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  3. Brainfood Live On Air - Ep410 - Future of Hiring with Matt Wilson, CEO of Jack & Jill
The Recruiting Brainfood Podcast

15 Sep 2026 · 38m · 17 chapters

Episode artwork

Brainfood Live On Air - Ep410 - Future of Hiring with Matt Wilson, CEO of Jack & Jill

In short

Future of hiring and recruitment in 2026, focused on “signal vs noise” in an AI-driven job market. The episode discusses Jack and Jill’s two-agent model for candidates and companies, how it searches public jobs (~14 million listings/day), and how it supports discreet/in-incognito hiring and candidate searches. It also covers incentive alignment, context-building over time, fraud/reputation controls, and plans after a Series A raise.

Guest

Matt Wilson, co-founder and CEO of Jack and Jill (UK/US team; launched <18 months ago). Previously co-founded Omnipresent, an HR tech platform for global employment/payroll/benefits; exited after ~18 months.

Key claims

Career/job search is inefficient and luck-based; AI increases noise; Jack embraces AI and uses reputation systems plus “context loops” to improve matching. Jill connects candidates to hiring teams with richer off-market context.

Notable examples

WhatsApp/email/Slack agent access; “incognito mode” for candidates; “block lists/black lists”; compensation benchmarking and negotiation support; Series A $40M; US launch and New York launch mentioned.

Written by AI. May contain mistakes.

Chapters

0:46

Introduction to Jack and Jill

Matt Wilson introduces Jack and Jill's unique recruiting agents.

“really hot off the press and the press, if you haven't noticed, is the huge news.”
3:33

Matt Wilson's Career Journey

Discussion of Matt's career and his transition from Omnipresent to Jack and Jill.

“And Jill is an AI agent for recruiting that is working for thousands of companies around the world with a similar idea.”
6:22

Inefficiencies in Job Searching

Exploring the inefficiencies of the current job search process and the need for innovation.

“But actually, you know, what we were doing every single day was changing the lives of the people that we were serving in this incredibly meaningful way, allowing people to get access to these incredible opportunities.”
8:39

The Role of AI in Recruitment

Discussion on how AI can improve job search efficiency and market monitoring.

“So that was really what the kind of through line was between both companies, just feeling like there's this huge problem that we can go and help solve and help make the world a better place.”
11:52

Jack and Jill's Unique Marketplace

Understanding how Jack and Jill operate in the recruitment marketplace and their advantages.

“Let's have a look at the mechanics of it with a little bit more depth, Matt.”
14:01

Enhancing Candidate Connections

Learn how companies can strengthen their connections with high-value talent.

“We all know the limitations of that textual sort of data, a lot more richness that will come from this dialogual way of extracting information.”
15:01

AI Conversations in Job Searching

Explore the experiences of candidates interacting with AI during job searches.

“Guillaume here has said, actually, it was a very interesting conversation.”
17:15

Quality of AI Recruitment

Discover how Jack and Jill achieves high-quality AI recruitment services.

“Please make, sort of stick more of those comments in.”
18:50

Signal vs Noise in Recruitment

Understand the challenge of filtering noise in AI-driven recruitment.

“outbounding, just the level of noise on both sides of the divide is just going up and up and up.”
21:00

Dynamic Job Discovery Process

Learn how Jack and Jill adapts to changing user preferences in job searches.

“who's going to get the most talented people?”
Show all 17 chapters
23:08

Meeting User Needs with AI

Find out how Jack and Jill's AI meets users where they are in recruitment.

“So, you know, that, how do we build functionality that is constantly building context over time?”
25:09

Diverse Roles and Future Expansion

Explore the variety of roles Jack and Jill is filling and future plans.

“I think the era of logging into a marketplace and just scanning for the latest stuff that's like brought to you is well passed.”
27:37

Confidentiality in Executive Searches

Discuss the importance of discretion in executive recruitment with Jack and Jill's model.

“So we wanted to go pretty broad from a role and from a seniority perspective to enable this word of mouth, and that's what we've seen over the last year or so since we launched Jack.”
28:03

Discretion in Job Searching

Discusses the importance of discretion in job searching for both candidates and hiring teams.

“How do you think that sort of Jack and Jill model fits in with that sort of frame?”
31:45

User Control Over Data

Explores how users can manage their profiles and data on the Jack & Jill platform.

