Social Selling, Combining Sales and Marketing for the Current Market with Ryan Scalera

About This Episode

Struggling in the new landscape to make a mark? Looking to gain an advantage in the Social Media world? Social Selling, or the combination of Sales and Marketing using social media, has been one of the more successful ideas to come from the Pandemic landscape, if done correctly. Ryan Scalera, of Dooly, drops by to talk to Brad about his experiences in the Sales and Marketing world, and what led him down the path he has found himself on now. Not having to use a resume for the last few years being just one perk of Ryan’s success.
Ryan Scalera is an Account Executive with Dooly. Don’t let that title fool you though, Ryan has found success both in sales, and more recently in various Edu-tainment videos. His success has led many to ask what makes it so unique. Simply put Ryan’s Social Selling abilities are making many rethink their current, some may say, outdated techniques to approaching the current market landscape.

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Social Selling, Combining Sales and Marketing for the Current Market with Ryan Scalera

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Episode Transcript

Brad Seaman: [00:00:00] So tell me how you got here. So give me, give me the background. You know, did you go to college and not go to college? How’d you get into sales?

Ryan Scalera: [00:00:06] Yeah. So funny enough with the, the, the music and everything. I actually went to audio engineering school. So I wanted to be a record producer had no real intentions of getting into sales or business in general.


maybe, maybe, yeah. So it, it was It was an interesting process, but I just started a new one to make money in between audio engineering gigs. Yeah. And I got into a job where I was basically selling frozen Italian food at farmer’s markets. And the first couple of days I hated it. And then all of a sudden I started to absolutely just crush it and love it.

And from then on, I just wanted to get into more sophisticated sales. Really kind of learn more about business and it it’s slow, snowballed over a long period of time, eventually gotten to insurance and then transitioned that career into technology sales, where I’m still at today. But as soon as I found tech sales software sales, it was like you know, I knew that I was going to be in it for the long haul there.

Brad Seaman: [00:00:00] So tell me how you got here. So give me, give me the background. You know, did you go to college and not go to college? How’d you get into sales?

Ryan Scalera: [00:00:06] Yeah. So funny enough with the, the, the music and everything. I actually went to audio engineering school. So I wanted to be a record producer had no real intentions of getting into sales or business in general.


maybe, maybe, yeah. So it, it was It was an interesting process, but I just started a new one to make money in between audio engineering gigs. Yeah. And I got into a job where I was basically selling frozen Italian food at farmer’s markets. And the first couple of days I hated it. And then all of a sudden I started to absolutely just crush it and love it.

And from then on, I just wanted to get into more sophisticated sales. Really kind of learn more about business and it it’s slow, snowballed over a long period of time, eventually gotten to insurance and then transitioned that career into technology sales, where I’m still at today. But as soon as I found tech sales software sales, it was like you know, I knew that I was going to be in it for the long haul there.

Brad Seaman: [00:01:11] What was

it? What would you say? I’m just going to grab a handful of things here. So when you, when you went through the process of trench kind of changing directions, so you’re going to do the kind of audio engineering thing and you’re like, okay, I’m going to get into sales. Was that a natural progression or did that, was that like a setback progression or did you come to a, like a T in the road?

Ryan Scalera: [00:01:28] Yeah, basically, I was my daughter my wife was pregnant with my daughter and I knew that I knew you get more stable work. And I was working a five to nine, not a nine to five in the audio engineering world. So it was like, I would go to work five, come back and then in the morning, and it was not sustainable.

And there was a, like three were three months of work at a time. Basically. It just got to the point where I needed to figure out something else that I could do with that, like a bachelor’s degree, but with what I was already doing. And I, I got very good at getting in front of record producers and artists and stuff like that back then.

And I started to correlate that they’re not really that different than CEOs and business people where people so if you can crack that code on how to get in front of, on someone, get their attention, help them with something that they’re trying to achieve. So that became a natural progression as it went on in the beginning, I wasn’t sure where it was going and now you know, life.

