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Sally Winter
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Jimmy
Welcome to Jimmy's Jobs of the Future. Today I'm joined by returning guest Sally Winter. Sally came on the show three years ago when she just exited her first company, a CBD gin company. I asked her at the end of that episode what she was likely to do next. She highlighted the careers system as being one that was broken. Of course, I agree. That's one of the foundational reasons of why I set up Jimmy's job as a free future. Sally has now launched a new venture to try and tackle this. It's called Hunch. It gets to learn applicants really well with its AI systems and provides them with up to 20 jobs a day. I think it could be really transformational because one of the challenges that young people have early on in their careers is they don't know the skills that they necessarily have for the workplace and they don't understand what jobs necessarily entail. Hunch looks to solve both of these problems. I think it's a really neat idea, and it's a reason why I've become an investor in the company as well. Onto today's episode, make sure you subscribe so we can continue to get bigger and bigger guests. Tally. Welcome back to Jimmy's Jobs of the Future. Not many guests come back for a second time.
Sally Winter
Sorry to hear that.
Jimmy
Exactly. But this time, you're doing something completely different. Tell us what you're working on.
Sally Winter
Yeah, I am working on something that two and a half years ago, I actually said I would be working on. So I was quite proud of that. It's a platform for young talent, job seekers, graduates to find, find out about the world of work, find out what careers are out there, what pays well and then how to land those jobs.
Jimmy
And why is it called hunch?
Sally Winter
It's having a hunch, the kind of going after, I guess fulfilling your potential, feeling that you've got an inkling that there's something out there for you but not quite knowing what it is. Yeah, not having the full picture, which I think is how most people, I mean before, you know, we go into this. Well for lots of people, corporate spaces or other space, the world of work, people have no idea what it is to operate like day to day, how you present yourself, who you're talking to, who each person in the business is like it's completely foreign territory. It's very much like a role playing thing that human beings in the, you know, capitalists world have to engage in and become an employee and you know, all those rules of the game, how you have to act, professionalism, all that stuff is very foreign to just being you, I guess. And so there's that weird dynamic.
Jimmy
So you, it's. I know primarily at the moment it's for graduates. Right. So what does a graduate do? They're getting ready to graduate in the final year and they sign up for hunch. And what is the processes that them
Sally Winter
the process on the platform. So we've got a, we've spent 12 months basically training an AI career obsessed agent. It finds out about you, it kind of scrapes a lot of data from either your CV, LinkedIn, it asks you a bunch of questions about your motivations and then it starts to show basically give you matched roles. So we bring the roles to you very different to a traditional job board where you, you, I mean especially for people entering the world of work, they don't know what job titles there are, they're seeing a lot of irrelevant things. So we only send you things that match. You get to kind of swipe yes or no, much like a sort of Tinder style dating app. And then we give you all the tools and the coaching to apply. So that's CV optimization, ATF making sure it's ready for ats, the system that she means. A human can see your application bespoke cover letters but mostly also our AI coaches you in. So it knows about, about you, it knows what you're looking at which is what's really dynamic about it. It can see you're looking at an account manager job. And it can be like, okay, so what do you think about this? Here's some experiences you told me you had that can help you get this role. Here's how to put your best foot forward. And also it can kind of answer looking further forward because, like, it's all a mystery when you get that first role. You're like, what the hell does that mean? What, what does a job title mean? I don't know what half the words on the job description even mean. And then what does it mean? Like, where is it taking me to Warhoods. So we try to like, demystify that a bit.
Jimmy
And what kind of questions is it asking then? Because that's really interesting to kind of reveal people's motivations because it's one of the big things I think that youngsters have going into the job market is you, you don't know what you don't know, to state the obvious. So what kind of questions is it asking then to sort of reveal that work type, personality? I suppose.
Sally Winter
So I guess like one of the most useful things about the fact he can see the job. You're, let's just use the job you're looking at example doesn't have to be that. Yeah, but it can say, okay, well, this, breaking down this job title, it's actually very much to do with organization, getting people together to do things on time, you know, delivering to lots of different people's needs. You know, is that something that, that appeals to you? Or, you know, is that a personality fit type? And then it can, you know, it kind of prompts off conversations and if you go, oh, actually I'm quite introverted, I wouldn't want to have to like, deal with loads of people, then it can start to steer you and open up other conversations. So that's interesting.
Jimmy
And how, how long does somebody have to use and play with it for? Right. Because that's one of the things I found about using AI. Like, it's amazing, but it does also take quite a lot of time for it to learn about you.
Sally Winter
Well, that's why our onboarding process, which is quite quick, but it's taking a lot of data that you've already got written down, so you're not doubling up. So CV and LinkedIn have a lot of that basic stuff and then that's enough for us to go on with a few other questions on kind of matching. And then our AI is. It's like a rag bottle, which basically means that it's learning as it goes. The more you use it, the better. It becomes but I'd say like very early on it's a very, it's completely personalized compared to all the other job like platforms that are out there. So we've got that feedback very, very clearly early on that people were like wow, this already feels like revolutionary compared to what I've been using because it's so antiquated the market, you know, it's super old school.
Jimmy
And what, how do you hire? I mean I, when I was listening to our podcast again this morning, like I remember one of the startling things about your previous journey was you didn't hire anyone and you did it all on, on your own. But like this time you've built like a, a small team. Right. And like co founders and so on. How have you found that as an experience of being the, the hiree?
Sally Winter
Very eye opening. I think it's interesting to have gone through the hiring process as well. I've got a couple people in my team on the marketing and comm side lot. Yeah, it's really interesting question actually because there's lots and lots of insights. Some things I guess I thought I already knew about but it was demonstrated like lots of people like not showing up, like applying but not following through, not replying to emails. It's amazing if you look at how tough the market is but then how many and how many people still don't email back when they're offered an interview or don't do the task, like whatever it is is like that's still incredibly high. And I'm sure behind that it's a complete mixture of reasons like confidence or lack of motivation. But that was really interesting.
Jimmy
Yeah.
Sally Winter
And then yeah, I think just, just, just being sitting on the other side of the seat. Right. Which I hadn't done before and knowing I guess what the candidate doesn't usually know which is the person interviewing you, like what they want to get the best out of you.
Jimmy
Yeah.
Sally Winter
Obviously for you just like oh my God, I need to perform and impress this person. So I was trying to bring in I guess empathy and like making that person feel comfortable through, through the process. But yeah, it was hard to hire, took quite a few weeks. We, I, this was way pre product as well. So we didn't have hunch to help with that process. But yeah, no, it took quite a few weeks which is almost bizarre when you look at how hard it is for young people to nail jobs and you know that they're applying for 6, 7, 800 jobs sometimes just to get an interview and you're like something's wrong here if it's still hard to hire kind of.
Jimmy
Yeah, but it is this, like the funnel has got like so much longer and wider with it. All right. Like, because it's just, it's, it's so much easier to apply for jobs now because you can do it in the day when you're working at home and like LinkedIn's made it incredibly easy where it's just like a couple of clicks to apply for things. But yeah, that sort of. Whereas previously, you know, you used to have to, if you wanted to apply for a job when I was sort of starting out 10, 15 years ago, you would have to do it in the evenings or at weekends. And so therefore you'd already kind of met a bit of a threshold as far as the employer was concerned of like, okay, well this person has taken probably half an hour at least to write, write this email in an evening at a weekend and send it in. Whereas now it's just become, you know, so much easier to kind of like, you know, LinkedIn easy apply, click, click and you put it forward.
