Finding your next role: Tips from YC's Talent team

[Music] foreign [Music] And with that, let's go ahead and get started. I'm Andy, like Paige mentioned. To give you guys just a quick background about myself, I've been recruiting almost for 10 years now. It's kind of crazy to think, but I started my career at Palantir. I was there for four years, and then I moved to a company called Affirm, where I started as the second technical recruiter. I was there for about four and a half years and focused mostly on engineering hiring, eventually leading the technical talent function. Now, I've been at YC Continuity supporting founders, specifically on technical hiring for about four, almost five months now. So, it's nice to meet everyone here.

Awesome! And I am Heather. I actually started my career in a bit of a different field in social work in San Francisco. I was new to the city at that time, and it was the first time I had really been exposed to the tech scene. After a few years of doing social work, I decided to do a bit of a career shift, as you can likely tell, and joined a recruiting agency called Bets Recruiting, where I partnered with a lot of different tech startups across the U.S. to help build out their go-to-market teams. I did that for about two years and then moved in-house and joined Stripe, where I was there for about six and a half years for a very wild and exciting ride. I joined when they were about 300 employees, and I was the fourth business recruiter, a business and GNA recruiter on the team. About a year after joining, I moved into management and was responsible for overseeing both the business and GNA functions for the Americas until I left back in April of this year. I've also been at YC for about five months now, joined the talent team here, and I'm working with founders and focused primarily on go-to-market and GNA exec talent.

Awesome! Thank you both for joining us. For those of you who don't know, Y Combinator is a startup accelerator. So every year, we have two batches of startups where we give them $500K, and then they go through a three-month program where they learn about the fundamentals of starting a business. We also have additional functions that Heather is going to tell us about, and I want to kind of frame who they are before we dive into why you're really here.

Heather: Yes, so we are part of the YC Continuity team specifically, or as we refer to it, YCC, which is basically YC's later stage investment fund. We are investing in the top one percent of YC batch companies. We've had about just over 4,500 companies that have gone through our batch program, and through our growth stage fund, we've reinvested in about 40 of those. We typically invest in companies that are around Series B or later. We've done some pre-Series B as well, but Series B tends to be our sweet spot, who are really kind of hitting the accelerator on growth from both a business and talent perspective. I will say that we don't just invest in these companies, but we're pretty embedded with our founders and provide support to them as they scale their organization through a lot of different programs that we run, working with our investment team on overall business strategy and then the talent team, which Andy and I are both on, where we are really focused on helping founders on anything related to talent, people, and helping them really build out their executive bench as well.

And for a little bit more context, could you share what your day-to-day looks like? You kind of went into it already, but I’d love to hear more.

Andy: Yeah, I'll give just a really quick overview. Just for everyone here context-wise, our day looks very different from being an in-house recruiter. As an in-house recruiter, our main focus is to really focus on that specific company and bringing candidates and employees into that specific company. Here at YCC, like Heather mentioned, we support many different founders at any given time in all different sizes and stages. For example, Stripe is actually in our portfolio, but we also have companies that are much earlier, like Series B and C. That could range for many different things. Specifically for me, I'm doing a lot of introductions for engineers over to founders, kind of being like a matchmaker there. Like Heather mentioned, we're also really helping with executive hiring, and we're also connecting founders with subject matter experts to really help them build out their executive bench. It can also mean running a diagnostic on their recruiting pipeline, so it really just ranges from day to day, but yeah, it's been really fun doing it so far.

Okay, now let's talk a little bit about the overall job market and what's been going on. What are some of the trends that you've been seeing?

Heather: Yeah, so I mean, the most glaring trend, obviously, you know we see it all over LinkedIn, has been layoffs. Companies that saw accelerated growth through COVID over-hired and now they're course-correcting, and their growth has really slowed. Unlike just what we saw a year ago, there are a lot of candidates on the market now, a lot more talent available. It was a job seekers' market, and now it's the opposite. It has become very, very competitive, and I do think candidates now have to go above and beyond just to stand out. But coming out of this, another trend that we're seeing is that early-stage companies, startups, are really the ones who are full steam ahead on hiring. They're really capitalizing on the available talent out in the market right now, and they're really trying to snatch them up. One thing I've noticed in particular is that companies are looking for candidates who have more experience, really looking at candidates maybe with like six plus years, like really kind of leaning more on the senior side. And we can get into this later, but for folks who maybe don't have that type of experience under their belt yet, don't be afraid to really broaden your search and include smaller startups. You don’t necessarily need to target FAANG companies; those are just going to be, in my opinion, a little bit harder to get into. Try to target smaller companies where you can have a really great mentor. And just know at this stage, maybe don’t be afraid to be a little riskier. Another trend that we're seeing is that most companies are still showing pretty favorable views when it comes to remote hiring. There are a couple of companies who are going back to more of a hybrid mode. Again, I think the recommendation here is just to be a little more flexible when it comes to location. And then another thing—just a quick plug—here at YC, we do have Work at a Startup. I definitely recommend looking on there for opportunities.

