The Pragmatic Engineer - Confessions of a Big Tech recruiter

Episode Date: January 8, 2025

Supported by Our Partners• DX — DX is an engineering intelligence platform designed by leading researchers. • Vanta — Automate compliance and simplify security with Vanta.—In today’s episode of The Pragmatic Engineer, I catch up with one of the best tech recruiters I’ve had the opportunity to work with: Blake Stockman, a former colleague of mine from Uber. Blake built a strong reputation in the recruiting world, working at tech giants like Google, Meta, and Uber. He also spent time with Y Combinator and founded his agency, where he helped both large tech companies and early-stage startups find and secure top talent. A few months ago, Blake did a career pivot: he is now studying to become a lawyer. I pounced on this perfect opportunity to have him share all that he’s seen behind-the-scenes in tech recruitment: sharing his observations unfiltered.In our conversation, Blake shares recruitment insights from his time at Facebook, Google, and Uber and his experience running his own tech recruitment agency. We discuss topics such as:• A step-by-step breakdown of hiring processes at Big Tech and startups• How to get the most out of your tech recruiter, as a candidate• Best practices for hiring managers to work with their recruiter• Why you shouldn’t disclose salary expectations upfront, plus tips for negotiating• Where to find the best startup opportunities and how to evaluate them—including understanding startup compensation• And much more!—Timestamps(00:00) Intro(01:40) Tips for working with recruiters(06:11) Why hiring managers should have more conversations with recruiters(09:48) A behind-the-scenes look at the hiring process at big tech companies (13:38) How hiring worked at Uber when Gergely and Blake were there(16:46) An explanation of calibration in the recruitment process(18:11) A case for partnering with recruitment (20:49) The different approaches to recruitment Blake experienced at different organizations(25:30) How hiring decisions are made (31:34) The differences between hiring at startups vs. large, established companies(33:21) Reasons desperate decisions are made and problems that may arise(36:30) The problem of hiring solely to fill a seat(38:55) The process of the closing call(40:24) The importance of understanding equity (43:27) Tips for negotiating (48:38) How to find the best startup opportunities, and how to evaluate if it’s a good fit(53:58) What to include on your LinkedIn profile(55:48) A story from Uber and why you should remember to thank your recruiter(1:00:09) Rapid fire round—The Pragmatic Engineer deepdives relevant for this episode:• How GenAI is reshaping tech hiring https://newsletter.pragmaticengineer.com/p/how-genai-changes-tech-hiring• Hiring software engineers https://newsletter.pragmaticengineer.com/p/hiring-software-engineers • Hiring an Engineering Manager https://newsletter.pragmaticengineer.com/p/hiring-engineering-managers• Hiring Junior Software Engineers https://newsletter.pragmaticengineer.com/p/hiring-junior-engineers—See the transcript and other references from the episode at ⁠⁠https://newsletter.pragmaticengineer.com/podcast⁠⁠—Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠. For inquiries about sponsoring the podcast, email [e-mail]. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe

How much can I negotiate? Because clearly you're getting an offer, you know, there's a baseline. Broadly speaking, wherever you are, just try to understand what it is of the recruiters working with. They're going to ask you to state what your compensation expectations are. I think that every candidate is best suited by responding respectfully. I would like to see an offer that the company thinks constitutes the value that I have to bring to the table. And sticking with that, if any company is not willing to give you an offer because you didn't state your compensation expectations up front, they're probably not the right company for you to

work at anyways. Ask them to put you a fair and honest offer on the table. Also, almost every single offer has some room for negotiation. What actually happens behind the scenes in tech recruitment? Recruiters at hiring managers working at big tech and startups do know, but they might not share their unfiltered thoughts. But this might be different for today's episode. Blake Stockman was a tech recruiter at Google, then at Meta, and we worked together when he was at Uber. He then recruited for Flexport, for Y Combinator and ran his own recruitment agency. After 12 years of being a big tech at startups recruiter, Blake left tech recruiting behind and is studying to become a lawyer now.

Leathes to say, I jumped at the opportunity to get some of his raw takes on tech recruitment. Today, we go into how the tech hiring process works at companies like Google, Meta, and Uber. How engineering managers and recruiters work together, using the example of myself and Blake at Uber. When you receive an offer, tips on how to negotiate it, and a lot more behind the scenes details.

If you enjoy this show, please subscribe to the podcast on any podcast platform and on YouTube. I wanted to ask you about a truth about tech recruiters. So in terms of as a candidate, I'm a software engineer on the market. I talk with a recruiter at a large tech company. Are you on my side?

Are you actually looking out to help me? Or are you someone who I need to win over? So basically when you're asking me questions, you know, should I tell you what I think you want to hear so I can pass your, you know, your screen, get to the interview? Or can at some point I kind of, you know, like, are you an ally? Because in the end, you do want to fill that seat probably as assuming you think I'm a good fit. I will say, when I had a good relationship and I genuinely believe that someone was going to be a good hire for the company, I would go out of my way to. go to bat for that person, to try to advocate for that person, or maybe we'll put myself on a ledge a little bit because I thought this was the right decision for the company and I

felt strongly about it. I think I'm probably a little bit of like an outlier there. I think especially right now where like a lot of recruiters have just gone through a lot of layoffs and hiring and maybe feel more fragile in their professional standing than maybe we did traditionally. I think that the primary thing that I would, it's like any professional relationship. And it has a lot of like asterisks to it. You just need to, you know, be authentic, like build a real connection with your recruiter

where there's an opportunity to. I think be wary around, be wary around overly disclosing information that's going to shoot you in the foot. Like maybe salary expectations. Any negotiating 101 will tell you not to give salary expectations up front because that's where people will anchor. If someone told me that this is an overly simplified example, but if someone told me that they

were going to say that their salary expectation was $100,000. And I knew my salary range was $110 to $140,000. But eventually I got to the offer, I'd be like, I know you wanted $100,000, so I wouldn't get you $110,000. dollars because at the end of the day, I'm an employee of the company and my job is to be an effective steward of the company. So recognize where there is some obvious inherent friction in the relationship. Be authentic in really what you want to get out of the relationship.