Career, hopefully

Brad Seaman: [00:02:23] also. So, so what would you say the biggest difference between selling insurance and selling software is,

Ryan Scalera: [00:02:29] Ooh, you can’t really sell insurance in the first place. There’s a lot of regulations and you can’t. You can lay out the options, but you can’t really make recommendations based on what you’ve collected as far as the information.

And it’s just so old school, the way that the industry is set up, there’s no room for creativity. It’s just an age old industry that is not innovating. And I love like very efficient companies that are very thoughtful about everything that they’re doing, driving the, the ultimate goal of business forward, where there’s some.

Awesome old school mentalities in that industry that I just could not I couldn’t hit my stride. And so when I transferred to tech, it was a huge difference. Cause it’s fast paced. You know, there’s a lot expected of you and it’s not by any means easier than insurance, but I just truly enjoy it.

Brad Seaman: [00:03:24] So what were you guys selling?

And everything benefits, just a benefit software benefits and HR tech.

Ryan Scalera: [00:03:30] So that was how that became a really good transition is they needed someone who knew the benefits industry. And I did it. It helped me a lot coming in as a, like a transfer into SAS that knew. Actual market in their industry and could speak on a multitude of different subjects that their software actually does.

And I had a couple of connections in the industry as well. So that definitely helped just get me kind of like go in early

Brad Seaman: [00:03:55] now, at what point do you, so, so I know you, so if anybody’s listening here and you haven’t checked out dually and haven’t checked out what Ryan and his team are doing on LinkedIn definitely fascinating for sure.

Lots of really cool videos. Do you, when does that, when do you sorta start putting that together on, on LinkedIn? Like, just cause when I, when I think about you, I almost think about you as like a Swiss army knife, past sales guy, half marketer, which I think at some level we’re seeing that it’s a change, which I think you’ll probably talk about.

We’re seeing a change in that, on how salespeople sell and how they generate exposure and opportunities. So I’d love to have you talk a little bit, just talk about your journey. Like at what point did you create your first video? I’m going to call you DJ Ryan Scalera for this episode. Like, so at what point did you bust out the mites and the video, and it start telling your VP of sales that you want to start doing something kind of crazy.

Ryan Scalera: [00:04:53] Well, that, that’s a great, and it was a transition just like that. I texted my VP of sales and central region. And I said Hey, can I grab the first 10 minutes of our Monday meeting? It was after a QBR. We did. And we had a sales trainer in named Keenan who was by the way, the next person I went to go work for.

And they, they basically, I recorded a song that I had done about the QBR, just as like a fun little thing. Cause he had joked that he is like, oh, someone should write a song about. And I went home.

Brad Seaman: [00:05:28] Keenan jokes are your VP of

Ryan Scalera: [00:05:29] sales. So my VP of sales, when I did it, he joked about it and I did the song about Keenan and and the training.

It was just so out of a field, they, they didn’t expect that at all. I never talked about that. I did music or anything like that. And I think people really like to re like they can relate to music when it puts other things in their life, into it. Like even just having a song with your name. Or things about your business.

It just resonated. And I kind of got the feeling that it would resonate with others too. And that’s when I started doing videos and little bits of like edutainment content on LinkedIn. And it was just immediately, I saw a lot of opportunity in it and I’ve been doing it ever since, and it’s brought a lot of opportunity.

So I’m glad that I did that, but COVID was probably. Like the real Firestarter for it. When I got laid off in the, during the pandemic, I couldn’t get an interview. I could not get a job over the next guy because they were basically the, the talent market was massive. So I thought, what can I do? That’s different that can make me stand out and get me in front of more people.

I started going way in with the goofy and music content and sales content. And it started to get attention almost overnight. Within two months, I had a job with Keenan. And then from there, transfer it into a, to Dooley when I saw a great opportunity. Now tell me a little bit about, tell us about Dooley.

Yeah. So Dooley is basically it’s software for sales and revenue teams. It’s connected workspace. We all know as sales reps that like we didn’t get into the job to do data entry, although it’s a vital part of our job and what we can provide for the business. So what Dooley does is it basically aggregates a lot of your different tech tools at a sales team.

