Startup Hiring Advice from Lever CEO Sarah Nahm with Holly Liu

Seren: Holly, welcome to the podcast!

Holly: Thanks for having us!

Seren: Yeah, pumped! So, Holly, you have a question to start it off?

Holly: Yeah, I'm super curious. Did you ever see yourself becoming a founder, a founding CEO?

Holly: Oh my gosh, I have to honestly say no. You know, growing up, I could not have grown up further from Silicon Valley. I grew up in Birmingham, Alabama, so deep south. Back then, I probably wanted to be a different thing when I grew up. Every three months, I was dabbling in different things, but probably one thing I spent a lot of time on was social justice. I volunteered at the Civil Rights Institute because all the amazing people that were a part of the Civil Rights movement are obviously still around, and they're still doing amazing work. That just defined my experience growing up in Alabama.

Holly: When I came out to Stanford—first school for college—I was the first person from my high school to go west of the Mississippi River for college in years. I had no idea what I wanted to do or who I wanted to become. I think that period at Stanford was really interesting. Pre-med was still the number one major, which has since changed, I think, to CS. It wasn't super obvious that you, as an undergraduate, could be a founder. My freshman class at Stanford was the first class to start with Facebook. I think that really changed so much in Silicon Valley, where young people now are seen as people that could innovate and bring game-changing ideas to market.

Holly: I remember so many moments where the people around me were stepping into those roles and positions where they were just going for it. I think subconsciously that influenced me, but consciously it did not. I studied design, and I always thought I was just going to go into design consulting. I was going to take a job at IDEO.

Seren: 100% what happened exactly?

Holly: Yeah, and I loved it! I mean, I was like drinking the Kool-Aid, mixing the Kool-Aid, distributing it in Detroit. For everybody else, design-thinking was supposed to solve everything. I have to admit it's still a huge part of how I see the world. It's still a huge part of what I bring to my company, so I totally thought that's what I was going to do.

Seren: Yeah, total surprise to me with that job?

Holly: Yeah, okay, yeah. I was very unfocused in my job search. I think the only way I even ended up, quote-unquote, applying to Google was I was dropping off some forms for a friend at Stanford's Career Development Center. There was somebody there who worked there and was like, "Oh, are you going to sign up for the Google interviews?" That's really fast.

Holly: I know, a part of me is sort of like, "Look, total privilege check," because it's not like, you know, it's not normal, so to speak, for there to be a clipboard with a pencil dangling from it for you to sign your name up for an amazing career opportunity. But that was right in front of me.

Seren: And you’re signing up for like where do you do design or...?

Holly: Oh, no, not at all! I think I just kind of went into it and was curious and engaged. I think I was one of those annoying ones who couldn't make up my mind. I just had this outstanding offer for like months—literally nine months—before I officially made the decision. I think even then I didn't know what I would do until my first day of work.

Seren: That's a whole story because you were in that program where you transfer around, right?

Holly: Exactly, yeah, the associates program. Okay, but it was super funny because I showed up to the new hire orientation and you get your laptop and all the things. Then they have this moment where you're all sitting around in the main cafeteria, Charlie's, and you're supposed to get picked up by your manager. Just sitting there, I’m imagining I’m waiting to find out what I'm doing, and I'm still sitting there at the end when everybody is all set, because my first job out of college was total, kind of like came out of left field.

Holly: I ended up being a speechwriter, which I never saw coming, and it was a job that nobody had had before specifically supporting Marissa Mayer. So you know, she was a little tied up, so she couldn't come get me. But I think in a weird way that was probably my crash course in a lot of what it is to be a founder because I had to kind of create something from nothing and figure out what I was doing and be really bad at it for a while. I think also in hindsight, so many lessons learned about leadership and strategy, and just getting to be a fly on the wall to conversations way above my pay grade. It was really an amazing experience, and I think, you know, to this day, I'm super grateful for it.

Holly: Obviously, I spent time on other things at Google too, notably, I spent a lot of time on the Chrome team, which was just incredible—amazing people. You know, Sundar was leading that initiative at the time. That was amazing! My direct boss was this amazing kind of growth guy, marketing guy, creative guy who would go on to be the head of marketing at Instagram. So yeah, like just some amazing people around me.

Seren: I’ve got to ask, though, when you speech write do you use post-its?

Holly: Oh, 100%!

Seren: Oh, that's impressive!

Holly: Yeah, I also take it the other way around, which is when I design mocks I use Keynote, the prototyping tool.

Seren: Yeah, I like that you like...

Holly: Yeah, no, I think there's so many insights from a design kind of practice that I think are super applicable to being a founder, to being a CEO. You know, for a while, I was actually really sad because I was spending less and less time on product and for someone who loves product, that was actually really hard. I felt like the sense of loss, but then I sort of started really reframing a lot of the work that I was doing as a founder around.

Holly: Hey, you know, I still work on a product. The product is this company, and I still have to do user research. It's just that my users are my employees and my customers. That same process for generating a clear strategy around user needs was just as needed, if not more so.

Seren: And then comes that design from being coming back.

Holly: Yeah, I know! So I really got to say to me, I think more designers should be founders. I think that that skill set is so, so relevant to the work it takes to actually get a lot of people together to work in a system and to create value from scratch. So, you know, definitely I think there are some amazing designer-founders out there, but a part of me wishes you know that there were way more.