Like don't be a robot. Because sometimes, again, you know, I would go. the extra mile on that extra 10, 15% of cases. When I would sit down with you and you were on the fence about a hiring decision, I would tell you my opinion. I actually remember some of these discussions. Yeah. I work with a lot of recruiters and I'm just going to say that most recruiters were not like you. I think the entrepreneurial spirit came through. But you did, so you did it both on, you did sit down with hiring managers. So like, you know, when you saw as I was on, especially with less experienced hiring managers, which I was in the beginning, where you actually gave me kind

have good advice outlook because you had placed a lot of people by that time, right? Hundreds of people at different companies and you saw how they worked out. So you sometimes, it just felt like honest advice. One thing I remember, which I haven't seen many, like some recruiters have done this. You know, I've talked with them. But one thing I haven't seen many people. There's on deep brief where it was a very like, like going back and forth and it trended towards a no.

You would rarely but inject yourself saying, hey, I know I'm the recruiter, but I've talked with this candidate a lot. and I'm also a bit of an outside observer. Here's things I'm hearing people be concerned about. For example, the coding interview didn't go as well, the second one, but the first one went well. And I'm just going to ask, like, how important is it for the role? Like, you kind of coached the room a little bit. And once or twice the decision was turned around, not because, you know, like, you clearly injected yourself because you felt that something was off and we weren't giving this a fair look.

And it was rare, but clearly that only happened because you had that trust with the candidate and kind of the broader content. Again, it always felt it only worked because you put the company first, right? So it would have not worked. Yeah, I think that was pretty unique to me, though, too. I think I was pretty unique as a recruiter and how I approached it. I think broadly, though, just to kind of round out the candidate side of it, I think just like recognize it the professional relationships and really what their goals are is to make the hire because that's what they're gold on. Right. Yeah.

And so there's some friction there of stewarding for the company. but also like, hey, if you're good for the job, great. It's one less thing I got to worry about. So I think that's important for the candidate side. On the like hiring side, I don't think, I don't think a lot of recruiters do this. I think a lot of recruiters because it don't come from technical backgrounds, you know, they're very wary or uncomfortable stepping in and having these sorts of conversations. I would push any engineering manager or any founder to maybe solicit that feedback more actively

because a recruiter talks to these people a lot. They can get a sense if there's any red flags or concerns that they should be aware of or if there are some supporting factors in conversations around how excited this person is for the job and what it means to them and what they'll really bring to the table and go that extra a mile. So I think from a like manager's side, don't be afraid to, now, you should probably give the Cody interview more weight than a recruiter's feedback. But like, it's valuable in borderline decisions. And I do think that some of the more effective hires that we made were not the straightforward ones. We're the borderline ones. No, no. They were almost all borderline ones.

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So let's talk about what hiring processes at big tech companies work like. Again, you were at Google, meta-Uber. I guess they're somewhat similar. I'd love to hear from your point of view, the tech recruiter's point of view, what did the process look like? Because as an engineering manager or, well, as a software engineer, right, the process is like, I get an invite for an interview. I go there, I get my feedback. I go to the debrief. I do thumbs up, thumbs down.

We have a discussion. As an injuring manager, I actually, I get head count. I then, you know, I'll probably talk to you. at Uber, we sometimes figure out a plan and I'm kind of involved, but oftentimes my recruiter does lead me, especially when I'm a less experienced injury manager, which I was when we first joined. What does it look from from your perspective when you're hiring software engineers or injury managers? Yeah, I mean, I think at the end of the, like, every company is different. How every company does headcount is different. Remember of Facebook, we didn't get our headcount goal

for 2025, I don't think until like February. I think at Uber, I think it was like, I think it did like March before we really knew like what our goal was. And then it would change like a month later anyways. Yeah. Uber was special. It felt like whatever account we had, if we hired fast enough, we just got more. Yeah.

So really at the end of the day, what Uber was was just higher as fast as possible. And that was the initiative, you know, from, from, you know, You know, from the top. Travis all the way down, right? From the CEO all the way down. But I think every company is different. So normally you'll get your headcount, right? And you'll work with maybe your VP of engineering, your engineering director,

whoever it is that your primary hiring partner is for your hiring group. And they'll say, hey, I have these hires. And then they'll say, hey, they're going to go to these managers. And then your recruiting manager will say, hey, here's your pocket. Here's your group. You know, here's what you're going to support. And recruiters will, every recruiting team has this nuances. The most effective ones that I've seen, you generally have more structured, direct partnerships

and relationships with your hiring managers. And so you'll sit down with them and you'll figure out an action plan. Once you get headcount, every engineering manager is like, my hire is the most important. And here's why. Oh, yeah. Oh, yeah. So your job, I think, is a lot of navigating that. and then figuring out how to tackle it.

So when we would hire software engineers, especially in hyper-competitive markets like we were, we're trying to figure out where is this person realistically going to accept our offer? And what do we need to do to close him or her to come join the broader organization? And so we'll get our headcount. You know, figure out what we need to tackle. We'll put together an action plan with the hiring managers. We'll go out.

We'll, you know, start reaching out to candidates, filtering through our networks, asking for referrals from the team. Whatever it is we need to do is start to get more people in the door, you know, fill the top of the funnel. And a lot of that now is done. You can do a lot with tooling. And there's a lot of productivity hacks. But I used to have to do with very old school hackerish ways.

So you fill that top of the funnel and then you just, you hope you have an effective hiring process. And if you don't, you need to figure that out, you run it, get good candidates through the door, try to close them. And yeah, and there's a lot of nuance. Every company's got a different way of going about that process. But yeah, it's it was always messy. No company has figured it out quite. Maybe we can talk over a little bit on how it actually worked at Uber at our time. Obviously things have changed and, you know, like it's definitely not not the same.