And allows them to capture discovery info, all their notes, Salesforce fields as easy as possible. Ultimately we bring in about an hour per rep, per day and productivity gains. I started using it when I was at Keenan’s cause he makes me take that a lot of discovery notes. And I became, I just got hooked because I was never too good.

At Salesforce administration. So it was something that, yeah, that, that spoke to me personally.

Brad Seaman: [00:07:58] Well, I, I saw him do a little video on, you know, I think there was some poll that went out there as like, can you be a good sales guy with that? You know, using CRM and his position was absolutely not. I mean, you have to be, you have to be organized.


Ryan Scalera: [00:08:12] It’s, it’s funny, man. Cause I, I commented on playing devil’s advocate on that post and he immediately called me right after he was like, Ryan, have you, if I taught you nothing, we started going into it. And we had a great conversation about it, but it was, it was funny because in reality, Like, if you’re running enough opportunities, you need to have this information somewhere.

It living in your head can work for a certain amount of time, but he’s right. Like good process adherence. Good use of a CRM. We’ll just make a sales person that much. Yeah. Yeah,

Brad Seaman: [00:08:46] for sure. Now do you, what’s the line between, so when you start, when you start started dually and you guys start putting out videos, Is there a conversation around like what the brand is or how these videos are going to go out or did they just say, Hey, Ryan,

Ryan Scalera: [00:09:01] you’ll get them.

So I am, I get to be a little bit of a lone ranger, cause I’m not on the marketing team, but I’m very tight with the marketing team. So I don’t, I’m not really as involved in the planning of content. However, I can freely come to them and be like, Hey, I have this great video or idea. And there’ll be like, how can we help support you?

So they have their own strategy. That’s very similar to mine. And I get to kind of jump in when I want to, but as a sales rep, like you said, like I’m a pseudos sales rep marketer, what that does for my pipelines personally. I’m addicted to it now, so

Brad Seaman: [00:09:40] yeah. Yeah. So talk about that. What, what do you feel like the, you know, from an observer?

Well, I think the one thing does, I’ll just throw it. I’m gonna throw in a couple of comments. So I think the one thing about being good at prospecting generating leads. However you want to do that, whether it’s inbound, outbound, bring into soup. Right. The better your brand is the better your inbound and or your outbound is going to be particularly the outbound.

Right. So if I call you from link me up at San Juan, Texas, that’s different than if I call you from LinkedIn out of Chicago. Right. So branding super important. So talk a little bit about it. And so as part of this, I think, Hey, you’ve created your own personal brand. So how has that impacted your how you’re perceived as a sales rep and, and just selling it?

Ryan Scalera: [00:10:24] So I will say this it’s definitely great for the career in general. I’ve got to meet a lot of my heroes, so to speak in both marketing and sales that I would, I just get to pick their brain, which is awesome. Just being in that scenario from the pipeline standpoint, I would say about half my opportunities are generated Personal inbound.

So they’re like reaching out to me. I had someone, a LinkedIn message me this morning. Hey, I think this is a good lead for, for Dooley. Just a friend in the industry across the sea. However, yeah, it it’s, it’s just it for self sourcing opportunities. It’s like,

Brad Seaman: [00:11:02] Well, it definitely creates a brand for yourself to go, like my guess is you’ll never based on what you’ve done to do what you’ll never have to do a resume

Ryan Scalera: [00:11:10] yet.

I have not used the resume in a little over a year and a half now. And it’s the coolest thing ever because I would spend countless amounts of time tweaking, making sure my resume was perfect. So I didn’t get kicked out in a, an algorithm. But yeah, I hope that’s the case. I do think that it, especially if I stay in the revenue tech space, I have a lot of opportunity to continue, like, you know, building upon it.

Brad Seaman: [00:11:36] I heard, so I don’t know if you’re familiar with Kyle Lacy. Lessonly here in Indianapolis had been an open view. He said his job for everybody on his team is that they would not have that. They would leave Lessonly and not have to get a resume. And I think that’s a great, I think that’s a great aspiration, especially if you’re a man.

Ryan Scalera: [00:11:54] A thousand percent, a thousand percent unless Lillian does great with their marketing too. I’ve seen a lot of Kylie’s stuff. I think he’s pretty heavily involved with the folks at Dooley too. So yeah, it’s, it’s something in this day and age where you can take it with you, you know, it’s not your personal brand and this is why it’s important, like to have that sort of separation.

