The founder’s guide to making your first few hires — Steven Bartel on recruiting at Gem & Dropbox

Brett: So I thought one place we could sort of start this conversation. I'm hoping to sort of broadly cover what you figured out in terms of building an early team. So maybe not the, the 50th or 70th hire, but the first and second and 10th and 15th, and you've written a bunch about this in the past, but was hoping to kind of explore that in our conversation and maybe a place to start would be, when you think more broadly about talent that is hugely successful in that fourth seat or six seat or seven seat?

What's kind of different about that type of talent relative to when you were maybe operating at scale previously, if there is anything.

Steven: That's a really great question. for early stage hires, thinking founding team members, The number one thing that I always come back to is doers, right? People who are actually gonna roll up their sleeves and, and get stuff done. I think there's also a certain scrappiness in the early stages.

That's really important. And in general, as opposed to at a later stage company where you need a lot more process, it might be more important to align with cross functional stakeholders in the early days of starting a company. You just need people who can do and build, What has that taught you about recruiting out of very large companies into call it the first 10 hires? And I think this is like a, a, a, a really interesting debated topic amongst early stage founders and CEOs. do you put it in the don't touch pile? Do you put it in? Absolutely. And what you need to do is get really good at filtering an evaluation in that pool, um, because you both have kind of this maybe bias towards action scrappiness dimension, you also have risk tolerance.

Brett: And what does it say if somebody spent the last seven years at a certain scale of company? Um, but I'm curious when you think about recruiting somebody that came from that world into a five or 10 person company, what are some of the things you figured out, or what are the points of view you've, uh, developed.

 first of all, if you're a startup founder trying to build out your founding team, you might not have the luxury of always picking and choosing where you hire people from. Right. So you might actually have to. Expand your lens and hire people from big companies or hire people that have startup experience or hire people straight outta school.

Steven: Right. It's so hard as it is to build out your founding team. So I, I don't necessarily think that it makes sense to apply a ton of filters on big company versus small company when it comes to, to hiring. I think the things that you need to make sure of are different depending on where somebody's coming from.

So if you're hiring somebody from a big company, I think that you absolutely wanna be transparent and give them a really great picture of what is it like to actually work at a small startup to make sure that their expectations are aligned. Cuz actually the, the place where I see this stuff go wrong is less about bringing on somebody and they can't figure out how to do the job.

It's actually more that they don't wanna do the job. Or that they're leaning away from certain types of important work to be done. that's where I've seen it go wrong more often is, is actually that you're bringing on folks that didn't know what the job was and then don't end up wanting to do it.

Um, so I think setting expectations is a really key part of that But then outside of that, I think there's still ways to really understand and test for people who are builders. Right? Folks actually rolled up their sleeves and, and built things potentially from scratch or maybe earlier iterations of things at larger companies versus somebody who took something and, and scaled the fifth or sixth iteration of it, or somebody who was really effective at working through others. which isn't really an option at a small startup

Brett: Do you think about early stage interview process as being different in any way based on what the person's experience was, meaning that you have two candidates and you're hiring for the fifth engineer on your team. And one spent the last eight years working at two big cap tech companies. The other had, uh, two early stage startup experience.

When you think about those candidate personas, do you think about evaluation in different ways or it's all standardized in

Steven: a little bit, um, on the edges. I, I, I definitely think there's there's room to test for slightly different things that you might be more concerned about depending on where somebody's coming from. But actually we did something completely. Non-conventional at gem for our first 10. Hires. And then we figured out how to scale it and it continues to be very non-conventional, but we actually had a lot of our early hires come and work with us for a day or two days, or if they were free and in between jobs, we'd just say, Hey, come, come work with us for a few weeks and really understand what is it like to work at a startup?

And actually the, the funny thing was this was a lot less about evaluating them. It was a lot more about them getting comfortable with joining our small startup and really understanding what that would look and feel like, uh, coming from a larger company but the added benefit of that is they gain such a clear understanding for what the role would be, 

But we also. Got a lot of signal on just hands on experience. What would it be like to work with this person? And now we, we weren't able to do this with everyone. Uh, a lot of people that interviewed with gem had full-time jobs, but even in those cases, we would actually have them come and work with us for a day, if possible, um, even to get, get some of that signal on both sides.

We actually had a lot of people self-select out of joining our company in the early stages because they realized that a startup just wasn't the right thing for them.

Brett: That's interesting. So to pick that apart a little bit, I guess two things pop to mind when you think about, uh, a candidate coming into, and let's just say a one day job simulation co-working what percentage of the time did they opt out? Versus what percentage of the time when a qualified candidate came in, did that experience give you net new information about that person that made you feel like they weren't a fit for

Steven: It's a good question. So I, I will say that our approach to building out our early founding team was to do a lot of hiring from our network. And so a lot of the folks that we were bringing on board to do one day or two day or three week work trials were folks that we knew and, and we at least knew of their reputation and they knew us.