But that was pretty cool because both of us were there. I was a less experienced engineer manager. In fact, I didn't have much experience when we started. So like I'll start from my perspective and then we can pitch in on, you know, like what, what information you had is I showed up. And my manager at the time already set up a weekly meeting with with you. Like every week we would get together. And so I would get my headcount approved or not approved. but I'm like, so like my leadership team needs to give me headcount or at least verbally tell me like, okay, you know, this, this year or this next six months, you can hire like, you have three headcount to fill. And with my, with my management team, I would decide what that head count will be. Is it going to be a senior mobile engineer back end? I mean, for me, this was mostly the two things. And once I had it, kind of put it in a table on our meeting, I would tell you like, all right, Blake, I now have clearance. We're going to start to hire for like these two back end and one mobile engineer. And then I would. And then I would. And then I would.

kind of like kind of handed over to you like how we're going to do this yeah yeah i think that's right i mean we would it was it was tough because we were we were in amsterdam we could hire from pretty much anywhere in the world and so when someone just gives you hey you've got to go hire you know 10 people over the next quarter uh here are your teams go figure it out um it's pretty ambiguous. And so, you know, we would figure out, um, as a broader, you know, recruiting team, hey, where are we able to really effectively recruit from? Where are, when we do a talent map. So this is something that I think is really helpful, especially starts to do larger hiring projects. Maybe not so much, you know, one to one. But like, when you have a new role,

you might sit down and be, okay, we need to hire a software engineer with this particular set of skills. And so if it was for, you know, our famous team was the largest one. So we'll say, hey, we need to find a couple, what are the companies that are going to have relevant experience? Or someone can ramp up really quickly, have understanding of our domain knowledge, and then we would map out those companies. And then we would say, okay, but which ones do we think also have like really good engineering talent that also, you know, would plant in really well with a broader engineering culture here? And then we would put together a whole outreach plan. So I think that was really critical is the pre-planning, the pre-calibration, making sure that we're aligned that

like the candidates that we would bring to your door, like, are you going to like them or do you going to have, you know, earlier opinions about them? And so I think the point in this is helpful for engineers or people that want to be founders one day or engineering managers is just like the upfront work of calibrating, really understanding and getting on the same page. is, I mean, it will save you weeks, if not months down the road. It saves you a lot of back and forth and really gets you ahead of the curve. And by calibration, what do you mean? Yeah, yeah.

I mean, if you just say, hey, here's a job description, go find me some engineers. And then I go out, I bring you some candidates. you're going to tell me, hey, I don't like these for this reason or this reason or I like them for this reason. I now actually remember when we're calculating. Yeah, yeah, exactly. So I would, and then sometimes I might ask you, I might be like, hey, Grigay, go find me five engineers that you're really excited about or that like if you could get them to like interview at Uber, like you would hire them like today. And like, why is that? And so I would have you bring some of those and then I would go back with my team and then we would go find a bunch and then we would sit down and we'd like write we'd

comment we spend 30 minutes an hour however long we needed to to get on the same page because recruiting time is expensive recruiting is very um operationally involved again it's becoming more and more automated there's easier ways to calibrate you could use AI systems to accelerate this process but there's there is some good old school calibration needs to happen because again Recruiting is a partnership function. Recruiting can't do anything on its own. And the manager is very, very limited in what they can do on their own. So you need to get those functions in the same page. Yeah. And I think one thing that I felt worked well, and it's kind of always hard to tell if I was in a bubble, if every company works like this. But as I understand, at a lot of places at large companies,

there's like recruiters and there's managers. And it's kind of transactional as in like, oh, managers get headcount every now and then. And when they do, they go to recruitment. They're like, bring me these people, you know, they kind of get something, maybe not what they expected, but they do it and they go away and they don't talk with them. Like what happened with you and me and like engineer managers and recruiter and your recruiting team is we actually worked together for a longer time. We, we figure it out. We did treat this as a partnership. I think, you know, my manager, Charles, he really always, he actually, he taught me as like, you need to treat recruitment as your partner. Like you're equal. Like you're not better than them because I think, especially

at Uber, a tech company, like, engineering was a little bit, you know, like, higher in the, I don't know, in terms of how we were, like, compensated or seen or valued. And so, like, he stressed his partnership, which was true. And I remember that when we put together, we were doing this calibration, we're trying to find senior engineers. And we realized we can't really find as many as we'd like, at least not in the near visit. You know, I think you came to us and said, like, all right, here's, we actually have, like, people who don't necessarily meet a senior bar, but they can grow into it and look at their

career director. Like, could we actually compromise on some of these? And then we could have more, more candidates, more diverse candidates. And I, I remember like being very pleasant and surprised, like, oh, really cool. So now you're telling me, but then I was thinking, like, you should be telling me because you know the market better than I do. You actually scout these people. And as a manager, I just remember that I had this thing in my head who I'd like to hire. And then reality just comes along. Like, like, those people will either not respond or when they do come in or they have like crazy salary requirements that even we can match even though we were we were there so i i felt that as soon as i as a manager i was like let me treat it as a partner in fact

let me learn from you it actually helped my recruitment and being more realistic and more flexible and adapting to whatever the market was and then i actually remember that uh i think it might have been your recruitment team like brought some ideas saying like oh hey why don't we do a recruitment trip to, I think, Brazil, because there was a lot of really good tech talent there. And it's like, what is the recruitment trip? And then you told me like, okay, here's how it works. So there was a lot of like, like surprisingly, I think we like as soon as we started to work together like that, I feel we got a lot of value out of this. Was this like a common thing in your experience at larger companies? Or is this how all the better teams work or they work differently? Yeah. You know, Google is,

again, this is like decade old information now at this point with Google, but like Google was very removed. They had one broad software engineering pipeline, you know, and like I would get a candidate that had interviewed with engineers across all these random teams, very unlikely that any of those people would ever interact with this person ever again. So very like emotionally removed interviews. and then you're like, okay, I've got a candidate. And then there's a team we would send it to who would say, hey, this person is probably a fit for these teams. And then I would send an email to the managers. They'd respond if they want to jump on a call.

