Season 2, Ep. 3 – How we think about sales hiring
Sometimes being a part of a sales team can feel akin to being in the desert on a broken bike six miles from the trailhead when it’s 115 degrees out, trying not to panic. And how do you hire for that kind of heat? This week we sit down with our VP of Revenue, Ben Kettle, to talk about what it takes to assemble a team of people that can put out any fire.
Well, hi Ben!
Hi. How are you guys?
Hi! Well Ben, we have officially invited Teja to be my co-host, so he is here to provide some comic relief and a little bit more—
He’s like your Andy Richter. That’s a—
Who’s Andy Richter?
No, we’re too young to get that reference, Ben.
Oh. He was Conan’s co-host. He was really good. Yeah, he had a good career. Everything was great.
Well, I think that’s a compliment for you, Teja. That’s fine, I think it’s a compliment for you.
Nice little backhand compliment. I appreciate that.
So I know we have a plan to talk to Ben about how we hire sales people and his views on doing it well, but Ben used to be a Mountaineer—and you know this about him, I think, right? And he used to live in Wyoming and Montana. (Ben: Yeah, yeah.)
And climb mountains, (Ben: Yeah) and be like a skier-snowboarder-avid adventure person. And so I think, actually, that’s a really interesting place to start, because like, from a personality standpoint, he spikes high, and like—independence, adventure-seeking, ownership, right? ‘Cause you’re out there, basically all you got is yourself. And you know, if I were to think about his philosophy in building his team, that’s what he looks for.
He’s like independence
Ownership. Yeah, totally.
Yeah. Can you start by telling us about that? Like about being a fucking Mountaineer?
Like how it all—how it intersects?
Yeah, do you mind, Faith? ‘Cause it—
No, this is great. Well and I mostly—maybe we can start the story with why you’ve withheld this information from me for over a year.
He a professional
It’s not relevant, and my friends who do know about it, they make fun of me when I bring it up. (Faith: Ok) Like occasionally I’ll be like, “Oh, yeah, like that time I was in Wyoming…” and they’ll like roll their eyes and be like, “Oh, here’s another story about how a moose attacked you.” You know? And so I might become very self-conscious about it. Going back to Teja— it’s pretty rare that anyone brings this up as like [something] that foreshadows what I do now, and [that] the values I learned then impact the way I think about teams now. So, it’s pretty rare that people draw that parallel, but you’re absolutely right. Teja and I have talked about this—not on the podcast obviously—but like, I like living environments where there’s a lot of things that can kill you. I think it forces you to like, think differently about how you behave, how you interact, who you trust, trusting yourself, right? Like I’ve had several instances back in those days where I would be with a friend, and we would be in the back country, and the weather would turn, and like a binding would break, you know, on a ski. And you kind of look at each other, and it’s like, ok, well, we’re gonna die. Like, if we don’t solve this problem, we’re gonna be dead, ‘cause like, it’s getting dark, whatever. And Teja, it has impacted how I think about the team. Like, I wanna hire people who I can trust to be autonomous and to like, have it be a stressful situation and make good decisions, and not let the decision, or like, not let the weight of the consequence effect the decision making. So yeah. It’s like you think about that— like my old life, it was— getting down was generally the goal. And like everyone knew that that was the goal.
And if, you know, people on the Gun sales team know that their goal is to, you know, bring in lots and lots of clients throughout bound, or like really, really understand if they’re in a client success role, like what makes our clients tick and what makes them successful, and that’s very clear, then they— we hire the right people; they will make the right decisions to make sure that happens. And my job then becomes kinda coaching them through it, if there’s something they haven’t encountered before, or to be a sounding board, or to like, just share some of my experiences, but not be prescriptive in telling them what to do. They know the goal. I have to trust them to deliver it, which is really no different from during that time period I was mountain biking in Moab in August. It was 115 degrees, my rear derailleur broke, and I was like six miles away from anything. And I was like, I’m gonna die. And I like had to fix—I like jerry-rig my bike with a single speed to get out, right? And like, I don’t need people that has that happen [and] they panic. Like, that’s not the people I want on the team. Sorry. That’s that’s a little too, like, I don’t mean to like equivocate the team. (Teja: No, completely.) That’s that helps inform it.
