Sales Hustle is now Sales Transformation
Nov. 11, 2020

Episode #18 S1-EP18 Wildly Creative Prospecting with Ryan Scalera

This episode of Sales Hustle welcomes Ryan Scalera who will discuss important points about Gap Selling and we will hear how he started his sales career. From selling Italian food to becoming a very successful sales person in the sales world.

Ryan Scalera is an Account Executive at A Sales Guy Inc. Ryan’s experience from selling Italian food, door to door Milk selling to joining the Gap Selling makes him very successful in different areas of sales. 

Ryan shares some of the golden insights in Gap Selling in this episode that surely sales people would love to hear. This is definitely an episode to watch as tons of takeaways to up your sales game. 

You can connect with Ryan via LinkedIn if you want to speak more in depth sales, leadership, coaching and training. You can also visit Gap Selling if you want to have a look around and check which areas in sales that can help you develop.

If you’re listening to the Sales Hustle podcast, please subscribe, share, and we’re listening for your feedback. If you are a sales professional looking to take your sales career to the next level, please visit us at and set a time with Collin and co-founder Chris.

Join Our Sales Motivational SMS list by texting Hustle to 424-378-6966. Please make sure to rate and review the show on Apple. 

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Episode #18 S1-EP18 Wildly Creative Prospecting with Ryan Scalera

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales change makers across various industries. The only place where you can get what you're looking for to up your sales game today's episode is brought to you by sales cast sales cast helps sales professional transformed the relationship building process and win their dream.

[00:00:29] Clients. I'm your host, Colin Mitchell. All right. What is up sales hustlers? I've got a fantastic guest for you today. I've got Ryan Scalera who is in sales at a sales guy, uh, which is ran by the infamous. Came in. Um, I actually, coincidentally have my, I am a sales bad-ass t-shirt courtesy of Keenan on today.

[00:00:55] I did survive gap selling live, made it out with a couple of bruises and scrapes. Um, but I was the only one to actually self Keenan thus far. So not too bad. Anyway, I'm going to let you guys learn a little bit more about Ryan and how he got into sales. And then we're going to talk about. Tactical stuff. I imagine we're going to talk about gap selling, uh, and we'll see where it goes.

[00:01:17] So, Ryan, thanks so much for coming on the show. I appreciate you for having me. And that is a trophy too, to where the only one to sell Canaan is a good thing. That's it we're me and Rachel are afraid of that show ourselves and we both sold Keenan. So it takes a lot, a lot. Yeah. I'd love to talk more about that.

[00:01:40] So first let's give a little, give folks a little context. Like how did you get into sales and tell them a little bit about yourself. And I love to tell everybody this, but I mean it, the short version, because we want to save this for the tactical stuff as much as possible. Um, You know, after, after leaving college, I would do what anyone who wanted to get into sales in New Jersey would do, which is sell frozen Italian food.

[00:02:11] And that was my, it was completely by accident. I found out I was about to have my daughter, um, that my wife was pregnant. It was really exciting time. And I was like, Oh my God. I left the music industry right before this. So I knew that I wanted to get into a job where I could communicate with a lot of people.

[00:02:33] And this was selling frozen Italian food at a farmer's market. I then went to selling glass, bottled milk door to door. So I did a lot of the really weird and tough sales in the beginning. And the road has been really winding and confusing, but the best route I've ever taken. Wow. Okay. So common, common story.

[00:02:54] People just kind of, I mean, one thing you said that stood out is you like anybody who wanted to get into sales because that's, that's a, that's an interesting thing because most people don't necessarily want to get into sales. Most people have a very. Bad taste in their mouth from somebody who's sold them or something like that.

[00:03:16] And they think, Oh, salespeople are evil or it's a dirty word. Or, you know, those are kind of the more common things that I hear. And they're like, Hey, I lost my job. Or I graduated in 2008. And sales was the only thing that was hiring and I fell into sales, but you said you wanted to get into sales. So tell me a little bit about that.

