Work at a Startup
by Jared Friedman, Matt Long

Jared Friedman is a partner at YC and before that cofounded Scribd (YC S06).

Matt Long a software engineer at YC and before that cofounded Crocodoc (YC W10).

Today we’re talking about a project Jared, Matt, and several other people at YC have been working on. It’s called Work at a Startup and it’s like a common application for engineers to apply to many YC companies simultaneously.


Craig Cannon [00:00:00] Hey, how's it going? This is Craig Cannon and you're listening to Y Combinator's podcast. Today's episode is with Jared Friedman and Matt Long. Jared's a partner here at YC and before that he co-founded Scribd and Matt's a software engineer here at YC and before that he co-founded Crocodoc. Today we're talking about a project that Jared, Matt, and several other YC people have been working on. It's called Work at a Startup and it's like a common application for engineers to apply to many YC companies at once. We're also announcing that we're hosting a Work at a Startup expo on July 28th in Mountain View where you'll be able to meet 35 of those YC companies. You can learn more and apply to attend at All right, here we go. All right, guys, so we are here today to talk about Work at a Startup. Let's really quickly do some introductions. Jared, why don't you start?

Jared Friedman [00:00:52] Hey, I'm Jared, I'm a partner here at YC. The way I got into YC was I did a YC company and one of the earliest batches was a company called Scribd and then I joined YC three years ago as a partner.

Craig Cannon [00:01:03] Cool. Matt?

Matt Long [00:01:05] Hey, I'm Matt Long. I was a co-founder of a company that went through Y Combinator back in winter 2010 called Crocodoc and now I'm a software engineer here at YC. Been here for a little over, little under a year now.

Craig Cannon [00:01:19] Cool. And you guys, in addition to a few other people at YC, have been working on a product called Work at a Startup. Matt, could you describe what it is?

Matt Long [00:01:27] Work at a Startup is a common application for engineers that are interested in working at a startup and, in particular, a YC company. They'll go through a lot of typical, biographical questions about themselves and their experience and background and then they're able to kind of choose their preferences for what sort of company and role they're looking for. We make all this information available to the founders of all of our YC companies who can then kind of browse and search through them to find what they're looking for, kind of indicate their interest and start conversations with them that'll hopefully lead to some hires.

Craig Cannon [00:02:05] Why make this? Why make this instead of just relying on the existing infrastructure out there?

Matt Long [00:02:12] Yeah, so I guess hiring is notoriously hard amongst startups and in Silicon Valley, it's just so much intense competition. The more established players in the tech industry and sure enough just like internal surveys we've done with founders of YC companies kind of confirm that we're overwhelmingly hiring and, in particular, hiring engineers is kind of the number one problem they face following going through the YC program. We, YC decided we should take the same approach we've done with everything and try to apply software to this whole scale, you know, find a good nice scalable solution and just another way that YC can kind of help out our portfolio companies and made our own kind of hiring portal that's a little bit kind of particular to the way and the types of companies that go through YC.

Craig Cannon [00:03:05] Jared, you have experience with this directly having hired quite a bit at Scribd before and you were also a part of the Work at a Startup before it was known as Work at a Startup conference in 2010, right?

Jared Friedman [00:03:18] It's actually not a new idea per-se for YC to try to help its company hire. Hacker News from the very beginning when we first created it back in I think 2009, part of the goal was to help companies hire. It's had a job section from day one and when I was at my startup, I used the Hacker News job section a lot and it was incredibly helpful for hiring. Probably half the engineering team that we hired came through Hacker News and that's not atypical for YC companies, so, we have sort of a long history of this. We have also long had an internal form for YC founders where they share candidates that aren't right for them but could be great for somebody else. That's also worked extremely well and so it was, the origins of this project were we saw that this was working and that there was tremendous demand for it and everybody wanted us to do more. The Work at a Startup product is trying to build just a better, more efficient, more sophisticated version of the Hacker News job board and the internal form that we've had for a long time.

Craig Cannon [00:04:31] In particular, what are the additions that differentiate it from HN job posting for example?