Um, so part of it was, was just alright, like. There's a little bit of, um, trust on both sides. Let's just see what this would feel like in practice. Now in practice, I'd say two thirds of those folks, maybe self-selected out of joining gem and a lot of times it wasn't necessarily gem. It was just, oh, wow.

This is, this is what it's like to be at a really small startup I might actually optimize for something different. And then, um, we absolutely got some signal on some candidates as well. And I'd say maybe a third or a half of them, we decided to not move forward with, but this, I think the signal that both sides got from a process like that was way higher than anything you could ever get from.

Whiteboard coding or, working through a few algorithmic pro problems over the course of a few hours. Um, now I share all of this, knowing that it's, it's, it's pretty actually UN unconventional and I, I don't necessarily have a playbook for recommending that, that every startup founder, founder do it.

Um, but, but that's actually how we hired our founding team for the most part, our first nine or 10 engineers.

Brett: I think when you talk about, I mean, the extreme case of this that you're getting at is contract to hire, but I think it's interesting kind of this middle ground, this one or two day, um, kind of working together, you know, most founders are like, well, the very best candidates have multiple offers and they're not gonna do that.

If you, if you had to guess, if you, if you weren't doing so much referral based recruiting or in network recruiting, do you think that can work or maybe as you've started to scale and modify this, do you think people's intuitions around that may be wrong?

Steven: I think that an approach like that mostly works for referral based in, in network hiring, which, which I still believe for your first 10 hires, building out your founding engineering team is generally the right place to focus. Um, there, there are different versions of this that, that we've refined and scaled over time.

And now we have a, I think a three or four hour. Pretty hands on, uh, coding exercise. That's standardized. Everybody goes through the same thing. I mean, the early days of jam, we were doing this, this wild thing where we would come up with a different project for every single person that interviewed with us.

And oftentimes some of these projects would even ship to real customers, which was kind of wild for an interview process. Now, I will say it was a lot of, uh, extra work from the full-time engineers at gem to make those projects successful a lot harder and more work to, to get those across the finish line than if they were to just code them themselves.

But so, so really it was a device for letting people learn about what it would be like to work at an actual startup. Um, but then over time, we, we did refine that and shorten it down to a couple hours, uh, real hands on coding exercise with several checkpoints with. Different interviewers. So to speak across the team where you would actually collaborate on real problems and do a code review and stuff like that.

Um, so there, there are ways to scale that and, and really boil it down to just the core pieces. But I don't know that we would necessarily would've landed there if we started from scratch. I think that was largely an evolution of, of this thing that we tried and had a lot of success with in the early days of having people just come and try working with us.

Brett: On that point, when you go back to those first 10 hires and you kind of did these one or two days, or maybe a little bit longer projects with them, uh, how did you architect that time? Um, and was it sort of a very, you know, Sally's coming in on Wednesday? What is she doing or how was that crafted?

Steven: Yeah. We, we put a lot of prep and thought into it. we had a running list of projects that we thought would be. Good projects for candidates to bite off. Um, we had to actually put a lot of time and energy into making sure that it was really fast to get your, your dev set up And, uh,

Brett: Yeah, I, I was curious cuz I think sometimes it takes a day or two for a new hire or more just to get set up from a development environment

Steven: it's really funny. One of the little side benefits of doing it this way was our dev setup would always take, you know, 10, 15 minutes max at any given time. Cuz we knew we we'd have candidates that needed to get going fast. 

Um, we would have conversations with folks before they, to. Give them a little bit of an overview of what to expect and, uh, share a little bit more about the technologies we use and stuff like that. So there'd be some prep. Um, and then there would be check in points. I remember that was really important.

Uh, we would check in an hour or two in make sure that they had dedicated time for, for questions and, uh, to unblock people as they're getting going. Um, there would be a, a check in point about a third of the way through about two-thirds of the way through, and then near the end, there there'd be more of a code review, and ideally we'd have time to do a iteration based on some feedback there as well.

Brett: When someone came in for one of these projects and you reflect on sort of how you all operated or behaved was, is it, was it a completely normal Wednesday? Were, were you thinking about salesmanship and Sally's coming in and we need to get her excited about what we're doing at. Like what was sort of the interplay between business as usual versus this is a sales and marketing activity.

That's gonna commence at 8:00 AM or 9:00 AM on

Steven: That's a really, that's a really good question. And the experience would vary a little bit, but my approach and I, I think something that served us pretty well for a lot of the folks that we were evaluating and, and trying to convince to come on board was actually to try to give them as, as clear of a picture as possible of what it would be like to be on the team.

And so if we had a candidate in, on a Monday, we would absolutely invite them to our weekly standup for 30 minutes to start the day. And they could just feel like they're a part of the team and hear everybody's updates. If we had an exciting prospect conversation on a Wednesday, We might do a little bit of a detour and say, Hey, why don't you come right along this, this customer or this prospect conversation?

And I, we would've no clue how that conversation would go but a lot of the times, like the reception to our product would be really strong or, or there'd be some really interesting thing that we could learn. And we could debrief a little bit afterwards and just give them as much of a taste as we could for what it would actually be like to work there.