To kind of build off of how people can think to narrow down their job search, are there any trends or specific industries that are ripe for disruption?

Heather: Yeah, I mean, there are many. Some that just kind of come to mind are developer tools. Despite layoffs, there's always going to be a need for software engineers, and companies are now starting to build tools to help automate development or to make the lives of developers a lot easier. Companies like Webflow, Build Buddy, Retool—those companies are doing quite well. Health Tech as well—I think this industry has been pretty ripe for disruption for some time, and we’re seeing more companies lean in, like Benchling and Modern Fertility. And then security—companies like Vanta and Salt Security as well. One other to add is Climate Tech. That seems to be a pretty big focus for a lot of larger organizations as well, helping to contribute to the state of the environment.

Here at YC, we love startups, and I personally love startups, but for some candidates, they might think that they're risky. What are your thoughts on that?

Andy: We love startups! So, I see, it's important to first call out that risk can be a very broad term and is very relative to the individual themselves. You need to spend a little time just defining what "risky" means to you personally. I'll say that there are definitely some advantages to joining either a startup or a large company, and it just depends on what you're looking for in your next career move and what's most important to you. Working at a large company might provide you with a bit more stability, or maybe better benefits, more formal on-the-job training, or opportunities to see what scale looks like. But I will say that swim lanes tend to be a bit more defined at larger organizations, and your scope of work is typically a bit more narrow. And then from a compensation standpoint, salary tends to be a bit higher, and if you do receive equity as part of your package, it is liquid. But then there tends to be a bit less upside on the actual value of your equity.

Whereas working at a startup, you’ve got a ton of opportunities to grow and develop at just a much faster rate. It tends to be more of an all-hands-on-deck atmosphere, so your level of exposure across the entire business and just ownership overall is much greater. You're digging in and really helping to build and scale the business, and can often see the direct impact that your work is having on the success of the company. You may also have more influence and more interaction with senior leaders or even founders. There tends to be more creativity and risk-taking because things are moving so quickly, and it’s easy to break things and then fix them without having some larger implications on the business. In terms of compensation, it is possible that your salary may not be as competitive or match offers that you would get at any kind of FAANG company. But you will have greater ownership in the company in terms of equity, which can lead to much higher reward potential as well. Just a quick perspective from my experience—joining Stripe early on was honestly the best thing that I could have done for my career. What I was able to learn in and accomplish in a matter of just under seven years would definitely not have been possible for me at a larger company. It just completely catapulted my career in a way that I didn't think was possible, and looking back, it's really rewarding to see all of the impact that I was able to have within the organization. It opened up a lot of doors for me, and I clearly got the opportunity to join a great company like YC.

And why do you think now specifically would be a good time for someone?

Heather: Yeah, so I might be stating the obvious here, given all the recent big tech company headline layoffs that we are hearing what feels like on every other day. But big companies aren't necessarily synonymous with stability, and startups aren't synonymous with volatility. Going back to what Andy had mentioned, many early-stage companies are actually doing really well, and they are full steam ahead on their hiring. If you kind of take a step back and look at trends in the startup world, you'll see that a lot of really great ideas and companies are born out of tough times. Some of today's biggest and best-known companies actually got started during past recessions. Take Airbnb, for example. The founders were very early entrepreneurs at the time and were struggling to pay rent back in 2008. They had the idea, “Hey, let's rent out an air mattress on the floor of our apartment for extra income,” and boom! From that idea, Airbnb was basically born. There are also companies like Uber and Slack, WhatsApp, Instagram, Apple, and so many others.