Seren: So, to me it’s not obvious. Obviously, you jumped around at Google, but it’s not obvious as to how a speechwriter goes on to found Lever?

Holly: Not really obvious to me either, which is probably fair for most people. But was there a point when you were at Google where you thought to yourself, you know what, I’m going to go be a founder? How did you decide? Why did you leave? How'd you decide to start Lever? How'd that go?

Holly: Yeah, I mean, I think like so many founders, my path is nonlinear. You know, I think you read in mainstream media about these lightning-strike moments that suddenly happen. I mean, I think that’s all just media, right? The personal experience of founding a company, it's first of all, it's a period of time. It's not a strike of lightning. I think even, you know, leaving Google, I didn’t leave to start a company. I think I left to just grow and experience more things and ended up pursuing a lot of different stuff—things ranging from just like personal projects to obviously working with several early-stage teams.

Holly: Personally, a lot of what I was doing at the time that was on the path to founding a company was experiencing working with a lot of different types of people. So, you could say that my co-founders and I were almost trying out working with each other for a while before we actually officially went for it. I think that’s a huge part of it, and I credit the fit with my co-founders for a lot of the success that we've had as a company. So, in a weird way, I don’t think I was doing it consciously at the time, but making sure that you’re finding the right people is probably the hardest to predict but most important part of the early stage.

Seren: Was it very... It seems like you found the people and you were working together, but the idea wasn’t quite there. I mean, Google was probably still on this rocket ship when you decided to leave, or doing really well. What was the most difficult thing to overcome? So, let’s just say I’m going to be blunt: what was the thing that propels you forward, and then what was the most difficult thing in getting you to leave?

Holly: Yeah, I mean, it’s cushy there!

Holly: Oh sure! I mean, first of all, I just have to say huge privilege check. Like having been at Stanford and having been at Google, I think it’s not lost on me that there’s a lot of opportunity open to you. At the time, I knew that. I knew that, you know, in a way, there was no good and bad choice spectrum. It was like all shades of good.

Holly: I think like a lot of people, I just knew that I had an opportunity just in my life overall to take risks and try things out and really grow my sphere of experience, and took that, which, you know, I think people who have it should embrace it. People who don’t have it, I mean, I don’t think should beat themselves up about, you know, having to think a little bit harder on taking a leap.

Holly: So in terms of leaving Google, that was easy. I think in a way it always felt like there was just more to experience. Starting Lever was harder, and that’s because, yeah, I mean, for one, I just didn’t know exactly what we were going to do at first. I think very few teams know exactly what they're going to do, and probably the biggest thing to truly getting started was, you know, again, people believing in the people that you're working with—believing in the people around you.

Holly: And then secondly, you know, I think believing in a change that’s happening in the world. I think distant third to that is believing that you have what it takes to bring some value that speaks to that change, right? That reacts to that change. So the change that we were really believing in that has really played out ever since was, you know, the world was—this is like 2012—when the founders of Lever kind of all got together and we just saw that the world was quickly becoming a world where revenue, competitive differentiation, innovation was all driven by talent. You know, like you look at what was limiting the growth of companies; it was that they couldn't hire enough engineers. They couldn't hire enough salespeople.

Holly: You think about what was causing some companies to win over others; it was because there was like some sort of ten-x talent thing happening that led to some sort of leapfrog in what they were bringing to market or, you know, some sort of better marketing strategy. Essentially what was happening is just like software was eating the world, knowledge work was eating the world, like as technology and digital transformation was playing out in every single industry.

Holly: Even the most blue of blue-collar work—manufacturing—was transforming into something that looked a lot more like knowledge work. You don’t just need undifferentiated assembly line workers; you need people who could program like a robotic arm or, you know, rethink a manufacturing process, right? So that was happening in every single industry, and it was really transforming how organizations had to think about people, and HR, and hiring because kind of gone were the days of my parents' generation where you like join a company and you work your way up the career ladder. My dad has had very few employers this whole career; he stays with them for decades, right?

Holly: Nowadays, Millennials and Gen Z are entering the workforce, and like people are staying at jobs for like three, four, five years. And in Silicon Valley, maybe even less! I think it’s eighteen months or something.

Seren: So did you guys feel that? Was there a unique insight in the beginning, or were you just like, "We see this change happening, and we’re just going to build a newer, better version." How did you approach product in the beginning?

Holly: Oh my gosh, well, like first of all, the beginning, that blurry period, probably lasted two and a half years. I would say we were super engaged in making sure we were defining the problem. I think in a way, probably different from other companies, we didn’t rush too quickly to solutions.

Holly: Well, I should say we actually did, and then we’ve always been kind of at the end of the day driven by our users and our customers and making sure that we're being honest to them and holding ourselves accountable to them. Like you can think you’re delivering this game-changing such-and-such platform, something something. But like what your customers say about you or what they say to their friends when they're talking about your software, I mean, that's ultimately who you are!

Holly: So I would actually say that first, we built an entire thing and actually had to kind of come to terms with, you know, what our customer feedback kind of was, and we had built just something incremental. We had built something that was just like a better version of what was there before, so we threw it out and I think we went back to the core fundamentals.