[00:03:34] So it was odd. I mean, I didn't end up liking it for the beginning because I realized I wanted to believe in whatever I sold. Um, and that was the challenge in the beginning was working for companies that I either enjoyed their product. Um, or I just believe that they were really good at what they did and they were helping people.

[00:03:55] I think that's like a key thing that people, when they get into sales or they, they see one of those kind of like sketchy salespeople. Um, it typically is something where it's like forcing. Or trying to, you know, pummel over someone into buying something that they may not want may not need for me. I love Italian food.

[00:04:14] I'm an Italian guy from New Jersey, so frozen Italian food. I don't. And the funny thing is that this guy who was at my wedding, like he was a good friend, he still is. And he inspired me as a one day. Ryan, you're gonna find, um, like a more sophisticated sale and you're going to leave this all behind. So he was very supportive and he knew that I was, I was crushing it when I did it, but I could just talk about the ingredients and people would start, their mouth would start watering and I would, I love cooking.

[00:04:47] So I started going into, Oh, this is how he does the role of teeny and it, Oh, it has this, and this is how you got to cook it. And for some reason I was able to. Out do any of the people that I was working with, who just kind of like opened the coolers and showed them the food and then was like, do you want to buy.

[00:05:05] Um, so I I'd strike up real conversation and that's something I learned in the music industry. So I like when I sat down after the music and I was like, what skillset do I have? And I was like, okay, I can get the attention of really important people. I got to meet a lot of famous people and I did it in very weird and slick ways.

[00:05:23] I find that so relevant to calling up CEOs and getting in touch with really important people in business. Is very relatable to how it was in the music industry. Cause you you've given you've even, you've even, uh, incorporated that into how you outreach, which I've seen. I finally got the skills sets to connect and, uh, allowed this show a little bit more of my personality.

[00:05:49] Yeah. Yeah. Okay. So, so basically what you're saying is like, Being creative can really help you in sales, because then you can really differentiate yourself in the type of conversations that you have, the way that you do your outreach or breaking through the noise of all the other bullshit that they're used to hearing from everybody else with their cold call script and their cold emails and their LinkedIn DMS that just are about features and benefits hands down.

[00:06:20] I mean, how many emails do you get in your inbox? Like that's what every. Salesperson, that's doing cold outreach should think they're competing with everyone else and crafting the most perfect educational email. Sometimes it's just how you get it. Even though their services could be 10 times more important if they can't figure out a way to break through the noise.

[00:06:43] And that's where creativity comes in, like, how do you get the attention? And then the back end, how do you deliver once, you know, once you get that attention? It's it's definitely, it's definitely an important point. Um, so listen up sales hustlers, because, you know, showing up differently, being creative and bringing yourself into the conversation can make a big difference now just to be devil's advocate for a minute, right?

[00:07:07] Because there's a lot of people and I've even thought this myself is like, it's hard to scale that. Right. Like, especially when a lot of these sales orgs are like, you gotta do, you gotta have this many meetings, you gotta have this many discovery calls. You gotta have this many demos. You got to make this many dials.

[00:07:23] And it's like, yeah, but it took me a half a day to create this perfect email with this perfect video. And it was a really meaningful outreach, but they haven't responded yet. So it's something that's hard to scale, but there's also an argument to be like, Hey, you need to be spending less time with more people.

[00:07:39] So. Tell me a little bit about that, do both. So I have a long list of people that I call that is pretty generic in my approach. It's somewhat volume, obviously quality. I work on my skills so that I can, you know, get results out of that. And I have a number, but at the same time, there's certain times where I think a little bit of personalization.

[00:08:05] If I can find a connective tissue, which those two videos, I did one for gong. One forget, except there was a connective tissue that I found that I was able to take my creativity and pull it together. That didn't take away from my other activities that I need to do to hit my number, get the right amount of meetings, get the right amount of revenue in, but ultimately it, I don't think you have to be siloed to quantity or quality.