No, that’s good. And I think it—like your management strategy is a lot like that. Like you and Teja have this in common where someone will mess up and your response is like, “Well, no one died.” (Teja: He fucked up.) We’re not, we’re not doing brain surgery or— (Teja: You fucked up, how dare you?!) Right. Well, I mean, it’s that, right? It’s like, you know, being accountable, but also, because—I think because we hire people who take their work so seriously, like it’s helpful for you to have that perspective, Ben, like I’m not six miles away from water in a hundred degree— you know?
Yeah. I’m not gonna lose a hand.
Totally. And that’s honestly—I mean, that’s what really struck me about Ben, when we first met, was like how much ownership he took for when there were, let’s say, you know, it’s like a simple, “Oh, hey, there’s a typo in this thing.” Or, “Hey, we’re not starting this initiative yet.” And he’s like, “Listen, I got it. I’m gonna do it. I’m stoked about it. We’re gonna get it done.” And it’s like—that tendency probably comes from being in those situations and maybe being attracted to those situations where he knows that he’s—it’s incumbent upon himself to solve the situation, you know? And I think he’s dope. And say with you, Faith, I mean, you’re so involved in the company’s hiring process. Like you guys have done an awesome job in bringing in people who have those values.
Well, Ben, today’s a very relevant day to talk to you about sales hiring, because we, as of 8:00 AM, just announced our Series A raise, which, you know, part of that process is gonna be building out some really high-impact roles on the team at large—specifically our sales team—which has traditionally been very, very light. So it’s, you know—you’re like in the head space already of like, “Okay, how do I think about scaling this sales team?” How do I identify like the metrics that are gonna tell me not only if someone’s successful in the role, but also how I know that they were successful in previous roles, and how I can use that to measure their potential here? So I guess to start, let’s just get square on the problem. Like people struggle with sales hiring, and if you had to summarize, why do you think that is? Like what makes sales hiring so hard?
That is—man. I wish I had a better answer, or the perfect answer, Faith. I think, what makes (Faith: That’s ok.) I think what makes it hard is sort of, I don’t wanna say antiquated, but like, like the prevailing attitude about what sales is makes it difficult to hire for sales. So, what are those prevailing attitudes? I’ve been in many, many situations as a candidate where I happen to be, you know, articulate enough, intelligent enough, very outgoing, very extroverted. And that is perceived as, you know, being high-functioning, being a highly successful sales person. I would argue that those things don’t mean anything. It may make me fun to be around at a bar sometimes, but it doesn’t necessarily make me a better salesperson. And I think people struggle, because they have a hard time. There’s this idea of like a Willy Loman type character or, you know, the really friendly guy at the car dealership, or whoever it is.
And it’s really—those people are like, good. They’re not great. And what makes great sales people? And this is, I think, the thing—the hump that we all gotta get over is that they are extremely persistent and diligent in the day-to-day. So one of the things that we’re implementing—and Teja and I talked about this yesterday—is like a weekly report of like, here’s our activity. Like, are we doing the right things every single day? So it’s this extreme persistence, extreme diligence, but it’s also having a process, right, that makes sense. And Faith, you’re very familiar with this, like our deal stages—but it’s also the discipline to follow it through. And a lot of sales people may be really charismatic. They may be really outgoing. They may be very extroverted, but they don’t have the diligence to follow through.
And they don’t like—they can’t like run a play in their head while they’re working. So they can’t think about—like, they can’t like remove themselves or put space between them and the client and think through, “Okay, here is this objection, how do I overcome it?” Or “I don’t really know what the buying process is for this client. I’m really gonna dig into that. And I’m gonna ask questions that may feel uncomfortable.” Like, are you the one signing the contract? Like, where are you in the—we’ve talked about this as a company—Like, “Hey, Mr. Prospect, where are you in your hiring cycle for this position? Did you post it a month ago? Did you post it six months ago? Let’s talk about your process and what’s going on.” So I think, I think the struggle is [that] people try to line up what society tells them is good at sales with what they maybe intuitively know makes someone good at sales, if that makes sense.
Yeah. That leads us really well into a discussion on evaluation, right? Because if the antithesis of sales hiring evaluation is looking for people who are outgoing and good conversationalists, et cetera, I guess the correct answer would be like, you know, we use qualitative and quantitative metrics and things that we’ve decided ahead of time before we actually start that evaluation process to then vet candidates. So I’m curious—and Teja, feel free to jump in whenever—but I’m curious about what kind of metrics you look for when you’re vetting candidates that aren’t just like, can they hold a conversation? Do I think they could sell me their left shoe? You know?