Sally Winter
Why was it only evenings that you could just.
Jimmy
Because if you were in a job already, like you couldn't apply during the day because, you know, you had to be in the office. Right. So like know you couldn't be sort of sitting there drafting out your CV in the office or it might raise questions.
Sally Winter
Well, I was going to say, I don't know, like, what's that, like 2010? I was like, yeah, you could have been getting away with more. Maybe. I'm not sure everybody else is playing by. Exactly.
Jimmy
Maybe I just do like model employee. But yeah, and so I just think, yeah, it's interesting.
Sally Winter
Like, basically it's easier than ever. Yeah, right. And that's a huge problem.
Jimmy
Yeah, and exactly. That does not make it easier for people to find the right, right work or right roles necessarily, because they're almost scatter gunning like, you know, and so on. You talk about how people apply, you know, 5, 600 applications and so on. It's just sort of mad. And AI is going to make it, you know, is, is, has got the potential to make some of the problems even worse. Right. Obviously that's what you're kind of like working to solve.
Sally Winter
Absolutely. Yeah. There's a, there's AI companies out there that will like auto apply for thousands of jobs and it's a huge issue because basically, obviously if the threshold's really low, I mean, I think like LinkedIn's Easy Apply is one of the worst, like best and worst, definitely worst thing to be invented simply because if the threshold's really low, you're going to apply for like 10 things and maybe you're only actually interested in two of those jobs.
Jimmy
Yeah.
Sally Winter
And then it creates, you know, 10 or 100 times more applications for the company to deal with, which makes it harder for them to find the right talent. But even if they find the right talent, that talent isn't even necessarily that interesting because it was that easy to apply. So I think the idea that it's just, you know, and there's incentive there because, you know, they're driving people onto the platform and if you make it harder, like, there'll be less people doing, doing those applications. But it's, it's a broken system basically. And it doesn't, it's, it's kind of damages both sides.
Jimmy
And that's where one of the things that your sort of unique offerings. Right. Is it is going to be 20 roles per day.
Sally Winter
Yeah. And you can only save 10. And I think once. One thing that's been really interesting is it's so demoralizing doing all of these applications. And there's like, there's no one to tell you, you know, that's, you know, here's how many you should be doing, don't do too many. So people are like, oh, if I just keep going, keep going, then eventually I'll land a role. And they sort of spray and pray. And that's not very effective for the reasons we just discussed about low quality applications and intent and all of that kind of stuff. But it's also just very demoralizing. So the idea is we want to use AI for good, to help people make fewer, better quality applications. And on the employer side as well. If there isn't a good match there, we're not showing it to people.
Jimmy
Yeah.
Sally Winter
So it's just, it's, it's fixing that issue.
Jimmy
And how have you gone about building this so far? Like you say you've been kind of 12 months in research and development. What we've been doing with that time,
Sally Winter
largely the credit is going to our engineers. So we've got incredible kind of tech team who've been, you know, kind of working very hard on building something that's, I mean, honestly, what they've achieved is, is, is really amazing because, you know, immediately in some of our earliest reviews for our, like, first version, we've had people being like, oh my God, the, the AI like versus LinkedIn who do actually have, by the way, this thing that's like, you're looking at a job, blah blah blah, let us help you. It fails one in three times. So it doesn't even work a lot of the time. And then it's really basic. I mean for the amount of stuff and you know, multi billion pound company, etc. It's amazing what we've pulled off a very small team in the space of a year. And then on the kind of marketing and user side, I've been creating lots of TikToks building up a WhatsApp WhatsApp community of, you know, 1200 plus graduates. Just helping them with honestly like some of the things that they need help with is really basic. I spoke to a couple of them who were like, didn't know what companies were out there to apply for. So every time I see a bus stop ad I'll Google and see if they have some sort of graduate scheme. I mean that's how lacking the market is at the, at the early stage.
Jimmy
And how have you gone about building that WhatsApp community? Where have you got, have you gone out, done your own bus ads or
Sally Winter
so literally just tik toks about the opportunities that are out there. So I started around the start of the academic year last year and very rapidly I was like, okay, so here's scheme going on, here's what roles they're hiring from. Very almost like job ads that's working on Tick tock, which is obviously where Gen Z is spending most of their time and then filtering through those people who wanted more information help to apply into the WhatsApp group. So quite a simple but very effective method for people who are job seeking and.
Jimmy
Yeah, and how have you found that? Because you do have a bit of background in TV as well beforehand. Right. So this is like kind of mixing all the Sally Winter skills.
Sally Winter
Yeah, a little bit. Tick Tock was quite painful to get on to, I've got to be honest. Yeah, very uncomfortable. I was in tv. Yeah. But I was always behind on the desk behind camera producing and things like that. So yeah, never. Yeah, I'm a reluctant tik tocker. But you know what, like it's been amazing to see a lot of, you know, again now, now we're on the other side of that act that like sort of hiring, you know, year which sort of runs for guards around September all the way through to like May. Ish.
Jimmy
Yeah.
Sally Winter
And then sort of pauses the summer. I'm now thinking people, oh I saw your video back in October and now I've gone through that long process. I've actually just started A role which is like, you know, it's really rewarding to hear that your output is actually doing something for someone.
Jimmy
And how is the grad market changing? Because I heard this interesting tale the other day about like, how it used to be, you know, in your third year you get ready to kind of do applications. But now that funnel is becoming longer as well in terms of people expecting, you know, they're almost using the internships kind of like program as a funnel for that, which was definitely happening when I was at university as well. But it wasn't perhaps as explicit as that. But like the big companies are now being much more. Yeah, basically, almost. If you haven't got an internship in your first summer at university, you're already kind of like falling behind the curve in that sense.
Sally Winter
Honestly, I was amazed to learn about like, just how competitive this space is because me as a, as a graduate, I mean, first of all, I did English literature, so basically I had no idea. So I was going to swear that I wasn't sure. I had no idea whether, like, what I was going to do. So, you know, I wasn't even thinking. I think like most people aren't even thinking about career until they're at least in their third year. But what I found is that if you want to be in these top companies, especially in spaces like finance, you know, you, like before you've even started uni, basically in A levels, you need to be like, okay, what spring weeks am I applying for? And spring weeks I hadn't even heard of until spring last. Last year. So spring week is like, it's the funnel into the internship, summer internship, which in turn is the funnel into the grad scheme.
Jimmy
Oh, my word. So it's got even further than I.
Sally Winter
So it's gone even further. So basically the spring insight week is basically like a week if, like just like shadowing, like going up and just work experience, like being in the office meeting people from the company and then you get invites through to the internships and then as you say, I don't think it's out there in the open, but I know firsthand from speaking to people that, yeah, a lot of the grad scheme cases are reserved quietly for people that go into the internships. But if you think about the kind of person that would know to apply for the spring intern week. Yeah, yeah, yeah, it's again, this comes back. It's certain backgrounds, families, network, etc. Which the masses don't have. And so it's just, it's compounding an issue of lack of social mobility and it's compounding all the way through to the companies and the good jobs and the well paying careers, you know, and I think that's, that's where my motivation comes from in being in this space. You know, it's trying to level the playing field just a bit because a lot of people out there, they just don't know. Don't know, don't know. They don't know what you don't know.