Jared Friedman [00:04:37] Yeah, absolutely. The way I think about hiring is like it's fundamentally a matching problem, right? There's a great company for everyone and for every company there's a set of people who would be perfect for them but it's really hard to make that match happen and it's especially hard for startups, for large companies like Microsoft, they hire people of all kinds and the matching just becomes easier because they're hiring for so many roles. If you apply to Microsoft, there's a good chance there's a role there that likely could be a good fit of you but with startups, you're only hiring for a couple of roles that don't have brand names, you don't know who they are, what they do, if you'd be interested, what roles they're hiring for, and so the matching premise is particularly hard for startups and that's why we've been working really hard on it. Matt would be a great person to talk about some of the ways we're trying to solve a matching problem. It's still in early days, it's a really hard problem, but I think we have some interesting ideas.

Craig Cannon [00:05:27] Cool.

Matt Long [00:05:29] The main thing we're going to be looking in is just kind of around kind of what sort of culture and company feel and potential employees are kind of interested in. Anything from kind of more objective measures like size of the company, number of people in it, whether or not they are profitable or not, like how important is that to a potential new engineer and then also, kind of course, kind of ranging in sort of like skills and technologies the engineers have mastered, the various degrees, and kind of lining that up against, the tech stack of that a given company's using... and then going more into the culture thing, just kind of looking for kind of what's more important to them just in terms of, excuse me, are they interested in solving more kind of like product focused questions or really digging in the deep hard technical problems, so things like that, kind of just what's most important to them and what they're looking for and then, of course, we can get all this information, exact kind of sort of information from all the companies that are going to be in the system as well. That would kind of give us kind of two sets of data, kind of match against each other and we think, you know, we're pretty confident this will be a nice way to kind of filter out the most interesting and the best matching companies to the top for these applicants and the founders as well of companies, just kind of show them which applicants

Matt Long [00:06:52] might be right for them.

Craig Cannon [00:06:55] How do the companies report and measure their own culture in these engineering problems? What questions exactly are they answering?

Matt Long [00:07:04] It's a good question. We actually haven't put these questions direct, in their final form in front of founders just yet but really, you could go to the application that's on and go through the career and culture section and then you can imagine there'd be like a fairly similarly worded question that we're going to pose to our founders and just, to start with, it'll kind of be kind of trusting them to answer them honestly, about what the conditions are like at their office and just the state of their company, whether or not we're going to have to sort of editorialize that or curate it all or make sure everything lines up with reality, it's kind of yet to be seen. But certainly, the start with speed that will be self reported from the founders themselves.

Craig Cannon [00:07:50] I'm curious about how you guys have been doing the matching thus far because this product has been around, when was the initial like early beta launch?

Matt Long [00:07:59] The very first beta was in the middle of December 2017 so just around six months ago.

Craig Cannon [00:08:06] What did it look like back then? Because it might be interesting for people to find out how this has evolved to this point.

Matt Long [00:08:13] Back then, it was just the data we're gathering from acting against that wasn't nearly as much as we have now and it's kind of pretty simple watered down version of what you might be asked at another kind of hiring portal like Hired or AngeList. Back then it was pretty basic stuff, just kind of who you are, what's your email address, a few free-form questions like, "Why do you want to work at a startup?" Things like that, and purposefully we steered away at that point from asking people for a resume just because there is a lot of kind of thoughts internally that it may not be the best thing or the best way to judge someone based on where they worked before, they look at them more holistically, which is especially true at startups. It's finding someone that's going to be aligned with your mission and can get on board with the goals of the company. Much more, we think, than, that might matter at a larger company with a much bigger head count. It's like a smaller and kind of different set of questions than you might normally see but we didn't really focus on work history at all or even education especially. What school you went to shouldn't matter nearly as much as what neat stuff you've done as an engineer, more recently. It certainly has evolved a lot since then. We actually now do ask you for a resume just because after not having it

Matt Long [00:09:39] for a long time, a lot of times the first thing founders would tell us, when we ask them how they're liking the product is, "Well, this is great but I don't know anything about them and kind of the first thing I have to do all the time is just go look at their LinkedIn profile and kind of learned a bit more." We're taking that feedback and iterating on that quite a bit.