Holly: So you kind of asked like, did we know we were building? I think that while we didn’t know literally what product or what solution we were going to bring to market from the beginning, what we did know was how we were going to hold ourselves accountable, and that was through listening to our customers.

Seren: Though you were in the startup game, which implies VC, which implies pitching VC. How does that process... You know, even your industry wasn't really as much of a thing as it is now, seven years later. What was that process like in fundraising in 2012? You were in the winter batch, right?

Holly: So we did our first meeting around a fundraising series A in October 2014. Okay, so I would definitely say 2012 to 2014 was that process of us figuring out what problem we're solving, how to achieve product-market fit, how to build that traction that you want to show.

Holly: In that period, we also discovered a lot about ourselves as a team. In that period, just for me personally, I went from being, you know, an individual contributing designer to literally kind of on the eve of our series, we had signed a term sheet, but we hadn't closed the round. Kind of we, as a team collectively, agreed I should be CEO.

Holly: So you figure out a lot in that period, and if you're not confronting those hard things about who we are and what we're here to do—who am I and what am I doing—I think that you can put it off just so long before it actually starts to intersect with what you can achieve as a company, as a team. So, you know, when I think of those early days, yeah, on all fronts we were figuring out who we were, and it's some of the most fun and terrifying chapters you've ever had.

Seren: Those are stressful years! So now, you know, we're way further down the timeline, and you do have kind of unique positions on recruiting, culture, and diversity. Back then, I assume you're just again figuring stuff out, right? A lot of our listeners are early founders, and they are competing against Facebook and Google—Google, I was going to call it "the Goog"—Facebook, Google, and every big tech company, right? How do you differentiate as a small start-up and land the top talent?

Holly: It's so true. It's a global talent market, and I think that it's competitive in so many ways. I mean, like every startup, I think, does have this experience of there's well-resourced recruiting machines that are kind of out there. On the flip side, early-stage startups have such a unique opportunity to offer.

Holly: I think the advice for our startups is to spend actually a lot of time thinking about what truly is your value prop—actually figuring out how you're going to approach hiring and what is kind of like the way that you can almost use your culture and all of its unique glory—as like, like go on the offense with it, because that's like you can run circles around a lot of the competition by bringing the experience of what it's like to work at your company into the candidate experience.

Seren: Can you give us an example of that you guys did at Lever?

Holly: Oh my gosh! Yeah, 100%. I think the first thing is proactive recruiting. So, you know, any startup out there that's just posting a job and waiting for great people to apply—that's all of you! Hiring is the strategy when you're a startup. There's a period at which like, you know, like you can be the best founder on the planet, and you will be holding your own company back if you haven’t figured out how to truly prioritize hiring, how to truly invest in it, and how to do it damn well!

Seren: Can we swear on this podcast?

Holly: Yeah!

Seren: How did you guys proactively do it? I mean, you’re usually so stretched when they are starting out.

Holly: No, this is actually like a concrete thing: proactive recruitment. I think it's like the outbound, right? In the same way, you wouldn't just like throw up a website and wait for customers to come find you; you’ve actually got to reach out to people.

Holly: So like the first thing that everybody tells you is reach out to your network. You'll tap that out at some point; you should still do it, still do it. But you'll tap that out at some point. And then I think what you have to start doing is getting really confident reaching out to people that you believe are going to be strong fits at your company, that you’re finding just on LinkedIn.

Holly: You should, and then you'll tap it out. Get creative: look at meetups, look at Eventbrite, look at GitHub. GitHub is a great place to find people if you actually, you know, kind of know like what your technology value prop is.

Seren: Or, you know, what's been the most surprising source for you guys? Like, is there something you just didn't expect? You're like, "Wow, I would not have expected to find a great candidate here."

Holly: That's cool! Honestly, we have so many amazing and unique hiring stories in our company. Our engineering org has largely been built up on my co-founder Nate Smith, who, you know, we are a recruiting software company. So, we think a lot about hiring—81% of his team was proactively sourced.

Holly: And I would say that, you know, you can genuinely find people and connect with people anywhere. The other thing that's been remarkable about our hiring strategy has been so many people that we actually hire—we actually met them and nurtured those relationships.

Holly: You use every year—do 2 to 3 years? Yeah, it comes back around! It's, you know, you're investing in... I don't want to call it like a database of talent; it's like you're investing in relationships. You may not see returns from those immediately, but you know those are going to be the people that actually when it is their right time, like when they're ready to make their next move, they're already going to be familiar with your team, with your culture, with your mission.

Holly: They actually get hired, like we have the data to prove this: like, 35% faster than people who are meeting you for the first time. People, I think, are familiar with the cliché that is a founder; you should be spending like 50 percent of your time on hiring.

Holly: I'm just like, it's a cliché because it's true. Hiring just takes so many forms. I think like one thing is obviously go out and meet people—no expectations, no strings attached; let's meet. Second thing you can do is encourage people on your team to do the same, and that's really tough.

Holly: I think actually for whatever reason, people feel awkward pitching their friends about job opportunities.

Seren: Can't imagine why.

Holly: Well, you know, I'm being a little facetious because yeah, it is a little awkward. It's awkward to sort of like—you know, sell something like that isn't so important. But then on the flip side, everybody has so much passion about why they joined, and everybody does feel really strongly about the startup they're working for.