From, I’m not just Dooley at the same time I work for Dooley and I love doing it. I’m very passionate about it. So I talk about it a lot on LinkedIn. There’s other things around just entertainment or education or opinions within the industry, documenting what I’m learning as I’m growing through my career.

Those are, those are all things that when I leave duly one day, I will have to carry on. Like it doesn’t go away. Now, is there a

Brad Seaman: [00:12:42] balance in your mind between, like when you put out a video, are you thinking about like your personal brand or you’re just like doing stuff that. No it’s as your fancy fancier that you’re having fun, but you think it’s fun.

Ryan Scalera: [00:12:55] There’s a, there’s a balance. You don’t want to become like the dancing clown which I’ve, I’ve thought about a lot. It’s like, I don’t want to be just like a parody or. You know satire. I really, so I tried to balance it out with content about the company I’m at the problems we solve the industry we’re in,

Brad Seaman: [00:13:13] I think that’s a distribution strategy.

Like if you think about like it being potent, like everything you do is not funny. And you’re trying to dilute it down with other material.

Ryan Scalera: [00:13:23] Yeah. I have like a running, like like list of types of posts that I do, types of content I put out. And I’m pretty methodical on what went. And so if I D I, I’m not going to do four music videos in a row, they’ll get old and it just won’t be as impactful as it is.

Same thing. It’s like, if I’m only doing like LinkedIn polls or something like that, it’s you got to mix it up and find like a cadence that works for you. But yeah, I started to get more granular with it over the. Well, I was going to

Brad Seaman: [00:13:52] say, I feel like you’ve done a good job. There’s a handful of brands that I can think of that I would sort of consider do a lot of content I would consider to be goofy.

I don’t consider you that way. You know, I think that you, I was going to say that. Before you got into the secret of Y Y Y I probably think that is that, you know, I see you as being bird balanced. Like I don’t, I don’t ha I don’t see you as the, I see you as being very professional, having a, maybe a, a point or like a position, and then you’re executing on that position.

And it does seem to be balanced. That would be my, that would be my perspective.

Ryan Scalera: [00:14:28] I think that’s, that’s good to hear that feedback because I think, yeah, in the, in the beginning, when I was doing the videos, it was all about like how to make people laugh. And at the end of the day, like when I got into sales calls, they’re like, are you going to rap for us?

Are you going to say for us? And it’s like, no, I’m a professional. I’m here to do my job. Do you have a problem I can help solve? So figuring out a good way to balance that, but then just like, you know, I don’t take myself too seriously. Like being able to joke around, just be really goofy. It’s just part of who I am

Brad Seaman: [00:15:02] now.

Do you have now what’s your process? Like it sounded like you have a methodical execution process. So how do you keep everything organized? Do you have a Trello board? What’s your content flow? Like when you think about content, it sounds like there’s videos. There’s polls. There’s probably like what’s your day look like?

How do you think about creating content and what’s your day look like as a salesperson trying to balance it?

Ryan Scalera: [00:15:24] So I have a there’s types of like, I don’t have like a Trello or like a content schedule or anything like that. I try to create a couple of different ideas. One of the big ideas, that’s like going to be a really creative video.

And then it’s planning out just how to execute that. Usually it’s on a weekend. After like my daughter’s soccer game, I’ll go and I’ll record and I’ll put something together and I have those structured out in kind of like a timeline. The ones that are like big, important that I’m going to put a lot of work into.

And then the other posts come to me during sales conversations. Like I think about something or there’s a theme in a conversation I’m having. And I can just quickly turn that into a LinkedIn post about my thoughts, get other people’s feedback and thoughts on it too. And that seems to be the most natural way for me to do it because if I sat there and tried to write out 10 points, They would all be kind of garbage.

But if it just hits me in a moment, I’ll immediately type it out on my phone. I may save it as a draft or I’ll, I’ll just. And like yesterday I did, I did something similar and it was not something I was expecting to be a well-performing posts, but it was, it just hit, it just hit at the right moment and the right vein, I guess.