Um, the, the types of things though, that we did gravitate towards over time, which were more for the candidate and not just a part of like every day company, um, tended to be around things like, uh, dinner. So, you know, if we had somebody come and do a day of working with us, or two days of working with us or a week or two of, of working with us, we'd try to do at least one dinner with the team so that they could get to know their, their teammates social.

 given your point about largely pulling from various forms of your network for those first 10 hires and kind of looping back to what you were talking about in terms of, um, you know, hands on doers, builders, et cetera. Was there anything that, you did to sort of identify those people in your network, or let's say you worked with a hundred people closely at Dropbox before you started and you sorted those by those that you thought would be the best fit other than them being sort of scrappy builders.

Brett: Was there anything in your own little internal algorithm that helped you sort that talent for the people that you thought could be a really great fit?

 I think that given the product that we build. Given a lot of what needed to be done at gem. We oftentimes were starting with a lot of the people that had pretty strong, full stack experience. I think that at, especially at large companies that the larger you get, the more specialization there can be.

Steven: So if we had to stack rank, that would be one of the things that floated at the top in terms of folks having a little bit more of a breadth of experience. But with that said, if we knew of a really talented topnotch infrastructure engineer, we absolutely talk to them.

and see if we could get them excited about the job, which would be talking to customers and building full stack. Product end to end. And generally we felt that if, if they were strong engineers and we could get them excited about the job to be done, and they were able to come in and do a full stack project with us, that was, that was somebody that I would, I would make a hiring decision on any day.

 How did you develop your narrative for the company in the early days, the narrative that you used to recruit talent? And I'm particularly curious because I would think it face value. Hey, we're creating some recruiting software for sourcers and, you know, blah, blah, blah, blah, blah. When you think about the craziest, most ambitious technical folks that you know, out of the gate, I'm not sure that, you know, connects with them immediately. And so other than I'm sure many of them were drawn to you, you had interactions over a long period of time. Did you have a specific narrative or a way that you went about selling the opportunity when maybe this one sentence description, wouldn't jump off the page for really ambitious technical folks.

Steven: Yeah. So I. The things that we shared with candidates to get them excited about gem. It was different from the pitch that I was used to at Dropbox at Dropbox, we could talk about all of the, the hard technical problems that we had, the scaling, the infrastructure, supporting hundreds of millions of users, right?

So we had to find a very different, unique reason to join gem, uh, from what I was used to at Dropbox and what from Nick, my co-founder was used to at Facebook. But the things that we got people excited about were were different.

We got people really excited about learning about all the different aspects of building a business. We, we attracted a number of people who thought they themselves might go on to start a startup. One day we found engineers that were excited about learning more about talking to customers and riding along sales calls and customer success calls and learning about fundraising and how to operationalize a business. And one of the, actually the, one of the core values that emerged out of all of this was, was this value of transparency, which, you know, we believed was the. really important for, uh, building a successful company because it meant having a, having a transparent company means everybody has as much information as possible to be able to do their jobs effectively.

But the side bonus, the side benefit for a lot of the early funding team was they would get a lot more visibility into how companies work and, uh, gain this unique exposure at a place like gem, where if they wanted to one day they could go on to start their own company.

Brett: How did you convey those things to candidates? And was it as simple as, Hey, if you join here, you know, you're gonna get to not just be an engineer, but be more holistically involved in the product building process or the company building process, or did you package this up or, or, or sell it or have it land with candidates in a specific way?

Steven: Yeah. We, we talked a lot about this with candidates and. I mean, we would go as far as to have candidates sit in on prospect conversations and customer conversations to get a taste of what that was like during their interview process. So it wasn't just talking at them about how we were gonna do all these things.

It was actually walking the walk and giving them a taste. the other thing we did is, is we had candidates talk to one, you know, once we had that, that early inception of a founding engineering team, once we had those first 1, 2, 3 incredible founding engineers, we'd, we'd set them up to talk directly to each other. And, um, you know, the next candidate we were recruiting could hear about these unique things and, and why these other founding engineers joined and how all these things had become true for them.

So it was a little bit of showing and then a little bit of. Telling through the people that had already joined.

Brett: I'm curious, you know, you are effectively the first hire of the company as the founder and CEO. And so why do you think you've had such outsized success? Or if you look at your own abilities or past. What is it about you that you think in enabled the, both the success of the company, but you to be successful as a founder and CEO?

Steven: Wow. Uh, never really thought of myself as my first hire, but I GU I guess I was the founding engineer, number one. Um, uh, no, it's really interesting. I, I think that for me, the, the thing that's helped me be successful and, and continue to be successful in scale in my role is I'm always learning. Um, actually at, at gem I've I've had to.

Pick up so many new things. My background is engineering, but at gem I've actually focused almost all of my time on the business side, sales, marketing, customer success, people, finance BI ops. And so for it, for, for me, it's, it's been really key to wrap my head around so many new things that I've never seen before and, uh, constantly be learning.

So I, I think I owe a lot of my success to some incredible mentors that I have outside of the company who have helped help coach me on all of these different aspects, every step of the way.