The other thing to note is a lot of companies that are created in this type of environment, like we’re seeing today, really have to learn how to preserve cash and extend their runway and need fewer resources to grow compared to some of the larger players—not having to scale back. Just to reiterate, there are tons of great startups hiring. It's just on you more so as a candidate to really understand what you’re looking for in your career, what is your own personal risk threshold, and also you need to do a little bit more due diligence on the viability of the business that you’re considering joining.

So, speaking of the viability of the business, what are some actual questions that candidates can ask to figure out where the state of the business is at?

Andy: Yeah, this is a good question, and so often candidates aren't sure what to ask or are even not comfortable with asking. But it's important for you as a candidate to have all the data points that you need to make a sound decision, and also it demonstrates to founders or hiring managers or recruiters—or whoever you're engaging with at the company—that you're doing your homework. So, I would encourage you to flex this muscle if you haven't already. Some of the questions that I would definitely encourage you to ask are: Does the company have product-market fit? This means basically they've identified their target customer, there's market demand for the products, and they're selling, and customers are buying. This tends to be a little bit more important for companies that are, I would say, Series A or earlier, just because that's what they're primarily focusing on as a business at that stage.

The next question I would ask is: How much runway do you have? So this means how much cash do they have in the bank, and how long will they last before needing to raise another round? You're not necessarily looking, nor will you get, the founders or recruiters or whoever you're engaging with through the process to provide you with an exact dollar amount of what's in the bank, but rather a timeline. Ideally, they would have about 12 months or more in runway. If it's less, then you should ask about future funding plans. What you're really looking to get from this question is ensuring the company is not going to run out of money in the near future or go under, and that they have a solid strategy on how they are planning to hit their next business milestones. Companies should know the basic math, and if they don't, I would say that is a bit of a red flag if they really can't speak to that.

The next question would be: What is the biggest—excuse me—risk to the company? And as a follow-up, how are you addressing it? This will just give you a preview into what's top of mind for the company and if they have a plan in place to really safeguard the business. And then what does attrition look like? I would say it's definitely important to know if the company is able to retain their employees. If attrition—the sweet spot—is around 15%, if it's above that, you may want to do a little bit more digging just to understand why people are leaving the company, so that you have more data points. One last recommendation: make sure that you are doing research on the actual current team, which you can do via LinkedIn pretty easily. Things to think about are: Are they able to attract good talent, and what is the tenure of the team as well?

So, now let's think about, as a candidate, when you’re assessing different companies and you're trying to get a sense of, like, is this the right company for me? Candidates might have some questions that are either uncomfortable to ask or they just want to know more. So, one of those that I hear a lot is: How do I ask about work-life balance, especially at a startup?

Heather: Yeah, I know candidates might be uncomfortable while asking this question because they don't want to come off as lazy or, you know, quote-unquote like unmotivated, or that they're worried that it might turn off the hiring manager and really risk the offer. Honestly, I would just ask it. I think I would ask, like, what are the working hours expectations? And then follow up with an explanation pertaining to your specific situation or your boundary. For example, there are a lot of mothers out there, parents who need to do daycare and other things. I think you should just set that expectation pretty upfront, and also making sure you're fully emphasizing that you are fully dedicated when you are on working hours would be really important. This is actually a very common question that recruiters hear all the time, and I think it's just really important to communicate on both sides. For example, for engineers, a lot of times you do have to be on call, and a lot of times the recruiter and even the hiring manager will let you know that up front. So, just communicate your options, and again, just to be very clear that you do have boundaries if that is the case.

Yeah, that makes sense. And another hot topic is compensation. How and when in the interview process do you ask about compensation?

Heather: Yeah, and I know this is a topic that can also be very uncomfortable for candidates, and even for myself. I know that’s always like very uncomfortable for me. What I do recommend is it’s really important to ensure that your compensation expectations are aligned with the opportunity, and you don't want to get to the end of the process and find out that there's misalignment. Before we get into how to ask, it's important to kind of call out that common practice for recruiters is that we typically share the pay range for what we are able to offer for a specific role, for a specific level, and that's because the interview process is a way to assess the candidates' experience as it's related to the role. We take into consideration the level, internal parity of the current team, and a lot of different factors.

In terms of how to ask, I would just maybe start out by saying to the recruiter, "This is not my biggest motivating factor, but it is an important aspect of how I evaluate an opportunity, and I want to make sure that I'm being respectful of everyone's time; can you share the pay range?" A lot of times the recruiters will be able to share the compensation range; it's typically not the hiring manager, so I would just defer to the recruiter. If you are interviewing at a smaller company and there is no recruiter, it will be the hiring manager or the founder who will have this conversation with you.