Jimmy
It's not even a level playing field in some ways because you can't even see the pitch that other people, people are playing on. Like, you know, just to run with that metaphor, but why did you study English literature?
Sally Winter
I was good at it and. Classic response, I was good at it and I was good. Basically. I was, I had a, like, I was very bad at school, my attendance was shocking. But the one thing I could turn up to and even like, even sometimes get, you know, 98, 100 in my work, having not even read the book was English lit.
Jimmy
Why do you think that is?
Sally Winter
That's quite a. I don't know, I don't want to say. Good story.
Jimmy
Okay.
Sally Winter
You know, stories. I mean, yeah, I mean I'm, I think having had a, you know, a lot of my success and things helped massively by the sort of following I built up on LinkedIn in the network because I'm, I, you know, I'm a good writer. I guess I write from the heart. That comes very naturally to me.
Jimmy
Yeah.
Sally Winter
And so I guess some, something in, in that I just had a good talent, natural talent for writing and obviously you don't. It's kind of like, it's interpretive, you know, it's all about making an argument or like describing something. It's like, you don't have to have it on facts and figures so much. I mean, you know, in chemistry, if you decide the right or wrong, you can't, you can't really get. And also, I didn't know, I wasn't even sure I wanted to go to university, to be honest. In fact, I took a year out to work and then I was still like, oh, I don't know about this. And someone was like, well, you know, when you're in your 40s, you're going for that senior management role. Is the, the difference between you and the next candidate might be a university degree. Which even at 19, I was like, that sounds like bollocks. But like, yeah, yeah, in the back of your head you're like, well. And I was like, I don't want to go when I'm older, because they sell you the university experience, which again, it's not. It's. Yeah, not everyone has.
Jimmy
But it's definitely the safe choice though, isn't it? I think that's the thing. It's like, it's the do this because society tells you to do it, but then, you know, it's now you're loaded with a load more debt as well. And look, I went to university. I had an amazing time. University, I think, is incredibly important for certain walks of life. But yeah, it is interesting just how much.
Sally Winter
It's a different ball game now, though, because the university degree obviously, like back when a relatively a handful of people used to go to university, Even like the 80s and 90s, it was some. It was an accolade. It was like, oh, he's got a degree. Like, that's when it mattered, you versus the other guy. And I can't tell you how far, far away we are from that having been a truth. You know, even when I came out of university, it was like. And now I'd say, yeah, it's worse than ever because also, especially since not only has it gone down, but employers are like, we just want work experience. And if you don't have work experience, your degree doesn't really mean a lot. And so. And again, this coaching isn't coming through from the universities either.
Jimmy
But also, what's, what's interesting about it was. And I'm not going to do this now, but I was about to ask you where you went to university as well. But it's like, literally the only reason I'm asking that is to kind of like make a judgment and like, therefore you have your own ranking in your head about, like, which.
Sally Winter
Yeah, and that used to drive me crazy as well, because I feel like the pathway through. Well, I'm not sure how much. I don't. I still. Yeah, this still happens. Definitely applied. You went to a good uni. Yeah, a good uni. It's like that immediately, like, puts a level. It makes an assumption. Basically, if you went to a good uni, you're smarter and brighter, with more potential. You're going to be a bit higher. And that's just like categorically not true. But also it, again, it leans into that bias that's carried through the system because, yes, there's obviously there's more diversity now in terms of who gets into those top unis, but it's, you know, so overwhelmingly a certain type of person. And so it's. Yeah, it's. It's very tricky. Like, I'm not saying there's a perfect system out there, there's always going to be some sort of bias. But yeah, that was one of the things that bugged me the most.
Jimmy
And yeah, you and I are both very keen on social mobility and signed up for the mission of it all, etc. What are some. I don't want to ask you, kind of like for the best graduate schemes, but obviously you spent a lot of time sort of looking at them, making these TikToks and so on. What's, what's interesting out there? Like who's doing interesting things, Doing it in a bit of a different way. Like, what are some of these. What were some of your most successful videos?
Sally Winter
I don't think I have a good answer for this because all my, all my videos have been like, on the big grad schemes so far. I mean, I think there's challenges in different space because it's been super like general.
Jimmy
But there must be a couple that stick out, right, of like even just the way they were presented or
Sally Winter
just all grad schemes, like crisis graduates.
Jimmy
But how are they trying to attract
Sally Winter
graduates and so on?
Jimmy
Like, what do they do? Like, because, yeah, you know, there is a bit of.
Sally Winter
I'm being slightly facetious. I mean, like, I think the companies that stand. I mean, if you look at Gen Z as a group of job seekers, they are very, they're very motivated by, you know, they're very passionate about kind of impact and, and things like DEI and things like that. They want to see that businesses are actually doing something. I think they're quite disillusioned, to be honest, with everything that they've grown up with, which is like, everything from the, like, financial crisis all the way through to Covid and they've had a very, very difficult run. And so I think companies that are acknowledging, you know, kind of having space for like mental health days and some flexibility and stuff, like, they very much expect that. And I think there is also this thing of companies that are demanding all the time in the office and them not like, them like having got used to flexibility working from home. So there's definitely some conflict there. But I would say companies that are like, providing an environment where there's lots of training and safety and like openness as well. So you can talk about things that maybe traditionally in an office, 10 years ago you wouldn't be able to. And the other thing is that they don't sign up to like just all the kind of corporate rules and regulations of how to Go about things, you know, dressing up in like suits and all of that kind of stuff. I think it's just not, you know, it's not been something that they've. It's just a weird time to have entered the market with COVID I think and having started and gone to university also remotely for a lot of them as well.
Jimmy
So what do you, because I. What do you think's happening in the jobs market more generally? Right. Because I've got this pretty sort of negative view about what's going on and it's partly a combination of, you know, some of the government policies but also geopolitical Trump tariffs, all of that like just pars more uncertainty and then also the ability that AI is doing a lot of these entry level roles. Right. What's your diagnosis?
Sally Winter
I mean who can.
Jimmy
Right.
Sally Winter
There's so many different factors going on and the economic downturn, the, the NI changes, like there's just so many contributing factors. And then as you say, I think every business out there is like we need to use more AI, we need to use more AI. And ultimately what is, you know, I don't think it's necessarily like by design, but what does AI do? A lot of what it does is those administrative tasks, the sort of, the more basic tasks that someone would get their foot in the door by doing.
Jimmy
Yeah.
Sally Winter
And so, you know, we've seen Klarna say, oh, we're not hiring any, I'm not sure was any talent, but certainly no new early, early stage talent. And then they've backtracked on that. And so I think you're going to see lots of companies. You know, we've seen an article recently about the big four cutting between 11%, I think 30% of their graduate and apprentice roles. And it's, you know, I think we are heading towards a crisis because I think if companies continue to go right, how can we improve our bottom line? How can we please our shareholders? More profits etc and they go, there needs to be almost. There needs to be some accountability to the fact that these are private businesses and they are for profit. Sure. There should be some accountability to the societies that they operate in.