Brett: Uh, maybe on that point and we can kind of take a, a quick, uh, left term before we come back to some of the early hiring conversations. one of the topics that I've, I've long been interested as the idea of commercial orientation. Um, and I think in product folks and engineers, it, it tends to be a population of, of folks that oftentimes actually don't spike in, in kind of commercial orientation, or how do you take a thing and actually sell it in a scalable, repeatable way, I'd be interested to hear more about your journey from engineer engineering manager, to product builder and business builder. And were there certain unlocks that you figured out along the way, that you think had an outsized impact or allowed you to actually cross that chasm in some way.

Steven: Yeah, there's one big thing. And I think this can make up for a lot of a lot of things early on. Even before we started gem, I internalized the importance of talking to customers. And I think I owe a lot of this to one of my close friends and, you know, who's ultimately become a mentor of mine. Uh, Spencer S skates he's he's the founder and CEO over at amplitude.

And I loved to pick Spencer's brain in the early days and how they got amplitude off the ground and what they did. And he would always come back to customers. You know, Steve, go talk to customers, Steve, what are customers saying? Oh, they don't like that idea that you're thinking about. What do they like, what are their top three priorities?

And, there's this trap that a lot of us, as, as technical folks fall into where we're really comfortable building product and writing code. And there's this trap that we fall into where we dream up a product we could go build, or some technology we could bring into the world in search of a problem and go build it and hope people will come.

And I, I, I think that's where a lot of. Folks go wrong. And, and because me and Nick, we were very well aware of this blind spot of, of having a lot less commercial experience, we told ourselves that before starting anything at all, we would go talk to at least 50 customers.

about the, the problem that we're trying to solve, how we're gonna solve it. And we would hold ourselves accountable to having pilot customers lined up and ready to go before we even wrote a single line of code. And what we tried to do is swing the pendulum in, in the complete opposite direction and lean into the part where we were worse at and knew least about I find the topic of talking to customers in the early days and as you're scaling a business, one of those things that make sense, but if you look at a founder and CEO's calendar on a weekly basis, it doesn't reflect the importance of that. And why do you think that is.

I think that for a lot of us, myself included until, until I did a lot of it, talking to customers can be pretty uncomfortable. It can be pretty discouraging. I remember the first many conversations we had with customers actually, before we landed on gem, we would get so excited about different ideas of things we could build.

And, um, you know, how we were gonna change the world and we would walk into a customer conversation and it would fall completely flat or they would get disinterested. Or we couldn't get to one or two folks coming out of 30 customer conversations who would be willing to sign up the pilot. 

So it was uncomfortable. And I think that there can be this urge to focus on actually the, the things that you're good at, the things that you're comfortable with instead of the things that are hard and, and most important and at least that was my personal experience. And that's my theory 

Brett: So, so if you were to create, uh, Steven's five minute class for how to talk to customers or talk to your first 50 potential customers, right? You're an engineering manager at company X, and you're thinking about building something from scratch, and you agreed with the idea that I'm gonna talk to 50 people before I do anything.

What's sort of the few minute class on how to actually do that in the most effective way possible.

 Oh man. And I wish I, I wish I had this class. when I was getting started, cuz so much of this we learned by trial and error and just doing different things. Actually the, the number one. Piece of advice that I would give is, is just to get going you could theorize and think about it and, and try to put all sorts of structure around it.

Steven: But there, there really is no substitute for just getting, going and, and going and talking to customers and, and trying things out and seeing what works and seeing what doesn't. And Hey, if your first five, 10 customer conversations are a flop, you can go file in five or 10 more to talk to it's , it's not like you're ever gonna run outta cus potential customers that you could talk to.

And if that's the case, your market's probably too small so you might have bigger problems to worry about. But if I were to think back to some of the learnings and things that we converged on from those early days of talking to customers, I think that we, we generally did converge on a few phases to these conversations in the first wave of conversations, maybe with the first 10, 15, 20 customers, we would spend a lot more of our time.

learning about their world and validating the problem that we were thinking about solving and whether it was actually a top priority. And I think that ended up being pretty important because if you jump straight into the solution space and don't spend enough time on, is this problem even worth solving, you might be missing the higher order bit.

There. One thing that we would always do as we were validating the problem statement and, uh, just learning about their world and their priorities is plant the seeds that Hey, like, we're really excited about this. We're gonna go talk to 15, 20 more customers. And if they're all feeling the same pain point that you're talking about, we'd love to circle back and get more time with you to walk.

you through our learnings and, and talk about how we're gonna potentially approach solving this problem. So you can always tee up that next conversation to jump deeper into potential solutions. So we did that and the second phase would be a little bit more about how are we gonna approach this? What are some of the value props we're gonna focus on?

Um, and then that would tee up the third phase, which is . We didn't have a product, we hadn't wrote written any code. So how do we actually bring that to life and convince some people to sign up as pilot partners? But we did, is we just built ball balsamic mocks? Are you familiar with the tool balsamic?