Holly: I think actually as a founder, one of the most impactful things you can do is help your team find its authentic voice about why they give so much of a damn about your company’s mission and why they joined and what it’s done for them and what they've learned and how they've grown.

Holly: You don’t have to say anything about the other person—just telling your authentic story is an incredible, incredible thing. So I would say that if any founder out there right now is trying to do a lot of hiring, you know, go book a team off-site where you actually help people come up with their authentic story for why they are so committed to this company and just watch it transform the conversations that they're having.

Holly: Build some email campaigns, if you will.

Seren: So related to this, you talked about motivation fit at the YC hiring event a couple weeks ago, which basically describes, like, is this person’s goal in their career and in like the near term at least aligned with where your company is at and their impact that they're going to have? How do you suss out someone's motivation when you're, you know, it’s like kind of crude to talk about it, but like building this two, three-year database of people you meet, like having coffees with or whatever? How do you figure out their motivation?

Holly: Yeah, great question. You know, I think the simple answer is really just ask, and the more complex answer is, of course, get really good at listening. So the simple kind of way is, you know, I think if you ask people what, you know, are where are you taking your career? What have you done in your past career decisions that have been most meaningful to you? What is it that you're doing at your current job that you like to do more of? What are the things you’re not getting to do at your current job that you hope you get to do in your next one?

Holly: All those are ways to get some of the facts, but I think fundamentally to me, like you know, at Lever, our first stage of our hiring process, it’s not a phone screen, it's not something like that's just screening. I can't; it's motivation fit. Like literally, that's what the name of the stage is, because I think it’s like at the root of your best hires and it's also at the root of your worst hires if you don't get it right.

Holly: So, you know, I think that what I'm listening for when I'm talking to people, what I'm asking people these questions, it’s usually to suss out, you know, is this the right stage for people. Ambiguity is kind of famously, you know, a huge factor of the experience at being at an early stage startup, and finding people that thrive with ambiguity or finding people that really love, you know, the diversity of problems that you're going to be solving, you've got to make sure to have an ear to listen for when people are really actually ready for that, when they're excited about that.

Holly: I think another thing to listen for is, you know, when people are sort of looking to say take a big impactful role at a company because everybody's going to say they're looking for impact, right? So when somebody says they're looking for impact, really do they know what that means for them? Is it generalities, or do they actually have something that’s really like revealing that self-awareness of what for them is like in it from their personal seat of experience?

Holly: I think that the more specific someone’s gotten about their own career, the more maturity they bring to the role, the kind of more they can probably up-level your team. So yeah, I think like simple answer: ask. Just ask. And then complex answer is really learn how to listen to how people express their thoughts about themselves at work and what they're looking to get out of it, what they're looking to do next, and what they're looking for in a team.

Seren: I certainly have a tactical question. They used to train a lot of interviewing around like tell me about a time when XY and Z.

Holly: Oh yeah, totally!

Seren: How do you like—do you still feel like those can help us out?

Holly: Totally! Getting concrete, you know, concrete examples, concrete situations as opposed to abstract, like brain teasers—I, you know, would summarize that as behavioral interviewing, and I'm a big fan of behavioral interviewing, especially for early-stage startups.

Holly: And here's why: you know, I think that you as a founder are hiring for a lot of roles you've never actually had personal experience doing those jobs. Expand beyond that! Yeah, beyond that, nobody else at your company may have ever done that job.

Holly: So you’re operating on a lot of theory at this point, and one way you can really like de-risk hiring and also not be too clever about how you're going to interview somebody is by actually just methodically asking them about their own career.

Holly: I think what you can get really good at hearing in their story as a founder is, you know, what are their patterns of success? What are maybe their patterns of failure? And just kind of like, you know, your company really well, so you know whether your company has like the contours for this person to be successful.

Holly: Therefore, I am a huge fan of, you know, we do a step in our process that we call career trajectory, and it's basically a behavioral interviewing interview where you go in and you just kind of start at college and then go step by step by step through people’s careers and allow them to tell you about it. It’s kind of basic, but it’s so impactful.

Seren: And you know, if anybody is really curious about looking into that, we kind of modified a version of top grading, which you can Google and find a lot of information about.

Holly: Yeah, I think it’s actually great to just give people the space to tell you about how they've kind of grown in their careers.

Seren: In the context of remote work, do you have specific advice around finding out someone's working style, their dynamic? I think what's a common one I hear is have they worked remotely before?

Holly: That's a good one right there! But are there other pieces of advice you have there?

Holly: Oh my gosh! I think this is where a lot of innovation is happening right now, and hiring people are sort of putting two and two together. Oh, it’s a global hiring market, and then also thinking about, like, what would it mean if we actually just tapped in really meaningfully to that global hiring market with hiring anywhere?

Holly: It’s tough! I think that there are clear benefits. I think obviously you get some advantages around, you know, beating the market so to speak and tapping into like a lot more like rare opportunities, and a lot of kind of like immediately upon hiring someone it’s kind of like being winning the game, you know?

Holly: But then on the flip side, you've got to build a culture that can support remote work as a first-class citizen. I think there are some people that really nail it, and they think about the details. They think about how meetings work; they think about how information is transferred; they think about tribal knowledge and how you're going to actually create systems for information to flow freely.