Jimmy
Yeah.
Sally Winter
AKA training young talent, which shouldn't just be about their own gain. It should be about like you know, training young talent, helping society, you know, get ahead and have, and have that initiation into the world of work. Because what's like where are we going towards here? If no one young gets trained up in any kind of roles, then they, there's no, eventually there's no funnel into medium and senior management, which is just bizarre. Like, so someone needs to, I don't know how I have a solution for that. But I do think that there's, I thought for many years actually that business needs to look at profit as more than just financial profit. They need to think about how are we, what are we doing for the human race, what are we doing for communities that we operate in and the clients that we serve in a bigger way?
Jimmy
I think what's interesting, right, is that like since the 80s you've had this kind of like big sort of like deindustrialization of work etc, and what we might be about, and that's kind of affected blue collar workers more than anything. And what we might be about to see is kind of like the D knowledge of vacation, of work, if that's even a word that I just kind of like made up. But the D knowledge base being eroded and I just think there could be like a white collar sort of revolt, etc. Like, I think it's, it's, it's kind of fascinating. What, what do you think if, you know, because you're a little bit into your kind of career now and so on and it's like shifted a long way already.
Sonny
Are you a fan of Jimmy's Jobs of the Future? Hi, I'm Sonny, one of the producers behind the show. And we don't just make this podcast. We produce some of the best business content out there, working with global brands and founders. Over the past year, we've flown around the world and demand keeps growing. And with four prime ministers trusting us with their appearances on this show, you're in safe hands. So if you're already in the market for a podcast or standout business content, why not start with us? Drop me a line at Sunny Boxlight IO, try our podcast calculator or book a meeting at Boxlight IO. That's Boxlight IO. Now back to Jimmy.
Jimmy
What skills and what do you think you'd be trying to focus on if you were sort of graduating today or if you're in your very early twenties.
Sally Winter
AI. AI. If you. Because that's the thing that I think is, is potentially, you know, gen Z is AI native. They, you know, my niece is like 16. ChatGPT is her Google. Yeah, she doesn't Google anything. And that's, that's becoming more and more commonplace. So I think that, that, yeah, if I was going in today and the advice that I give is like, understand it's difficult again because I haven't been in the world of work, but Studying what businesses are using AI for, what they should be using AI for. And if you can walk into an interview and be like, I can save your company xyz, because here's. I'm really familiar with these tools and I know that they would, you know, fix this, this and this business need or whatever, then that. I think that's the number one biggest thing that you, you know, that would be an absolute 100 hire. Because there's so many businesses out there that are like, we need to use AI, but we're terrified of it. Like, we don't know where to start. It's overwhelmed. There's new releases every few months. The capability is, you know, going sky high. But we haven't even done the most basic processes. So it's like a huge undertaking. And so I agree.
Jimmy
I think that's the biggest opportunity for young people. Right. Is like. And actually, whilst the job market is really tough at the moment, if you can master or at least get to grips with AI more, then actually you're able to go into an organization and probably help it quite a lot. And that you've almost got like, possibly the first kind of like the almost potential generation that can leapfrog the people above them because they're able to kind of come in and be able to. This is the way that you could do it. That you're basically having that almost now for the first time in 20 years, probably since the Internet kind of really took hold. I do think that's quite, quite an opportunity for young people, which sometimes gets.
Sally Winter
Yeah. And then of course, there's a thing that doesn't get talked about that much, which is all the vocational things, which are, you know, which a lot of people are like, well, that's. AI is not going to replace, you know, plumbing and all these other jobs. Which is. Which is very true. So, yeah, I mean, you know, it's. It's always a bit more doom and gloom, I think, than it is on the ground. There are still tons of jobs, but, like, for sure, it's difficult. I mean, you have to be. You have to become. You have to be right now a professional at job seeking. Right? So, like, doing the application, ticking the boxes isn't going to cut it. You need to go above and beyond. You need to stand out. You need to email the. The director, the managers, you need to connect with everyone on LinkedIn. You need to, like, follow up again. You know, everything needs to be done. That's the only way that you're. You're going to come out of the thousand applications for each job that you're going for.
Jimmy
Finding a job is a job, is
Sally Winter
a job in itself. It's an unpaid, you know, a bit like kind of women taking care of children in the home. It's, it's unpaid labor. It's literally becoming that because I know so many people that are job hunting for almost a job, you know, a 9 to 5 role each week for at least, you know, two or three days worth, which is, yeah, it's, it's, it's crazy to be honest.
Jimmy
Let's talk a little bit about personality in work because one of the things that I think there is in danger of happening with AI is that we all become a lot more kind of formulaic. We're all able to write brilliant CDs etc and all of that and basically it just raises the, the stakes and how you stand out is going to become even more important. And I think whilst we've done a bit of LinkedIn bashing in this potential Jimmy Stills partner, is the, is that actually like having a personality, having a bit of personal brand is like increasingly important? I think you've been very good at kind of building it on LinkedIn, etc. And I can totally see why and how you've kind of like transferred to doing this for hunch as well. But yeah, talk to us about the kind of reflections on building a personal brand.
Sally Winter
Very uncomfortable. I think you have to be a, you know, only 1% of people post on LinkedIn so you have to be that 1%. You have to get comfortable being uncomfortable. And then I'd say it's putting out the bits of personality or the bits about you which are interesting because I think there's, there's, there's this a lot of AI, a lot of LinkedIn content which people. Which is kind of gives it a bad rep, especially actually amongst Gen Z. Is that kind of like it's nice to have been awarded this award. My, you know, I mean with, with my work and it's like you'd never talk to a mate like that. So when I'm talking to people about personal brand, we're saying like talk. When you're like getting really like het up about a subject and you're talking passionately about it to a friend, that's maybe minus the swear words. That's how, that's how you should be talking on LinkedIn. You should be talking about things that really bug you. You should be showing passion and not afraid to just like keep it professional. Which I think is one of the Things that people worry about the most. Easy to say, I'm an entrepreneur. I don't necessarily have like a boss that's like looking down over me. But yeah, I think it's. Someone said this to me the other day, he's a reasonably successful on Tick Tock. He was like, take the two weirdest things about you that like don't necessarily match. He's like ex rugby player and he, he does like book talk. So he like reads books and gets kids into reading. That's an interesting like thing that you think. Oh, I remember that. So if you think about all the people, I guess that you see on social media, what are the things about them, you know, that you remember and that's the things that you should be putting across. I don't know, maybe you like canoeing and like knitting or you know, whatever it is, it doesn't have to be that like interesting. It just has to be different. Right. Because no one remembers companies, people remember people. And so you have to put across your personality, whatever that is. It just has to be different. It doesn't have to be on paper. Like you're really cool and I don't know, you'll go yacht sailing, Miami every weekend or whatever. Like it doesn't have to be on
Jimmy
paper like knitting on canoes. I mean that would wrote that on top of a cv, right? Like probably would sort of like, I
Sally Winter
mean I would follow that channel. Knitting on canoes, like, I don't know, it's just, it's just putting across people like to see people who are either angry about stuff or really passionate about stuff. So whatever it is that does that for you.