Brad Seaman: [00:16:37] Well, I know the last one that I, that I saw, which may be a couple of weeks old at this point is the G the G2, which I, which I thought made me laugh. It was creative. Right. So does that

Ryan Scalera: [00:16:47] one? That was not me. That was the marketing team. They, it was such a silly, funny concept, but they call me and they’re like, Hey, can we do this?

And I immediately just heard it. And I was like, that’s ridiculous. But. Something nobody’s ever done when they got a, got a, a G2 leader category or whatever like that.

Brad Seaman: [00:17:09] You gave me so many good ideas. Cause I’m like, oh, from a market. So we can take, we can take all the people who are on G2 and like come up with a Jew.

Like there there’s so many ideas I got from that that maybe just maybe Chuck, like instantaneously check on what I kept when I saw what I saw.

Ryan Scalera: [00:17:24] It’s it’s funny, man. I love it. That the Dooley team is really all about that brand. And we’re doing things a little bit different. We’re trying to, you know, shake things up a little bit and I have fun with it when they

Brad Seaman: [00:17:37] bring, so when they bring sales reps on, so it looks like at this point, like how big is your, how big is your.

Like how many sales guys were on the sales team? How big is the marketing

Ryan Scalera: [00:17:45] team? Oh, I don’t even know how big the marketing team is now. Cause they’re adding a lot more seats there. I started, I was like 16th employee, I think. And then. Now we’re over 40. We’re going to be somewhere beyond that. Pretty soon scaling really quickly hiring a lot of folks.

We have four sales reps, including myself. We have our head of revenue, our head of rev ops, and we’re hiring like SDRs right now. So probably like six now going to be like 10 in the near future. Okay. So

Brad Seaman: [00:18:19] when they, so when they’re bringing it, so my question was going to be, and I want to know the size of the team.

When they’d bring, so I know one of your counterpart, or I don’t know her, but I know that you have another person on your sales team. Zoe, I see her do a lot of stuff. Are they teaching, are you guys sort of, indoctrined indoctrinating people on how to be a kind of sales marketers online or like what’s the, what’s the process?

Like, are you guys already thinking about that? Like, okay, we’re gonna, we’re hiring SDRs is the SDR as part of the job description, going to be like. You know, make videos and interact online.

Ryan Scalera: [00:18:54] Not at, so it’s not a forced thing. We don’t, we wouldn’t want to create a culture where it’s like, you have to be creative, that doesn’t breed any creativity.

I think it’s just, we really lucked out and Zoe is technically on, on marketing. But like we all have a similar kind of idea, even across the sales team. Like I’m probably the only one that puts out like content across the

Brad Seaman: [00:19:16] sales. I’m not seeing anybody else in here.

Ryan Scalera: [00:19:19] But like, we’re all really, like, I love working for the same.

We’re all really good in, and each of us have a like different like strong suit or like skillset that we’re really efficient at. So like, I like it. It’s not, we’re just hiring carbon copies of each. And building this, like where the real Ryan

Brad Seaman: [00:19:38] Scalera, please stand

Ryan Scalera: [00:19:39] up. Yeah, no, I have to rap or sing to work at Dooley skew.

We’ll feature it like

Brad Seaman: [00:19:47] looking for rappers and singers to sell enterprise sales software.

Ryan Scalera: [00:19:52] The amount of people in sales that I found out were like really into music is. Astronomical. I think it goes hand in hand people that are like creative and, you know, some, some sales folks are very analytical and they don’t want to touch music at all.

There’s others that really just like connect to art music all the time. It’s it gives a

Brad Seaman: [00:20:12] human thing. Right. I mean, it’s the one place that you can sort of like. I think in most cases, unless somebody is just into something that’s maybe atrocious to somebody else, you know, most of the time you could find some common ground, right?

You can find us song across genres that you can relate to somebody. I think. I mean, do you find that in most cases, like when it comes to music, you can find something.

Ryan Scalera: [00:20:33] I that’s, like, one of my hobbies is trying to find songs that I think someone else would like, I like ask them, like, what kind of music do you listen to?

