Skip to content
November 8, 2022 · 21 min read

Season 2, Ep. 15 – What we’ve learned from 5xing our sales team with VP of Revenue, Ben Kettle + Head of Strategic Accounts, Jessi Soler

A lot of things have changed at since we first started, but no department more than sales. In this episode our Head of Strategic Accounts, Jessi Soler, and VP of Revenue, Ben Kettle, talk about what it has looked like to grow the sales department by 5 times its size.


Read transcript

Faith (00:05):

Well, Ben and Jessi, welcome back to the Frontier podcast. You’ve both been here before. Thank you for continuing to humor me.

Jessi (00:14):


Faith (00:14):

Ok. Well, first and foremost, apologies in advance, if there’s any background noise. As you know, my life is chaos, so if there’s—actually just heard a hawk screeching, and we just put the chicks out, like they’re officially kicked outta the baby coop and they’re like out in the world—so could be a really fun recording. I don’t know, guys. 

Ok, Jessi and Ben! Let’s start with Jessi. Jessi, hello. Can you introduce yourself? What do you do here? What’s your job?

Jessi (00:52):

Of course. I’m Jessi.  I’m the Head of Strategic Accounts here. Pretty much working on client—it’s anything client facing. Actually, that was my answer. I guess it’s changed a bit. So right now, my goal is to identify, you know, good accounts for the developers on our platform. Go after them , get ’em to work with us, and then maintain those relationships.

Faith (01:16):

Sweet. Ben?

Ben (01:19):

I’m Ben. I run the revenue teams here at Gun. So short term, what that means is I am setting up different capabilities to get new clients as well as our account management program, client services program to maintain our relationship with existing clients. And then in between that, helping Jessi any way I can—which is usually pretty nominal—with like her day to day and like getting her freed up to do the work that she needs to do, like working with clients and making sure that we have everything we need for them.

Faith (01:56):

Alright. Well, we’re here to talk about sales. And I think specifically, the thing that’s gonna be interesting is the evolution of how we’ve thought about sales over the last four to 10 years. And I feel like the talking point is like, “We’ve 5xed the size of our sales team!”, but that’s because our sales team used to be one person. So now we have five people, but there’s like lessons learned, I’m sure, within that umbrella. So Ben, my first question’s for you—probably be helpful to just like lay the foundation around like—what does our sales team do? How does it function? Like, set that up for us, and then we can get into it.

Ben (02:39):

Well, the answer to that question is like the subject —what our sales team does is changing. So Gun started out and was for a majority of existing a bootstrap—from its existence, a bootstrapped company. And what that means is that all growth was funded by profit. So there’s not a lot of outside investment, and because of that, growth is like kind of very deliberate and steady. And as a result of that, I think—and I’m curious to see what Jessi has to say—so Jessi was sort of really the sole salesperson for a long time, and she got more and more work, right? ‘Cause Faith, you and the marketing team started sending more leads, more inbound leads, and Jessi worked them and closed those deals. Where we are now, though, is we’ve kind of come to this realization that just relying on inbound leads alone is just not gonna be a great way to grow the business and scale the business. So now what the sales team does is a bit different. So we’ve hired some of these new people to go out and generate pipeline alongside marketing’s efforts. And that’s really what we’re in the process of setting up today and establishing today.

Faith (03:57):

And as like a function in the business too, I think that’s like a critical difference as well—between our sales departments and probably what other companies think of as sales, but also between what’s true for us today and what was true four years ago—like our sales department was essentially doing two, maybe even three departments’ worth of work, right? So like everything from matching to presenting to consulting with clients and figuring out what they needed was Jessi’s thing. And now we have like a full DevRel team full of senior developers who are doing the majority of what I just listed. We have an account management team that’s maintaining those relationships and making sure that clients and developers are kind of like getting the most out of working with each other long term. But specifically today, our sales team—I’m gonna say this, and you guys tell me how I’m wrong. Our sales team is primarily responsible for making sure that the clients that we’re taking on are good fits. So we do a lot of vetting on the front end and then also making sure that the hiring process progresses at a pace that respects both parties’ time, right? So we’re not allowing companies to kind of sit on job posts for months and months and months and not get back to developers. Would you say that’s true, or am I missing like a whole kind of like block of work in there?