Jimmy
I know it's funny you met. So I did a post last week about the AI job. Big four dropping between 11 and 30% which you were mentioning earlier. And I just like fired off a thing about it and I was just like, I think it should be front page news because it was like page 9 of CM and I was like, we are storing up a massive, massive problem. And that was basically all I said. And what's interesting about a. I managed to spell front page wrong and. But it's the post that has taken off most in the last two months that I've done. Yeah, like, and it's kind of like
Sally Winter
you probably spent the least time on it, right?
Jimmy
Oh massively.
Sally Winter
It's like hit send. What? You know, I mean I've, you know, I've worked with lots of kind of founders and business people in the past to do ghost writing for them and help them with their LinkedIn. And so it's very much the story. It's like. And also the more they're like, oh, say, I'm not too comfortable with that. Can we like make it more safe? It's like, yeah, you can, but no one will see it. Like, you want that toe. That's the thing that AI is the worst for is it makes everyone into this like M Dash. It's a certain tone, it's a voice, it's not your voice. And so yeah, yes, it makes people who are terrified and they can't start, maybe they won't ever start posting. So it raises it gives them an ability, which is great. I also think that there's something interesting that people aren't discussing, which is people whose English isn't a first language for them, it's there. They depend on it a lot to kind of get the grammar right and put things out. I've noticed. And it's very powerful in that sense. But yeah, it's when you get really passionate, you just put it off into the ether because people can feel that passion. And also the one thing you did as well as I, because I remember that post, is you had an image and you put very little text where people make the mistake of putting an image with lots of text or a video and then loads of text. It's like, which one do I look at?
Jimmy
Yeah, yeah, yeah, yeah. I think that's a fair. A fair point on that actually. Yeah, it is. It's funny how it kind of works, but. Yeah. How have you found doing some of the gate. I mean, I know you sort of had a bit in between jobs or in between founding empires, but like, how did you find the sort of ghost writing for founders and so on? Because I think it is one of those things. It's really. Well, I get pitched people all the time to do it and yeah, I just don't. Yeah, I find it quite hard to subcontract that out.
Sally Winter
I love telling people stories. I think everyone thinks they don't have a story. But when I listen to someone, it's. It's all actually weirdly like you realize this respectively and you look at your career, you're like, oh, it's all intrinsically linked. But like, I'll listen. I used to do video editing and stuff and some directing and stuff, but. And I would know when I was listening to the filming being done, I was like, oh, that's the bit I'll edit later so I can listen to someone saying, I don't know, talking about themselves and their bits. And I'll be like, I intuitively know that's the bit, that's the bit people will connect with. I have like this weird connection with other human beings where I'm like, this is what people buy into and that's, that's my superpower. So I get a big kick out of helping people to tell the stories they don't know they have.
Jimmy
Yeah.
Sally Winter
And I'm very good at it, so that helps because I like seeing it blow up and be able to make people happy and do the things they do. And that's everything from like, I don't know. I helped a guy who was like, he had an amazing project up in the north around Leeds and he basically, you know, puts food, surplus food into good use war zones and schools and all this. And he did a post saying, you know, it's, it's closing down because our landlord doubled or tripled our rents and business rates and we're about to collapse. And I was like, oh my God, this guy needs help. So I got together our wrote the post. I think he raised like 40 grand in 24 hours and managed to get his location back. So I just, I like helping people. I like, it's, that's, that's the thing for me.
Jimmy
Yeah, that's interesting. And you're basically going to be doing that for younger people now, right? That's part of the whole thing, just helping them tell their story and like
Sally Winter
how to put themselves across.
Jimmy
Yeah, I think it's, it's so important. I mean, it's why like, you know, I'm investing in it and whatever and so on as well. I just so passionate about it and I think that you just don't know what you don't know in those early parts of your kind of career and therefore you end up making decisions about it from kind of like a point of weakness. Which is a real shame because people are just desperate to get a job and like get on with their kind of career and it's difficult to explore things as well when you don't really know what you want to go.
Sally Winter
So hard to explore things. So that's super interesting because we live in an age where there's more information than ever. Right. But if you look at like, if I type in how to become a X, I don't know, product manager at Google, I'm sure, like, sure I can find some roots. But the thing is, people like you might have gone to the same school, university, but you might be completely different to someone else that you Know, whatever on paper looks similar for you, but your ambitions, the things you hate, the things you're motivated by, completely different. And that's why I think it's such a difficult thing to solve.
Jimmy
Yeah.
Sally Winter
And, yeah, you can't. I think, like, some of the people I speak to, they go on LinkedIn and they just look at like, okay, I'd like to be in this industry. It's. First of all, it's this much jargon in it. So it's like, what the hell does. Does any of this stuff mean? Like, in English?
Jimmy
And every industry does that to kind of.
Sally Winter
Every industry does that.
Jimmy
Put its own barriers. Yeah, abound it, I think.
Sally Winter
Yeah. I mean, I used to work in, like, broadcast news, itv, and there was all these, like, acronyms. They were all different from BBC, was different from itv, was different from another broadcaster. And so, yeah, I think that we need almost like a giant. So the thing is, because everyone's different, there isn't. No, there isn't one path. There's also not something to say that just because you're on path A, you couldn't be on path B, like journalism, which I was in before, really similar to entrepreneurship. Has anyone written about that? If you Google it, probably not. Because in a sense, you have to get really obsessed about something, go really deep dive, and then you might move on to something else. That's very similar to entrepreneurship. Very similar kind of personality qualities. I guess that's probably not out there. So what you almost need is a giant map of 10 or 11 examples of individual routes. So someone can see themselves and be like, oh, well, I was quite interested in. I don't know, I was quite good at English literature at school, and this guy's gonna do X and so maybe I could do that. And that's. That's what we need. We need a giant map. Basically. People could just explore.
Jimmy
I agree, we should. We should create that. But I. I think one of the. It is interesting about the. Particularly the switch to journal, the switch to entrepreneurship, because I do think until people do it, it's very difficult to kind of like, test it. Like, there have been some good friends of mine who've been journalists as well and, like, haven't been able. It really does take a sort of certain type of kind of like, characteristics to. To do it, I think. And it's just. Yeah.
Sally Winter
The journalism or the tradition.
Jimmy
Well, the entrepreneurship. I mean, yeah, I've been journalism as well. Like, yeah, there are definitely transferable skills of journalism to entrepreneurship, like, as they probably are in almost any Anything there are.
Sally Winter
Right. That's the thing. It's also so general, like detail orientated. Okay, great. Like English literature is detail orientated. It's like it's, it's voting on a perfect thing and like really deciphering multiple meanings from that thing or like and honing down and making an argument. Now those same skills lean obviously into journalism. That's like more of an established route, but they also lean into tech because having that, that emotional intelligence I guess that I have and sitting down with loads of, you know, kind of our target demographic way before we built the app and going like understanding who they are, what their motivations are, what their fears are. That interviewing process, that was something that I didn't think. Oh, okay. That's a transferable skill into tech and that understanding your users is one of the most fundamental things in tech. Whereas when you think tech, you think coding.