So, like, it was very, very removed. And I remember, again, to go back to like, why did I go to Uber? Like, I think I ever, I think I only saw the hires that I made like one time, if ever after they started at the company, you know? So it was like so removed. And any of the partnerships were happening at a very, very high level, but not between managers and recruiters. And I always remember, I thought that put us in the back foot when things started to change around Google. I remember around the market, around how many other exciting companies were out there like Uber at the time, right?

And so that was really interesting to then see like Uber. We were very directly involved. Recruiters were tied directly to particular teams. we would have these regular syncups. And I think that made me a lot more effective in navigating really difficult closing scenarios where I couldn't say, hey, we're Google, accept our offer. I'd be like, hey, can work for Uber and all the baggage we bring along. But here's why it's a really, really good place to be.

And then we would, you know, lean on our partnership. I would talk in depth about why I, what would make, you know, like your team, for example, like really, really great or why it might not be the right fit. So I can then help that person navigate. And I think the best recruiters are able to have that honest conversation and navigate some of the complexities around like what makes something like not the right fit as well. And I think for founders, like when you're recruiting, it's very easy to say all the best parts of what makes your, you know, what makes your company exciting. But like being able, especially for early employees about like, hey, here are the risks, here are the challenges,

here are the things that I'm worried about. And I want your help solving these. How might you solve these problems? Let's dive in. Let's jump in about that. That can also be a signal for them if it's the right fit because that's what the real day is going to be like. It's like solving real problems, not just folks in the outcome of closing them and then trying to figure out if it's the right fit, when you go in with transparency and openness, you're more likely to land on it being the right fit for everybody. And it also means that it'll stick with you, like they'll stick with you for a long time. And so the partnership that we had, I think, with the back and forth around Uber and some of the teams, I think that that's why some of the hires that we made are still there, right? Like, we go on

that Brazil trip, like, some of those people are still, like, they're the leaders now of the office. which is crazy to see. Almost all of them. This is like seven years later. They've all grown into like senior staff engineers. And yeah, that was the Brazil trip, which again, it came from. I want to stress, as far as I remember, it came from yourself and the recruitment team. I don't know exactly who.

But it was like, oh, let's do this. And we're like, oh, we don't know about this. Yeah, I think it came from other members of the team. But we were all involved. And I think it was very, very interesting to like see some of my colleagues, like, really drive some of that and I think some of the results. I was a skeptic of its like ability to work, but it, I, it worked really well. And the folks that we hired are exceptional, clearly, you know, have come standouts in that culture. And I do think this speaks to exactly what you were

talking about before. Sometimes you hire people with real potential, um, who can grow into roles. And I think you have this freedom to do this a little bit more at larger companies. You can't do this when you're hiring two or three engineers total for your whole company. But when you're hiring for a larger team like that, you can make these tradeoffs that like can pay very large dividends down the road. And that trip was a great example of exactly that, I think. Totally. So can we talk about how hiring decisions are really made in the sense of you've been in so many debriefs, you know, with hiring manager discussions.

But once an engineer goes to the interviews, talks with the engineering team, you know, we know there's the software engineers the usual, most companies, coding interview, well, there's the recruiter screen, coding interview, system design, hiring manager interview. And when that person, you know, like they do pretty well on all of those, oftentimes it's not necessarily an easy decision. I've been on many of those hiring committee decisions or even hiring manager decisions. what have you seen in terms of how do hiring managers decide? Is it hiring managers or is it groups?

And how much input did you have as a recruiter to champion people, for example? Yeah. The larger the company, the more decentralized the hiring processes. Right. So like at Google and Facebook, you have committee after committee and review after review that look over large packets. You know, you're talking earlier about Cloudflare, like looks over every offer before it goes out. Like larger companies can sometimes have layers and layers of reviews and approvals and you need to basically validate your hiring decision all the way up the chain. This could be really painful,

I think, for candidates and also for the manager who's like, hey, I've been trying to find this person for like three, four months. Oh, yeah. And they're not going to start for another month. And then it's going to take them a month to ramp up. And then we have this to look. So like, I always found those types of processes to be very in contention with rapidly changing business priorities. And so that's why a lot of startups and I think more efficient like companies that were more efficient at like really scaling like Uber really brought it like as close to the manager as possible with like one layer of removal and of like approval basically just as a gut check making sure that you're not just making desperate decisions but making effective decisions and so we would do debriefs right so that was our

standard process i have generally carried these through and i use them even with my earlier stage startups that i used to work with where you have your hiring process of who's in like who's interviewing what and what subject matter we want to dive into and you can talk more about how hiring process is work but like basically you get all these people into the same room, you put out there, hey, I'm a yes, I'm a no, I'm unsure, you have a broad discussion. And then I also find that it's really, really effective to do written feedback so that people can come review it asynchronously and then have more informed valuable discussions. Instead of just like resuscitating like notes live. And so you come in, you make those, everyone discusses.