“I've got a couple more questions for you.”
33:06

Addressing Candidate Fraud

Examines how Jack & Jill verifies profiles and addresses potential candidate fraud.

“The stage at which we can then is with, this is true in both directions, is with reports from users.”
34:40

Future Plans for Jack & Jill

Matt Wilson discusses the future development plans and funding goals for Jack & Jill.

“Final couple of questions for you, Matt, because I am totally respectful of your time.”
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Transcript

Automatic transcript. May contain errors.

0:05So, brilliant stuff. And yes, we are live, everybody. Welcome, everyone, to Brain Food Live on Air. I don't know what episode this is. We're on episode like 5 ,000 or something. We do tons of these, probably like over, over, sort of exposed at this point. But there's so many great conversations that need to be had in the world of recruitment in 2026. and so we have to keep having these conversations particularly when we've got so much innovation happening in our space. Folks, I'm delighted to be having this sort of chat today. It's really special because it's breaking news. It's all happening and it's happening right now really hot off the press and the press, if you haven't noticed, is the huge news.

0:51I think it announced today that our good friends at Jack and Jill have raised a stonking amount in Series A. I think it's$40 million or something like this. That's right. And a huge raise for a company that's already making like a huge wave all over the recruitment world. Matt, you'd be interested to know out in San Francisco and New York, two independent meetings and events last week. And Jack and Jill were mentioned two or three times in both events without my solicitation by U.S. recruiters.

1:27Matt Wilson: That's great to hear. We launched in the US at the start of the year. We just launched in New York recently. So it's good to hear the words getting out. Already sort of happening. So brilliant to have Matt Wilson here in conversation. Matt, let's just introduce you real quick. Why don't you quickly say a couple of sentences. Who are you? What is your due? Yeah. So I'm Matt Wilson. I'm one of the co-founders and the CEO here at Jack and Jill. Jack and Jill, we are just less than 18 months old as a company. and we're split between the UK and the US as a team. And what do we do? We've built two different agents, Jack and Jill and Jack works for professionals, is an agent that goes to work for an individual professional to help them find their dream job.

2:15Matt Wilson: So Jack will spend about 15 to 20 minutes on a phone call with somebody much like going for a coffee with a recruiter. that recruiter is working for you. So Jack gets to know who you are, what you've done, what you're looking for, what your dream job is in really, really rich detail. And then using that information, he then works for you as a professional to help you find that dream role. So he does that through looking every day at every single job listing that gets posted anywhere online, can support you with your applications for those, can help you with doing mock interviews and giving feedback and building confidence ahead of going into a process and all the way through to helping you benchmark compensation and even helping you dry run negotiating your compensation at the end of the process.

3:05Matt Wilson: So really, how do we build Jack as this personal recruiter that is working for the individual end to end, whether they are figuring out what they want to do and they want to do some career coaching all the way through up to negotiating an offer. And Jack works for about close to 400 ,000 people today, all around the world, but with concentration in London, in San Francisco and in New York. And on the flip side, we've built Jill. And Jill is an AI agent for recruiting that is working for thousands of companies around the world with a similar idea. How do you really understand and load this agent in Jill with as much context as possible on who you're looking to hire and what the skills are, what the culture is like at your company, who's going to be a great fit.

3:57Matt Wilson: And then Jill is going out and connecting you up with people in Jack's network and beyond to help you place incredible impressions at your company. So Jack and Jill together form the largest agent social network in the world today. And yeah, we're just getting started. So the goal is to take this to a billion people over the next couple of years. that's an amazing vision and i love the vision of it i love the scale i love the name as well i think everyone loves the name um matt because it's one of those that immediately we rock it you know it's one of those where you know what i can't understand exactly what this is without even having to press into the even experiencing it it looks like we've got agent to agent communication let's talk to it we've got already people in uh in the chat saying a big fan of jack so whoever is doing the conversational experience there for Jack big thumbs up there thank you very much Randy um so and I guess I need to start off with a bit of an origin story Matt um because you you obviously have got a very interesting career I don't want to get into the the sort of physicist type of work you're doing I want to do that at another time because you're brilliant trajectory but you have already been a successful recruitment entrepreneur um when you set up launched a sort of omnipresent you exited that to deal um why do you going why did what inspired you to give it around too so quickly like most people think okay great exit i'm off on the beach for a couple of months like what made you think right actually no i was only in that i was only a hors d 'oeuvre i did i did go to the beach for a couple of months i uh i i had it was 18 months between leaving um omnipresent and starting jack and jewel just for context for people listening I mean, Omnipresent was a HR tech platform that offered global employment, payroll and employee benefits services.