Jimmy
Yeah, completely. What's your vision for hunch 10 years time? What would you like to achieve with this
Sally Winter
big question? So much. I mean the space as it is, it was tricky about it is there's so many things to solve. Yeah. So you think there's career discovery, there's putting your, putting your best foot forward, there's the interview. There's just so many, you know, and then there's supporting those young people once they're in. So I think kind of we've, obviously we've, we've built for a lot of that. The vision ahead is having more like data points on really understanding an individual. Right. Because right now we're relying on like CVS and very much like 2D pictures of I understand you because you went to X University or you've worked at S company and so I'll form my opinions based on that. But obviously we've now got the tech and we are building the tech as well to understand someone who someone is in a much more intricate, multifactorial way in terms of their motivations. How much do they, how deep is their curiosity, how much do show up to do certain things. There's so much more things that kind of we are building out the tech to be able to track so we can go and say we can tell you so much more about, you know, Claire or whoever it is. We can tell you how, you know, what she thinks about what she's interested in, you know, kind of what her ambitions are. So much more of a wholly rounded profile, I guess than what we have now. And I think that's really important because if you break down all of the stuff all the stuff around cvs, the applications, the rounds, they just want to know that that person at the core of it is a cultural fit with the company. Yeah, it's going to show up, can and wants to be and is motivated to train and learn new skills and then obviously further on the market has certain skills already. Fair enough. But that's all of these layers, all of this stuff.
Jimmy
Yeah.
Sally Winter
Is just trying to get to that and it's doing a very bad job at it. But the, the ability we have now with, with models, with AI, there's. There's so much more of an opportunity for us to know the candidate in deeper ways than ever before. And therefore the matching with what companies needs and all of this like stuff in between should be able to be reduced down to almost nothing, basically. Yeah.
Jimmy
It's interesting when you talk about that somewhat. You know, there's an argument that a hunch will know the person better than they might know themselves, which feels a little dystopian. But actually at the start of your career you probably need somebody that, that kind of does that. I'll tell you one of the problems I think I might run into AI at some point though is this is just running like, you know, sort of my own business is that it's gonna remember stuff and I just, it's gonna be like interesting in terms of like when that stuff is no longer important, it's still going to rank that quite like highly. And I just. It was when you were talking about some of like things about what people want from work and whatever. It's like, well, they sort of, you know, oh, I want it to be sustainable environment. I worry, tell AI this one and then basically it's just never going to forget it. And your views on that stuff, you know, it can, it can change with different priorities. It's almost like you're going to need like a quarterly review with your, with your AI, where it sort of go for what you want to achieve etc and that type of thing. It's very interesting. Think about it like that.
Sally Winter
Yeah, I mean you can, you can kind of build that in though. I mean there's, yeah, ranking and systems where you can be like, okay. I mean there's probably also studies on, you know, okay, if so and so is really important now in 18 months, statistically, how important is it supposed to be? And there's obviously the data points you can continue feed in and so. But yeah, I think, yeah, it's amazing the rate at which AI is just every month. You're just like, yeah, being Blown away by the next. By the next thing.
Jimmy
What have you used it for lately in your kind of, like, personal life?
Sally Winter
In my personal life. Sorry, when you said that, I was just thinking, like, so many people now are using it as, like, therapists as well. Yeah, yeah. Which I don't count myself in for. But, yeah, there's been so many funny skits around that I think for me it's very useful. And here's the interesting thing. So it's very useful for brainstorming, I would say.
Jimmy
Yeah.
Sally Winter
And also building out, like, basic structures of ideas for content. So, yeah. Oh, and again, like, AI is only really as good as you prompting it, but then you also need. And this is why I think, like, AIs will replace all the jobs, etc, because you still need someone that knows what good is to assess for now whether the AI has captured that or not. And so I will use it sometimes to the base of posts or like, okay, I want to talk about xyz. Put the words for me when I slow a brain brain day. Or just to like, get ahead. And so, yeah, I think it's just very useful at making tasks faster and slicker. But as you say, because so many people are relying on it, it's just copying and pasting out what it. What the output is. You know, there's the AI sludge era that we're in, which is.
Jimmy
Yeah, AI slop. Right.
Sally Winter
Yeah. And people are going nuts about it because on LinkedIn, for example, like, there's so many. Every day I see a protest. And the funny thing is, I know some of them are written by a. There's too many ad posts on here. Everything's AI. And I've also had the. I find quite funny that the people who were like, loyal EM dash users who are now, like, I have had to stop using EM dashes because everyone thinks it's chatgpt. I was using it for decades before this and it's like. That is a weird thing, the EM dash thing though, because even if you prompt ChatGPT to not use it, it still uses it. Yeah, it's a weird, like, AI, like, no, we're actually type thing.
Jimmy
Yeah, yeah, yeah, it's. Yeah. I haven't used it for much in my sort of, like, personal life lately. I just. I think I'm asking you because I might get some interesting tips or something.
Sally Winter
But their research tool is really good. That's what I would say. So looking into, like, really detailed, long research tasks.
Jimmy
Yeah.
Sally Winter
Around, for example, like, it can scrape the deep research tool, for example. Can scrape like, I don't know, give Me the top 50 graduate schemes in consulting and the opening dates and the closing dates and the salaries and things like that. So it's very good at like organizing data and bringing in. You're like, oh, wow, this would take me days of really laborious tasks.
Jimmy
Yeah, yeah, yeah. I did ask it the other day to do like the top sort of 50 employers in the UK and it was, it was nuts how quick it kind of chucked that back out.
Sally Winter
Did you use the deep research or just regular? Yeah, it's good, isn't it?
Jimmy
Yeah, like the research is definitely. And the thing is as well is like it's only 10 or 15 minutes now, but it's going to be able to run for longer before we know it and already can in some places anyway. And it's just going to be, you know, imagine what you could do if you could put it on for like seven, eight hours to find this stuff.
Sally Winter
Imagine what would be in just 12 months time. I know, yeah. One of the interesting things, I think that people have said this kind of a rhetoric that gets spoken about a lot is like, oh, AI knows us better than ourselves. And I'm like, I don't think people know themselves very well. Yeah, I really don't think people. I think people were experiencing like their version of maybe 10 of who they are. But actually only when you ask people like who do you think I am? That's like a very big learning experience. And I honestly just don't think people know themselves very well. I think like we are the stories that we tell us ourselves. And yeah, I think it's an interesting concept that people were freaked out by. When I'm like, how much do you really know about who you are? Like on paper. Yeah, you know those bits. But
Jimmy
that's a really good point. I don't think people know themselves that well.
Sally Winter
I think most people were governed by like a lot of anxiety, insecurities, like ambitions and things. But like, I mean there's who, who you are is largely like who are you to other people? How do you come across? I think self awareness generally is really, really poor.
Jimmy
I actually, I mean one of the things that fascinates me is the kind of like changing nature of status. Right. And like how status has changed. And this is one of my views of why there'll always be jobs while there'll always be work because it's one of the fastest ways that you can kind of like navigate somebody. You're kind of like states in the social Hierarchy. I just think that's why people will always want to work and humans will kind of create work for ourselves because of that. But I'd be interested in you because you're, like, a bit younger and, like, basically every generation comes into the workplace and slightly redefines itself against generation that went before. Right. Like, that is just the way the generations and cultures shift. But what. Yeah. What are the things that you found that really matter to you? Like, also, you know, you had an exit in your 20s as well.