But really at the end of the day, you know, it's not the engineer on the next team over who's helping you with a particular skill set interview. It's not, you know, the senior engineer on your team who, you know, has a broader understanding of architecture than you do. It's you as the manager who has to own. own that decision, both the positives of making that particular hire and maybe any tradeoffs you have to make because it's very rare that everyone's going to perfectly fit what you're looking for. We're talking about human beings after all, right? Like, not robots. And so I found that

the biggest thing you can do from a candidate side is just like be honest with the hiring manager about like where your strengths are and like where you're trying to grow. Don't. try to, you know, BS your way around it. And because that's the person who's really going to have to own the decision and go to bat for you. And who's going to either give it the inevitable yes or no. If you're on the manager's side of this, remember like when you're interviewing people, very rarely is everyone going to be a thumbs up? Yes, across the board. This is the perfect hire? Let's make it. I think that was maybe 20% of the.

the hires that we would make is where everyone is unilaterally, yes. So the thing that I would talk to a lot of the managers about is like, okay, here's this candidate. You have all these signals. Again, they're imperfect. They're quick snapshot conversations. And as anyone who's managed people before knows, it can take months or even maybe a year before you really understand people's strengths and weaknesses as a professional. Yeah. So how can you possibly get that in a short interview? but here's these signal points. Let's make a trade-off discussion here. Like, knowing what you know about the team,

knowing what you know about this person, how it all fits in, like, what do you want to do? And so how hiring decisions get made, I think it really lands on like, how desperate is the team to hire? How cleanly do you fit in with the overall need? More and more,

it's becoming about particular specialized skill sets or having broader, like, architectural understanding of what it is that you're actually building, not just being the fastest coder or, like, quickest hacker, you know. So I think it's more about, like, nuanced, broader understanding and, like, being able to navigate those tradeoffs. So I'm happy to dive into, like, any particular area that you find interesting there, but, like, a lot of the times people want to think that it's. like, I have the skills for the job and I either did or did not get the job. Why is that?

I think there's a lot more nuance always going on behind the scenes that doesn't really get talked about openly. Did you notice that large tech company, like the startups behave very differently in terms of hiring or is there just more subjectivity? Is it more based on the, you know, fewer people making decisions? Yeah, yeah. I think the pros and cons. of a hire and how it fits in and how much impact a bad hire can make or how much impact a good hire can make is so much larger, the smaller the company it is. Oh, interesting. And so I do think that there is an inherent, like, introducing of bias for sure into hiring

process. And I think that a lot of companies struggle, struggle with this part of it for sure of, like, making really effective informed decisions that are not based in bias, but like actual rooted, like, how good do I think this person is really going to be in this job? But yeah, I do think a lot more, there is a lot more risk aversion, I think, at earlier stage companies initially, and then they get really desperate when sometimes it takes them a while. And I think they overcorrect. and that's where they make hiring mistakes.

This is the second time you're mentioning a company being desperate. You previously said don't make desperate hiring decisions, but clearly you've seen that the companies do. Can you talk about how this happens? Because it sounds like you've seen a bit of a pattern here. It happens. You know, I think when you're facing a big push or a big deadline, right? Sometimes as a company, you realize, oh, we have this huge opportunity here, but we need to hire someone to actually, you know, build out this project or take on this product area or whatever.

Then you put together a recruiting process, then you either, whether it be you're doing it yourself or you bring on a recruiter, by the time you actually spin it up and probably get going, it might be a week or a couple weeks or a month, right? Depends how effective or how high priority it is. You need to warm up the pipeline, you need to reachouts, etc. You got to calibrate. You got to start bringing people into the pipeline, running processes. So it can take a very long time until you start to actually get people in the door. And then you have to actually get them to start. Now, there are more candidates in the market now than there were, you know, a couple years ago.

I think that's the nature of tech hiring right now. But it does take a while. And so I think that what will happen is that especially, earlier managers or earlier founders that haven't done a lot of hiring before, you know, going with these expectations of what the process will look like. And then they end up finding themselves two months later, three months later. Maybe they made an offer and the person took a different job or, you know, they didn't quite navigate the tradeoff decisions effectively or maybe just didn't find the right person, which happens, right? So then you're kind of facing

this like, well, we've got this okay person that we think would work, at least for, this maybe this context. And if we don't hire them, maybe we don't ship this product, which could be feel like life or death. Everything feels like life or death early in your company. So that's where desperate decisions are made. And I think the downsides of a bad hire for a company at an early stage, they're very, very high. They're very, very high.

So that's where, yeah, that's where desperation. And let me add one more desperation, which you might remember. It's a weird type of desperation. Maybe this was specific to Uber. If we did not fill our headcount allocated with hires by the end of the year, we would lose it. Yes. So basically, this created this really weird thing. And I was in a situation in Amsterdam.

We had a lot of headcount and we were like lagging behind. We were not on track to fill it. So at the end of the year, as a manager, you know, like, you know, clearly we initially worked with the recruiting team saying, hey, can you get more candidates? Let's get in more interviews. Let's like have engineers like work less on projects, push back on projects so we can actually hire. But as a manager, we did face a decision of like, okay, there's a person who's kind of a maybe, maybe yes. Do we hire this person and then will help fill the headcount or will we just lose the headcount, which feels again, I don't think this happens right now, but a, uh, uh, uh, a, uh, then this was a thing. It was such a weird situation to be in. Yeah. Yeah. I think because if you have to remake your case of why you want to hire that person in the first place or why it's important. And I do think headcount discussions are very, very, very political, right? It's everyone fighting over limited resources, particularly right now where it's not a boom market. In particular, sectors like AI it is, but like broadly across the board, it's not as much of a boom market as it

used to be. I think very rarely making desperate decisions leads to good outcomes. And that's why you generally, at larger companies, have layers of checking to make sure that this is actually a really good business decision broadly. And that's, I think, the primary purpose of exactly what that's supposed to, you know, supposed to serve. I would just advise anyone, if you you think the primary reason, the primary and secondary and maybe even tertiary reason you're making a hire is, oh, God, we need someone in the seat. You're going to probably regret it. Yeah. Yeah. Over time, it usually goes like this. But it's, this was more of a case. When I personally was a less experienced manager and I didn't see, I think once you do those mistakes, you learn from

them. You do. But maybe you can learn ahead of time and not make them in the first place. So now that we've, we've gone through the, you know, the hiring committee decision is settled. on a yes, one way or the other. It's a very exciting time as a candidate. You're getting on, you know, you get the email, you get the call saying, hey, we want to extend an offer for you. And then, you know, we're setting up this call, which is in your lingo, it's the closing. What happens on this call, which is a recruiter, candidates think about it as a final call. You know, recruiters think of as a hiring manager as a closing call. The goal of the company is to have the person accept. What typically goes through how do you prepare?

and, you know, like, what does your feel look like? Because you've done this so many times. Yeah, yeah. I think the preparation for that, a recruiter is going to go back to their finance team, if they have one, or the founder if they don't, right? And they're going to tell them, hey, this is what you can pay. You know, here's the salary, whatever. Here's the equity that we're going to offer.