5:49Matt Wilson: So really kind of at its core, the mission behind that company was there's amazing people all over the world, there's amazing opportunities all over the world, but administratively, it's really difficult to connect up these people and these opportunities. And there's all of these legal, HR, administrative, financial barriers that come up to a great person being able to work for a great company. And I just loved what we did every day. You know, we were doing pretty mundane work, right, of building payroll engines, of working with health insurance providers all over the world, of handling people's pensions, of dealing with employment law.

6:27Matt Wilson: But actually, you know, what we were doing every single day was changing the lives of the people that we were serving in this incredibly meaningful way, allowing people to get access to these incredible opportunities. And on the flip side, I learned companies to access incredible employees to go on and contribute to the missions of those companies. And I think, you know, coming out of omnipresent, I took, as I said, 18 months figuring out, you know, what's that next thing that I want to go and spend the next 10, 20 years of my life building. and I just kept coming back to this idea of like I think the way that you know the things that are most important in our lives our health our relationships and then it's our work and our careers and the way that people navigate through their careers is just like insanely inefficient and insanely luck-based you know how do people get jobs probably there's a few different ways you go and browse through a job board you browse through LinkedIn and you send off some applications and increasing volumes of applications being more and more people and just never hearing back even if they potentially are a good fit for that role.

7:35Matt Wilson: And it's just this incredibly inefficient process. The way that you actually search over these platforms is really poor. You're not searching for what you really want. So you've just got to morph that into some set of filters. And that's a really inefficient and pretty horrible way to go about finding a role. The next thing that you might do is if you've got a network, maybe you can get some introduced to somebody, but not everybody has a network. And if you do, you're maybe only getting introduced to like 1%, if that, of all of the potential opportunities that are out there in the world. And wouldn't it be better for such an important thing in our life to be able to cover everything that was possible out there?

8:10Matt Wilson: And thirdly, you might go and work with a recruitment agency. But again, those agencies are only working with a very small number of clients at any one point in time. So it's getting very, very little coverage. So I think it was looking at this, you know, this is one of the most important problems for us as individuals, for companies, for the economy more broadly, and it's just done in such an inefficient way. And actually looking around at who was innovating in this space with AI, it felt like most of the vendors were kind of supercharging the inefficiency rather than were actually going, you know, how should this work and what would be a much, much better and much more optimistic way that we could build the labor market connectivity to make this much better for people and for companies.

8:54Matt Wilson: So that was really what the kind of through line was between both companies, just feeling like there's this huge problem that we can go and help solve and help make the world a better place. Yeah, amazing stuff, Matt. You actually mentioned the inefficiency of it. And I think everyone immediately understands sort of that's the case. And I just wonder how many people actually end up like having really life-defining sort of situations just happen to them and they end up with something suboptimal and they just you know that's that's what they've just driven down to and before you know it they're locked into a certain career path I think that's almost everybody in the world I think is uh is making suboptimal decisions in their career you know right from the very start of going okay what am I going to even do you talk to most people in their careers and say how did you get into this well I kind of fell into it you know I you know I was coming out of school or university and I was thinking about what to do and like I happened to get this thing and then I happened to be in this role and like fast forward 25 years and like I'm now still doing that.

9:52And, you know, I think that's true

9:54Matt Wilson: on this kind of like career spanning trajectory, but it's also true of every individual decision that gets made. Oh, why did you move from this company to this company? Like what process did you go through to analyze, you know, the whole spectrum of what was possible that you could go and do? And it's just the tooling and the services haven't been there for people or for companies to have this full kind of spectrum of consideration. And it's now for the first time it's possible to do that. We've got technology that can really deeply understand nuance, really deeply understand domains, not the set of Boolean filters that are being applied to a search, but taking in the real requirements on both sides with all of the trade-offs and then be able to do that with scale.

10:38Matt Wilson: So unlike the kind of human-led services that have come before, where it's only happening over a very small network or a very small number of clients. We're able to do this at kind of the scale of the internet with this depth of nuance and domain understanding that the latest all comes out, which is really remarkable. Yeah, and the challenge, by the way, folks, if you didn't know, I mean, we are embodied intelligences with basically two eyes, two ears and one mouth and limited time. So even the most diligent job seeker is going to have a narrow window. pre-AI that have a very narrow window that they're able to look at.