And I try to find something, maybe they haven’t heard that they would like And like, honestly, the, the choices of the era of music that I choose when I do my content is very methodical based on the ICP that I go after. Okay. Tell me

Brad Seaman: [00:20:55] about this is going to be really so awesome. Tell me about.

Ryan Scalera: [00:20:58] So, yeah, I like I was doing like nineties hip hop early 2000, like songs like green day and closing time.

Like I choose those particular songs for a reason. A they’re like ear worms. Most of the time, my ICP kind of fits into that elder millennial, gen X. Window and we’re all about nostalgia and it’s really, it’s trying to go after that audience. So if you want some to speak to something, to speak to someone, it may not be the newest hit on the chart.

I try to, I mean, when I

Brad Seaman: [00:21:36] listened, when you did some of those, well, one, you did the, I did you do, I want to build a snowman? What are the, what are the recent ones you’ve done? Like throughout the songs? Okay. I mean, I checked, I mean, I saw that with my kids, right. So I was like, you know, I’m guessing guys, you’re talking to have two or three kids.

You know, you nailed some, one of the three kids they have is going to have one on one to watch that for a grant, even a grandkid,

Ryan Scalera: [00:21:58] right? A thousand percent. Yeah. It’s a, it, Disney is like, I’m waiting for them to come out with another banger because like, I need more material. No, I thought

Brad Seaman: [00:22:06] you were going to say, wait, I’m waiting for them to come after, before we use it.

Always. It is. Oh, so that brings up a good point. Is there any, like when you’re doing the songs, is there any limitation to the music in terms of, or no? Cause you’re singing it.

Ryan Scalera: [00:22:20] I

Brad Seaman: [00:22:22] suppose too, if you, if you I’m just kidding.

Ryan Scalera: [00:22:25] No. So, I mean, I’ve talked to a lot of people. Cool. And you know, the music legal side of things to understand if what I’m doing is legal, fair, you know, use whatever.

Ultimately if I ever got like a cease and desist, I would take the videos down. There’s nothing really tying me back. I’m not profiting off. There’s no way to trace if I’ve closed a deal because, and it’s falls in an interesting place in like the laws of like parody and cover

Brad Seaman: [00:22:54] denture wrestling. So there’s okay.

So there’s parody laws, right? Like, Hey, you know, creative consent, maybe not Kurt, what would you call that creative intent?

Ryan Scalera: [00:23:04] It’s yeah. So I know YouTube like took down a lot of parodies and. There there’s like some legal, gray area in it, but yeah, you like, if you’re just taking someone’s song and posting it and then monetizing it, that’s an

Brad Seaman: [00:23:21] issue.

That’s an issue different than, Hey, we’re making a parody or whether that’s poking fun, but like

Ryan Scalera: [00:23:26] I’m not going to pump ad dollars behind the cop. I do ever. It’s only going to be organic if I’m using other people’s music and then there’s other songs that I’ve done. Like I did one in the very, very beginning of the pandemic.

I’ll working from home. And I produced and recorded the whole thing. So it’s my music. I own all the rights to it.

Brad Seaman: [00:23:45] Okay. Okay. Now, do you have, do you have kids? Yes. Your kids. Are they like, did they think dad’s a sales guy or they dad’s a DJ?

Ryan Scalera: [00:23:53] My, I have a seven year old and an almost two year old and my seven year old loves it.

Like, I think she. She tries to like write and come up with songs because she’s watched me do it VSL. Sometimes she’ll get my car. She’ll be like, dad, can we listen to some of your music? I’m like, okay. She loves it. She, she definitely knows I’m inside. We have a John Barrows book. I like, I want to be in sales when I grow up or something like that.

And it’s one of her favorite books. So she wants to be in sales one. Yeah. Maybe, I don’t know. She may find out what it’s all about and say, heck no,

Brad Seaman: [00:24:28] she might be in marketing, you know, who knows, who knows what marketing will look like when

Ryan Scalera: [00:24:32] she’s in? I know, I know I’m excited for that. I, you mentioned a great point is that like salespeople are starting to act a lot more like marketers.