Craig Cannon [00:09:57] Any other surprises that you've learned from founders who are getting all of these applications come through their door?

Jared Friedman [00:10:03] One surprise is actually the diversity of candidates that companies are looking for when we first stated we worried that it might be hard for us to find great companies for people who are not in the Bay area because so many of the companies that we have are based here. Turns out not the case. We actually have companies now hiring in over 12 countries, we have a ton of companies who are hiring for remote only roles and just the range of like the different skillsets that people are looking for, everything from full stack web to data science to dev ops and sort of a whole range of experience levels as well. We were able to find good matches for almost everyone who signs up.

Craig Cannon [00:10:50] I'm curious about, before we talk about the conference, I'm interested in talking about the recent HN thread and what were the learnings from that. Earlier this week, you, I think it was Jared, I think you posted it, right? Basically a question to the community, right? What are the pros and cons of working at a startup in 2018? What were the takeaways?

Jared Friedman [00:11:12] It was a pretty amazing Hacker News thread. We got about a thousand comments in response to the question and they were really insightful like people share some amazing experiences of working at big companies, of working at small companies, of founding their own company, of being a consultant and how all of them compared. The reason that we did it was we wanted to really understand what people liked and didn't like about working at a startup and, in particular, what YC could do to help because we're in a position to be able to help with some of the things that aren't working as well as they could be. Some of the things people really like about working at a startup is for sure the autonomy, the feeling that you're able to really move the needle on an organization, that like, the company that you've worked at might not have been successful if you hadn't taken that job, the ability to bond with a small team, the ability to work on really interesting problems and with the newest technologies, the ability to have control over the technologies that you use rather than just inheriting a tech stack that's already set. Certainly some interesting pros and then on the cons, the most prominent one was compensation and what we heard is compensation is important to people. If you're going to take a job, you got to feel like the compensation is fair and startups have to be fair, have to be paying fair compensation in order to attract the best talent and that's always been true. It's gotten a little bit harder recently

Jared Friedman [00:12:58] as compensation for engineers across the industry around the world has gone up but what some people on Hacker News may not yet know is that the compensation of startups is gone up a lot as well. We may be closer than they think but there's still more that startups have to do on that front. Transparency is also very important where people need to feel like if a big part of their compensation package is equity in the startup that they really understand how to value that equity and how to compare it against other offers, that's a basic thing that all startups can really do better when hiring people. Job security is very important to people. Sometimes when you're working in early stage startup, it can feel less secure than working at a big company, the startup can go out of business. This is actually something that YC and Work at a Startup can help with a lot because while working at any individual startup may not be as secure as working at a large company, hopefully, working for startups in general can be even more secure because if the startup that you're working at now doesn't work out, there's going to be 20 other startups who are going to value the great work that you did there and want to hire you immediately.

Craig Cannon [00:14:26] Especially within a network such as the YC community. Another thing to be clear about, if it hasn't been mentioned, Work at a Startup is working at YC companies. Startups around the world just in general. Matt, did you learn anything from the thread?

Matt Long [00:14:42] Just that compensation came up so frequently was a bit surprising to me because I guess for me that was kind of already a known quantity that going to work at a startup, you're probably in the general case going to be taking a somewhat lower salary than you might get at one of the larger paying companies. Just that it's very black and white around that. Some of the comments are like, "Why would you go work at a startup when you can make double the amount at a large company? This just doesn't make sense." At face value that might be true but there's other kind of non-financial reasons you might choose or want to go work at a startup, which I think it's really important that you have to have these other kind of issues, like Jared mentioned. Forming these close bonds with a small team can be really appealing to people and certainly, that was one of the big kind of things I look back on from my startup experience. Granted I wasn't an employee, I was a co-founder, but the bonds I've formed with them, they're still, to this day, some of my closest friends and it's just things like that are one of the unique kind of things that startups have to offer and just that wasn't... Kind of got brushed over a lot and a lot of the comments

Matt Long [00:16:00] was a bit surprising to me but it makes sense again because finances are important and if you're a software engineer right now it is possible to make a pretty nice salary at a lot of places with relatively low risks.