Brett: Yeah, for

Steven: Yeah, so we, we

Brett: I, I feel like it's less en Vogue, but probably five years ago it was the, it was the Figma of

Steven: I don't even know if it was in Vogue back then. I, I just, I didn't didn't know about any other software and.

Brett: I thought you were gonna use HyperCard.

Steven: um, but one of the things I do love about balsamic is, is that it is low fidelity and kind of by design. So, so people don't expect higher fidelity, good looking mocks. And you could literally, uh, mock up a few core workflows in a few hours in balsamic. And we would show that to customers as here's the MVP that we're gonna build you and try to convert, to getting folks to say that they would be pilot partners 

Brett: When you think about that early process of talking to customers and refining the value prop and refining the early product and understanding what's going on in their world. Did any of those ideas translate over to the way in which you thought about recruiting the early.

Steven: Mm. Yeah. I mean, one of the advantages of building recruiting software and working with so many amazing companies is we had a ton we could learn from our customers about how they were hiring that translated into how we, we built our early team. So being in the recruiting and town acquisition technology space.

Like I think even more than most founders, Nick and I leaned into putting in the hours and putting in the time to building an incredible founding team, um, both on the engineering side, but also on the go to market side with some exceptional talent, um, because building the right early stage founding team, that's the foundation upon which the rest of your hiring is going to be built.

And it's what it's, what can really propel your company forward. we knew from the early stages that, yeah, we'll, we'll have a career site that we can direct people to, but. Posting a job. Like that's, that's not gonna be how we hire. That's not gonna be where we get a bunch of applicants.

And so we knew that lesson from early on, I think a lot of founders maybe don't realize that though, is that actually early stage hiring is all about going out there and finding people and pulling them in versus waiting for them to apply. But, you know, that was also the core thesis behind gem . And, and one thing that we, we, we learned from all of our customers.

 One of the things that I think is, is kind of interesting about both you and Nick is that you each kind of had a couple internships, but basically had one formative technical experience

Steven: Yep.

Brett: you at Dropbox and Nick at Facebook, how did you figure out what are the things you wanted to take from those companies and apply at gem versus back to first principles or do it differently.

 because at that point in time, Kind of the 20 10, 11, 12 sort of that time was both when Dropbox and Facebook were the most dominant brands, the Silicon valley, darlings of that generation. And I would think it would be easy just to do a lot of copy paste copy.

Brett: Well, we did it this way at Dropbox. Well, we did it this way at Facebook. Um, and so I'm interested. Did you intentionally think about what are the things we want to take versus not?

Or was it a kind of a much more organic process for you

Steven: we did actually, there was some, uh, or organic process to it, but there was also a lot of intentionality behind it. And let me just maybe share a few examples Facebook. A lot of the way the product was built and the way that folks made decisions. And I interned there. So I know a little bit of this but Nick was there for a long time, so you can speak to this even better than I can, but Facebook was very, ship off and shipped fast and then run experiments and rely on data to make decisions. We actually, we loved the ship off and then shipped fast. And that actually became one of our core values around velocity.

Um, but Facebook as a large consumer company, and to some extent, Dropbox as well, had the luxury of having hundreds of millions or, or billions of users. And in, in that world, you can rely a lot more on experiments and data to make decisions, whereas for gem. And I think for a lot of B2B SAS companies, relying on customers and talking to customers is, is the right way to make decisions.

So, so that led us to a second value at gem, uh, around customer focus at Dropbox, a lot of our decisions, at least while I was there for new products were design led. Um, and actually apple works very similarly to this. where a lot of the way they build product is, is design led. Um, and I think that can make sense for certain companies where you kind of need to figure out new products and, and do it based on a lot of vision.

Um, but, and, and where you have to do these big releases, that roll out to tons and tons of users all at once. And, and for, for Dropbox, it was actually really important that when we ship stuff, because we had so many users that it worked out of the gate and because we were dealing with people's files and data, like attention to detail was really important for gem though.

We decided that we wanted to be more scrappy than that, um, and that we would make as many of our decisions as possible by going and talking to customers and understanding what they want. And that actually we'd be okay with. Not sweating every detail because that might slow us down a little bit. I wanted to loop back to where we started and, and pick up the thread on some of the, the early things you figured out around, um, hiring. And one of the things that you sort of talked about at a high level was the fact that a, a bunch of the early hires just came from people that you had interacted with, or were somehow in your network.

Brett: But if you go back and, and you think about the first 3, 5, 7, 10 hires, what, what was the sourcing strategy within your own network? Did you just sort of open LinkedIn and create a list and then sort it in some way? Like, what are the nuts and bolts of actually how you figured out who to target for those first five or seven folks?

Steven: Yeah, and we actually did end up using gem for a lot of this, even when it comes to sourcing from our own network, We actually have a free for startups program at gem. So if you're doing any sort of sourcing from your network, whether that's first or second degree connections, you can actually use gem for free until your company grows past that 15 employee.

For up to two years. But yeah, we were, we were focused pretty much a hundred percent on our network and the lowest singing fruit and the place where we started was first reconnections. So we went on LinkedIn. Um, we went through every single person we had ever worked with.

