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Season 2, Ep. 21 – Promoting from within: why we love hiring people who are new to tech

In this episode, Faith sits down with our VP of Operations, Tyler Newkirk, to talk about how we’ve traditionally approached growth and promotion at It turns out our secret sauce is hiring talented people and giving them the space and tools to thrive, even if their background isn’t in tech.

Faith Benson
Faith Benson
· 28 min



Faith (00:03):

I feel like it’s 9:00 AM, and it’s 3:30.

Tyler (00:06):

Yeah. it’s been one of those days where I can’t believe the time has flown by as fast as it has. Just a lot more to get done.

Faith (00:14):

Yeah. There’s something with the time change too that I just like cannot get my bearings. I know that’s not a hot take. Like everybody is talking about how much it ruins their lives, but oh my gosh. It feels like it’s 10:00 PM a couple hours after I wake up, and that just like, doesn’t make any sense.

Tyler (00:33):

Yeah. Is this is the last year in Tennessee, right?

Faith (00:36):

Wait, what?

Tyler (00:38):

Am I making that up? I think that’s true.

Faith (00:40):

I think you’re definitely making that up.

Tyler (00:43):

It’s possible.

Faith (00:45):

Alright. Well, we’re gonna fact check that before anything goes in the podcast.

Tyler (00:48):

Please do.

Faith (00:49):

What if we started that rumor, and then the Tennessee legislator just like had to pass it, because everybody thought it was true?

Tyler (00:56):

I mean, if—you know, I wouldn’t be mad.

Faith (00:59):

No, I feel like they would make a holiday in our honor. You know?

Tyler (01:03):

They should. If—yeah, if this is where it all started, then I think that’s appropriate. 

Faith (01:06):

Then everyone would listen to the Frontier podcast. <Laugh>

Tyler (01:09):

Mission accomplished. Right.

Faith (01:11):

We’re down here. Tyler, we’re talking about something that I think you and I have pretty decent experience with here on the team, which is why we love hiring people who are a little bit more green, and maybe in some cases don’t even have experience working in technology. And it’s probably worthwhile to start with both of our stories, because neither of us came from like a storied history working in technology. The myth is, Teja found you working at Home Depot, which—I don’t know how true that all is. So what were you doing before you came here?

Tyler (01:54):

Yeah, it’s—I mean, it’s mostly true. Isn’t that a fact check response? Mostly true.

Faith (02:00):

Yeah. It’s mostly true. There’s a blog post about it. So <laugh>.

Tyler (02:04):

Yeah. No, we—I mean, we met prior to that, but you know, the reality is the business of the time where they couldn’t afford to bring me on, and I wanted to work here. And so we just—that’s what I was doing to string along the bills until, you know, I was able to to come on full-time. So yeah, there is a lot of truth to that, but I obviously knew Teja before.

Faith (02:26):

And you were working—well, you majored in something relevant, right?

Tyler (02:32):

Mhm. Yeah, I majored in entrepreneurship from Belmont outta college. And obviously I’d spent some time, you know, within the EC network here in Nashville and really enjoyed that space. And so obviously taking classes and coursework, in that, and had just the tiniest bit of experience from that. It’s nothing, I think to the—you know, what you learn once you’re in it, but it’s where I wanted to be, and so yeah, I mean—I knew at least enough to know that was interesting to me, and I wanted to learn more and just kinda steep myself in that. So that’s what, you know, drew me into this kind of space to begin with.

Faith (03:11):

And then—this will be easy to fact check. So is really your first kind of like technology company that you’ve worked for.

Tyler (03:20):

Yeah, I mean, I’ve done a couple contract stints here and there with a few other firms, but yeah, this would be like the first real, kind of tenured position with any sort of longevity to it. 

Faith (03:35):

Same. I mean, I did not major in anything relevant, as you know—I thought I was gonna be working in the Middle East, and when that didn’t pan out, I was a teacher for eighth and ninth graders for three years, and then did a couple stints with startups, none strictly technology-based, before I landed here. So obviously when we both landed at like five years apart from each other, we were pretty green.