In terms of when to ask, I definitely recommend doing it before the on-site or the face-to-face interview. Just again, like you want to make sure there's alignment—don't want to get too far along where by the time you get an offer, you know both parties are surprised. My advice really is to do your research ahead of time, either on Pave or Level Set, to understand what the market is paying for someone at your level and in your role.

Given the current state of the economy, do candidates still have the ability to negotiate their offers?

Heather: Yes, yes, yes, yes, yes! The answer is always yes. Don't ask, don't get is the motto. There are a few companies that will say that this is our best and final offer, but it's always best practice to do some research, come up with your data points, and see if there's any wiggle room with the offer itself. Keep in mind you want to make sure that you're doing so within reason and in a respectable manner. One pro tip before going into a negotiation: I would take some time to figure out what is most important to you with regards to the offer package itself. Is it base? Is it maybe equity? Is it sign-on? Companies are usually able to get creative on what levers they can pull across those three different categories and will often ask you what’s most important to you to get you to sign today, so go in prepared and again with reasonable asks.

Just one other reminder: companies are typically working within some parameters for offers, and they do take into consideration internal parity of their current employees as well when they're figuring out what your offer package is actually going to look like. Finally, just to reiterate, please don't forget to be respectful to recruiters or whoever is negotiating with you. Thank them for their help and for going to bat for you when it comes to increasing your offer, at least trying to increase it. It might be that they're not able to, but I think just showing that appreciation will go a long way.

Yeah, that's a great point! It's hard work to be a recruiter, to always be talking to candidates. Now, let's go back a little to the beginning when a candidate might be engaging with a company and thinking about how candidates can tell their story and kind of come off as a strong candidate. For candidates who are recently let go or have recently left their companies, how should they kind of talk about that? Should they share if they were part of a reduction in force?

Heather: There should be no shame in letting your recruiter know that you're part of a RIF, especially in this economy. I think everyone’s very empathetic to that situation, and it really has no bearing on your candidacy. This question will likely come up on why you're looking for a change, and it's better to be honest. I don’t think the recruiter will harp on it; I don't think you need to harp on it either. You don’t need to explain why. I mean, we can give a one-liner, but I think when you are talking through it, just really focus on your experience, focusing on the impact that you've made at whatever company you're coming from, and kind of move forward from there. I don't think anyone should be scared to share that they were part of a RIF.

In terms of just making yourself stand out as a candidate, what are some ways to do that?

Heather: A few things come top of mind. First and foremost, leverage your current network for any introductions. The power of your network can often be very underestimated, especially in today's environment. I'm sure you guys see it all across LinkedIn right now—everybody, to Andy's point, is very empathetic if folks were impacted by RIFs or are looking for new opportunities. People are more than happy to make intros or get you pointed in the right direction, so definitely take them up on that.

For companies that you're interested in, I would do some digging on LinkedIn, connect with leaders, and send them a nice note. If you can find some kind of common ground in that message, do that just to try to penetrate and get in outside of just maybe sending your application in. I would also include any kind of letter of recommendation or references from past managers in your application or somewhere early on in the process as well. That could just help you get a little bit of a boost or signal boost early on in the process. Make sure your LinkedIn profile is up to date and get specific about your accomplishments and, to Andy's point, your impact that you had in your previous roles. Recruiters and hiring managers definitely do review those, so make sure that your LinkedIn matches your resume as well because those are things recruiters will pick up on.

Attend networking events. I think we've all probably noticed that we're having more in-person events, but even events like this where we're over Zoom. Whatever you can do to get in front of people and get your name out there and just meet folks will also help you. This goes without saying, but always come prepared to your interviews. Have your personal pitch down; if you have to practice in front of a mirror, do it. Do your research on the company, the people you're meeting, come up with really thoughtful questions for each point in the process as well. Again, make sure that you’re sending thank you emails and follow-ups after each interview to each individual.

What was the most standout or the most impressive thing that a candidate has ever done to get your attention?