Jessi (05:37):

No, I think all of that’s right. And then the one thing that I’d add is it’s a lot—it’s kind of on us to make sure that we’re understanding their needs. You know, obviously like tech skills and everything, you know, what type of developer they need, but then also like, you know, how they want this person to work with them, how they want them to communicate, you know, prior experiences, personality, anything in there. So that’s a big part of like, you know, once we vetted the company and the position, it’s really about then identifying and understanding exactly the type of person that they’re looking for and relaying that to our DevRel team in hopes that we have that person.

Ben (06:18):

I agree with that, and I’d also add that there’s—and we’re still very early days in this as well, but you know—you mentioned the account management piece, sort of like making sure we’re a valuable partner, not just for this engagement. For all the engagements to come, right? So understanding and anticipating their needs in terms of talent, in terms of technology, all those different aspects that like ultimately help our clients grow and scale their businesses. So like that’s the next piece. And prior, before we had any dedicated people on that function, it was, candidly, whatever Jessi could fit into her day.

Faith (06:54):

Mm-Hmm. Which—weirdly, she has the same day as all the rest of us. 

Ben (07:00):


Faith (07:01):

She’s not having any extra hours. Ok, Jessi, obviously we’ve been alluding to this so far for the whole episode, but what are some key ways that your experience as a salesperson here at Gun has changed over the last almost four years that you’ve been here?

Jessi (07:19):

I think the quality of clients that we get in and how we work each one has changed a ton. You know, when we were first doing this, or even up to like a year, year and a half ago, like we didn’t even necessarily have a call with a client before we started matching ’em with candidates. They would send us a job post, send us their specs, and then we worked on, you know, presenting some people to ’em. So I think it’s become a lot more hands-on in terms of like the sales process and understanding their needs and how we can best work with them, which I think has led to better placements, better long-term relationships. I mean, that’s a big thing, I think. And then also, you know, we didn’t do as much like company-client vetting, you know, a couple years ago. So I think that’s shifted a lot. And then really like focusing in on who we want on our platform, who we want our developers to work with. So that’s definitely changed a decent amount, especially in the past year, honestly. 

Faith (08:23):

I would agree with that. I would say it became very clear to us maybe like two years ago that our client, our primary client is really developers. (Jessi: Yeah.) Right? Like, we know that that software talent is very hard to come by these days. And just like what you said, Jessi, like we used to take every lead and immediately start working it. We would get jobs shared with the community, we would pull applicants, and that back in those days, we didn’t have a web app and we used to hand make every single profile so that they were all like, consistent and branded. So you would like design these profiles and send these PDFs to clients who maybe we would never hear from again. Right? So I think that that was a huge change. And it’s scary too to like get the net a little bit smaller, because before, we were like, well, you know, if we just—if we treat every client like this, chances are somebody’s gonna bite. But I think when we made that switch and we realized like, no, this is actually a lot better—not just for developers, but also for like the clients that were ultimately able to serve. I think that was very clearly the right move.

Jessi (09:41):

Yeah, a hundred percent.

Faith (09:43):

I mean, this could be a good question for either of you, so we’ll see who jumps in at first, but I’m curious about what is something that as a sales team or like a sales organization, we have gotten so good at that we could write a book about if we like pooled everybody on the team’s knowledge?

Ben (10:04):

Jessi, please take that one.

Jessi (10:07):

I think—and I mean it’s kind of along the lines of like what you were just saying and what we’ve been saying is—I think we’ve gotten very good at acting as an advocate for our talent. Like not letting them, you know, undercut in terms of budgets, anything there, I think that we’ve gotten significantly better at, and I think everyone does a good job of that. I think the coordinators do a good job of it. I think, you know, the AEs are doing a great job of that, too. It’s showing, you know, it’s providing, showing the clients like the value that we provide and giving that to our developers as well is something we’re very good at. I don’t know, Ben, what else are we really good at?

Ben (10:50):

Thanks, Jessi. So we have four new people on the team who are ramping up—like very new, like less than six weeks. So I don’t know if they’re great at this yet, but one thing that we’ve definitely hired for, and one thing I think that the team, you know—Jessi certainly did a lot improvement in this way, and I’ve tried to screen for in these hires is—I don’t—I want us be really, really good at being more consultative other than—rather than salesy. So I don’t want us to get meetings with prospects based on tricks and cuteness. I want to get meetings with prospects based on authority. I don’t want us to take a deferential approach when we talk to a client, whether they’re newer, existing, or prospect. I want us to like, take the lead and be able to really like—again, like to Jessi’s earlier point, like advocate for our talent and be able to do so intelligently.