Tyler (04:05):

Yeah, definitely.

Faith (04:06):

And I think it’s interesting that that’s been like pretty thematic with folks that we’ve brought on since.

Tyler (04:12):

Yeah. In a lot of cases, I think that’s definitely true. I mean, we’ve certainly worked with people that are not green, right? That have come in with domain expertise in various areas, and I think at times, that’s definitely necessary. But there’s been a lot of cases where that has not been the case. To your point where we’ve, you know, we’ve hired and we’ve worked with people where they have a foundation of a given skill set that we think they’ll need to succeed in a role, but then can build on that. They have a lot of room to grow and really blossom into that. And so that’s been fun to see, too. But you know, I think there are times that that call for one or the other, but we’ve certainly done a fair amount where we’ve hired people that have just given them a lot of room to grow in their roles too.

Faith (04:58):

There’s so much in what you just said that I wanna circle back to, you know, like I wanna talk about how we decide when to bring in an expert and when it’s okay to bring in someone with just like a lot of hustle who’s a little bit more green. You mentioned how we give people kind of the space and resources to grow, which I think is valuable to talk about. But maybe a good place to start is, you know, you mentioned, obviously there was a time when we were a young company, and I think we still operate sometimes a lot like a really scrappy startup. And oftentimes in those cases at smaller companies, cost is really a hurdle.

Tyler (05:39):

Yeah, like a huge driver of decision making.

Faith (05:40):

Yeah, exactly. And so when there’s not kind of an endless amount of cash to work with for your hiring strategy, something that we’ve done that seems to have worked pretty well is we said, alright, here—here are the domains where we certainly need an expert who has a point of view, who’s done this several times before, and can bring that context here to our team. We can’t always afford those people full-time right away. Right? And so our strategy has been let’s work with these domain experts, fractionally, whether that’s kind of a short term engagement where they audit something we’re doing, or we bring them on as, you know, long term fractional employee. And then let’s augment them with green folks who can learn from them, be kind of their legs on the ground, do a lot of the implementation level stuff. And that seemed to work pretty well for us over the years, right?

Tyler (06:33):

Yeah, certainly think that’s true. I mean—and in more ways than just the level of expertise that somebody brings, right? I mean, there are opportunities that are just smaller sized in terms of like the projects and things that need done, where fractional makes a lot of sense. And, you know, I think it allows people a chance to feel us out as a company in a culture, and is this somewhere that they wanna be more involved with or less over time? So, you know, I think there are other benefits to that too, but I think that’s a big piece of it, right? Is like, what do you envision, what are your needs for a given role? And, you know, what does that mean? You can sort of—you can accommodate in terms of the person, how experienced they need to be.

And some of that’s obviously obvious too, but I think—but it plays into the needs of the role. Like, do you need somebody to come in and get results right away? And is it a highly specialized thing, or is it a role that you anticipate you know, growing and having people growing under it? And so, I mean, lots to consider there, but especially when you’re early on, and you don’t have the ability to always bring in somebody, you know, really experienced and an expert in a given area, you kinda have to make do with what you can.

Faith (07:45):

There’s also sometimes when we’re running a hiring cycle and we realize that there are some things that might even be more important to us than that skill match or expertise.  Like, one that comes to mind is passion for the space that we’re working in, right? If we’re interviewing somebody—let’s say it’s a PR role—and they’re like, well, I’ve never worked at a PR firm before. I’ve never done PR anything, but I hate the way that hiring works today. And I am so passionate about fixing it. I feel like yeah, that’s a lot more compelling to us than somebody who’s maybe an expert in the domain.