I think marketers are starting to act a lot more like salespeople too. And both of those are good signs. Like I think they’re both signs that their people are doing well. W where, where

Brad Seaman: [00:24:51] would you draw the differentiation between? I mean, I think I saw online, like, you know, marketing is not sales and sales is not marketing.

There’s definitely some overlap, right? Like in specially I think if you’re thinking about lead generation, because like marketing a sale and marketing a lead or an interest is, is a little different. So I’d love to hear your

Ryan Scalera: [00:25:10] storytelling. I think that that’s the, the absolute great, like common thread between marketing and sales a story.

Right. They’re telling stories to two different audiences at two different parts of the journey, but ultimately the salespeople that are telling a story more like a marketer and, and, you know, going out there catching attention and they’re having better luck on generating opportunities and the marketers that actually understand not just releasing a boring white paper, but how can we entertain and provide value?

In whatever we’re doing in marketing so that it helps the, the prospect kind of self-actualize what it is that they could get out of your product and service. That’s where I think like now that a lot of these teams have like marketing teams have a revenue number over their head top of the funnel, you know, whatever leads, whatever it may be.

But I think that that’s, you know as a sales guy, I think that’s awesome. I know attribution is hard, but. Well, I

Brad Seaman: [00:26:13] definitely think it makes sense. I mean, so I think, yeah, so Kyle hears it. He’s in here in Indianapolis. I think I ever heard him refer to it as like a revenue first team. So like his team has a number we’re trying to hit, we’re trying to impact pipeline.

We’ve got us percent. I don’t know if he referred to it as a percentage or an actual hard number that they’re trying to hit, but they want to be able to say, Hey, this amount of the pipeline, we’re able to contribute back to market. Which would fall in line with that, you know, I think he’s a sales minded marketer.

Ryan Scalera: [00:26:46] Yeah. Mark young on, on my team same needs like me and him clicked pretty much immediately. And I found out about the job opening through him, honestly, but it really helps. I know they say like marketing and sales alignment, marketing sales alignment, but when marketers start to understand, like, not just about like setting up.

A system to pump out, but actually like we’re both going towards these results. It can create such like a better experience for the sales reps or the customers.

Brad Seaman: [00:27:18] Yeah. Yeah. I love it. And I don’t know if it, you know, I think of myself as a marketer as much as I think of myself as a sales person. And I wonder if some of that’s just due to the size of a bit of, you know, being an entrepreneur and starting a business and You’re when your team’s small, everybody’s got to work together, right.

When you get big, then people started getting separate, you know, start getting separated. But when you only have, you know, eight or 10 people sales, marketing team, you know, everybody’s got to collude. So where would

Ryan Scalera: [00:27:45] you say you enjoy spending the most of your time? Is it more on the sales or more of the marketing?

I mean,

Brad Seaman: [00:27:50] it’s probably more on like marketing strategy is probably the place that I think, you know, I have lots of items. Endless reams of ideas and post-it notes. And you know, there’s not enough bodies to execute all my, you know, oh, wow. Oh my ideas. And then I gotta be careful, like getting around idea people too.

So I like to hire people who have good ideas and then all of a sudden everybody’s just running around, coming up with ideas and I’m like, man, we gotta fight. We gotta find some executor’s or there

So I was going to get this stuff up.

Ryan Scalera: [00:28:24] Yeah, that’s a, I think an execution is I think usually the harder part I had to create like a literal filming schedule and like ask my wife to just like, be like, Hey, listen, I’m going to take Saturday and I’m going to go get these things done. And now it’s more of like a smooth, like a well-oiled machine.

I was not a great at executing. And I had to kind of force myself into that behavior. It’s not like natural on that side for me

Brad Seaman: [00:28:52] on that side. Now, when you put out the videos and they’ve got all the background I don’t know if you consider it or, or you consider it, you know, like, are you using Canva?

Like, what do you put? What, like, what’s, what’s in the stack of stuff that you use to put something,

Ryan Scalera: [00:29:06] are you using it? Yeah, so I have a, I have a green screen over there with lights. I use my iPad. To film everything that no fancy camera. I use a software called Filmora nine and it’s, I think it was like $45 for like a year.