Hopefully the recruiter has a good understanding of the equity. Hopefully they can speak to it. I'm assuming that equity as a part of the package, I think it's pretty, pretty standard in most technical offers these days. Tech and startups, yeah. Yeah, at least in the startup sphere. And I think that I'm a nerd, so I like to really understand the equity and speak to it and how it plays into the market and maybe how we got our valuation. At Flexport, I used to like, I talked to our FP&A team and I was like, hey, we want to, I'm going to get information of like. I think it's a finance planning and an and and analysis.

Analysis. I think they're like they're like they're like financial wizards, man. They're just like forward projection, you know, thinking about like. And they and they really understood the company valuation, right? Like the other ones doing the investor. You walked up to them to understand all this. Yeah. And we would and we and we had a recruiting team trained on how to speak to and sell the valuation.

We were not going to beat Google. Facebook and Uber and even other competing startups that offered more money. Fluxport did not give the largest packages. So we had to tell a story about the startup, where it was going, why it was going to be big. And so, like, we taught our team, and I think this was effective because we got it. I mean, again, our baseline was 20% offer acceptance when I started there. And so we trained the team how to sell equity. And so not all recruiters are going to be able to do that. Not all recruiters are going to have a good understanding of the financial projections and

futures and valuation nuances. But what an engineer should know is that like you're going to get the base level information. Hopefully your recruiter can speak to things like the strike price. The, you know, where's the valuation coming from? When is the company going to raise again? Because you're basically deferring cash compensation to be an owner in the company. So ask about, ask questions you would want to know as an investor.

If you're willing to go do some like day trades on the side over a couple hundred or a couple thousand dollars, shouldn't you take that kind of dedication and nuance and understanding and like understanding the equity, which is a major, you're basically deferring cash to invest in this company. That's a lot of what you do when you go work for a startup. So if they don't have the information, be polite, but just ask them if you could speak to someone who can give you that information. Sometimes that's the engineering manager. They'll give you their authentic take a lot of the times, how they think about it for themselves,

right? Because it's going to be their job. If you join, they're going to have to help you navigate these compensation conversations. So get this information. And then sometimes they'll connect you to the. CEO or someone from the finance team to talk through it. But this is important information. I think a lot of people gloss over it and don't understand it because it's messy, it's scary, it's unique. And yeah, pretty gray. So, but yeah, I do think that when I was

a recruiter, we would prep, get the information, understand what the offer is, lay it out there. And then we would always set up another call. Okay. When can you talk to the hiring manager? Or, you know, what does next steps look like? Can you accept this offer? What is your timeline? And so I think being able to ask his questions to really understand the offer, but then also be ready for them to ask you for when you're going to make you a decision, whether it be

on the spot, a couple days, two weeks from now. And that's very situation specific. Yeah. Now, one thing that I think is on everyone's mind is who is, who is, who is, who is, in the situation is how much can I negotiate? Because clearly you're getting an offer, you know, there's a baseline. And, you know, normally this will be a tricky question if you were working for a company right now. Because, you know, I couldn't be certain if you're talking to a company or not.

But now that you're not in the profession, for now, at least, what looking from a candidate's perspective, as a recruiter, clearly you wanted to close the candidate, what leverage do Candidists usually have? And we can talk a little bit about maybe about like seniority, how that weighs into these things. So if you had to advise someone who is like, I got an offer, it looks good, but I like to make the most of it. How does a good professional negotiation look like? Ones that you've seen succeeded. And what are maybe some pitfalls that actually, you know, people don't succeed? Yeah.

So I'll say first off, some of the laws around transparency and compensation, at least in the United States, are changing very quickly. We have new laws coming in place in Illinois, just this next year about pay transparency. We're saying this already that it's been in place in California for a few years. It's been in place for New York for a few years. And so you should be able to get some baseline understanding of like, what's the actual range that I'm working with? And I think that's a good starting point. It's just like understanding. And if they don't have it, you should be able to ask for it. Again, this is very like region specific. It's very, if you're in the United States, it's very state specific. Broadly speaking, wherever you are, just try to understand what it is of the recruiters working with.

They're going to ask you to state what your compensation expectations are. I think that every candidate is best suited by responding respectfully. I would like to see an offer that the, company thinks constitutes like the value that I have to bring to the table and sticking with that. And if anyone, if any company is not willing to give you an offer because you didn't state your compensation expectations up front, which I've never, ever seen by the way, but like they're probably not the right company for you to work at anyways. So, uh, ask that to put you a fair and honest offer on the table. Also, almost every single offer has some room for negotiation. There are some

exceptions. Sometimes interns don't have an ability to negotiate, things like that. But most offers have room for negotiation. So just be prepared for that. If you're interviewing at a bigger company or if you're interviewing at multiple companies and have the privilege of getting multiple offers, the best thing you can do is get all that information in the same place, go to the company you're most excited about, and get them to compete, get them to like step things up. Because what I would do when I was a recruiter is,

and this is true when I was at Uber and pretty much every other place, I would take in all this information. And I'd be like, hey, give me all the information that you can or that you're willing to disclose by your other offers. If this is where you want to be, that's the big commitment I'll get. Tell me you want to be here. I'll take all this information.