Craig Cannon [00:16:14] For sure. Did remote work play a big role in the thread? Were people looking for that or--

Jared Friedman [00:16:21] It did. A lot of the feedback centered on the insane cost of housing in the Bay area and in a few other large cities and asked the question why tech is so concentrated in this area and a lot of people suggested that one way that startups could compete with big companies for talent is to be more flexible on that, to allow remote work, to have offices in other markets where the housing is not so insane and that's really interesting feedback and it's definitely a trend that we've seen among the YC companies, more and more of them are taking advantage of that.

Craig Cannon [00:17:00] Yeah, absolutely. Zapier is a great example of one of those companies. They were paying people to delocate from the Bay last year which was interesting. I think they got a couple people to do it. All right, let's talk about the conference. You guys are doing a Work at a Startup conference in July, correct?

Jared Friedman [00:17:17] Yep.

Craig Cannon [00:17:18] What are the details?

Jared Friedman [00:17:20] The Work at a Startup conference is actually not the first time YC has done it. We did it a long time ago back in 2010 and I know because I presented at it and it was great and the only reason we didn't keep doing it was that it was a lot of work and YC was very short staffed at the time and so we just sort of like paused it for a number of years but I'm really excited that we're going to bring it back and YC has grown a lot since then, we're 10 times the size and so the conference is going to be about 10 times the size that it was back then. It's going to be really big. And so, how it works is it's similar to YC's Demo Day but for employees instead of investors. We're going to start with a keynote, Justin Kan and Sam Altman are going to give keynote talks about working at a startup, why you should work at a startup, how to judge startups, what kind of compensation we should be looking for, how to negotiate an offer, and then we're going to have 35 rapid fire pitches from the founders of YC companies. We've got an extremely broad range of companies coming who are hiring a very broad range of roles. We have everything from like establish successful companies like InstaCart, DoorDash, and PlanGrid, their founders are going to come and give a personal presentation and then we have a whole bunch of really small companies that just raised a seed round and are looking or engineers number one or two are giving out large amounts of equity and return and then sort of everything in between.

Jared Friedman [00:18:51] And we have companies who are hiring for roles like the most common are probably like fullstack web, backend web, and frontend web, but there's a whole range of other roles as well. We have companies who are hiring for like co-founder/CTO roles, we have companies who are hiring for machine learning and A.I. and devops and robotics engineers and embedded system design. I found that particularly cool just how broad the range is.

Craig Cannon [00:19:23] What's the experience going to be like for an attendee? What can they expect?

Jared Friedman [00:19:26] The most compelling reason to go as an attendee is if you think you might be interested in working at a startup, but you're not really sure which one or how to think about it. You come to a Work at a Startup event, you'll get, in a short period of time, a really compressed view of what's out there on the market, what your options are as an engineer right now in 2018, and you'll get to talk to the founders because after the talks, we're going to have just like a mingling session where you can just walk up to the founders of any company and get to know them.

Craig Cannon [00:19:57] As an engineer, Matt, you're an engineer right now, how do you think someone ought to prepare themselves to attend the event or should they not worry about it and just show up?

Matt Long [00:20:10] It kind of depends on your background, where you're coming from. If you're an engineer that's already worked at a startup or might be familiar with what's going on and what employment might look like at a startup, then you probably don't need to do much. You might want to research a list of companies that are presenting, anyone should do this, just so you know what to expect and which ones you might be interested and listening to because I believe there is kind of going to be a separate track of other talks going on at the same time, so sometimes you have to pick and choose between, if you're going to be listening to the presentations or something else that's going on. Familiarize yourself with the companies and then for someone that hasn't ever worked at a startup before, you probably have a set of ideas of what it would be like to work at a startup based on what you've read on Hacker News or elsewhere on the internet. I would say kind of try to push all of those out of your head and kind of come with an open mind because, you know, we like to think that especially YC startups are going to present you with kind of a nicer all-around employment offer and try to ignore any horror stories you've heard before and how bad it might be, but also, recognizing like we talked about earlier that you may need to take a hit on salary if you are coming from a larger company

Matt Long [00:21:30] and everyone's going to have their own kind of take on whether or not that works for them in their current situation. Coming with an open mind and kind of being willing to think about working in an industry or for a sized company that you've never thought about before would be the best way to get ready for it.