11:15And they'll have to make choice really on a very small sample. That's right. That's right.

11:22Matt Wilson: And sorry to interrupt, I think that's true of the most active job seeker that is going out and spending all of their time on their job search. But it's 100 times more true for the passive job seeker. And we think we should be living in a world where you have an agent that is constantly monitoring the market for you, regardless of whether you're in a traditionally what we would call an active state or not. Everybody should be having a vision, continually monitoring the market and seeing if there's something that's like bar hurrying for them that's out there. Yeah, fantastic. Let's have a look at the mechanics of it with a little bit more depth, Matt.

12:01You mentioned sort of you've got Jack and Jill, two opposite agents, basically dealing with the two-sided marketplace. What is that marketplace? Is it actually a wall you have to apply into? So for instance, are the jobs that Jack is going to source for me as a job seeker, are they the ones that have to correspond with what Jill is doing? Or is it open web, it's going to scrape everything and then sort of see what's what? Where are we currently with with the product on that side, Emma?

12:32Matt Wilson: Yeah, so for candidates, we do both. So we will have Jack look over every public job listing that we can find. So I think it's about 14 million a day that Jack is searching over on behalf of the, roughly 400 ,000 people that are working with their own Jack. And we don't have relationships with the vast majority of those companies, of every company in the world. We don't make any money out of those. the consumer product is free. So we are, you know, Jack is there to work for you, not to work to get us a placement fee. And that's really core to how we think about two agents, there has to be this incentive alignment, where Jack works for the professional, Joe works for the company.

13:16Matt Wilson: So, you know, what's good for the, what's good for the professional is seeing the entire world of opportunities out there. But, you know, better than here's a job description that's gone up this morning, which looks really interesting, is Jill has spoken to the hiring team at this company. It looks like a perfect fit for you based off of what we've discussed. And I think, you know, based on what I understand about your background, I think you'd be a really good fit for what they're looking for. Let me connect you directly up with the hiring team, and you can go straight into a process, you know, like you would if you're working with a great exec search partner, they wouldn't be making you go and apply for that job.

13:52Matt Wilson: And they would have a lot of context on, you know, what was going on in that company and why that would be a great, great fit. So, you know, we think about how do we bring the entire universe, those that we work, those companies that we work with directly, where we can offer this like direct line into the company and a whole bunch of off-market information, as well as bring the entire universe of what's out there publicly as well. Yeah, fantastic. And we can see the organizations that do interact with Jill will probably end up having a much stronger ability to connect with the high value talent simply because you're going to provide that additional nuanced context that can't be captured in a 300 word sort of job description plus career page.

14:31We all know the limitations of that textual sort of data, a lot more richness that will come from this dialogual way of extracting information. And by the way, we've got some sort of compliments for you already, Matt, on the chat there about the conversational style. A quick question for everyone watching. Have you had a conversation with an AI agent, quote unquote, on the job search to date? Have you tried that? How did it make you feel? Let me know in the comments. Guillaume here has said, actually, it was a very interesting conversation. I'll read it out. Better than the actual humans, goodness.

15:09And I know Guillaume's probably missing this up here, So I understand his comments there with a bit of context. But the first time I spent a good time on something and not someone, a weird feeling, but a suggestion of jobs after a few refinements, it was absolutely spot on, which is something you verified. They knew the people in the companies that the business was referring to. That seems like a ringing endorsement, Matt. How did you get to that level of quality when so many other sort of AI agents have not been able to do that? Can you tell us a little bit about how you got to that level of quality?

15:43Matt Wilson: Yeah, I mean, I think it comes down to my CTI and the engineering team that we've built. The reality is it's never been easier to build a first version of a product. But when you're working at the kind of cutting edge, the bleeding edge of what's possible with these agents, it's really hard to build something that's market leading. And we have, I think, you know, one of these strongest engineering teams of startups worldwide, but particularly in London and in Europe, we have an incredibly high bar for the team, or Gourley, but for the engineering team, as working with these agents, operating this, you know, the largest agentic social network in the world, brings a whole kind of slew of challenges in terms of trying to, you know, make that work as best as possible for people.