I think Jessi’s gotten phenomenal at that, just over the years. I think that our team now is oriented that way. We’ve, you know, hired two account managers who are very like, proactive and like, they’re more interested in having a real conversation and like running through, you know, the general sort of like checklist. And I want our SDRs who just started with us to also be that way. You know, one thing that we catch them on is like, ‘Hey, you’re providing real value and like, don’t cheapen that. Don’t be too deferential.’ And, you know, we did a role play the other day, and one member of the team to one of the SDRs who had gone in the role play, like, you’re using way too many modifiers, and you’re hedging too much. Like you should have the confidence to like say these things without adjectives and adverbs. And again, I think that the ramped members of the team are good at that. But it’s part of those things–one of those things that I really wanna develop early and like have it be our secret sauce.

Faith (12:56):

Mhm. One of the challenges of just kind of like what we do is that our sales team isn’t selling software, right? Like, we’re selling a new, better way to hire technical talent, and to really understand what that means and why it’s so valuable, you have to be like pretty steeped in that process, right? Like, you have to have seen lots of engagements. And Jessi, I think like if I were to answer this question for you or if someone asked me like, what would you want Jessi to teach you? It would be like, how do I know two things? One is if I’m building my BokTok™ app—my TikTok for just chicken videos—and I need to hire a developer, how do I know if I should hire somebody who’s just like a grinder who I know can turn out the code and might have like a lower hourly rate, or if I should hire somebody who’s like super senior, way more expensive, I could probably only afford them quarter time, but I know that the foundations of my app are gonna be awesome?

And there’s a ton of arguments for either of those options, but I would go to Jessi to tell me, to get her opinion and probably trust that, because she’s seen hundreds of these engagements, and she can really advise me on what works and what doesn’t. And the other thing is like, let’s say I hired a developer. I’m not a developer, right? Like I’ve never managed developers before. And I was like, you know what? I don’t know if my dev is performing. I would also go to Jessi and be like, ‘Hey, are my expectations way too high for this? Am I not managing it appropriately? Or is this developer just like not doing what they should be doing?’ And I feel like those are things that you did not—like, you didn’t come to Gun as like an expert in those two things, Jessi. But I feel like now, you could write a book about them.

Jessi (14:58):

Thanks, Faith. Yeah. I do think that we do a good job of that. So yeah, but it’s just because you’ve seen all these scenarios over and over, you know? I feel like that’s the only way that you’ll ever really understand that. 

Faith (15:12):

Yeah, that gets into actually the next question. I’m wondering if either of you will call that out, but what do you guys think is the next big challenge that’s on the horizon for the sales team?

Jessi (15:26):


Ben (15:29):

I can’t agree more. Jessi does listen to me. I think it’s figuring out a way to start the conversations in a meaningful way. But like—and which is another, fancier way of saying outbound. We’ve tried it before to varying degrees of success and it like—we just have to get really, really good at being interesting and getting attention and differentiating very, very quickly. And I think that’s a challenge for any business, particularly one like ours, right? Where we’re like—so often we’re just seen as like a recruitment shop.

Faith (16:07):


Ben (16:07):

Right. Yeah. But if you talk to any of our clients, the reason they love us is because we are not a recruitment shop.

Faith (16:13):

Right. Again, like the thing we’re selling isn’t like a nice, clean product or like piece of software. Like the thing we’re selling is a radically different way to think about technical hiring, and that’s really hard to convey in a subject line. Like Ben, obviously, like you come to us having done outbound a lot previously, but we, as a business, have been inbound—like a hundred percent inbound—for as long as either Jessi and I have been here.

Ben (16:43):

Yeah. It’s a really fun one, right? Faith, like—one that you and I are collaborating a lot on and you’re with the team on. It’s really, really hard. It’s really, really hard, and it’s really, really hard to do it and combine it with some degree of client education. So like it’s again, we get lumped into like we’re—oh, you guys are recruiters all the time. And again, like we solve a similar problem that they do, but we do it in a very different way. And like taking the time to, you know, educate and differentiate on that is not an easy task.