Sally Winter
Yeah.
Jimmy
So, like, that was obviously, like big stakes, marketplace, etc. But also. Yeah. What then was like. Okay, what drives Sally then?
Sally Winter
Well, it's interesting what you just said there about how every generation will go into work and we'll create jobs for ourselves around status. I think intrinsically humans want to come together with other human beings. Like, that is like the core life experience and build things. Building things gives you a sense of achievement. Now that I'm not just talking in terms of entrepreneurship. I'm talking about, like, you're at work, you're doing tasks, you're building towards something. There's a mission, there's a gathering of people. I mean, like, what is even work? What is work? What's the difference between work and, I don't know, journaling?
Jimmy
Yeah.
Sally Winter
Is it money? Like, it's an activity that you're doing?
Jimmy
Yeah.
Sally Winter
Like, you know, I mean, it's like, it's even the definition in our minds of, like, what's work versus not work? Well, I don't want to be working. Well, what is work? You know, fine, you're getting paid for it and things like that. Or maybe you're not. Maybe it's volunteering work. Like, but there's this interesting differential in our brains between, like, it's categorizing, it's choosing to see something in one category and something in another category.
Jimmy
Yeah.
Sally Winter
And I think that's really interesting. But fundamentally, it's. People want purpose. They want to come together with other human beings, exchange ideas and build stuff. You know, that's what we are as a species, I think. We like to build stuff, and that gives us a sense of achievement and discovery. And we are curious, you know. So, yeah, it's. It's interesting from. For me, I think I'm very much zoning on. Like, it's the people, those interactions with other human beings, like, learning things, having that. That desire, I think, to elevate ourselves and, like, always be kind of changing, growing. I think that's. That's what's fascinating on the Ground and also just seeing what happens when you get lots of different people together. There's not, I guess, just, you know, cohesively building. There's also conflict, different ideas of how something should be done. There's how you navigate communication. You know, there's so many interesting dynamics and almost all of them come from people to people interactions.
Jimmy
Yeah, I, I, that's true. I, I do think that, and this may be one of the big things that changes, but where the word work originate. Originates from is French. And it's like to press and like, that's the sort of, like, you know, the old, to kind of press things. And it's just the, the language that we use around work is very kind of like, I just think it's stuck in historical.
Sally Winter
It's quite negative.
Jimmy
It's quite, it's quite negative.
Sally Winter
Something you have to do that you don't necessarily want to do. There's some, yes. Hesitate, like, there's some like, oh, I have to, I don't really want to.
Jimmy
Compensation, like, I think like being used as a phrase and like, you know, even the open AI guys talk about like their tc, their total compensation. I think, you know, being compensating for the loss of time.
Sally Winter
Lots of time. Yeah, yeah, right.
Jimmy
Like, but also it's like one of the things, I always think it's funny when you're like, football commentators are like, when a player has worked really hard on any given day, they're like, oh, they've put a shift in. Like, it's that kind of like, oh, you know, it must be.
Sally Winter
If it's really hard, it's work. And work is something that is slightly negative. It's like a sacrifice basically of some kind. But obviously there's also on the reverse of like, well, if you do something you love, you never work a day in your life. And so there's this interesting psychological piece about what is, when does it become work and why. Yeah, I mean, I can give you lots of answers why work is viewed negatively. And that's largely because most people have to work to live.
Jimmy
Yeah.
Sally Winter
Which is like a horrendous state to exist in, to be honest. I mean, especially if you're really up against it and you're in that system where you have almost no control, but you're just having to go in to be alive, to, to pay, to be alive, to eat, to have a roof over your head.
Jimmy
Yeah.
Sally Winter
And so that, I mean, that's obviously where the negative com. Connotations come around, that word. But obviously work can also be Work is a massive part of self esteem, by the way. Huge part of self esteem, esteem, responsibility, achievement, you know that that's what you get. You. And identity as well. Like, I think not just through business, but, you know, the things that we do very much like, define us, our sense of ourselves. And so, you know, that's also tough, I think, as an entrepreneur is your. Your identity is very much tied into what you're working on, especially since you don't clock out. It's on your mind 24 7. You're dreaming about it, you're thinking about it, you're just living in it, really. And so, you know, I mean, do we have a lot of identity outside of work? Like, I think we. Like, we do and we don't. Maybe that's just coming from a workaholic. But, you know, it's. I think in the uk, we are. One of the first questions we asked each other is, oh, hi, what's your name? What do you do? Yeah, you know, we are that kind of society.
Jimmy
But I think it's weird. There's something interesting you say there as well, about identity as well, because I think we end up sort of like. And the point you were saying, about not knowing ourselves as well, because I think we almost subcontract our identity out through different things. So, like, my identity's definitely changed since having kids and a family and whatever that's like. But again, it's like it's. It's through something else. I now have an identity as a dad, dad of daughters. And, like, that is part of it. And then it's also, you know, we still contract it out for our football teams as well. The university that we attended, we go around looking at all these different, like, status markers, but it's not just. Yeah, we're not very clear at explaining.
Sally Winter
Yeah. What we are. Easier than trying to bear your art, like, bear into your soul. Like, who am I deep down? It's so much easier. Like, well, I'm a dad and I like football and I'm exactly a consultant, you know, like. And also our identities are very fluid. So it's like when you're. I'm assuming when you're at work, you're, you know. Sorry. When you're at home, for example, being a dad, you're not talking to your children as a work person with, you know, you know, proper terminology and stuff. So we very much like, inhabit different identities depending on who we're with, which very much means your identity is almost. It's a project you're projecting it out depending on actually who, what they. What the person exteriorly needs from you.
Jimmy
There was one. There was another thing I want to talk to you about, because the only thing my kids been excited about, work wise, is the fact that we're doing this partnership with McDonald's and they know that I'm going to go and work in McDonald's for a day and they just think this is the most exciting.
Sally Winter
Are you actually? Yeah, yeah, that was my first job.
Jimmy
Exactly right. I. When I listen to this. So what, what did working McDonald's kind of like teach you?
Sally Winter
It taught me. Oh, God, it taught me a lot, actually. Yeah. I think I was 16, possibly 17. I remember because I was still doing my studies and so I'd work, I don't know, a couple shifts a week. I think it taught me about my place in the world, how fortunate I was. Like, I don't come from a, you know, privileged background in the uk, but by God, like, more global, globally. And there was lots of staff members from different parts of the world, like, wow. I mean, having English as a first language, wow, the privileges that that brings you. So I found it quite grounding and it also taught me, you know, a bit of humility, I guess, because, you know, you are dealing with lots of customers who will treat you like crap. I mean, you're, you're just a McDonald's worker. You're seen as like a, you know, a kind of disposable asset that people can, you know, shout out or whatever. And you're, I don't know, like it was. It just. I don't know, it taught me hard work. It taught me not to have an ego as well, because I think there's a lot of people, like, I would never, you know, I think it's really important not to have. I'm too good for this and that, because in that way, again, like you said something about latching on to different things.
Jimmy
Yeah.
