Juicebox's AI recruiting agents go deeper than LinkedIn filters — now serving 5,000+ customers across industries

Apr 23, 2026 · Full transcript · This transcript is auto-generated and may contain errors.

Featuring Ishan Gupta

Uh eventually owning a majority stake in Spirit, which has struggled with high operating costs, stiff competition, and surging jet fuel costs amid the Iran war. Well, we will follow that story more in the future, but we have our next guest returning to the show, Isan Gupta from Juicebox. Welcome to the show. How are you doing?

Hello. I'm doing awesome.

Thank you so much for taking the time. Uh,

great to have you.

Introduce yourself in the company.

Yeah, so I'm one of the co-founders of Juicebox. We are an AI recruiting platform and we help companies find and engage talent using LLMs. We build agents that will go out there, find the right people for every role you're trying to fill and get them into your process.

Okay. We have a friend who's an executive at a big tech company. He's been getting absolutely spammed with new outreach from what appears to be a new Gmail account that is been created. And what's so remarkable about this this cold outreach is that it even nails the sort of like cringe footer that says like, you know, do not print this for the environment's sake and like, you know, a little quote and like it it it doesn't feel just like a prompt box shot in there. Uh it there they're all there's a huge variety, but it's not it hasn't been successful. Uh he he's he's he's annoyed by it. So, how do you think about actually targeting the outreach so that you're not annoying potential new hires?

Of course. Yeah. I I think the main problem so the exec side is almost like the extreme side of it because they're getting like so much outreach anytime an exec is available and everyone's kind of spamming them.

Yeah.

The thing is that for the average role, the best way to guarantee that you're reaching out to the right people is to spend more time on the search. What ends up happening in organizations today is that there's a hiring manager who really understands what they're looking for and then there's sort of these pattern matching that happens afterwards where talent teams are basically relying on these like really hard filters like oh I'm going to reach out to every software engineer at Google. That's not a smart strategy, right? What LLM are able to do is they truly understand

are you interested? Yeah, it's it's like LLMs are able to truly understand what makes someone successful in a role and try to actually find people who are good at that. And instead of just pattern matching based on what company you're at or what job title you're at, we'll actually go in there, we'll analyze your real work product, we'll see what you're doing on GitHub, what are you doing on different platforms, what companies you've been at, and develop a more deeper understanding of who's going to be affected and then reach out to the right person so that that in fact like reduces spam.

Yeah. Let's flip it around to the person that's looking for a job. They want to get spammed with great offers. Uh what should they be doing? Because there's a lot of software engineers where they can't contribute publicly because they work for an important company. Uh there's a lot of folks who their work happens behind the scenes and maybe they are sharing it on LinkedIn. But can your scrapers reach into LinkedIn? Should they have a a personal website and then uh you know put that in some sort of robots.txt txt and webcwler filter so that they get indexed properly. Like how can job seekers show up in results more aggressively at a time when more people are looking for jobs more aggressively than ever?

Essentially put your work product out there. Talk about what you're working on. Putting out blogs, putting out open source contributions, putting out any projects that you have worked on, those things help because

would three hours of live daily content help?

I I'm sure. I'm sure. I mean, it ends with an acquisition.

Yeah,

that's true.

Just talk about AI comms for for three hours a day and yeah, you turn some turns raise some eyebrows. Anyway, uh what yeah, what about so are you purely focused on technical roles because you keep coming back to like GitHub contributions, breaking down, uh breaking down example work products, and I'm just wondering for someone who's in more of a knowledge role or they work in PR or marketing or bisdev or finance like should they be educating people? Should they be explaining their strategies? like if they're not a natural writer or they don't just have a piece of like a side an obvious side project that they can open source, how can they show up to the AI researchers or the AI uh recruiters of the future, your company included?

Yeah, of course. So we we we started out more tech focused because that's the industry we understood the most and we started out working with tech startups and we started working with companies like like RAM scale all these kinds of companies

and then eventually what has happened in the last year is we've grown way way past that. So like now tech does not represent the majority of our customer base. We have more than 5,000 customers and a lot of them are larger enterprises and they're looking for all sorts of people. So what what we are able to do is we're able to join profile data and your experiences on all the company data that we have. So essentially if you put a little bit of information about yourself on different platforms, we're able to take that information, enrich that and do a deeper research on every single company at every single skill you've had, everything you've worked on and build a better understanding of exactly what your area of expertise and then make better matches using that. And it applies across industries. So for example, we have people looking for traveling nurses in the Midwest. Very different type of role. But what we can do is we can look up profiles. There are registries available for nurses on on the internet as well. We'll look up those profiles. We'll understand the different places you've worked at. We'll try to build a good understanding of what these different environments are, what kind of people do these other companies hire, where you've been at in the past, and then make a good inference on whether or not they are fit for the role you're looking for. Okay.