Faith (17:26):

Do you have like a secret weapon, Ben, for somebody else who’s spinning up an outbound program? Like what is your—what’s like the one ingredient that you think they must have? 

Ben (17:36):

I’m not proud of this one, Faith

Faith (17:38):

Tell me.

Ben (17:39):

But I’ve—it’s the one—and we’ve played around with it on our team. I think anytime you’re setting up outbound, you benefit a lot from defining what you are not early. Which is another way of saying tribalism, right? Like so—we are not those people, we are these people. An obvious example of this would be—let’s say you’re like productivity software and you know, you have all these features that are unique to you and your branding’s great. And you have like really talented product people and engineering people, and your marketing team’s tight, but like, you’re still kind of put in that productivity bucket. Like the way I would sell that is, Hey, you know how Jira sucks? You just like call up an engineer and be like, ‘Hey, you know how Jira sucks?’ And like, inevitably—like Jira, don’t me wrong, Atlassian’s a great company, Jira’s great software, but like people are all like, ‘Yeah, they kind of suck. Like I do know that.’ It’s like, ok, well we’re not that, and here’s why. But like, I think whenever I’ve had a lot of success with outbound, it’s been because I was able to really quickly frame what I was not. My first job was selling mobile software—or my first like big sales job. Now, I talk to these clients, and I’d be like, ‘Man, you know, these like, dev shops don’t really get mobile?’ And they’d be like, ‘Oh my god, yes. They they never have enough iOS developers, they never have enough Android developers.’ Like yeah, I know. Well like we only do mobile. And they’d be like, really? Like, Yeah. And here is why. And so I was like really able to kinda differentiate us from people that were winning that work who were, you know, they couldn’t say that.

Faith (19:27):

Yeah. I’m like curious to do an experiment and go back in my inbox and see all the outbound emails that have actually gotten me, and see if that was a strategy that they used. Because I feel like that’s something that I can grok really easily is like, if somebody calls out something that like strikes a chord with me as like, it sucks. I’m like, ugh, yes, I will open this email. Absolutely.

Ben (19:49):

You get a lot of credit for being the person that has the, you know, the moxy to say, ‘Hey, this isn’t good and here’s why.’

Faith (20:00):

Yeah. Like, you don’t have to do it this way.

Ben (20:03):

Yeah. And that everyone’s like—some people love the status quo, you know?

Faith (20:09):

Yeah. I’m curious if you guys think it’s going to be a challenge for us as we scale. Like obviously, we’ve scaled a lot, at least in terms of head count on our sales team over the last year, and we’re just talking about how like Jessi—in my eyes—is an expert on understanding what kind of talent I would need to achieve a certain outcome. Not just, you know, tech stack, but like actual kind of experience and engagement type and all that. And then also you know, how to like gauge the success of an engagement and understand kind of those nuances. How are we thinking about scaling that institutional knowledge that took Jessi four years to become an expert on and empowering more people with it within, you know, their ramp period, however long that might be.

Jessi (21:05):

I think at least what we’ve been doing is just—what’s so funny?

Ben (21:11):

<Laughing> It’s just not an easy question. 

Faith (21:13):

No, it’s not an easy thing. That’s what I’m wondering. Like is it—do we think—are we calling it a challenge, or do we think we’ve got a pretty good plan for it?

Jessi (21:21):

I mean, we’ve just been doing as much shadowing as possible, because I feel like there’s so many different situations that come up that it’s really like impossible to just like put together a doc and be like, ‘Hey, you know, learn this, you know this, and like you’ll figure it all out.’ It’s very much so like just being involved in it and seeing how things play out and seeing how we handle ’em. So we’re doing a lot of shadowing and I’m so sorry, Strayla is–

Ben (21:48):

Going crazy?


Strayla is also shadowing the sales team.