Tyler (08:29):

Yeah, I think—I mean, I think you have to index, you have to understand like where you wanna index when you’re hiring, right? You know, is this something where like passion is a big piece of it, or is it, Hey, we need somebody who—maybe they’re not super passionate about this thing, but they love to learn, or they wanna be more familiar with a given discipline or a given space. Right? And, you know, passion’s a great example of that, but I mean, I love it when we find people that are like naturally inquisitive and say, this is something I don’t know much about, but I can learn. I’ve shown my ability to learn in other ways throughout my career, and this is something I wanna really jump into. Or, you know, making sure that they match over the next few years of their career trajectory. Does that align with this role? Is this again, something where they are really looking to step up quickly, this is something where they’re okay to come in and really learn and feel it out and all those things—again, kind of go into consideration set, but finding out what you really wanna index on is a big piece of where you fall on that spectrum for any given hire, versus super experienced or less so. 

Faith (09:34):

Yeah. And I think we do a good job of planning that before we actually start the hiring cycle.

Tyler (09:40):


Faith (09:41):

Yep. Just getting a sense of what we’re willing to compromise on—what’s most important. Yeah. You mentioned, you know, it’s great when we find people who are super curious and eager to learn. And I’m wondering if you wanna talk a little bit about how we support folks who are really hungry to learn and get better. You know, what kind of guard rails do we give them, and how do we support them in that?

Tyler (10:06):

Well, this kinda goes back to your original point of, you know, for a lot of years in this business or that I’ve been here, most of the business is history. We’ve been fairly constrained from like budget and cost, you know, perspective where we’re not able to go out and make 20 hires and hire leaders for different, you know, departments right off the bat. And we’ve kind of had to build into that. And so as a result of that, you’re sort of creating intentional spaces for people to grow and become those over time. And so, you know, out of necessity, right? Not always like first choice, but just out of necessity. And so, you know, I think having that expectation up front and then making sure that whoever is stepping into that role is open to that ambiguity and kind of to that open space of, Hey, we know that this role is gonna evolve a lot over the next 6, 12, 18, 24 months. Like, are you okay with that? Like, does that excite you, or does that make you really nervous and anxious? And is that not a good fit? Or, Hey, this role may change, right? And it may branch a little bit here, it may branch a little bit there. Is that something that’s exciting to you because you just wanna learn more about the space in general or the field in general? And so all those things I think are key to asking and finding out for anybody that’s, you know, gonna be in a new company. But specifically with this, when we have roles where we know we’re hiring somebody who hasn’t been in this exact role for years in their career, I think it’s exciting to be able to like watch people grow and see, Hey, we’re gonna give you more responsibility. Or as the company grows around them, like they’re also sort of leveling up, you know, in tandem with that. And so that’s like really fun to watch and see that there’s always that inherent space, I think, for people to grow and level up into, if that’s something that they wanna do. Right? Not everybody desires that, but I think for the people that do, there’s, you know, with startups, small companies, there’s a lot of opportunity for that in the earlier days.

Faith (12:07):

Yeah. And I think it’s one thing to say like, Here’s space to grow into—now grow! <laugh>, and it’s another to be like, Let’s figure out together what it is you need to supplement the areas that you’re not an expert in yet. It’s been my experience that when I need to go deeper in a subject, whether it’s Google Ads or SEO, or the way that our content is interconnected on the website, there’s always an opportunity to bring on a coach for a couple months or have an external audit done. Or if I like, take time outta my day to take a course about any of these things, like, that isn’t something that people are confused about. Right? Like, it’s definitely kind of like baked into the expectations of my time is, I’ll be spending time executing, but I’ll also be spending a lot of time learning. And I think that’s pretty unique here.

Tyler (13:05):

Yeah. I’ll say, I think what we’ve done well—and you teed this up early in the conversation, so kudos to you—is when we kind of sense that, Hey, nobody on the team has this particular skill. We can go and get that from somebody at out of, you know, in a fractional way. Hey, come in and work with, you know, someone on this particular thing, so they can learn more about it. They can be more informed over the course of a quarter or two quarters, right? And it’s not a full-time hire. It’s not somebody replacing somebody in a role, but it’s, Hey, come alongside so that we can learn in an accelerated fashion. I think we’ve done that fairly often, and for the most part, effectively, I think where we can, we’re just starting to explore. And maybe—and I would say this—room for us to improve as a company is like providing actual, like formal education, you know, for the team, and ways that they wanna grow. I know we have recently over the past year or so, been pushing, you know, things like the <inaudible> project, which is super cool, right? Anybody comes on the team that’s not a developer already we’ve got this sort of set open source project that they can jump into, which is so great. 