Holly: Whereas if you're all co-located in the same office, you kind of get it for free. So, you know, Lever actually didn't really embark on remote work until we were pretty late as a company, and that was for people that had already worked in our company for a while and then like for maybe personal reasons or whatever.

Holly: Needed to move. I would say that we're just getting started with a second office. We're now starting to experiment meaningfully with our team composition, but we had the other side of it where we stayed together as long as possible, and I think that was pretty intentional.

Holly: It allowed us to, I think, really quickly, you know, I guess like spread a lot of best practices, and it led to us certainly like sharing a lot of the load of skilling the team really effortlessly. So, you know, again, pros and cons.

Holly: I would also say that we had to get real good at hiring, and a tight talent market here in the Bay Area to do that, so I definitely think it’s a really huge talent strategy question that any founder that’s building a team right now has to ask themselves: What trade-offs do we want to make?

Holly: And go eyes wide open into like how if you’re going to, you know, accelerate hiring by like really casting a wide net, hiring remote—okay, how are we going to prepare our culture for that?

Seren: Another thing you mentioned in your talk was how you write job postings, which I really liked. You described it as basically just describing the impact that job can—you know, can you elaborate?

Holly: Absolutely! Well, I can tell you kind of the story. So, we just, after we raised our series A—a big moment for us—right? Like we started talking about what we were going to do next. We started really strategizing about it, and something that we knew we would be doing that we hadn’t really done up until that point was hiring a lot of people, right?

Holly: We had been a really tight small team for a long time, and here we were about to double the team in a matter of months. So being a recruiting software company, we were like, "Okay, well, we know a lot about recruiting. We know we really want to invest in building a great recruiting process."

Holly: So we decided to take, you know, an off-site. We all loaded ourselves into a van—company small enough that we fit in a van—and went to like Tahoe or something like that for a few days to actually really design how we were gonna hire and what our hiring culture was going to be like and how we were going to design our candidate experience.

Holly: By the way, I'd recommend anybody who's about to do a huge amount of growth to do something very similar. One of the things that we kind of asked ourselves was like, "Well, when we start hiring for roles, how are we gonna know what jobs we need?"

Holly: So we actually developed this little exercise—like it's literally a Google Doc that you know has text boxes and stuff—that laid out, okay, like what would someone with this job need to achieve in one, three, six, twelve months, right?

Holly: And specifically, we tried to make them not like tasks or like, you know, start doing blah, but to focus on impact results outcomes, right? Like, well ideally, they'd like improve web conversion from this to this or they, you know, actually like nailing the results of success!

Holly: So we pat ourselves on the back. This was a great way to define a lot of jobs to be done. Like now we had carved out all these amazing, you know, I think you're hiring a lot of generalists; you're hiring a lot of athletes at that time.

Holly: So here we had this great way to define our work, and we thought we were like really proud of ourselves. So we actually were able to go out and like start hiring with confidence, interviewing with confidence, and we got all these amazing people in the door.

Holly: And like when they got pretty late stage, we’d be like, “Oh yeah, like here, let’s share this internal doc that we have with you,” and people would just light up when they saw this. Oh my gosh, this is so clarifying, so amazing!

Holly: And then it took us an embarrassingly long time, like probably six months, to like be like, “Hey, why do we even write these like boring job descriptions?” Why don’t we just take these impact descriptions that candidates and people that end up actually joining the company find way more interesting and, frankly, like accurate and you know, all sorts of other adjectives? Why don’t we just use that as the way that we talk about the jobs we have? And ergo...

Seren: Yeah, yeah!

Holly: So do you find yourself, do you still list required skills for instance? So say you know, I’m looking to apply for a job at Lever and it's like you’re going to increase X, Y, and Z and I’m like, I’m on it and then you read the application like this person isn't none of the required actually do that?

Holly: You know, every once in a while I think for some of our entry-level jobs, when we do know that there’s like a few things that really do feel like great to have coming in, we list it. But actually, if you go to like our career site, like actually most of our jobs—like the vast, vast majority—are actually just written this way.

Holly: I would attribute, you know, this impact descriptions as opposed to job descriptions as not just being one like a great way to get the most talented people—like the top 10%—I love the talent market interested in your opportunities. It's also been a huge driver for us of diversifying the people that are self-selecting into applying because by having this lengthy list of skills and requirements, I mean you're basically, you know, broadcasting to the world assumptions about what kind of people should apply.

Holly: I think the beauty of impact descriptions is you are putting out kind of like a statement about what you're looking for, and it welcomes people from non-traditional backgrounds—like, you know, kind of tech outsiders, so to speak—to throw their hat in the ring.

Holly: And so I would say therefore that it’s not just more effective; you’re actually getting the top talent interested, and those are the people that you want to hire, right? It's also, I think, more inclusive, and it’s really, I think, more clarifying also.

Holly: Teams do hiring, and I think getting everybody aligned on what you're looking for as a founder is a huge accelerator to being able to really scale hiring to do it with confidence to get lots of people who are all contributing to all be on the same page.

Seren: Yeah, I mean, it's related. YC has the same thing: a lot of people from non-traditional tech backgrounds who might be in tech look for reasons to disqualify themselves. They're like, “Oh, I didn’t go to Stanford and drop out! I didn’t go to MIT or whatever!” And like, there should read you the YC application!