[00:08:31] I think you can run both strategies simultaneously and maybe just save the creativity for some of the more important or bigger accounts. Like if you hit it good. If you don't, you know, you're still playing this other more volume. Um, you know, slight personalization game. Right? Right. Yeah. So making space for both, you know, your quality, your, your quality that are maybe, you know, the, your dream list, right.

[00:08:59] Everybody's got their dream list. Um, but tell me one thing that stood out that you said, as you found this, you know, connective tissue to be able to. You know, open up your creativity to reach out in that way. So tell me about that. Like, are you looking for opportunities to do something creative? Are you creating time or space to like, do research around people on your dream list?

[00:09:20] Like walk me through the tactical steps of like how you're finding time to reach out differently in a very personalized way. Um, On top of also doing your more volume driven activities. So it's something that I definitely stumble upon. Gong was someone I wanted to speak to and I love their company. I love their product.

[00:09:41] I was just such a big fan in general of them. And I started to create a strategy. I knew I was going to do something around this. I had to figure out what it was going to be. So when they announced their, their series, D I knew a lot of people were posting this video of congratulations, gong, you know, you're so awesome.

[00:10:00] Talk to me. Uh, kind of thing. And I saw so many people doing it and, you know, I just figured out how could I take it? We'll take what I know from them. And just instead of reinventing the wheel, just turn it just a little bit, do something different to get their attention. So I connected with a ton of their salespeople.

[00:10:19] I was already speaking with some of them. I was already speaking with the marketing team. Um, and I started to create, uh, an approach where I knew that. These many people had read gap selling. They call themselves gangsters. Everybody keeps, uh, quoting, uh, living in a gangster's paradise. So I decided to change the song to another one that was, uh, from office space to be a little more relevant.

[00:10:43] Then I wrote the lyrics, I recorded it. I put the video together and I made it really funny. And I knew that if I did it this way, they're also a LinkedIn heavy organization. I knew that this would speak their love language, so to speak there. It's getting in front of their ICP too. So I'm connected to all sales leaders, they're selling to sales leaders as well.

[00:11:08] So that's why I chose get accepted the same way is because I knew it would do a similar thing. The salespeople would all kind of rally together and be like, Oh, you have to take this meeting. Now. This is, this is very creative. Like we wish we could do this kind of stuff. So it was very thought out and I repeated the exact process for get accepted as well and plus a little extra branding for them.

[00:11:32] So I think, um, we're a little over 10,000 views, bunch of sales leaders, comments. So it's, uh, it was fun to do. So what w ha has, has have you, number one, did you get the meeting? I don't want to, it's not like a kiss and tell thing. Yeah, I got, I got both of the meetings fairly quickly. Um, it may, it will. Is it out of social pressure?

[00:11:56] Possibly a little where it's like their sales team. As a matter though, you just eat, it's got to get the meeting and then it's up to you from there. If you're PR if you're following a proper gap selling framework, which I'm going to assume you are, then you can see if it's a fit or if there's something you can solve for that.

[00:12:17] Right. Well, it's a work in progress. I don't think anybody is a perfect gap seller. Uh, and I've even seen Keenan be like, you know, even though I wrote it and it is me, like it's not easy all the time. Sometimes you miss something. So I think it's an ideal, uh, to be able to live up to it kind of thing. Oh yeah.

[00:12:37] I mean, it's, it's, it's hard to, uh, it's easy to see things in other people, but that it's harder to see it in yourself sometimes. So especially in a sales person, right. Like you can. You know, see a colleague that's like, Oh, they should have said that they shouldn't have said that. Or why didn't they ask that?

[00:12:52] Right. But then it's harder to see it in yourself, but in my experience, going on gap. So Keenan live, like I would thought I was doing a decent job, but every time his face lit up, I knew I had something coming at me that, uh, you know, it's almost like stopped me in my tracks. Like, okay, what's he going to say now?