We started to organize them into projects and we used gem projects for that. But of course you could use a spreadsheet or something like that. And we also went and got creative and we thought about former internships who were all the people we worked with there, we went and thought about all of our classmates from MIT that we knew.

And we ended up hiring several people from that pool. And then every week, we were carving out time to . Uh, do more sourcing and especially from first degree connections and, and continue to build and expand on our lists. But we were also in parallel starting to reach out to those folks and engage with them and catch up with them and see what they were up to in their life And, you know, whether they were starting to think at all about what was next. And for many of these people, it was actually a really slow and long, uh, nurturing process where we would catch up with them every month or two over the course of six months, nine, 12 months, two years before, before they were actually ready to make a move.

 and then actually consider working with us. We did actually develop a, a pretty fun trick though for sourcing second degree connections. Um, I like to call it the, uh, the connector node, uh, trick.

Steven: So essentially what we did is we, we came up with a list of 15 or 20 people that we really, really respected, and they would say really good things about me or Nick, my co-founder. And then we would actually go in and source from their connections and name drop. Hey, saw you were connected to Albert ne, um, who we think super, super highly of add some personalization, add a little bit about gem.

Would you ever be up for grabbing a coffee? And the cool thing was. Folks would actually go talk to Albert and say, Hey, how do you know this, this Nick guy or this Steve guy? and it, it almost turned into this warm referral and, and recommendation where they would back channel the connector node. They would say good things.

And then they would get back to us. And, and we, it would turn these kind of second degree connections, colder connections into warm ones. And actually that's how we hired. Uh Enno um, our first engineer from Uber, she, she joined us from Uber, where we had no network.

Brett: That's that's really clever. Are there other tricks like that, that you deployed in the first couple years in building the team that might be interesting to explore?

 we pretty quickly, as we started to scale out the team and, and have. More and more of our founding team helping with recruiting. We discovered that it was really helpful to have a steady drumbeat of things we could invite people to because having some sort of compelling reason or, or thing to have people swing by for made it feel a lot more natural to our team, to reach out to their network and say, Hey, we're, we're having this, this happy hour or the, the team's getting dinner, or like we're hosting a game night.

Steven: Do you wanna swing by and say, hi, it's gonna be a lot of fun versus, Hey, can I introduce you to Steve or Nick to talk about job opportunities? so having a steady, uh, drumbeat of, of things that we could invite people we were interested in working with together that were lower pressure. and weren't as direct and head on as we wanna sell you on a job opportunity, um, was, was another really important thing that we discovered and started to do when we were about 4, 5, 6, uh, founding engineers.

Brett: When did you go from sort of in network, previous relationship style recruiting to, um, some sort of sourcing out of network, extended network recruiting and how did you know it was time to make a concerted effort to, to move outside of that?

Steven: So the first thing I'll say is that we, we never stopped doing really heavy in network, referral based hiring. So. Sourcing has always, for us been purely additive on top of that, I would say that we started to source out of network when we started to have specialized roles that we might not have as big of a network for.

Um, that was also, uh, an interesting place to use agencies in, in certain key select ways. for our first marketing hire. For example, some of our sales hires where we just didn't have as strong of a network. But then on the engineering side, I'd say probably when the company was around 25, 30 people is, is when we started to do more sourcing outside of network.

And around 25 people is when we brought in our first recruiting slash HR hire who ended up becoming our head of people and scaling with us in that role until we were about 150 people. Um, so, so she started to help source and then we, you know, started to hire one or two recruiters as we, we got into the 50 to a hundred mark and, and then we started to rely even more on sourcing.

 It was more that we added it on to start to supplement a lot of the in network and referral based hiring that we were doing. one of the main benefits of doing that, um, was we were running to all sorts of problems in the early days with, um, building a diverse team because.

Steven: and, and this is, this is something that we decided when we were, I think, 10 or 11 people like as gem as a company, that's in the recruiting and HR space, it's gonna be uniquely important for us to build a diverse team. It's important for every company out there, but for us, so that we can build the right products so we can, um, develop best practices internally that we can then share with the rest of the market.

We decided to really try to invest in building a diverse team. Early on sourcing was actually one of the few ways that we could supplement our other channels and sources of hires to offset what was inherently a less diverse network or inherently less diverse inbound applications. 

Brett: Something we didn't, uh, we didn't talk about a minute ago is when, when, when you were doing referral based recruiting for, within your own network or people that you had worked with, did you interview them as well in, in sort of a rigorous way? Or did you assume that the work you did together was proxy for, for an interview?

Steven: We did every referral. Every in-network person went through that same interview process, um, where we'd actually have them come and work with us for a day or two or in some cases for a little bit longer, if they had the time.

Brett: And other than sort of working together on a project, were there other parts of, of the actual interview process for those first 10 or 15 hires?

Steven: so

 Working on a project actually had a bunch of different elements and parts that went into that. There was the actual coding. Um, there were midpoint check-ins on the project. There was back and forth and questions being asked. So, you know, we would, we would get some signal on, on collaboration.