Faith (14:18):

Huge fan. Yeah.

Tyler (14:20):

Yeah. Huge fan of what they’re doing there and all the work that’s gone into that project, because it’s—even for somebody who’s not a developer myself, it’s still learning. You still learn so much from the basics. Even though I’ve been in this business for, you know, years, and I understand some of the terminology, it’s like, Oh, interesting. You know, you’re always learning something new at a foundation level. So yeah. Things like that. You know, we’ve done more recently, and I wanna do more of—I think as a company, as we continue to grow and have more people to be intentional about, you know, finding those spaces of not only if you wanna level up and maybe it’s adjacent, right? And giving abilities to do that. So that’s a place that I wanna continue to explore and how we can do that more over time, too.

Faith (15:04):

Yeah. Something that the marketing team has been doing is maintaining a shared bookshelf. So in notion we just have a bookshelf database, where we post like podcasts, articles, books— whatever it is that we’re consuming. 

Tyler (15:21):

That’s super cool.

Faith (15:22):

And it’s cool because, you know, the nature of notion is you can annotate things, you can leave comments. And so that’s been fun as like a member of the marketing team to see the team kind of like level up together and kind of build the shared context around like, alright, cool. Like all of us have read this piece about what makes an exceptional landing page, and we all have this context now when we’re building things for the website.

Tyler (15:47):

Right. That’s great. I love that. I didn’t know you guys were doing that, but I wanna implement that now myself. That’s super cool.

Faith (15:52):

Well, I think we should make it company-wide, for sure. Maybe we’ll do like a resource that’s public as part of a—this is actually a spoiler alert that is on the content calendar for next year.

Tyler (16:04):

Very cool. Yeah, I’m on board.

Faith (16:06):

I was also thinking when we’re prepping for this episode that like, there are some things we win by hiring people who are new to technology that I don’t think we’ve thought of before, consciously as wins, but we’ve certainly benefited from them. Right? Like for example, when we bring in people who’ve never worked in technology before, they’re not bringing kind of like preconceived notions around what’s possible or what’s good or what’s bad, based on what they’ve experienced at previous teams. And I think in a lot of ways we’ve seen that pay off, right? Like the example that I’m most familiar with, because it’s in my space, is our newsletter, right? Like, we started writing this newsletter almost five years ago.

Tyler (16:56):

We have a newsletter?

Faith (16:57):

Yeah. We do have a newsletter.

Tyler (17:00):

Just kidding. We have a newsletter. Wayfarer, it’s very great. Faith writes them. 

Speaker 1 (17:03):

You know, if I was a seasoned marketer, the Wayfarer would certainly not be what it is, right? Like,  if when I joined I had been writing newsletters for someplace else before, there would be CTAs everywhere, there would be a hard sell—

Tyler (17:19):

You’d be so much less authentic.

Faith (17:21):

Exactly. But instead, it’s literally just my diary on the internet, and people like it and subscribe to it without actually being like on our platform, which is cool. Yeah. Also, like empathy for non-technical hires is something we win when we bring in folks who are new to tech. Like we work a lot with people who aren’t developers themselves, and we can really understand that when it’s something that we’ve experienced recently. 