[00:13:11] Yeah, it's, it's funny because like that is a lot of the coaching. It's great. It's not, as, I think it's, it's a lot easier to work for Keenan than people might think. He goes hard on the feedback on the live, because I think we need to call attention to that. Most people rely on their product. Or they're, they're trying to sell on technical problems.

[00:13:31] So I get that, but at the same time, like I had a perfect, not perfect, but a very good discovery call I did. And the feedback was you could have gotten to that problem quicker. So I think there's always ways to improve even the perfect call where you close the business. There's a way you could have served the client better, could have done it better.

[00:13:50] And that's one of the best. Uh, benefits of working for Keenan is the amazing coaching that I get, um, which I feel like is for free. Mm. Yeah, no. And that's huge. Something you said stood out right. Is, is, is, is that, you know, there's always room to get better. Right. So I think that's where a lot of salespeople fall short, especially people that have been in sales a lot.

[00:14:13] Sometimes they think that they know it all right. Or, Hey, this is what I've been doing. And it's been working and got me this far. So why am I going to listen to somebody else? Right. But the minute you stop. Learning or stopping open-minded to getting better. You're in trouble. I totally agree. And that's, I think coming here was, I even said to him, I'm like, I was a little afraid, but the reason I was afraid because I was afraid to shine a light on where I need to improve.

[00:14:42] And just coming to that conclusion made me realize that I had to do it. Mm. Mm Hmm. Okay. So now tell me a little bit about, um, like just, you know, for the fo you know, with the current situation and lots of people unemployed and getting laid off, there's going to be a lot of stories that are the more, really common traditional story of like fell into sales or lost my job, got a sales job.

[00:15:06] Like, what do you tell those folks? Like, just getting into sales, you know, being in sales for a while yourself, like what advice would you give them? Uh, don't be afraid to ask for advice from the people that you want to be like, even though, you know, maybe you don't want to be in their position when they are, like I reached out during, when I was unemployed during COVID, I reached out to everyone.

[00:15:32] Uh, everyone that I saw that was doing something I thought I could learn from, and I asked for time, And I mean, sometimes they're just not able to give it and that's fine as well, but a lot more people and a lot higher profile, people are willing to give you advice, give you support and be there for you if they see you taking the steps to do so.

[00:15:53] So you know, the same way. If you get into a company and you're newer, Go find the top performers and maybe do something for them first, instead of just asking, but like try to learn what they're doing, try and figure out what's working and then emulate it and then try to advance on your own as well. But you know, in the beginning, it's, it's all a learning process and a grinding process.

[00:16:18] So you have to do the work. You have to do the work to stay there, to be able to learn more and improve. Yeah. Yeah. I mean, asking for help is really hard for some people, right. Especially in like the, you know, colleague environment. Right. Especially in a sales environment, right. Because if everybody's so competitive by nature too, but you know, something that I've seen a lot, especially what's really ramped up during COVID is a lot of these like peer communities, right.

[00:16:44] Peer to peer. So there's a lot of, you know, salespeople in B2B sales, SAS sales, you know, Different levels, SDRs BDRs, AEs zeroes, all over the place that are just meeting in these places and helping each other. Cause it's just, it's a very safe environment for you to just come and, and get help, you know, but you got to ask, you got to speak up, you got to ask for help and people, human beings like helping people.

[00:17:10] So there's going to be somebody that's willing to step up and give you that help. Hands down. Um, and I've had several peoples starting to reach out to me now asking for advice, help, stuff like that. And I love, I love doing it. Um, I, I'm trying to work with my little cousin right now. Who's thinking about getting into SAS and, uh, I'm starting to work with her and I'm like, well, you know, you've never done sales.

[00:17:35] So let me see where I can tap into my resources. Here's where I think you should start reading. Here's what you should start thinking about, because these are the truths about the industry, but here's the result that could come from it. If this is really what you want, but I want you to soul search and figure out if it is, um, I think asking for help is hard and people don't feel like worthy enough to ask for help, but at the end of the day, people are people.