Steven: There was code review. Uh, there was a discussion around how would you extend this project? What would you do next? What were the things you didn't have time for? What were prioritization decisions you made along the way? So actually working on a project with all these different. Pieces added up to a pretty comprehensive set of things that we were able to test for over time, though, we did add other things like a values, fit interview.

Other folks, other companies might call that a culture ad, uh, interview, where we started to, to actually test for, uh, our, our values in the interview process as well, but probably not in the first, uh, we didn't have that until we were close to probably 50, to a hundred people.

Brett: on that point. How did you structure that part of the interview process when you did, uh, implement it?

Steven: So at gem we have four core values, transparency, velocity, customer focus, and diversity. And so we have a set of questions that we have interview users trained on and calibrated. that map to those four values. So for velocity, for example, we might ask, tell me about a time where you had to cut corners or, or make a trade off to ship something sooner, or to get a project over the finish line more quickly.

And you could imagine a, a full roster of questions, maybe three or four, each that map back to each of those four core values. And then we train up interviewers on those questions and what to look for and get them calibrated. 

Brett: Do do you remember other specific questions in sort of this area of, of culture ad that you found or your team found particularly useful?

 one of the things I come back to with transparency is that transparency is easy when things are going well, but it's, it's important when things are, are not going well. my favorite question there is, um, tell me about a time that you messed up and how did you handle that? 

Steven: And I think asking about a time that somebody made a mistake can, can help you get a, a picture into how they're gonna handle, um, That in practice and, and whether they're gonna be transparent about it, whether they're gonna own up to it. for customer focus. That piece actually was a little bit more specific to the role that we were hiring for because being customer focus as a sales rep or a customer success manager it could be a little bit different from a PM or an engineer or a designer.

But for PMs, We actually developed a two part interview where the first is a mock customer conversation about an actual product problem where somebody pretends to be the customer and the candidate is the PM interviewing the customer.

And then the second phase is with an engineer on the team where the PM has to translate back their learnings from that customer conversation. And the engineer has to pretend like they weren't in the room for that customer conversation. 

Brett: the nature of your product and what you were sharing in terms of reaching out and starting to build a little bit more of an outbound muscle. What are some of the things that you've, uh, learned and figured out as it relates to positioning and messaging to potential candidates, maybe other than the more obvious things personalization and sort of some of the things that people already know are, are there some more nuance points that you've figured out just given where you sit in the ecosystem, both as a tools provider, and then as somebody obviously using all of this yourself to build and scale your own team.

Steven: Yeah. So, I mean, so you mentioned some of the obvious things like personalization personalization is really important, especially as a small startup. I think that just the value of, of follow ups is, is also oftentimes overlooked. A lot of folks that are getting started for recruiting for the first time might just send one message or, or feel bad about sending a second or a third or even a fourth.

But actually our data shows that only about half of the positive responses to initial outreach come from that first message. So by sending messages to three and four, you. Double the positive responses compared to just sending off one message and, and forgetting about it. So follow ups are, are really important.

I think that follow ups give you an opportunity to sprinkle in new things and new information about your startup and your opportunity. So if you have things like blog posts or a fundraising announcement, um, or what it's like to work at gem, for example, or something around values, if you have them at that stage, adding in content over the course of three or four messages so that folks can learn about your company and your culture a little bit, um, is, is definitely a great, great technique.

One, one of my favorite techniques, though, for the initial outreach is, uh, what, what I like to call the breakup email. Where the last email that you send, uh, is something along the lines of, Hey, uh, I know you're probably super busy, uh, figured I'd give this one more shot. We'd all be super excited to talk to you and, and connect, uh, about this opportunity.

If not, no worries. You won't hear, hear from me again and having that, that last email signal that this is gonna actually be the last time that you hear, uh, tends to be this, this interesting psychological thing that gets people to actually respond to it.

Brett: Why do you think that is.

Steven: I don't know. Maybe people just kind of expect that they're going to get another one after that. so, um, I, I don't.

Brett: There's some sort of loss,

Steven: I think there is some sort of loss aversion thing. Uh, and there, there actually is. There's been a lot of research on loss, aversion and how that's actually a more, a more powerful effect, So an area we haven't yet explored is, is how do you approach closing candidates, maybe the fifth candidate, the 15th candidate, the 25th candidate. What have you sort of learned and, and sort of what are some of the things that you've done at gem in terms of getting people over the line?

So the, the, the first thing that I would say about closing is that a lot of people think that closing happens at the very end once you're at the offer stage. But actually if you're doing your job, right, closing starts with that very initial conversation, it extends into your interview process. you know, all the way to the offer and then even well past the offer until someone actually physically starts, um, I've even seen.

So I've seen many candidates back out after accepting offers in, in my career. Um, so closing doesn't even end with the offer, but continues until their start date. 

I think another really important thing when it comes to closing is it's actually less. Selling and pitching and having like the perfect narrative. That's gonna convince everybody to join your company. It's actually a lot more about understanding what's important to them and asking questions and really developing a deep understanding of what's important to each individual candidate.