I'll go to our finance team and I'll make them get you the best and final offer that you could then make your decision. So I think for negotiation tips, don't go first. More offers is better as far as like getting better compensation and take your time

so you really understand exactly what it is that the company's offering. Yeah, and I guess it's good context to understand that the recruiter is not the decision maker, but they can do, you know, when you're respectful, they will try to help you. You've already gotten the offer. Yes. Like, as an engineer manager, like, we don't want to lose a candidate if we can close this candidate at that point. I had no incentives. I had no goals. I had no, I never had any sort of structure tied to my performance that was. associated with paying people less money. In fact, when I ran a recruiting firm, I was paid a percentage of the salary. Now, I took my professional obligation pretty seriously to not like abuse

that position, but a recruiter does not have professional incentive to pay you less. Their professional incentive is to get you in the door. If they're making you an offer, their job is to get you in the door. So help that if you want to go work there or if you're really serious to considering it, work with them professionally to like make that happen, but make them go first when it comes to compensation negotiation. You've worked at a lot of startups and you previously mentioned, you know, like finding great startups. How can engineers and engineering managers or even execs find great founders or startups to work at? Do you have some advice on on how you can scout those things out. Yeah, how to find good founders, how to find good companies. Yeah. So,

first off, I wish there was one place where every startup could go and post all of their jobs and you can make an effective decision. It's very disparate. Probably not LinkedIn. Probably not LinkedIn. Tell me more. Well, you have to pay a lot of money to post an effective job on LinkedIn. like they charge companies thousands and thousands of dollars just to even put up a job in the first place and so if a company is spending thousands and thousands of dollars to post a job you know like I don't know they're probably larger right yeah um there are good jobs on LinkedIn I found a job through LinkedIn is how I found Flexport but like the market is changing um and especially the earlier and earlier of a startup that you're really interested in like if you really want like small

gritty startup, they're not going to be posted on LinkedIn. Large companies probably are, later stage companies probably are, but not the really early stage ones. And those are probably more easy for people to find anyways, the larger startups. Earlier stage startups, Ycomiter has a great website, worker to startup.com. They've built it to where their founders are, have like permanent access, they can run a lot of their recruiting searches entirely through there. And so you can go on there. I would contact people on there all the time to try to get people to come work at different YC startups that I was helping or, you know, that we thought would be unique fits for those individuals. And so, um, I think every candidate who's interested in

working at a startup should start at work at a startup.com. Now, again, these are only YC companies. This is not going to be everything. But there are a lot of great YC companies all over the world doing all sorts of things. So there's number one. Next, you can look at a lot of the best venture capital firms. A lot of them have job pages or have lists of recent investments that they're making. And so you can go to their career site and like find great repositories of like great startups at the best venture capital firms are working at. I don't think that working with a really big brand name VC is everything, but it's certainly a signal, right? It's certainly a piece of information that you can rely on. There's probably something there. If Drason Horowitz is writing a

$10 million check to someone, there's probably something there because they spent time. They're not does give in out $10 million these days. So if there's, if it's, there's probably some reason. I, I think that, um, um, a lot of these conversations that you're going to have again, like, you're about to spend a lot of your time working on a very, very hard thing, um, with people. So I think every person who's taking a startup seriously, um, make sure you really get to know these people, you know, Like, you are exposed to so much more of the hardship and the ups and downs and whole journey of it, the earlier of a startup you go to.

And it's much easier to take that journey on when you actually like the people around you. And so when you are evaluating startups, you have to think about it on an interpersonal level as well as a professional level because you're all working to make the other, like to have each other. succeed and you need to have each other's back. It's a little bit like going to war, you know, like you really, like you really, really need to. And so I think that's important when like you're evaluating. But yeah, as far as like where to even find these people, I think those are really good places to start. A lot of this is through networking. A lot of this is through referrals. So just trying to connect with a lot of these people. Different venture capital firms have talent teams that work in house that are constantly trying to find people to go work.

So maybe you can try to connect with them directly. But you kind of have to hustle and you kind of have to go out and do your own research because these early hires, everyone approaches it differently and there's no like single place that you can go. And as someone who's used LinkedIn a lot as a recruiter, what advice would you give people to kind of, you know, update their LinkedIn, right? Like the first time you're like, I'm kind of going to be open on the market. I'm not going to like put an open to work and I have a job.

But I'd like recruiters to find me. How did you find either both software engineers but also engineering leaders that you kind of like felt worthy enough to, you know, message? Basically, what advice would you get people to like, you know, make yourself a bit more attractive or maybe subsequently indicate to a recruiter as like, hey, if you message me, I'll probably respond. Yeah. I don't know if I, I never really thought too much about if someone would respond, because if I'm there, I should probably just send the message and see. And I think most recruiters are probably just going to send the message and see. Now, if you're on there like, don't contact me unless, you know, like, I'm probably not going to message you because I think you're being kind of a jerk. So I'm probably not going to message.

We see some of those software engineers. I see them less these days, but it used to be big a few years ago in the market was hot. Yeah, just don't be a jerk. It's fine. If you don't want to, if you're not interested, respond, hey, thanks, not interested, or just don't respond, right? Very simple. But I think for your LinkedIn profile, just put the basic information, put what you built, put what you're excited about, put the basic technologies that you've worked with. Some companies care about that, some don't. Put the domain that you've worked in. Sometimes I would work with fintech companies and they really wanted people with like particular fintech experience. Sometimes I work with people that, that wanted operational experience like Uber. Like you're building software that's like moving the real world around. So like how are you doing that? So put put some of that contextual information outside of like I build software. But like what type of business problems have I really had to understand to like go build effective stuff around?