16:33Matt Wilson: And then it's just spending lots of time with people being really user-centric in terms of how we build, how we iterate. And also, the underlying technology is changing so quickly that I think probably every quarter since we started the business last spring, we've totally torn down and rebuilt the agents because just what's possible almost week after week at the moment with new models and new capabilities coming out, is changing. So it's just important that we're kind of constantly, you know, even as a less than 18 month old company, like thinking about how to disrupt ourselves and what's going to, what's going to, what could somebody else produce would be even better.

17:13Matt Wilson: So I think just like very relatively product focused as a company. Yeah, fantastic stuff. Folks, I see questions flying in. Please make, sort of stick more of those comments in. We're going to get to each one of those as we go through. But I'll pick a mix as we do it as well. And one of the questions I want to ask you, Matt, is really firstly on the context of the wider world of this mass supply sort of scenario where everyone's using AI of some sort. They've increased their applicant sort of capacity. And that's led to what people say, you know what, increase of noise, reduction of signal. How is it that Jack and Jill have tried to resolve that problem?

17:51Because isn't there also a situation where I could enter into Jack experience a little bit disingenuously, let's say, you know, fine, I'm going to pick out some of these amazing jobs. I want 500k starting salary. I want all of this. It's basically stuff that, you know, I've had to input it. How do you kind of understand that I'm not, you know, a really good signal candidate compared to someone actually is, you know, a real high value sort of prospect for an employer?

18:19Matt Wilson: Yeah, I mean, signals noise, I think is the phrase that is repeated more than anything else at Jack and Jill. and it's really in the, you know, the kind of founding principle of the company is, can we provide incredibly high signal to noise, career services to people and creating services to companies? And yeah, I think you're right. As AI is, you know, as candidates are using AI more to support with, you know, kind of mass supply, as companies are using AI more for sourcing and outbounding, just the level of noise on both sides of the divide is just going up and up and up. And it's so hard to kind of break through.

19:00Matt Wilson: And that's really the kind of insight behind the company is how do you, this is going to happen, like everybody's acting rationally in this world. And like that is going to happen more and more. And I think we're still in the very early innings of that happening on both sides. How do you kind of find signal in a world like that? And for us, it's just kind of skipping to the end game. If everybody's going to be using an AI, well, let's embrace that. And let's have you brief your AI with what you want. Your AI has got infinite patience to look over all the opportunities. And the company hiring AI has got infinite patience to look over all the candidates.

19:34Matt Wilson: How do we build, you know, within that, we've got to build good reputation systems, fraud detection to make sure that, you know, the agents are faithfully representing their, the professionals and the companies that they're working for. but if you can do that you can then really look over everything and find this incredibly high signals noise matches within that I think this idea you know one of the beliefs we have also is that there isn't really such a thing as you know top talent that is a different thing for every single company and you know anybody that's been that's worked in in recruitment for a mixture of different companies will know that they'll go around it all of those companies will say that they only hire top talent.

20:17Matt Wilson: And then you go and you talk to other companies, what are you actually looking for? And it's totally different from one company to another. And it's the same for candidates, what an individual wants out of work is very different than the than somebody who on the surface may look quite similar to them. So for us to say, how do you not judge what somebody wants or what somebody can do based off of you know, a very thin LinkedIn profile or a resume, but actually take that, you know, really full picture of who this person is, what they've done, what they're optimizing for, and do the same thing from the company's perspective.

20:49Matt Wilson: And view this as how do we match in this high signal to noise way, people or opportunities they're going to be really well suited for and vice versa, rather than just how do we rank everybody from one to seven billion and then say, okay, well, who's going to get the most talented people? That's not how humans work. That's not how jobs work. yeah really good Matt I love the um basically the quality measures is contextual isn't it um I'm reminded of like football teams and what have you you know when you have a star player for one club transfers to another another club suddenly performance collapses I mean you know what it's just context um you know what is good for one team is not good for the other so um so a really important sort of thing for a person recruitment to uh to recognize um things do change though Matt As we go through the job discovery process, as we go through the job search process, and on the other side, as we go through the recruitment process, how does Jack and Jill sort of keep up the dynamism of changes of motivation?

21:54I may start a conversation, for instance, with Jack to say, you know what, I really want this, this, and this. I then have a chat with my partner who then says, actually, have you thought about this? And I think, oh, no, I didn't. And my view has changed. So how do you track sort of the change of posture, I guess, without being like overly, you know, intrusive to the person? Is there a way you've done this?