Sally Winter
I think people latch on to ego and they tell themselves it's about status, but actually it's about fear of being in uncomfortable situations. It's about fear of what other people think. And so, yeah, I'm very proud to have done a very basic job like that because it taught me lots of. Lots of bits and bobs. Yeah.
Jimmy
You cannot always tell if somebody has worked in hospitality, but you can always tell when they have not. I think, like, it's a real thing. You can see when you're out for dinner with people and whatever you think you've never worked in hospitality. You see the Way you're treating people like that is a really good point.
Sally Winter
Do you think you teach like empathy and things like that or like patience? I mean like really important skills actually because you know, as, as therapists will kind of talk about, everyone wants to be seen. And so actually I think having those skills to make someone feel seen, heard, comfortable, like cared about.
Jimmy
Yeah.
Sally Winter
You know, sure there's lots of CEOs that go around working their way up to the ranks, being absolute monsters and blah blah. But I actually think the power is in. Is an empathetic leadership helping people to like lift them up ultimately. So yeah, hospitality is great. I feel I was in food and drink and so I. Yeah, well, yeah, something about.
Jimmy
It's amazing to sit in that chair and talk about therapy in one form or another. Yeah. I think it's really interesting and what you're doing is almost like. Well it's not quite career therapy, is it? But it's helping is guiding people on their careers.
Sally Winter
You must be. Yeah, I mean it's giving them a space to ask stupid questions and stuff. And I think like again, you know, knowledge is power. Understanding what's out there, understanding who you can be and that coaching bit of like you're allowed to do this by the way. Like it's not like growing up for example. You know, I didn't, I didn't know. I think I didn't know that you could work at Google first of all. I just feel like it's like okay. Prompted me, you know, be maybe coders or whatever but on like a self esteem and confidence level. Did I think I was allowed to ever work in places like that? Like no. So there's also that thing of like giving permission that like, you know, you're just as good as anyone else. You can go out there and like you can be in the spaces that you're not necessarily.
Jimmy
There's a really good point about asking stupid questions and you can do that with AI and this kind of amazing kind of careers tool you're building in hunch. But yeah, no, that's important. Those early stages. Cool. Well Sally, thank you very much for coming on. Jimmy's Job is the Future game. We're definitely going to get you back on.
Sally Winter
Like to hear about that was a very broad chat. It got quite deep. It did.
Jimmy
I was just exactly what ended up happening last time as well. But yeah, no, I think that's. That was really, that was really good and yeah but like you say like, you know, I'm investing in hunch and whatever. Like. And I'm really excited about it. I think it's like a big opportunity, so I have to get you back on. You can tell us about the journey. Where do you think you'd like to be by the end of this year? With Hunch?
Sally Winter
I'd love to have made a big dent. Well, I think, like, we're pausing for the summer, but, like the next academic year. I think we've got some huge university partnerships. We've just worked with our first pilot employer and so I'd love to have sort of like 40, 50 of those running by next year.
Jimmy
Yeah.
Sally Winter
So, yeah, it's, yeah, really excited to start. Kind of just seeing emotion and seeing and having people come to us more and more and more. I think we've had like 20 already. Just being like, thank you for giving me a, you know, an opportunity for guiding me and helping me get to something that's now really fulfilling and building my identity.
Jimmy
Brilliant. Sorry. Thanks so much.
Sally Winter
Thank you very much.
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Podcast: Jimmy’s Jobs of the Future
Host: Jimmy McLoughlin (Boxlight Creative Studio)
Guest: Sally Wynter (Founder, Hunch; Entrepreneur; Former Downing Street Adviser)
Date: August 5, 2025
In this episode, host Jimmy McLoughlin welcomes back entrepreneur Sally Wynter, who previously exited her CBD gin company and now spearheads Hunch, an AI-driven platform seeking to revolutionize early career job matching and guidance. The conversation dives deep into the broken job search ecosystem, the impact of AI on hiring, social mobility challenges, the changing landscape of graduate recruitment, advice for young job seekers, building a personal brand, and reflections on the meaning of work itself. Throughout, Sally and Jimmy share personal experiences and candid insights, making this a wide-ranging and thought-provoking discussion for anyone interested in the future of job hunting.
[01:00–05:00]
[05:00–06:30]
[06:30–10:00]
[11:49–13:00]
[13:00–15:30]
[15:42–18:06]
[18:15–22:00]
[22:29–24:31]
[24:31–27:15]
Quote:
“We are heading towards a crisis because I think if companies continue to go right, how can we improve our bottom line... and use AI...there should be some accountability to the societies they operate in.” [26:26, Sally]
[28:40–31:24]
[31:51–36:48]
Quote:
“AI is the worst for... it makes everyone into this, like, M Dash. It's a certain tone, it's a voice, it's not your voice.” [36:48, Sally]
[37:22–38:49]
[39:31–41:26]
[41:26–42:56]
[43:07–44:53]
[45:16–50:09]
[50:09–52:08]
[52:18–57:50]
[58:42–61:19]
[61:19–end]
On the scattergun application problem:
“It creates, you know, 10 or 100 times more applications for the company... even if they find the right talent, that talent isn’t necessarily that interested because it was that easy to apply...” [11:18, Sally]
On the hidden ladders into top jobs:
“If you want to be in these top companies, especially in finance… before you’ve even started uni… you need to be like, okay, what spring weeks am I applying for?” [16:22, Sally]
On AI-empowerment:
“If you can walk into an interview and be like, I can save your company xyz…that would be an absolute 100 hire.” [28:51, Sally]
On building a public narrative:
“No one remembers companies, people remember people.” [34:38, Sally]
On social mobility:
“It's not even a level playing field...you can't even see the pitch that other people are playing on.” [18:06, Jimmy]
On learning from hospitality jobs:
“I'm very proud to have done a very basic job like that because it taught me... humility, and empathy.” [58:52, Sally]
On job seeking as a job:
“Finding a job is a job, is a job in itself.” [31:24, Jimmy]
On the limitations of self-knowledge:
“I honestly just don’t think people know themselves very well… we are the stories that we tell ourselves.” [50:09, Sally]
| Segment | Timestamp | |-----------------------------------------------------|---------------| | Hunch introduction and purpose | 01:00–03:30 | | How Hunch’s AI works | 03:47–06:08 | | The application flood & Easy Apply critique | 09:07–10:54 | | Quality over quantity in job applications | 11:49–12:42 | | Building a WhatsApp community via TikTok | 13:00–15:28 | | The internship “funnel” and social mobility issues | 15:42–18:06 | | The diminishing value of degrees | 18:15–22:00 | | Gen Z workplace values/expectations | 22:29–24:31 | | Crisis in graduate recruitment (AI & hiring cuts) | 24:31–27:15 | | Advice: Mastering AI as a job seeker | 28:40–31:24 | | The importance of personal branding | 31:51–36:48 | | Building Hunch’s deeper candidate model | 43:07–44:53 | | Do we know ourselves?/Career self-discovery | 50:09–52:08 | | Hospitality work & empathy | 58:42–61:19 | | Hunch as “career therapy” | 61:19–62:14 |
For more insightful and practical future-of-work conversations, subscribe to Jimmy’s Jobs of the Future.