Andy: Oh, at Stripe? Oh gosh, I don't— I think it was a sales candidate. They sent in some cookies, which always, like, desserts will always get my attention! But then we also had a marketing person get really creative and send in a package that they had kind of like come up with some creative Stripe marketing ideas that they had, which like clearly that’s a very creative outlet and definitely got us to get on the phone with them.

I remember at Palantir, we were interviewing for a coordinator role, and I remember one candidate we actually did end up hiring. She just went above and beyond to basically showcase she didn't have any experience, but after the interview, she sent a really long document showcasing what she could do as a coordinator. To me, that just showed she was already kind of doing the job already—like just basically showcasing her skill set. She had graphs and charts and all these things, and like she did a model of how many people she could schedule. It was just that was just, like, crazy and above and beyond, and it’s not the norm typically.

So yeah, that’s definitely one way just to stand out. We know that there are a lot of companies out there, so in your opinions, what are some of the companies that you're most excited about?

Heather: Well, we're very excited about the companies in our portfolio. To name a few: Zip—Zip is a very common name, but if you guys welcome to Zip HQ, they're hiring engineering sales, post-sales, marketing. Pave, I think we mentioned that—they are a compensation benchmarking company, and they're hiring a bunch in the tech sector as well, so data scientists, designers, engineering sales. Deal is also another good one. Kolshi—they're their very first federally regulated exchange where people can trade on virtually anything, any event. So they're really cool. Checker: they've been around for a long time, background checks. Build Buddy—they are, I think I mentioned this like in the developer tool space. They're pretty small; they're like a 12-person startup, but definitely check them out. Vanta—they're in security, and then Whatnot as well—they're in the marketplace space.

Okay, that has been a lot of really good info. So if there's only one piece of advice that you want our attendees to take away from this talk, what would it be?

Heather: Oh gosh! One, I would say that I know things may feel a bit heavy right now with all the recent layoffs and slowing of hiring, but there's still a lot of really great opportunities out there. I would just recommend that you take the time to do the upfront work and discovery phase of what you want from your career so that you're clear on what you're looking for going into your search. This will just give you so much leverage throughout your interviews.

You have to really get good at marketing yourself and really pushing yourself outside of your comfort zone with networking, asking for intros, asking really tough questions, as we talked about, but honestly this will just reinforce and help you grow professionally and personally. So, I guess if I were going to—I guess I'm going to borrow Nike's slogan and say just do it! Like get out there and go and try things and get creative, and if you fail, that’s okay. Just don’t get discouraged. You just have to be a bit patient right now and make sure you're doing some due diligence, but there are great companies out there and great opportunities.

Andy: Similar to Heather, I mean, I think just do your research. To give you guys more insight, I also did—a really I started in marketing during my first job, and I really hated it. I didn’t know what I wanted to do, and I knew recruiting was actually a field I wanted to get into. I was not working a lot with some friends who were already in there, and an opportunity happened to come up; it was a contractor role, and I just went for it. I was like, “You know, I'm just gonna do it,” because I knew I wanted to be in recruiting. And so that’s how I landed at Palantir.

Funny enough, I actually interviewed at Stripe after Palantir; I didn’t get the job. I was devastated. I realized, actually looking back, I probably was just so new, and I just wasn’t a good interviewer, I had realized. What I did after that was I actually talked to a friend who’s really good at interviewing, and she basically prepped me so much. We went to a Barnes & Noble—I don’t even know if those exist anymore—but eventually a coffee shop, and she basically threw a bunch of questions at me and really prepared me for my next interview, which was for Affirm. She honestly over-prepared me. Going into that interview, I felt so confident, and I got the job with them the next day. I really recommend everyone just to maybe be a little bit more self-aware: If you don’t get the job, maybe just do a little digging as to why, and then don’t be afraid to just ask for help. Really, just do it! I was really devastated over my rejection; I shed a couple tears, and then it was just kind of like, “Okay, I just need to do better.” So, that’s some advice I would give if anyone's in that situation.

Oh, I want to jump in and just touch on one of the questions in the chat, which is: Is there anything specific or different when looking at senior leadership roles? One thing I would definitely leverage for more senior, director, and above leadership roles is VC talent partners. Start connecting with those individuals because they are very plugged into the startup scene and can often help. If they don’t have anything within their portfolio specifically, like we will often make introductions to other talent partners across different VCs to try to get good talent plugged into good companies. So that's also another avenue to try if you're on the senior leadership side.

Yeah, definitely a plus one to that! [Music]