Holly: It’s not a bad angle!

Seren: So related to inclusion: Ava Zhuang sent you in a question. She writes, “What’s the biggest roadblock you faced in trying to make hiring more inclusive to diverse candidates?”

Holly: Wow, there's so many things going through my brain as I’m thinking about this. I mean, so there's a few levels. For one, we as a recruiting software company, we're trying to actually scale out how all of our customers—how the entire industry—can make hiring more inclusive. So you know, we've got things that we’re doing on a product level that I think answer Ava's questions, and then of course we are a company that's going through a lot of scale that is trying to figure out our own culture and how to be more inclusive internally.

Holly: So there’s also like that side of it. So, you know, in terms of the road block of making hiring more inclusive for the world... Gosh, there's so much to be done there, and there’s so much to be done there completely outside of software.

Holly: So I think the biggest roadblock is sometimes you're sort of caught up in this tension where people would love for software to solve the problem. And you as the software, you know, as a technologist, you have an opportunity to move the needle that way.

Holly: But also, I think it's really important when we're talking about a more equitable world that people do have to change, and so the biggest roadblock probably is when people maybe hope that the problem can be solved easily without confronting kind of like these questions of what are we as people doing.

Holly: I think it's an opportunity for, you know, companies like Lever to actually drive a richer conversation around that and to make people maybe more aware that there's things that they can do.

Holly: I think in particular with things around diversity and inclusion, there really is that will. I feel that year over year, more and more people care, more and more companies from more and more verticals and stages are all coming forward and saying this is something that they want to invest in—that they can’t ignore.

Holly: If anything, you know, this isn’t a roadblock, but maybe something that would remove roadblocks: I think people need more success stories out there because they're happening, and I think we see a lot of news reported on all the bad.

Holly: It’d be great for, you know, the stories about what is working and like what is taking to be out there. In terms of like what we have done to make our hiring more inclusive—oh my gosh, I think we're constantly running experiments.

Holly: I am really happy to say that diversity and inclusion has been something that the team at Lever has made a huge part of our culture from like day one, and it’s not because we were diverse from day one.

Holly: You know, for two, two and a half years, I was the only woman at Lever, and it took us a long time also to diversify in other dimensions like race and ethnicity or having parents and people with different family situations—people with different backgrounds—all those different facets also came kind of later.

Holly: But we always cared, and I think we always had a vision for what the culture could be. I would say like probably the biggest roadblock people face to making their own teams and hiring more inclusive is thinking that it’s about demographics and thinking that they have to reflect the demographics of diversity before they're allowed to make their culture, you know, more diverse or inclusive.

Holly: I actually give a lot of people advice: look, before you’re about to do a big investment into diversity in your recruiting and making kind of your hiring more diverse, I actually think it’s really critical to start by making sure your culture is inclusive.

Holly: Because what’s the point of hiring all this, quote, diverse talent, right, if when they get there, they’re not ready to succeed?

Seren: Yeah, yeah!

Holly: So, yeah, number one roadblock when founders think that because maybe they're in a majority, they don’t have a credible ability to lead their company to, you know, have a strong D&I culture.

Seren: Well, I mean, it’s what we were talking about before we started recording. Like now founders are not only tasked with leading the company, thinking of a great product, hitting product-market fit, doing all this other stuff. Now they're in charge of being clued in completely with whatever is going on, whatever social issue.

Holly: So let's like spell this out a little bit more: like inclusion. What does that mean at a company that’s five people? What's an example? How do I do that?

Holly: Oh my gosh! Well, I can definitely tell you how the conversation got sparked meaningfully at Lever, and it was "Who does the dishes?"

Seren: Oh interesting!

Holly: Did they all look at you?

Seren: Hopefully not.

Holly: Well, I wasn’t the only one, but I was one of them. But like a very obvious kind of group of people did the dishes, and a very obvious group of people did not do the dishes.

Holly: Everybody knew, you know? It wasn’t like a surprise; like everybody knew. And it was not something we’d ever entered into the domain of like something that we realized was the surface area of our culture.

Holly: At some point, I can't remember how this came up, but somebody shared an article about how like findings, your research shows that disproportionately women do office chores.

Holly: Sharing that article also pointed out like, hey that was happening here, and what did we want to do about it? And literally, we care improved the next day or maybe like two or three days later, we just decided to do something about it.

Holly: We built a Slack bot that assigned rotational dish duty, and it would just tell you in the morning, “Today’s your dish duty day.” And then we just like made it completely equitable, and people didn't shirk their duties.

Seren: Wow! That's a whole other question!

Holly: Actually, it took a long time even when like, you know, I think it was until like we were like actually a like significantly like maybe a hundred-person company, and then we actually had like maybe somebody who’s like facilities team that was like taking care of it.

Holly: We did this for a long time, rotational dish duty. It became part of the culture—it became something that people would talk about, unlike it’s like, “Yeah, it was something that actually I think was us doing something about it.”

Holly: A more kind of at-scale answer, you know, if that's like the five-person company version, you know, one year, you know, launched our vacation calendar: here’s our official Lever office, like you know, like vacation schedule and holidays schedule.

Holly: And you know, we shipped it; we moved on, and then we found out later— like maybe a day or two later—that there was a lot of like critical feedback from the team about our decisions about which holidays we had chosen to recognize and not recognize.