So, the thing I rely on the most is generally an industrial organizational psychology referred to as a work sample test. And coincidentally enough, Deividi, who vets all our developers on the platform, takes the same approach. So, if you wanna be a developer on Gun.io, and you have an interview with him, the interview isn’t about your philosophy around code. I mean, I’m sure he covers some of that, but like the real crux of it is he has you walk—he has the candidate walk them through a project and their code and explain why they made the decisions they did, right? And why they put it together this way, and why they decided to work on that thing. And I do the real—I do the same thing for sales. And generally what that means is if you are a candidate for a job, you are selling yourself, right?
So I’m looking for, are they checking a couple different boxes? Are they asking—are they genuinely curious about Gun.io? What we do, are they curious about the team and the sales team’s goals and what they’re gonna—the standards that we have? Are they curious about me, personally, or anyone they’re interviewing with at the company and like the problems that we have and how they can solve them, right? So like I’m looking for them to—‘cause if they know those things, they can then position themselves to have an honest conversation about where they fit in or where they may struggle, even. And so I’m looking—I kind of, you know—the great thing about sales is that when you’re interviewing for a job, you’re selling yourself, and I get to actually see their work sample test, right in front of me, like I’m on the receiving end of it.
You know, like a really bad sign is someone coming in and I’m like, “Oh, you have any questions for me?” and they’re like, “Not really, but here’s a rundown of my resume.” Well, that person’s gonna get on the phone with their prospect and just talk about how great Gun is without knowing anything about the prospect, and they’re not gonna close anything, right? So, that’s how I’m approaching it with really all our roles, but particularly for like AEs, client success folks, and even SDRs. I have an SDR interview I think in 20 minutes. So I’ll see what they do.
Well, kind of on that note, I think a lot of folks that are listening to this are probably in similar shoes as us, right? They’re smaller teams, they’re trying to be really judicious with how they spend to make sure that there’s kind of an ROI with every dollar, and obviously that’s what we’re going through right now. So I’m curious if you could walk us through, like, how do we decide from a sales perspective—and keeping in mind we are a services based business—how do we decide who to hire? What kinds of roles are gonna have that impact for us?
Thanks to your work, Faith, we’ve been successful in that, like with inbound, we don’t—the company to date has done really well with inbound, right? And so we haven’t really hired for skills like prospecting. We’ve never really hired—I think in the past, maybe we’ve hired some SDRs, but they didn’t work out. We haven’t really hired anyone in client success, because for the most part, the community’s sort of taking care of that. We have a very strong product, so we haven’t really needed client success. And I think to answer your question, what we’re hiring kind of for now, for that next step, is like, well, we do need to have people that have skills more along prospecting and outbound reach out, and those types of things. We do need to hire people that are familiar and can set up a client success function to deepen our relationships with our existing clients, right? And to grow with them, and to ensure that as they grow, we grow along with them, right? So what we’re looking to hire is really in those areas, not necessarily because what we have now isn’t getting it done. It is, but we need to diversify a little bit, and we have to get a little bit more niche in who we’re going after. And going back to being a small company, you know, we’re at the stage where we’re fortunate enough to do that. Like the balance sheet is strong, the business model’s there, right? It’s time for us to sort of diversify our custom acquisition strategies and hire specialists who can do those things.
And I’m curious to get Teja to way in on this too, because obviously Teja’s been operating this business for a decade and has done so, you know, in a really kind of lightweight way across all teams, but, you know, sales specifically included. I mean, I have this experience too, you know, trying to grow the marketing team. Teja’s super open to getting pitched on team growth. But it is like, rightly so, you know, very, kind of tough to convince that we need to scale teams. So it’s not an easy feat to say, you know, I think we need to hire an SDR, or a team of BDRs, or account management, and just kind of snap your fingers and have that be so. There’s kind of a lot of back work involved, and it’s a question of well, how do you prove out? Like, Teja’s question is always gonna be well, what is this person gonna drive for us? Right? And it’s kind of hard to have an answer ready for that, when we haven’t had anyone do that full-time. So how do we kind of manage that on the sales team?