22:18Matt Wilson: Yeah, I think there's probably two things that we think about here. One is how do you build functionality that is adding value to the user, whether it's the professional, whether it's the hiring company, that is also allowing the agent to build context over time and calibrate better over time. both in understanding you more deeply over time, but also as your wants and needs change and your preferences change, or as you even kind of realise what it is that you want, kind of changes through a process. And again, anyone who's worked in recruitment, this kind of period of calibration with the hiring manager of taking the initial brief and then sharing candidates.

22:55Matt Wilson: And what they said in the initial brief is actually different than what their revealed preferences are when they go and actually start talking to candidates, or maybe through some early interviews, opinions change as people kind of start to see the reality of what that role could look like. So, you know, that, how do we build functionality that is constantly building context over time? So, for example, if you were working with Jack and Jack was sending you some publicly listed jobs and you were then, you know, over time, maybe your opinions would change in terms of which ones you'd be saying, yeah, like, let's look at this one that looks like a great fit.

23:28Matt Wilson: That one's not a great fit for whatever reason. through that Jack is then learning what your kind of current preferences are at that point in time and that can then influence the companies that we might match you with if they're interested in those opportunities or not so it's about building these kind of context loops inside of the agents so that you're continually collaborating continually learning on both sides and just like a human would if you were interacting with somebody over a period of time, you wouldn't have to say, okay, let's sit back and talk about what you actually want. You'd just become.

24:04Yeah.

24:05Matt Wilson: Fantastic. I love, sorry. As I say, the other side of that is just meeting users where they are. So, you know, our Jack is not just there in a web app whenever you want to go and like do a bunch of recruitment, do a bunch of job related activities. Jack is there in WhatsApp. You can just drop him a note at any time. You can drop him a voice note. you can go back and forth there. Jack will be sending you emails and you can be emailing back and forth. And likewise, on the company site, Jill is there in Slack with their users. Jill is there over email. Jill is integrated into the ATS. Jill is there through that web app as well.

24:44Matt Wilson: So, you know, a big design principle for us is like these agents should meet the users where they are. Just like if you're working with a great human, you would expect that they would be able to message you over whatever channels and be able to drop them a WhatsApp or send them a message in Slack. And, you know, that closeness and decreasing the friction to actually update the agents is a big part of how you drive that context-wide rule as well. Yeah, fantastic. I think the era of logging into a marketplace and just scanning for the latest stuff that's like brought to you is well passed. um and folks if you if you were sort of one of the ogs you'd remember like 13 years ago i launched a talent marketplace um which tried to do uh you know the talent matching uh solution didn't work as none of them did um and we i think we're all waiting for agentic ai to make that match human person screening jobs going through that paginated experience that's not a good way to do job discovery.

25:43Same thing on the recruiting side, paginated searching of hundreds of candidates, not the way to do it. We don't have human patience, but AI doesn't have these constraints. And it could go through all of those things without sort of any drop in performance. Got some brilliant questions coming through in the chat here. Matt, I'm going to put them through to here. This one from Miranda is very interesting. What industries, actually I'll rock this in with what Nuna has said at the bottom. Firstly, what types of roles are you seeing Jack and Jill kind of performing best at or where the core ICP is currently?

26:26And then I guess the follow-up is where might they expand? Where's it going?

26:29Matt Wilson: Yeah, so today we primarily see success we've primarily focused on working with tech companies, startup scale-ups, larger companies in primarily hiring either remotely in San Francisco, in New York or in London and and we work across the full spectrum of roles and the full spectrum of seniority levels. So we place a software engineer, a mid-level software engineer but we've also placed an entry-level customer support person. We've also placed executive and board level roles as well. So it is a huge spectrum in terms of the role types and the seniority types. And that was a deliberate decision to say, you know, we're not just going to focus on one role or one seniority level, because the biggest growth event that we have, building a consumer product is word of mouth, and building an amazing, remarkable consumer product.