Holly: And specifically, we hadn’t chosen to recognize Martin Luther King Day because we had recognizing Presidents Day or something, the same month. And you know from the people team’s perspective, they were just trying to like their heuristic was low: just balance out the holidays as evenly as possible throughout the year.

Holly: But we realized in that moment that our holiday schedule was surface area to our culture. So I think in thinking about making your culture more inclusive, it’s really about what are you choosing to make your cultural surface area? What are you choosing to say like this is part of it and this is not?

Holly: That’s like one decision a founder has to make, and then second, it’ll change over time. Literally there were, you know, at one point our holiday schedule is not part of the culture, that was right?

Holly: I think that’s like how dish duty was not and then it was. And that’s just a dynamic part of culture. But I think the important part about being conscious about building inclusion into your culture is that dialogue.

Holly: What a founder can be responsible for is that any time something comes up—because it’ll come up right?—it’ll just come out of nowhere, is to make sure that you’re the kind of company where people are able to bring it up, and where you’re able to sort of like give it back to the team like, “Okay, what do we want to do about this?” and where people take action.

Holly: I think that’s actually at the heart of getting, you know, this really murky world of how do you be a socially responsible founder. You’re not gonna know, but what you have to do is build that capability inside your company to question yourself and to have a dialogue and then to take action.

Holly: That’s, I think, at the heart of what early-stage founders in particular have a real advantage on, yeah versus these companies that are trying to add this on later. You have so much ability to shape how your culture talks about itself and how like employees are shaping that conversation.

Seren: So, Holly, it’s really funny. I’ve actually visited the Lever offices, and I noticed in the kitchen they have wine, which I’m super appreciative for! They have a bunch of cups, and then there’s this one lower shelf that says, “Please leave for the vertically challenged.”

Holly: I mean, you’d be surprised! Like obviously the diversity and inclusion conversation, it's so driven by certain kinds of categorizations. But you know, one of the most profound shifts for us when it comes to diversity was to talk about how we didn’t want to buy into the idea of technical and non-technical people.

Seren: Oh interesting! Can you tell us a little bit more about that?

Holly: Absolutely! Like, you know, I think Silicon Valley has this deeply ingrained stereotyping around technical people and like for the most part I think that's a seat of privilege. Like if you are an engineer, if you’ve got coding chops, if you’re a hacker—like there's all these kind of attributes about you maybe being like a more worthy or valuable or like higher potential founder or employee, right?

Holly: I think there is even some companies where like the technical parts of the company get free lunch and then the non-technical parts of the company do not.

Seren: Ugh, right!

Holly: And of course like with hiring being as tough as it is for like software engineering and wills data scientist roles, I think that like there's this value placed on these people that, you know, I think frankly a lot of people buy into, too, right?

Holly: Like a lot of the people that are not on that side of spectrum—like the quote non-technical people—have almost self-handicapped about it. We actually for a while recognized that not only was that kind of against like some of our cultural beliefs, but also it was holding us back.

Holly: We needed our quote non-technical people to embrace and adopt like designing systems that were as sort of like scale sophisticated and have that sort of engineering mindset about their work.

Holly: And then we also needed our technical people to understand our customers, understand the value proposition, to like really embrace some of the qualitative aspects that we as a B2B software company really needed them to like actually really, really know our customer and why we were doing some things.

Holly: And get our go-to-market motion and our sales pitch, and why we're doing these things like on a deeper level. We just realized that that stereotype wasn’t serving us.

Seren: That's a great insight!

Holly: Yeah, it’s like I’ve met many technical people with no product sense.

Seren: Yeah!

Holly: I mean, I’m guilty of it too, right? Like, I sort of embraced the idea in hindsight—in a weird way—that I was like proudly are non-technical founder, but I have a BA in mechanical engineering from Stanford. So it’s sort of like what—you know? Like it just was like confusing.

Holly: And so we actually, yeah, we ran a training of like "I'm technical and so are you!" that we just like had a few like brown bag lunch seminars. One of our early employees, shout out to Jennifer Kim, she runs a blog called "Inclusion at Work," check it out!

Holly: She helped us kind of build, and we just like ran a bunch of people through it and like tried to like, you know, spread this empowerment, I think, that it—yeah, like I think again just like my missive of like there should be more designer-founders. I think like there’s a lot of people out there that are limiting their own potential by not thinking that they can access any part of what it takes to get creative and solve problems.

Seren: Yeah, I couldn't agree more!

Holly: So related to all this is, like you said before, having the conversation about it. I think people are often terrified to have the conversation about this at work because they're like, “I don't know what I'm supposed to say. I don't know what I'm not supposed to say. I might know what the prevailing thing to say is, but maybe that's not how I feel.” Or I'm just curious, how do you set up a culture that allows those conversations? Is it like with your manager directly? Like how does that happen?

Holly: Oh gosh! It’s like layers of an onion! I wouldn’t even say Lever solved this problem, but I’ll just enumerate some of the things that we do to help. We do everything from the superstructure to the super just human skills.

Holly: So we have a new hire onboarding that we call Ramp Camp, and it's the week kind of where you get on boarded to the full 360 of the company. It doesn't matter if you're salesperson, engineer—we onboard everybody to every part of what makes the business successful.