Craig Cannon [00:21:51] Cool. Just, in practical terms, should they bring a resume with them?

Matt Long [00:21:55] That's a great--

Craig Cannon [00:21:55] Or many.

Matt Long [00:21:56] That's a great point. We didn't mention this but actually there is going to be a sort of a selection process for who gets to attend since, unfortunately, we don't have unlimited space at YC's office in Mountain View and so everyone will be required to fill out the normal application that's on right now as if you were going to be using the site online. There will be a special section where you can indicate that you're interested in attending the conference which will treat your application a little bit differently and it'll just tell us who's all interested so we can then go through or we're going to have the very difficult job of selecting who gets to attend. That's the main thing. Whether or not you need to bring paper resumes, if you really want to, we're not going to stop you from doing that but we are going to try to have a little bit of a technological approach to just kind of making it easy for people at the conference to kind of indicate interest in companies.

Craig Cannon [00:22:56] Is it open to people not currently living in the Bay Area?

Matt Long [00:23:01] Yeah. Anyone that wants to come we're not going to stop you. Of course, you'd have to pay your own way here and all that but, it's more about if you're willing to work in a location where most of these companies are located. If you're willing to relocate there then that'll probably be the bigger... will drive the decision a bit more but certainly, anyone not from the Bay Area is very welcome to attend.

Jared Friedman [00:23:30] We are also going to livestream the conference online for anyone who can't make it out here and I wanted to mention one other thing that I'm very excited about for the conference which is for the first time we're going to have hardware demos, so we do this for Demo Day for investors, and back in 2010 when we did the first Work at a Startup conference, we didn't have really any companies for building hardware but now we have a lot of companies who are building all kinds of cool stuff. At the conference, there's going to be a full sized self-driving truck from Starsky Robotics that will hopefully be self-driving itself around the parking lot. We're going to have an actual satellite from Astronus which is a replica of the one that's currently in orbit around the earth. We're going to have, well, we're working on getting permission to land a giant industrial drone in the parking lot of Mountain View, that's a drone that's made by a company called Valanci and it's so large that we need to get permission from the city of Mountain View to have it land there.

Craig Cannon [00:24:33] Wow, cool. Reframing the term startup to be much broader than SaaS companies is an important thing that you guys are doing.

Jared Friedman [00:24:42] That's a great point. A lot of engineers don't realize just how many options there are in startups these days. We have several companies attending who are doing really hard science stuff. They're doing autonomous driving and mapping and hardcore machine learning computer vision kind of things.

Craig Cannon [00:25:01] You guys have been working on this now for over six months, what are the metrics you've been tracking and how is it going?

Jared Friedman [00:25:08] Yeah, so far it's going extremely well. We haven't really announced it at all, we've just been running it very quietly. We added a link on the Y Combinator homepage and so far we've already gotten over 3,000 engineers to sign up and fill out a profile. More exciting to me is that of those 3,000 engineers, the vast majority of them have gotten at least one message from a YC company. Companies are actually really using the product and if you are an engineer and you sign up the odds are good that you will get in touch with a company. Over 80% of the YC companies who are hiring engineers are already on it, they filled out their own profiles, there's a directory on the site where you can browse all the companies who are hiring engineers, so, the response from the YC community has been great.

Craig Cannon [00:25:55] Awesome. All right, guys, thanks for making time. What's the URL if people want to sign up or apply to go to the conference?

Matt Long [00:26:03] Yeah, so you can find all this at

Craig Cannon [00:26:06] Great, thank you.

Jared Friedman [00:26:07] Thanks, Craig.

Craig Cannon [00:26:07] Thanks.