27:28Matt Wilson: People will use Jack, and then they'll tell all their friends about it. But if they can only tell the friends that have the same job and at the same seniority level of them, we're not going to get very much word of mouth. So we wanted to go pretty broad from a role and from a seniority perspective to enable this word of mouth, and that's what we've seen over the last year or so since we launched Jack. and um yeah the uh in terms of like where we're going next from an industries and uh and segments perspective i mean we already serve a whole bunch of stuff around the edges there so i think you know it's kind of expanding into more of those white collar industries over time yeah brilliant the seniority piece i think is kind of under probably understated somewhat because i can imagine at the exec search level or the senior sort of c level you've got different types of issues when you're looking for job opportunities, primarily things like incumbent in place and, you know, requirement for absolute confidentiality.

28:24How do you think that sort of Jack and Jill model fits in with that sort of frame? Because we can imagine, you know, if it works at exec level, then probably it will cascade down to all sectors where you want to have an agent that's permanently looking for you in a discreet way. Because if we could do things with discretion, we probably would always be semi-permanent job seekers. This is looking for opportunity, but we can't do it without these massive signals into the market, which we don't necessarily want to have it reflected back in business.

28:55Matt Wilson: I think that's true on both sides, right? There's good reasons why you might want to run a search discreetly as a hiring team. Maybe there's an incumbent that you don't want to necessarily find. Maybe you don't want the market to know. So maybe you don't want a whole bunch of people inbounding to you because you want to run this very, very precise search. On the candidate side, yeah, this is not true at an executive level, but you don't necessarily want the market to know that you're looking for a role if you're in a role. You don't necessarily want this huge volume of recruiters reaching out to you.

29:31Matt Wilson: Right. So, you know, we've designed into the products that both sides on the professional side and on the company side can choose the visibility level of the of the role or of the of that profile. So, you know, if you're happy for this to be public, then the thing you're posting a role and candidates may be able to see that role and register their interests first before you then review them, as well as you reviewing candidates and requesting introductions to the candidates inside of the network. But if you want to run that as a discrete role, you don't need to have that listed anywhere publicly and you can be the first mover in all of those outbound messages.

30:14Matt Wilson: On the candidate side, you can go into what we call an incognito mode where you wouldn't show up in the search profiles for any of the hiring teams, but you'd still have opportunities brought to you and you would then just have to be first mover in those engagements and say, yeah, okay, that role looks really interesting. Would you please flag my profile to the hiring team? And then they'll review that only once your profile has been, only once you've opted into that interaction. And even in the public mode, there's also, you can put in place block lists or black lists. So you could say, okay, I don't want anybody in my current employer to be able to see my profile they're using Jill.

30:51Matt Wilson: I don't want anybody at this company that's there's some sensitivity around to be able to see my profile either. So that's the functionality we built in to enable people to go through this process with discretion. And I think that is one of the problems with the LinkedIn profile. The LinkedIn profile has service serves so many purposes in people's professional lives, so that it has to be quite a thin profile on what you've done. Whereas with Jack, you can share all of this context and it's only shared where there's an interesting opportunity on the other side where Jack thinks that that's going to be interesting for you.

31:25Yeah, really, really interesting and fantastic. You've been so thoughtful on the product development there. I think a lot of people would have forgotten about the confidentiality aspect altogether with this. Matt, I realize that we're eating a lot of time. I hope you can still hang around with us. I know we said initially circa 30 minutes, but if you're still okay for another five, I'd love to keep talking. Let's do it. I've got a couple more questions for you. I would imagine people might develop a really quite interesting relationship with their Jack because the context grows over time. Jack's going to get to know you better over time and all the rest of it.

32:00This is fantastic. But there may be a situation where I'm thinking, hang on, I actually want to delete that because I'm a new guy. Or I've decided, you know what, I've just done a massive career shift. I want to just not actually have any of that additional context go into my next future direction. Is that something you offer? Or do you think that's actually really dishonest in the sense, you know, we're deleting information that is relevant for potential employers?

32:28Matt Wilson: I mean, I think it's important that the users have control of the data and how that's used. So, yeah, we offer you can delete all the context that's on your account. You can start fresh. I think over time building more ways for the users to have much more control over the context and how that gets built and how that's then utilized. Yeah, I think it's really important that that's in the hands of the users, whether they're on the professional side or whether they're on the company side. And yet again, maybe an advantage over working with a human in that is you couldn't ask the human to kind of wipe their memory of all your prior conversations.