Is that for me?
Yeah. Do you wanna take a shot at that one? And I can—‘cause we went through this process together, so yeah.
You know, so I think the experience probably differs, depending on what team you’re leading, with my encouragement around hiring or lack of encouragement around hiring. I think Ben has received a lot of encouragement from me about hiring. (Ben: Yeah. Yeah.) And you know, I think the best we can do without ever having done any of these activities at scale is to at least have a working model that has some assumptive inputs on what we expect in terms of performance and cost. And then we can, you know, make sure that lines up with the way we wanna spend the money. And generally, given where we are today, it probably makes sense to ramp. I don’t know. I like to think I’m not that tough on it when it comes to approving hires, you know?
Well it’s just different. It’s different than what you would have working at like, an Amazon, where it’s like, well, we have this, we have a headcount addition of 10 slated for this year. So the conversation is much different than us, where we grow in a really agile way where quarter over quarter, our needs are gonna be different. We don’t have a set head count because maybe we need to hire a hundred people. Maybe we have to hire zero people. And that’s kind of all on the table, just depending on how we structure the case, you know?
Totally. So maybe I can share a little bit about capital deployment philosophy when it comes to hiring well. So it’s like, we’re a really small team, and the level—we have a nice balance sheet—but the level of money that we have to go against any specific growth plan is gonna be less, probably, than a large old- school staffing firm or recruiting company, right? And so we have to have a model that, in relative terms, is gonna be way better ROI, right? That means we have to actually hire better. Like at the individual level, they have to be directed better. They have to be managed better. And that’s the only way we can take market share and grow faster and start to create gaps between us and other companies. And so I think the philosophy that you and Ben have for your teams around being really judicious with the use of funds while scaling is—it makes sense for our stage of business. That’s trying to get to, you know, the next step in size and scale. And so, you know, it’s not sufficient for us to copy-and-paste an inbound or an outbound strategy from another company. We have to do it better than them, right? We have to, to be able to continue to grow and continue to be the capital efficient business that we’ve been.
Right. Ben, if someone’s listening to this, especially kind of your introduction into sales hiring, and they’re like, “Shit, it turns out I’m really bad at sales hiring” which I think, you know, probably a lot of folks feel, whether it’s in feedback—like the people I hire turn over really fast, or I spent three months on a hiring cycle, and I know I could be more efficient than that. Or I keep hiring the wrong kinds of people, and they’re doing a great job, but it’s not delivering benefit. Like what advice can—go ahead, Teja.
So, we tried to scale our sales team before, and I can give you a postmortem on why it wasn’t successful. It wasn’t successful because we did not have somebody like Ben being able to quickly assess success in the role and have the tenacity to quickly off board people who were not having success in the role. And instead, we almost took a co-dependent posture when we were like, “Hey, it’s us. They’re not managed well, this and that.” Right? And maybe that’s true, but we had pretty clear targets. We just weren’t following through on building a process to continue to bring in good SDRs, good account managers, good AEs, and make sure that people were performing once they were onboarded. And I think that’s the magic of having somebody like Ben. You know, we think back to his level of ownership and what he looks for in his team is that as an exec, Ben is not just thinking about getting people in. He’s thinking about managing them and off boarding them if they are not performing. And that repeated process of growth, you know, change, growth again, that’s what builds a good sales team over time. So I’m not actually convinced that off boarding somebody in three months is so bad. (Faith: Right.) It’s like, you have to have that, because we will hire poorly. Every company does. You just have to have the tenacity to make the decision when that happens.