So I think don't write an essay, but like put the basics and be a human being. and that will help recruiters find you when you want to be found. So, solid advice. Thank you. And what is an inspiring story about recruiting someone that you have? An inspiring story. I mean, that Brazil trip was pretty special, I think, for a lot of reasons. I'll say recruiters are pretty thankless job.

and it's very emotionally draining. You spend a lot of time going to bat for people, whether it be your managers or your candidates, and no one really stops and says thank you too often. But that trip to Brazil, I didn't go, but when our colleagues came back, there was only two of us that were really kind of helping the candidates navigate the actual process and offer negotiations. So it was pretty complicated to make that all happen. And I remember one of the individuals when we made the offer and he accepted, he came up to me after he started and he told me, hey, thank you so much. Like you changed my life. You changed my family's life. This is a big step for me, moving me forward. And I don't know what it was going on in his life where he felt like he needed to make that change so much or move away from his home country and move across the world to Amsterdam, right? Like he.

Huge change. I've done it. It's really, really hard. And a lot of people do it to move to the U.S. or now to Amsterdam. So I remember when he came up, he said, thank you. He told me this story. And it sticks with me because, like, maybe these people just don't say thank you. But like, I really think what it was is that I was respectful, I cared, I put in the extra effort. I tried to tell him why this would or would not be a good move for him. I didn't try to sugarcoat it. And it ended up being the right decision for him. And so I think that's great. Like you're helping people navigate one of the most consequential things in their lives, their jobs, right? And I think giving it their respect and time it deserves, like has a lot of value. So I guess good takeaways.

If you're hired somewhere, go stop by and say thank you to the recruiter. Because when you say it, I actually realize you say to thank this job. And as an injury manager, why I was working with you, I'll be honest. Like, I didn't say thank you too much to you. Maybe I did. But, you know, it kind of just hit me now. Like, it does feel like a thing because the hiring managers kind of take you for granted, which I'm just going to say that I did.

Yeah. It's okay. You were still in a recruit when I would apologize. Like, sorry. It's not that I didn't appreciate you, but I never thought it was just, you know, it's part of a job. Like, you know, you helped me hire you out. Yeah.

good job high high five and i think as a candidate's uh like it's easy to complain and i i've heard so many engineers complain about recruiters but i've never really heard people be thankful even when they and they don't see the stuff that that you do for them so yeah yeah whatever and whatever it is just remember again this is a people business right we're working with people on all sides it's very messy it's very difficult um yeah i don't think i think you would hurt but i do think that when you take that extra step, that's the type of thing that make people remember you that will go to bat for you. You know, there's one piece of advice I always like to give people is that careers are long, you know, people will remember the, they will remember how you made

them feel. They won't always necessarily remember all the things that you did. And so if you give people good impressions where they have a good general vibe and emotional connection to you as a person, they will be willing to go to bat for you in the future. They will become the network that you will rely on to go get your next job. I'm getting responses now and help from people who are willing to go to bat and help me find really interesting internships as I'm jumping into this new career, right? They have no reason to respond. I'm going to be a legal intern in a different department, potentially in different companies in them entirely. They only were doing it because I left positive impressions on them, or at least I'd like to think that I did. And so,

whatever it is, whether it be a thank you or just being cordial and professional and kind in your professional interactions, it goes a really long way in ways that you can never predict. Awesome. And with this, let's wrap up with some rapid questions. If you're okay with that, I'll ask a question and then you'll tell me whatever comes to mind. What was the most successful cold email reach out that work for software engineers? There was this one guy at Uber and he would email out, hey, this is Chris from Uber. I'm interested in chatting. Let me know when you're free.

And he got more responses than anyone else trying to be crafty or creative or unique or selling. He was, hey, this is Chris from Uber. Let's chat. And like a lot of people, you know, like, hey, great Chris. Let's chat, dude. What's going on? So, yeah, I remember that. Chris, Chris Adams.

What a guy. I asked this from a few recruiters, and I sometimes got the same complaint that some recruiters put so much time and effort, they researched, they did super personalized, and then they did have that person, which, and by the way, when those recruiters tried this, it didn't work for them. Gurk, did you ever read a three-paragraph long recruiting message telling you all the nuances? No, there you go. No, even I didn't.

What was the hardest role to recruit for throughout your recruiting career, technology role? We were hiring a chief data officer for Flexport, and no one had the same idea of exactly what a chief data officer was supposed to be. And even our data analytics team was like, why do we need a chief data officer? Like, what does that mean? And let me tell you, when no one can tell you why you're hiring? to someone, no one will be able to make the hiring decision. So still doesn't keep me up anymore. But yeah, Chief Data Officer at Flexport, that was a lot.

What is a book that you would recommend and why? A book that I would recommend in why. I'm a big science fiction fan. I think we all spend so much time reading professional books, I mean, this is a professional podcast you're making. you're making. Right. Sometimes you've got to get out of it.

A three body problem is a amazing science fiction novel. Hugo Award winner was on President Obama's reading list. Three body problem. Go read it. I could not agree more. I have some friends who tell me they find it very slow to start, but I don't know. I think it's part of the book. If you're an engineer, you have an inquisitive mind.

You like to understand how things work. the book goes in a deep depth trying to explain science fiction and that just to me as a nerd is impossible to put down if you started it and you went you gave it a chance yeah yeah yeah with you so that's the book this is awesome blake this is very nice to reconnect talk a little bit about the the good times and just going deep into recruiting thank you so much for sharing all these details yeah my pleasure happy to help it was really nice to reconnect with blake and thanks to him for sharing these behind-the-scenes details so candidly. Good luck to Blake in finishing law school, though I have a seeky suspicion. We'll see him around in the tech industry, even after he graduates. If you've

enjoyed this podcast, please do subscribe on your favorite podcast platform and on YouTube. And if you're interested in what the tech recruiting job market looks like, check out the deep types from the pragmatic engineer linked in the show notes below.