[00:17:59] And as what you said, they want, they want to help, um, some may be too busy to offer their time, but they'll usually send you some sort of advice. Yeah. Yeah, no, I want to go back to something you said early on, right. Is, cause you talked a little bit about like being passionate about what you sell, either making a difference or something like that.

[00:18:19] How important, you know, this is something that people have different opinions on. How important do you think that is and why? Uh, I think it was about 90, 90% important because listen, every, every product, every service has its flaws. So you're not, you may work for a company that's the third best in the industry.

[00:18:39] Um, that might be for a reason that may not be, but I think that believing in what you sell is extremely important. It keeps you away from selling a product and it puts you towards solving problems. And when I, like, I fully believe in gap selling, that is just so I went through it. I saw the results that had, for me, all the things that they were claiming that it was gonna improve my win rates, increase my deal sizes, stop my discounting, get, you know, bad leads out of my funnel.

[00:19:13] It did that really quickly. So I was like, this is amazing. I would love to do this. I also wanted to sell the sales leader. So it, it just kind of lined up. But if you're, if you truly do not believe in what you sell at all, and you're just using pricing tactics and all that stuff, go find another job like that.

[00:19:33] That's mine. Go ahead and listen up. If you're not passionate about what you're doing, go find something that you are, um, because you know, it's only getting, you're only going to, not that you couldn't sort of make it work or survive, but you're, you're limiting yourself. When, when, when you have a deep reason why you're doing what you're doing, you can go a lot further.

[00:20:00] And, and, and that doesn't mean that like, if you're just getting into sales, that you have to be super passionate about the first sales job, but maybe it's just too, you know, See if you're a sales is a good fit for you, right. Cause it's hard to turn down a job, especially in today's economy. Right. But, um, you know, you're only going to go so far.

[00:20:20] You're going to be limiting yourself. If you're not passionate about what you do, if you really think that you're serving, helping others or have a deep seated, you know, um, reason why for yourself personally, I like what you said. I actually had the turn down a job that paid more. And was kind of like a guarantee that it would all work out.

[00:20:40] They were just set in such a good position that I knew I could get through and I could do it too, but I was just maybe 15% less passionate about that, that I was about what I'm doing. And I, it was a hard convince for the rest of my family and my wife, but at the same time, I was like, I know that it'll keep me happier, long term to do what I'm more passionate about.

[00:21:04] And I think, Oh yeah. It's because you, you, you can't, you can't show up as your best self at work. If you're not, if your personal needs aren't being met. Right. If you're not okay. Happy. If you're not, you know, different things balanced. If you're not, you know, being fulfilled by what you're doing, there's so many personal things that need to be in good order, even, you know, eating healthy, sleeping, well, taking care of yourself, meditating, whatever it is like there's so much personal work that has to be done to be able to show up as your best self and your professional job.

[00:21:40] Yeah. They say that like, if you're five to nine is not good, it's likely that your nine to five won't be. Right or the, or, or vice versa, right. Or the flip side, I had to think about that. But, but yeah, if you're not taking it care of yourself personally, then you're going to show up with a shitty attitude every day and not perform.

[00:22:02] Yeah. Right. Um, and so, yeah, I mean, your personal and professional definitely need to be like integrated in if one is suffering, the other will, for sure. A hundred percent. Hmm. Um, all right. So now what about folks that have been in sales for a while? Maybe they have a, I guess for lack of a better term, shitty leadership, um, or they're not getting the training that they need or they've kind of hit a ceiling.

[00:22:31] Like what do you tell those folks? Um, I mean, this depends on their specific scenario, but I've been a big fan of taking a step backwards to take a step forwards. I've seen a lot of people do it, especially now with, with COVID and lack of jobs on the market where maybe a VP has to go take a director position to build back up to a VP or.

[00:22:56] Become a, you know, a CRO or, and then on the lower side, like if you're an IE, don't feel ashamed to take a step back and become, uh, uh, you know, a hybrid or an SDR. If you know, you can execute and then grow your career from it. Um, I think that people kind of get, they feel like trapped into where they are.