You have to know what good looks like to you, right? And so Teja mentioned the model earlier. I’ll use a very specific example. We hired a new AE, two, three months ago. She was—I would argue she was kind a nontraditional hire, in terms of background. (Teja: Yeah.) But when we put together this model for the sales team, I used my best guess, based on my experience, of what her ramp should be. And the great news is that she’s hitting it, right? But like, I wasn’t shy about what her ramp goals were. I think a lot of times sales leaders—to Teja’s point—they kind of adopt that codependent relationship. And it’s like, “Hey, come in.” This happened to me early in my sales career. It’s like, “Hey, come in, just really do the best you can. We’ll talk in three months.” You know? And it finally took. And thankfully, I was self-motivated enough and figured it out. But I had a boss who came in several years later, who set me down in a room. He’s still by today. He’s still a mentor today. And he was like, let’s talk about how much money you wanna make. And let’s talk about how much you want your—how you want your career to progress. And let’s just do the math. And no one had ever done—oh, it’s embarrassing to admit—but no one had ever done that with me, right? And so now when, especially bringing on someone who’s on the revenue production side of things, it’s like, “Hey, here’s what we expect.” There’s no ambiguity, right? (Faith: Right.) Now, my job is to help you get there. And I’ll be honest, anyone who I’ve ever let go, I’ve let go because they lacked activity. Not because they lacked results. Someone who has a lot of activity and is willing to learn and willing to be coached, and if I’ve screened correctly, they’ll get there. They may be a little slower to ramp, but they’ll get there. And usually they end up having this weird exponential curve. Like there’s nothing, nothing, nothing—and then they just fly up. But yeah, you just have to be very clear, and that—the codependent thing’s a great word, because it’s like: Hey, this is just what we expect. (Teja: Right.) This is nonnegotiable. Now our job is help you get there, but you gotta, like—you can’t lead a horse to water.
Yeah, and if it’s clear, then everybody knows, you know? After three months, it’s not a surprise that you know, that the performance isn’t there.
If you could kind of determine how every company in the world did sales hiring, what would that look like? Super high-level. What are the bullet points that should exist in that sales hiring process? And this can kind of double as advice for those hires who aren’t confident when it comes to sales hiring.
So, I mean, I can tell you the things I look for—
In a hiring process?
Yeah. So these are people who are talking to clients, right? Trying to close—and this—I ripped this off. I can’t take credit for it. But HubSpot, actually, in the early days, did this big test on the traits they were interviewing for and assessing for, and number one, to the CRO’s surprise, was curiosity. So I want highly—I want people that like—I want dilettantes. I want people that—they not know much about, you know, drones, but if you own a drone company, and you’re talking to them, they’re gonna just learn everything they can about your business, right? So that’s number one. And I think that a lot of sales people just aren’t curious. They’re just gonna go through the motions. I think the other thing—and this is a big one for me, and it may be less for other people that have really robust training programs and really big teams—but I want people who are self-accountable.
And so the way I screened for that is I asked them about something they wanted to improve personally or professionally and had them walk me through how they did it. And the best answers always have several things in common. One is they used data to know they were getting better. Two is they relied on outside expertise, whether that’s, you know, going to YouTube, reading a book, whatever. Three is they developed some sort of accountability and then their community around it. So they got like a spouse, they got like a coworker, even their boss, they created a community. And four is they understood that the process always wouldn’t deliver the outcomes they wanted, and they were able to adjust, right? (Faith: Right.) So those—self-accountability is huge for me, because I want someone that I don’t wanna be watching their numbers all the time. I want them watching their numbers all the time, if that makes sense. (Faith: Right.) And lastly, they gotta be somewhat competitive. Like they have to want to win in some capacity. And that can manifest itself in different ways. Like, you know, Teja does Jiu-Jitsu, I race bikes. Faith, you teach a cycling class. Right? Like, we all have like these things that we’re trying to get better at, and trying to improve on. And I’ve yet to meet a salesperson that isn’t at least somewhat competitive.
I feel like this is probably true for you too, Ben, ‘cause I’ve spent kind of a lot of time—there’s a lot of crossover, obviously, with sales and marketing and kind of when we hand things off—so I spent a lot of time over the last four years thinking about the customer experience. When they sign up for Gun.io, what is it that they’re coming here looking for, and what do we deliver? And as a result, I’ve gotten super critical of other people’s sales processes. Do you feel that way as well? Like thinking about this all the time, and kind of thinking about how to measure performance sales people, do you find yourself being more critical?
Yeah. And I’ll tell them a lot of times. I mean, Teja saw this yesterday..
Oh yeah. Yeah. There’s a company that I introduced to Ben, and we won’t mention the company.
We won’t mention the company. And look, I’m gonna hear the guy out, but you know, he’s like, “Hey, Teja sent me to talk to you, blah, blah, blah.” And I was like, “Look, man, last time I entertained you guys as a vendor, it was a horrible experience. And not only did the product not deliver, but your sales process I found to be just almost offensive.” So like, not only, Faith, will I notice it, but if they come back at me, or if they approach me and they ask me what I think, I’m gonna tell them. (Faith: Yeah.) And I hope they change.
