so it's a big advantage when you're in very very early days to um have some existing relationships you know definitely i think it's i think it's really i've talked about this a few times but i think there is a very interesting podcast content series of people that go and work at startups early doors like we first employee yeah like we we really lionize the the founders i totally agree the early employees like uh do so much in shaping the company yeah and um yeah i think they're under they're underrepresented and underspoken about yeah yeah exactly exactly um brilliant it's been amazing to have you on like it's been fascinating seeing all the stuff that you're doing and the way that you're going about it and yeah it's amazing to have this company being raised in london right um so yeah congratulations on all you've done and yeah awesome thanks for having me on pleasure fall has never looked or tasted this good sweet greens fall harvest menu is back with seasonal favorites dressed to impress and made to be devoured warm roasted sweet potatoes crisp apples maple glazed Brussels, and crave-worthy flavors in the autumn harvest bowl, maple glazed salmon plate, and roasted bacon Brussels side.

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