Why do you why do you think there hasn't been a like a big like a like a decacorn scale outcome in in recruiting tech to date?

What is Indeed?

I I would actually argue against that. Like LinkedIn's a pretty

LinkedIn Oh, got it.

Indeed is a pretty massive outcome. Uh

holdings 70 billion enterprise value, bro. Come on.

But that so so that's but but that's but that's like kind of where I'm kind of where I'm going. Isn't that like a a holding company? staffing and recruiting firms.

Yeah.

So more more like labor intensive, but I can imagine

it's not the database market. Let's just be like it feels like you could have you could have like if you execute properly, there could be an outcome closer to that holding company that you just mentioned than

some of these other kind of just like recruiting tech platforms.

Yeah. Yeah. I guess like where's the source of like uh economic power and lock in and scale that would allow for a really really broad outcome here as opposed to okay there's a whole bunch of AI recruiting firms and companies sort of bid them all down and there's not insanely high margins good businesses but not the hundred billion dollar outcome like have you been thinking through that I know it's early but uh have you been thinking through like what does this look like at me mega scale

of course yeah we we've thought a lot about that The the thing is that the main value in the recruiting industry always acrews in the services layer. So far it has never acred as much in the software layer because it's really actually the work that goes into finding people. It's the ability to search for the right person and get them into any role. That is what people pay for, right? And so far there has been no way of actually automating that because you cannot do that. It requires judgment. It requires actually understanding what someone's working on or what their capabilities are. That is exactly what agents are able to do. So this is really the first time when you have a massive opportunity in a market that's incredibly important and you're able to build that with RLMs because it's just not been possible until now. And most companies have traditionally in recruiting tried to target this like software layer which is like hey we'll build another CRM we'll build another ATS and all of these different platforms but the main value always occurs in being able to find the right person. That is what someone wants to pay for and that is exactly what we're able to do with LLMs.

Very cool. Well,

yeah. I I remember first discovering that just everyday recruiting services companies could be big because Hey, there's a there's a public company called Haze. Haze.com.

No way. Really?

It's just a public I've never heard of

like staffing firm.

Wow.

Uh good business. That's very very big opportunity for you.

Congratulations on the Teal Fellowship. Thank you so much for coming on, breaking it down for us and hope to see you soon. I'm sure there's a lot of milestones in the near future. Great rest of your day.

We'll talk Thank you so much for having me. It was awesome.

Goodbye.

Cheers.

Up next, we are running one minute behind, but we're going to catch up because we have uh we have Derpetual next. Building infrastructure to enable derivatives trading on any asset. Interesting. Okay. Derpetual. Uh Anthony Hizuki.

Before we go there, let's pull up this post. Yes.

From none other

than who?

Than Ben Horitz. Not Ben Horowitz.

Ben Horowitz

with the anti- Grammarly. Mess up your emails with AI. If you're worried about people accusing you of a of using AI to write your emails, use sincerely misspelled to use more AI to add misspelling.

Yes. It it it condenses down that long boring email that you were about to send that says to whom it may concern. I wanted to reach out to express my interest in connecting regarding potential synergies between organizations and it just dumbs it down to wanted to reach out let's talk and uh this is news flash this is how people actually email and communicate uh when it's personto person and I think everyone would be better off with a little bit uh tighter communication methods especially in the age of AI so uh I don't this this seems like a joke or a drop but I would imagine this being a good product and I think people might actually pay for this.

I like there are so many times

I think it's actually a real product.

I hope so. They're going to charge five bucks a month.

Alex Lieberman said uh such a good viral drop idea, but I I think it's not I don't I would not expect this to go away. I think this is a business and I think this will be successful and I think this is a valuable tool and it's something that uh that probably it would be hard for uh Google to justify baking into Gmail. It's like it it is a little bit counterpositioned against

Yeah, it's a tough pitch.