I mean, I feel like that’s the only way you get better.
Right. And like, here’s the thing. I actually respect the person who emailed Teja and then me, because I sent that, and then they responded with, “Hey, I hear you. Like, some things have changed, ask me some clarifying—” Like, he’s doing the right thing. He’s not shying away from that. He’s addressing it. So I think I’m talking to him Friday now.
Well that’s good. Right? ‘Cause you called it out as like a critical skill of sales people is like, they can’t shy away from difficult conversations. And I think that’s kind of a great way to test it. Well, Ben, I feel like there’s some golden nuggets in here for both sales people looking for their next role, but also people who are charged with hiring sales people, and kind of ways that they can create structure around what otherwise kind of feels like a pile of very chaotic resumes that they need to vet, so—
We have a big pile right now, Faith. Thank you for your helping with that, by the way.
Yeah. What are the takeaways? The takeaways seem to be work sample—look for a work sample. (Faith: Yeah.) And index is highly on three qualities: curiosity, competitiveness, and diligence.
And to identify those traits up front, because a lot of folks will kind of fall back on this shtick of like, “Oh, a sales person should be salesy.” When really, the traits that you’re looking for are not being salesy.
It’s not extroversion.
Some of the best people I’ve hired have been introverts (Teja: Yeah, totally.) and I’ve gotten out of that interview, and I was like, I would never be friends with this person. And then like, if I met him on the street, it’d be like, “Nice to see ya. See you later.” But they like, you listen to their sales call, and they crush it.
It’s interesting. I mean, you know, one thing is, Tyler and I have both been—and Faith too—like we’ve all been at the tip of the spear from a sales standpoint. And I would say Tyler’s probably a little bit more introverted than us, and I’m maybe a little bit more introverted than you two, right? And I think, you know, I do think that it probably takes more energy to be on a sales call if you’re not highly extroverted, like it’s more draining, but to your point, I think if you have the discipline to overcome that, it’s not a big deal. But they have to index highly on accountability then, right? And be like, “Hey, I’m gonna get this done.” ‘Cause it is harder. It’s harder to get on the phone for six hours.
It’s more draining. Yeah. (Faith: A hundred percent.) Energy is just less. Yeah.
And I’ll say one more point, which is maybe to go meta. If you wanna hire a sales leader who hires sales people, you know, one thing that seems to have worked for us and I think is working for Ben is that at our company, we really like people who spike in some sort of independence, self-ownership, accountability. And I think Ben’s story about being a Mountaineer in Wyoming and Montana—and you know, I’m not even—it’s like whatever personality trait you had, Ben, that made you go out there to be reliant on yourself, and then you cultivated and developed by being there—that’s like, that’s what has led you to have so much success in your career and, you know, building the team here. And same with you, Faith. I mean, right? You you’ve done so much through TFA and through having your own business and, you know, I don’t know, like your house projects. So there are things that show up in a non-professional context (Faith: Yeah.) that I think are attractive.
Well, it’s whole person hiring, right? (Teja: Yes.) You have to understand, you know, who they are as a whole person. And the only way you can get to that is, you know, talk to me about life outside work.
Yeah. I mean the second AE we hired is like—she’s a strong woman. Athlete.
Yeah, she’s a powerlifter, which we didn’t know when we hired her.
Yeah. We didn’t know, which is—that’s on me. I should have known. I knew in the first week, but hey. In my book, the hiring process doesn’t end when you get hired. It lasts.
Exactly. Exactly. Well, Ben, we’re obviously very lucky to have you here building up the sales team. For listeners, you can find Ben everywhere on the interwebs. Twitter. I know that you are there. If you’re interested in working with Gun.io, joining Ben’s team, you can find us @Gun.io. And then our jobs are always posted on our LinkedIn page. But if you think you are a fit on the team, you don’t see a job that fits your skills, shoot us an email. We’re always happy to chat.
Yeah. I have a bias towards action, reaching out, ‘cause I’ll always respect that.
Alright, you guys. Well, Ben, you gotta jump for an interview, actually. So hopefully this is a good pregame for it. (Ben: Yeah.) Go hire some awesome sales people. (Ben: Thanks Faith, Thanks Teja.) Alright. Bye, guys.
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