Ben (21:50):

So, I think this is— it’s a really interesting question, Faith. The good news that I’ve noticed, that I’ve seen is the shadowing and the role plays work, right? And so like we’ve gotten better at like getting their reps in, ‘cause like, as Jessi said, there’s tons of different permutations. I think the other aspect of it though is that, you know, there’s not an insignificant number of our prospects who—like, they haven’t quite thought it through to the extent that we know that they should, based on our experience. And I don’t mean to bag on ’em, I get it. Like, I’m the same way. So I think that for our team, is like asking the questions to really pull that out of them. Because if we can do that, like—they won’t do that with other vendors. They wanna do that with other people. And so understanding like more of their motivations, not being afraid to ask kind of harder questions about the business and the business impact of these people they wanna bring on. You know, I think that gives us a leg up, and it’s something that even someone who’s non-technical can understand pretty quickly, which is again—kinda goes back to what we were talking about earlier about like the team feeling like empowered to be consultative and like ask more questions and ask the why’s and ask, well, hey, what does this mean? Or, you know, like none of that really requires you to be really proficient in like the latest backend technologies—what the client needs. The DevRel team and Deividi, they can take care of that. 

Faith (23:29):

Yeah. I think that’s like often kind of the biggest hurdle—is understanding that to be able to talk about the work that needs to be done, you don’t actually have to be able to do the work yourself.

Ben (23:46):

No. You have to really understand the motivations for the work and the goals for that project. And look, we understand the technical end, too. Like that’s again—what DevRel does—but you’re right. Like, so often people don’t ask those questions. Like a great one is, you know, hey, like what’s this one—like what’s this one role’s KPI? 

Faith (24:09):

Right? Like what’s the—how do we know that they’re successful?

Ben (24:14):

And like, people don’t think of that all the time.

Faith (24:16):

Right. It’s so true. I feel like we’re just not often in the headspace, as busy people who are trying to do a job, of imagining what it takes to do another job well, if it’s not the job that we actually are tasked with doing, if that makes sense? (Ben: It does.) Like, I think that’s what makes the work that our sales team does so kind of like nuanced and difficult is, because it’s not about—yeah, they’re like—they have to be like super kind of meta <laugh> and think about things that most of us don’t in our careers.

Ben (24:54):

Yeah. They have to–I mean, we have to–in a way, everyone on our sales team is sort of like a hiring manager, right? And they’re—interrogating is probably not the best word to use—but they’re interrogating these prospects, like as a fellow hiring manager. (Faith: Mhm, right. Yeah.) And one, that’s unique—like I don’t have many friends who I sit down with and they tell me about their jobs and they’re like—they’re surgeons. And I’m like, well, like have you really thought about why you’re suturing this person? (Faith: Right.)

<Laugh>. Like, you don’t do that. Like, you don’t like typically like really force introspection on other people in like your day-to-day. But we have these calls all the time.

Faith (25:40):

Yeah. And I’m just not that naturally curious. So that’s why Ben would never hire me to be on his sales team. I’m just Podcast Girl. 

Ben (25:50):

But you podcast! I mean, that’s curious. Don’t tell yourself you’re not curious. 

Faith (25:54):

Right. It’s curious enough. I’m no Diane Sawyer, but we’re gettin’ there. 

Ben (25:59):

I love that Diane Sawyer is your pinnacle of curiosity. It’s like, Diane Sawyer. Curious. 

Faith (26:05):

Of course. I mean, who else? We’ll talk about this later. I need to know like who wins a curiosity award? You know who probably does it is Stanley Tucci, actually.

Ben (26:17):

He’s a very curious guy. That’s true. 


I’ll give you the Tucci.

Faith (26:19):

For Halloween, Dan was Stanley Tucci, and I was a bowl of spaghetti. 

Ben (26:30):

Stanley Tucci is a very attractive man. I don’t mind saying. 

Faith (26:34):

Oh, there’s just some—I don’t know what it is. I think because like attracts like, and I know that we would have an excellent time dining together. I think that’s why.

Ben (26:48):

I mean, on paper, not a lot <laugh>, right? Not a lot on paper, but really—

Faith (26:54):

In my heart… In my heart, I know it’s true. <Laugh>

Ben (26:59):

That was a fun tangent. Let’s leave it in.

Faith (27:02):

That was great. Yeah. Leave it in, Bill. 

Alright, you guys. Well this has been very insightful. I don’t wanna take up too much more of your time. I know we’re kind of nearing the end here, but I really appreciate it, and I’m excited to talk to you guys maybe in six months and see how the challenges that you guys called out are evolving, changing, if there’s still challenges, or if we think we could write a book about them.


I’m excited for that too.


Yeah, this is like our little—our live diary.