Although I used to use a free system on my phone called a video shop or in shot, it doesn’t take much to create pretty like good enough LinkedIn efficient, like sufficient content. And then obviously, like, I, I do have the audio set up and I can record like actual songs. And then, well, you got


Brad Seaman: [00:29:47] good voice too.

You got a good voice too. I try, I try to sing in my house and my family is like, Hey, if you God wanted you to sing it and giving you a better voice, I’m like, come on. We gotta be that. We gotta be that. I’m

Ryan Scalera: [00:29:57] I’m okay. So I grew up with a sister that was like incredible at singing. And I was always like, kind of like I didn’t go towards it until recently, but I thought I’m like, well, if I can’t sing, maybe I can learn to rap.

And it took like years and years, and I put a lot of time into it, but I learned basically that, cause I thought I couldn’t never, you thought you’d

Brad Seaman: [00:30:21] never seen that. Hey, what’s the one thing that you’re really passionate about, right.

Ryan Scalera: [00:30:26] That’s a, that’s a good question. I guess I’m really just passionate about exactly what I’m doing and trying to find a real balance to, to kind of keep doing this.

I, I love making the industry and the job fun and, you know, light-hearted and entertaining. I think there can be like a negative connotation around sales and there can be, you know, just. It’s a tough role in general. So if we can make it a little bit, yeah, yeah. More fun. If we can make it a little bit more entertaining and still like, be very successful in it.

Like I want to bring that out and show people that they can completely be themselves and it will actually probably benefit them more than they think, because I buttoned it up in the insurance industry for a long time. And I actually am. I just, I’m doing way better now that I’m a hundred percent honest with who I am

Brad Seaman: [00:31:20] you feeling like a little stodgy on the insurance?

I mean, insurance seems like a lot of handcuffs, right? There’s lots of you can’t say you can’t do. It’s probably personal. Like people are buying you, the product is sort of the product, right? I mean, there’s, it’s not like software where there’s features in there.

Ryan Scalera: [00:31:37] There’s not a major problem you’re trying to solve when you buy insurance, you’re it’s maybe risk avoidance or, you know, but at the end of the day, like software is something that an every, every salesperson dreams of selling a software that solves a massive problem.

And that’s why I seek out companies that solve a large problem or really changing something that a lot of people will be excited and happy about because it makes the process a lot easier. Then it’s really about doing a really good consult, consultative sales process and digging in and seeing like, well, what’s going on in your business?

How can we help? Let’s try and map this out together rather than like, here’s your different premiums for this insurance? You can make the choice and let me know when you want to write a check kind of thing.

Brad Seaman: [00:32:27] There’s no, and you’re right. There’s well insurance. We could go on and on about the, you know, the differences.

I do think you’re probably selling yourself more than, than in a software situation where you really are selling software. Not to say that people, you know, look, if you’re a jerk people, aren’t gonna want to buy your software, but if you solve a big enough pain you can be a total, you know,

Ryan Scalera: [00:32:47] you can be at the, you could be a lot bigger of a jerk than you could with that

Brad Seaman: [00:32:51] pressure.

All right. Hey, well,

Brad Seaman: [00:00:00] So tell me how you got here. So give me, give me the background. You know, did you go to college and not go to college? How’d you get into sales?

Ryan Scalera: [00:00:06] Yeah. So funny enough with the, the, the music and everything. I actually went to audio engineering school. So I wanted to be a record producer had no real intentions of getting into sales or business in general.


maybe, maybe, yeah. So it, it was It was an interesting process, but I just started a new one to make money in between audio engineering gigs. Yeah. And I got into a job where I was basically selling frozen Italian food at farmer’s markets. And the first couple of days I hated it. And then all of a sudden I started to absolutely just crush it and love it.

And from then on, I just wanted to get into more sophisticated sales. Really kind of learn more about business and it it’s slow, snowballed over a long period of time, eventually gotten to insurance and then transitioned that career into technology sales, where I’m still at today. But as soon as I found tech sales software sales, it was like you know, I knew that I was going to be in it for the long haul there.

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