33:00Matt Wilson: You can, you know, your jack can get its mind wiped and start from scratch. right brilliant and fantastic you're clear on that on the value side that's brilliant matt um kind of segues on to the fraud issue okay how are you dealing with candidate fraud here's where we're talking about basically people who are lying about their uh sort of credentials and so on um how do you how have you thought about that issue matt yeah so we we we verify the profiles with uh with other public sources so to try to get a good read on on that we actually can't control that any more than an application with somebody lying on their CV or somebody lying on their LinkedIn profile.

33:40Matt Wilson: The stage at which we can then is with, this is true in both directions, is with reports from users. So if we see that somebody's gone into multiple interview processes and that's then been flagged that the user's misrepresented their background, then that's something we look into and have a process for looking into that. And if somebody's persistently misrepresenting themselves, themselves, then blocking them from using the platform. The same is true in the other direction. You know, it's also you get companies that will misrepresent themselves, their recruitment process. And it's really important to us that we deliver an amazing experience for all of the candidates that we work with and that Jack is representing.

34:20Matt Wilson: And so, you know, these reputation systems, whenever you're building a network or a marketplace, reputation systems with both upfront controls, but then also reactive user-generated reputation systems are really important. And that's something that we're building out more and more. Yeah, fantastic stuff. Final couple of questions for you, Matt, because I am totally respectful of your time. You've got actually 40 million quid to spend. So I don't want to sort of stop you from doing that. I have to ask you a question. What are you going to do with the money? What's the plan with the raise? how is that going to impact sort of customers and candidates?

34:58Matt Wilson: Yeah, I mean, it's really simple. You know, we are here to build the best product on the market to help people manage their careers and find the next step in Jack. And we're here to build the best possible agent on the other side, connecting people up into that network with Jill. And, you know, there's a lot of product development work still to be done. There's, you know, constant trying to stay ahead, trying to plow forwards in terms of what's possible and just build better and better products for both professionals and for companies. And then with those products, take them to more and more people and more and more companies.

35:36Matt Wilson: Our goal is to have a billion professionals working with Jack, working on the network over the next few years. And we've got a hell of a long way to go before we get there. So just continuing to run as fast as we can at expanding the network and building better and better products and something like this is better every day. Fantastic stuff. Matt, I'm going to have to let you get on with that plan because I could continue speaking to you for another 45 minutes, no fail. But it's been a brilliant sort of conversation with you so far. And I've got to let you get on with your day leading this business.

36:12Final question for you is if they want to find out, anybody here wants to find out more about Jack and Jill. How do they do that? What is the entry cost of entry? How do they kind of get the first taste?

36:24Matt Wilson: Yeah, so go to jackandjill.ai. If you're a professional or you want to see how it works from the professional's perspective, it's totally free. You go get signed up, enlist Jack to help you optimize your career and help you find an amazing role or just to monitor the market if you're not actively looking. And on the company side, again, go to jackandjill.ai. You can get started for free and you can, yeah, all the details of the commercials are there on the website, on the business side. Fantastic stuff. Matt Wilson, thank you very much for your time. It's been a wonderful pleasure speaking with you.

37:00Congratulations on everything you've done so far. It's been a fantastic journey and I'm sure I'm speaking for everyone who's listening to this. We're all kind of watching with very keen eyes and to see what you're going to do with this race. so thank you very much for your time well done and uh yeah uh let's see what what happens with jack and jill going forward in 2027 very exciting stuff thanks so much see you later

From the publisher
The Future of Hiring, with Matt Wilson, CEO of Jack & Jill   Matt Wilson, CEO of Jack & Jill, joins Hung Lee live to discuss what happens when AI makes applying almost effortless, application volumes explode, and the traditional signals recruiters rely on start to disappear.   Key Themes We'll Cover:   The End of the Application? - What happens when applying becomes effectively free, and why more applications plus better filters may not be the answer   An Agent for Every Candidate - What changes when people have an agent that understands their experience, ambitions, salary expectations and what they actually want next   What Recruiters Do Next - Where agents can assist with searching, matching and introductions, and where human judgement, persuasion and relationships matter more than ever.   The Job Market in 2030 - What hiring could look like if agents continuously search the market on behalf of people and companies, without candidates needing to apply at all   Whether you're sceptical about AI agents or already exploring them for your team, this session will give you a clear-eyed view of where the technology stands and where it's going.   Follow Recruiting Brainfood here (recommended) and register (save my spot) now to join the live discussion on 15 September at 2pm - bring your questions, because this one is going to get interesting!

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