Tyler (17:48):

I think that’s a big piece of it. But even, you know, to add to that—you know, people bring in a lot of experiences that are unique to just other industries too. And I think there is crossover, right? In different ways. And so, I’ve seen that a few times even, you know, with an operations of how, Hey, this is how I’ve done it at the sold role I had, and you know, it was very customer centric and I wanna make sure that like, this is how we implement a new process here. And I’m like, that’s great. I love that perspective. Let’s keep that in play. And so I think you get a lot of benefits that way. And not that, you know, tech is devoid of those things as an industry, but you know, when you get people that have had a variety of career experiences, that also brings a richness, I think, to to a role, to a team, and then obviously, you know, to a company. And so I’m glad that we’ve got kind of a diverse mix of backgrounds from a career perspective on the team so far. It makes it cool.

Faith (18:51):

Yeah. Something that I actually had under the column of like, what we lose by hiring more green folks is insight into other companies and like a broader context around best practice for their role. But I hadn’t thought about what you said, which is like, yeah, maybe we lose that, but what we gain instead is insight into best practices at other industries and in other roles. Right?

Tyler (19:20):

I think it’s still a valid point. You know, I think when you have people that aren’t as familiar with your space or they’re newer to a given role or function, I think you just have to be more intentional about seeking out things like best practices and standards and common KPIs, right? If you’re not coming in with that knowledge, then you have to build it. And to build it, you have to sort of seek it out and understand. And so I think that’s just a place where, you know, for our business, we have to be intentional about doing that in some areas where, you know, we don’t have that expertise at every single seat, or we’re building it over time or in the earlier days, right? We really had to seek that out from domain experts in different ways, and one that—like you said—that enables us to learn ourselves. But that is, I think still a valid point where you’ll, you know, you’ll bring in some really good things from people that are not—haven’t been doing the same thing for 10 years. But on the flip side of that same coin is you also have to make sure that you’re watching out for those flanks, if you will, in a given role. And, Hey, where are we gonna be weak? You know, just because there’s a knowledge gap or an experience gap, and really leaning into that. So I still think that’s a valid point.

Faith (20:36):

Yeah, that’s interesting. How, for folks listening who are like, Yeah, maybe I need to kind of rethink the way I plan out these hires—What’s your advice for folks as they’re considering like, Do I need need a domain expert, or can I hire someone a little bit more green?

Tyler (20:54):

That’s a good question, and I don’t know that there’s a single answer. I know some of the things that we’ve looked at are impact—like time and the degree of impact. And so if this is a role where we need results really fast or they need to be real needle movers in terms of results, I think that’s something that can inform whether or not you need somebody who’s done this before who can quickly get up to speed and have an impact—if it’s a role where that’s less of a concern, it’s more of an ongoing thing, or just by necessity of the role itself, it doesn’t affect maybe growth of the business—there’s maybe more opportunity to have somebody come in and learn over time and build around them. I think that’s one area to look at. And then I think the other two is what is the rest of the team around that role? How are they able to support or facilitate growth? Do other people on the team have adjacent knowledge, even if it’s not their sole responsibility where they can help somebody get up to speed really quickly, or, Hey, if no one on our team knows how to do this, should we then go and hire somebody else who doesn’t know how to do this?

Faith (22:04):

Right. And when we can’t coach them.

Tyler (22:06):

A hundred percent. And so, you know, those are a couple different things. Now, I will say one of the things that we’ve done that I think has at least helped with that is we typically try and have, you know, somebody do a new role before we hire for it, just for even for a short time, right? So that we have some experience and that we can at least speak from an informed place on—even if it’s just our own context of Gun, you know,—we can still say, Hey, we’ve done this ourselves. When somebody new comes in, we’re able to at least understand, empathize with the role. And I think that’s helped too with having people who are less experienced in a given responsibility set kind of get up to speed because we’ve—we know what it’s like to be in that seat, even if it’s for a short time. And I think that’s something smart that Teja has implemented that we’ve done over the last couple years that I think has been effective too.