And so for me, closing is a lot more about doing discovery and actually there's so many parallels between recruiting and sales. And I, I think this is one of the, one of the strongest ones where you wouldn't jump straight into a demo, or you wouldn't jump straight into talking about commercial terms in the same way as an offer letter without first developing a really deep understanding of the prospect and their needs and what they.

So you can figure out how to position the product that you're selling and how to best position your demo. And you similarly, wouldn't talk about pricing and negotiation and stuff like that until first you validated that you're the right long term partner for them. 

Brett: On that point about the, the sort of qualification throughout, what are the types of questions that you ask or, or, or if I were to watch you on the 10th, hire the 11th hire sort of end to end from, Hey, Jane, I just wanted to catch up and tell you what I'm up to through. You're ready to give an offer. What are you doing along the way to gather that information to both do sort of the final cell, but to be planting those breadcrumbs throughout that process?

Steven: Yeah. So early on in the process, I'm always starting with pretty broad lines of questioning just to get folks talking about what's important to them. So if I reached out to somebody cold over email, or, you know, somebody from my network and asked them to catch up for a coffee or something like that, I'm walking into that conversation.

First of all, I'm just spending a little bit of time , uh, catching up and easing into the conversation. But then I'll probably ask a, a pointed question like, Hey, you know, it sounds like you're thinking about what's next. Ha have you thought at all about what's important to you and just get them talking along the way.

I'm starting to ask questions that are a little bit more targeted. Um, I like asking folks, well, what other things are you considering just to get a, a feel or a sense for the full spectrum of the types of opportunities that they're looking at? Some candidates are a little bit uncomfortable. , uh, sharing all of the specific places that they're interviewing at, which is totally fine, but you can ask them more broadly, uh, like, you know, what types of companies are, how big are they, um, are, are they other, are there startups like us or are they larger companies later stage startups and, and really try to get in their head in terms of like the full range of things that they're looking at?

Um, timing. I always like to check in with candidates about when they're looking to make a decision. Where are they at with their other processes? Things like that. It's funny. I mean, even this translates back to sales, uh, simple qualification framework, like, like BANT budget, authority need timing. right.

Timing is one of the, the four key things that, that you dig into on, on sales to qualify people in or out, um, same is true for candidates, right? So if, if somebody's just having exploratory conversations, like maybe you don't rush them so fast into an interview process, but if somebody's at late stages and expecting an offer at the end of the week as a small startup, you might have to drop everything and , and get them in, in process as soon as possible.

But one of the advantages of being a small startup is you can actually move fast like that. And you can take swings at candidates where the process might be a little bit tighter.

Brett: So as we kind of wrap up the conversation, you mentioned sort of the role. Mentors have had in, in the building of gem and scaling you from founder to CEO. And maybe we could kind of build on that. And, and by having you share, when you think about some of the people that have helped you the most, what are the big unlocks that, um, that you've experienced from their mentorship and guidance?

Steven: So how would, how would bucket into a few different categories? Cause I have a few different types of mentors. I have a set of folks that are also B2B SAS CEOs that I can go to. And. Those folks tend to be really, really helpful. cause there there's, there's so many similarities from one company to another, when it comes to just general company, building things and even go to market things.

And how to think about this new leadership hire that we're gonna make, or how do you scale all hands from one phase to a next, when do you introduce all hands? What do we do about this weekly standup that we're doing that doesn't seem to be scaling anymore? 

And then there's also mentors that I have for specific functional EF uh, areas. So one of my, one of the things that I've prioritized. In every funding round for gem all the way from C to series a, to series B. And even to our most recent series C is to get really strong operators onto the cap table, as angel investors, who I can get help from.

And as part of that, I also have some of the world's best marketing leaders, CMOs VPs of marketing revenue leaders, CROs VPs of sales. We've got product leaders on the cap table, and these are folks that we can call up for very specific when, as it relates to functional expertise, or if I'm kicking off a CMO search, I can go talk to five people on my cap table about the different flavors of marketing leaders, and that for a B2B SaaS company around your size, you know, scaling to a hundred million in ARR over the next, however many years, you might want this flavor of marketing.

Um, that those kinds of conversations where you can go straight to the source are so impactful 

Brett: and other than sort of organizing your network like that, have there been certain ways that you approach leveraging them that you think has positioned them to translate their advice to what you're doing or to have sort of an outsized impact on some problem you're trying to solve?

for me, the way that these folks have an impact on me and, and our business, that's entirely up to me. I have to be really proactive here. I have to be thinking about what are my top three priorities as, as a CEO this quarter, or this month. And then who can help me in my network or on the cap table who has experience in these things that I'm about to go do that I've never done before.

Steven: So it's very self-directed and proactive. in the sense that I'm thinking about what are my top three priorities, and then figuring out who do I know who can go help as opposed to having a monthly check in with every single angel investor on my cap table. Awesome. Well, thank you so much for spending all this time with us.

You got it. My pleasure.