Holly: One of the sessions is on diversity and inclusion. So like literally your first week at Lever, you’re hearing us talk about it. You're hearing us talk about where we’re at with that. You’re receiving an explicit invitation to be a part of it.

Holly: Other structural things that we do, we have a lot of employee resource groups—so these are like of course, you know, a lot of companies have them. We have Leverett for the women at Lever. About 65% of our employees are a member of one of these groups, and we actually not only have them and support them, we actually asked them to help us build policies.

Holly: Like the Lever Parents ERG was a group that we like my VP of people like went to and asked like, “Hey, we’re trying to revise and improve our parental leave policy. Can you actually help?”

Holly: Using these groups to inform real decisions is kind of the next level. We also do kind of programmatically a lot with our management groups or management layers.

Holly: So I’m a big believer in coaching. We do a group coaching program. So every twice a year, every six months, we do like a six-month program that we run all our managers through. Some who are promoted internally, some that we hire, to be intentional about our management culture.

Holly: I think that they can be such great advocates in terms of spreading great practices that do make work more inclusive. And, you know, if you're not already engaging your management team on D&I, like, you know, hello! That’s really impactful!

Holly: So that’s some of the structural stuff, and then some of the things that are just more human. Oh gosh! Well, here’s a funny example: We really encourage people to engage with each other to solve problems with each other, but you know sometimes having difficult conversations, like you’re kind of navigating these murky waters of, you know, you don’t want to kind of go over the net and like accuse into something, but maybe you’re trying to surface or highlight a difference in point of view or assumptions or background.

Holly: And what we didn’t want is for people to resort to stereotypes.

Seren: Yeah!

Holly: Yeah. Well, you're like, you know, an introvert and I’m an extrovert and say blah blah, or you're a salesperson and I’m an engineer, and therefore blah blah!

Holly: One thing that we also built into Ramp Camp is we have all the new hires kind of take one of these assessments, and like the output of one of these is like a color.

Seren: Yeah, number one, a color one?

Holly: Yeah! There’s even an animal one, so, yes!

Seren: Yes, we are also big fans of spirit animals!

Holly: Awesome! But yeah! So, you know, now everybody has the shared language about how to talk about difference that isn’t about like how you were born or, you know, socio-economic background or anything like that.

Holly: I think that that’s really empowering for people. So now we even celebrate it. I think it’s become a way we can celebrate difference.

Holly: So at the end of Ramp Camp, obviously, you kind of complete it, and then we actually do a happy hour for that month’s Ramp Camp class. They come and exit kind of their last session of the day where they get their colors and enter, you know, Commons—our Commons area—where we have this whole company like clapping.

Holly: We kick off this happy hour to celebrate their first week, and this sort of like it's the colors reveal is at the happy hour. So, all the new hires are wearing leis that correspond to their color stories. Like green, you’re like...

Seren: Right!

Holly: You know? I think that, you know, whether you’re doing it kind of in these structural ways or you’re just giving people like tools to work in, that’s personally huge!

Seren: That’s huge, yeah!

Holly: Yeah! It's about how you create a common language and then kind of celebrate it and say like it's okay to talk about it.

Holly: We're kind of huge dorks, certainly! I love it. Obviously, I’m horribly biased, but yeah, we’re kind of like goobers in that way.

Seren: That’s great!

Holly: Yeah! So much of it is just, I mean, like comedy even. Like it’s just in tension, right? It’s like coming from a good place! Like okay, like we can work with this!

Seren: Yeah!

Holly: And you know what? Like those ideas I just described are bottoms up. Yeah, it’s not like I’m some architect of all things diversity and inclusion; I’d ever quite the opposite, actually. I credit like the team collectively as really being the drivers of this.

Holly: I think that's the opportunity that the early stage founders out there really have—if you do get this into your culture, what you get long term is this, you know, collective ownership over everything cultural. But certainly, diversity and inclusion as part of that, if you can get that seed planted, it just like is a little bit self-reinforcing.

Seren: Yeah!

Holly: And so I would not leave that! It sets you up for scale!

Seren: Yeah! It pays in dividends later!

Holly: Yeah! Well, like get ramped up into this culture and they would just know.

Seren: So, Holly, wrapping up here, we have YC. We have a batch going on right now. All of these companies are quite early. What’s your advice to the companies in the batch to make the most out of it?

Holly: Mmm, you know, I think that the number one thing I would say is, you know, your culture is your people—it’s who you hire; it’s who you fire; it’s also who you’re recognizing, who you're promoting, who you're rewarding, and how you do all those things.

Holly: You probably feel like you have a million things going on. Everything's on fire, and you have so many things to get done in a given week, but the secret to solving all these problems is through really, really getting great at building your team.

Holly: Yeah! And so like I found this to be true. I work with thousands of companies at every stage of growth with hiring. I think like you have to get great at talent. You have to get great at hiring.

Holly: And I think that if you can really embrace that as a true part of being, you know, an authentic founder, you know, I think you will attract the right people that will run with all those things that you’ve got to do in a given week.

Holly: And it is the shortest path to building strong culture; it’s the shortest path to building your results. So, you know, embrace that—founders’ number one job is recruiting!

Seren: That’s excellent advice!

Holly: Alright, thanks for coming in!

Seren: Thanks, thank you!