Faith (23:00):

Yeah. I think that’s huge to identify, like, reasonably, what can we expect from somebody, like what’s a really aggressive KPI, and what’s kinda the base level that would tell us if the person’s performing or not? Something I think about a lot too, with hiring folks who are more entry level is—especially in technology—our candidate pool for more experienced folks tends to be pretty homogenous. And that’s kind of true regardless of role, maybe except for marketing. Something that we win by hiring entry level folks is access to a much more diverse talent pipeline. And I think we’ve won a lot there as well. But obviously like  your recruitment is only as good as your retention. And so I’m really excited to think, to continue kind of implementing these practices around supporting folks in their growth, right?

Like whether it’s access to coaches, academia, like you mentioned, getting sense in the Oden project. But also, you know, I feel like the most impactful thing that was done for me here was just introducing me to a professional network. Like both Teja and Grey have been so helpful in identifying other growth marketing leaders and their networks and introducing me so that I have some sort of benchmark for myself and I’ve got like kind of a peer board that I can go to and say, Hey, like here’s a challenge. I’ve never dealt with this before. Like, what do you guys do? What do you think? 

Tyler (24:41):

Yeah. That’s so key. That’s what somebody who has experience and is not green in a role can bring to a team, can bring to the table, right? Is that network for, if not themselves, then other people on the team, potentially. 

Faith (24:54):

Absolutely. And I think, like as I’m reflecting on this, I’m thinking about how we can do this for folks in every role at the company, not just in leadership roles.

Tyler (25:05):

One last thing that that’s come to mind as we’ve talked is just asking these questions too, of the people on your team, of, Hey, do you feel like you’re growing? Is this role that you’re in, like the direction that you wanna stay in? Or if not, how can we maybe accommodate that? Or is there space for that here? It’s prudent and helpful to be mindful of where people want to go. And that doesn’t always mean you’re aligned forever. That doesn’t mean every employee that you hire is gonna be with you forever, should be with you forever. And I think it’s okay to understand where those paths might, you know, diverge too. And so the more that I think as a leader that I try and challenge myself you know, is just to make sure that I have a pulse on that team wide. Are people where they wanna be? Are they able to grow? And if not, like, have we identified that? Do we—are we aware of that? Is there a space for that? And just making sure that you’re checking back in on that. And it’s not a one time conversation that happens at the point of hire, but it’s a continuing thing, too. Which stuff deals along with continuing education, other opportunities to grow. But I think just being intentional about asking those questions, even will, at least for me, has opened up like new ideas, new thoughts, Oh, I didn’t know that about you. Oh, that’s interesting. Or now that you’ve been in a role for six, 12 months, you have a better sense of where you wanna steer yourself going forward. Again, speaking for myself, those are things that are sometimes easy to not prioritize conversations, but I’ve learned that as we’ve can get in a regular cadence of having those, they can be impactful, right? Because that could be the difference of somebody sticking around for a few more years or saying, This isn’t cutting it for me. I wanna go find something else. There’s a lot of just potential there, I think with a simple conversation, that you can learn. 

Faith (27:01):

Yeah. If you are a manager, a leader listening to this and you’re like Yeah, that sounds great, but that sounds freaking terrifying. <Laugh>, there’s two resources that we’ll link in the show notes. One is a bit called Difficult Conversations, which is an oldie, but a really goodie for having kind of those conversations with folks who you’re leading, or anyone in your life. And the second is much shorter and more consumable. Blog post by Teaming, and Teaming makes software for leaders and managers. We find a lot of value in it with managing one-on-ones. Yeah. But there’s a great blog post that’s just a list of questions to ask in a one-on-one, and I just have those in my one-on-one folder and pull one every week when I’m talking to someone on my team. And a lot of them fall under the category of like, Let’s talk about professional development, and how do you wanna grow? You know, and how can I support you in that? 

Tyler (27:58):

Yeah. I love that. 

Faith (27:59):

Love that. Well, Tyler, this has been awesome. I think this has been one of my favorite conversations, actually, on the podcast.

Tyler (28:05):

Likewise! Yeah. This has been fun.

Faith (28:06):

Yeah. Cool. Well, we’ll provide those resources for everybody, and we’ll see you next time!


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