[00:23:20] And therefore they think that if they make a move, it'll be damaging to their career. There's a lot of talk about job hopping, but at the same time, there's a lot of companies that say, have you executed. Uh, what were your results? And I don't really mind the fact that you've been at other companies. What did you do with those companies?

[00:23:40] So for me, I'm starting to, I, I don't just try to get education from Keenan. I reach out to the other people and other thought leaders, and I really try to absorb as much as I can from them. I think people used to. Tastes state too siloed to their company and what they could provide them. Were there any educational resources out there, as you said, those community groups?

[00:24:05] Um, I see a bunch of people jumping on like Thursday night sales you're you're, you know, Scott Lee's like all these people are putting stuff out there. It depends on what you're willing to go out and consume. Some people have a time constraint, but I have two kids, a wife, and a lot of other stuff I'm juggling.

[00:24:23] So I'm, you know, if I'm able to do it every once in a while, I think that other people should start doing that. Yeah, no, I totally agree. In the couple of things you said, you know, stood out, right. Is if you're in a, if you're an a, and you have to take SDR job, like that's that's okay. Right. If you're, maybe you're not passionate about what you're doing and you're limiting yourself.

[00:24:48] But to you, you know, to get in somewhere where you can really, you know, feel fulfilled by what you're doing and really feel like you're serving people well, might mean taking a step back and also, you know, people are different, right? So every environment. Maybe the environment you're in is not the best.

[00:25:08] Some people do well in more of a full sales cycle, you know, the type of role right, where they're doing lead gen and, you know, selling, you know, um, some people might do better in more of a startup environment. Some people might thrive more in a larger corporate environment. So, you know, see maybe, you know, That's something to consider as well.

[00:25:30] It testing out where you, yeah. I, I think that I really enjoy startups, but I've never worked. I have, but not in a tech, a large, large tech company. I have the assumption, but I could be wrong. I could go work for a large company one day and love it. And all the structure and processes already built out. But I I'm just someone who likes to be able to have flexibility, to build those kinds of things and figure out what.

[00:25:57] Is going to work best and where we could take it where I don't think that might be conducive. So like if you're in a startup and you're trying to get to a larger company, there's probably a play that you could do in that startup to help you start leveraging, to get into that next role that will get you where you want.

[00:26:15] I also, like I was an account executive for a couple of years. I'm basically taking a step down into more of a hybrid role because I really want. To lead a sales development team one day and grow one. And I knew that I was only an STR for like eight months when I was one, because I crushed it and just got promoted.

[00:26:37] But I was like, I want to put my money where my mouth is. If I'm really going to coach and train people to do this, I want to be able to prove that I can still do it and I can do it at a level that most people like take time to reach. So that's an issue. Yeah. That's an interesting thing because, um, you know, there's, there's the common scenario where bestseller gets promoted to promoted, to managing a team or VP or manager or whatever, and it's not the right place for them.

[00:27:08] It shouldn't be not every great seller is a great leader or manager or motivator. Um, but then there's also the argument that like, People who lead or manage or motivate, like, do they need to be actively selling or practicing what they preach as well? I think to, to stay sharp, you need to have some essence of it.

[00:27:29] Um, I think that understanding what, not, what your reps are going through, but. Really all intimately knowing where they could be working to improve. But I think that there's more of this like coaching type of role and, and all these like outsource enablement functions that are starting to come in, but sometimes like the basic sales skills.

[00:27:51] Are something where you need your manager to be listening in and coaching you and saying, Oh, I noticed you keep doing this, read this book, or let's try to go through this exercise. Let's, let's uproot your thinking. And I think that if you haven't done sales in 30 years or 20 years, and you've just been in management, you're really good at understanding managing situations and people.

[00:28:16] But I think there's an element to these leaders that still do what they, what they manage. And I think that makes them just that much more dangerous, so to speak. Yeah. Yeah. I agree with that. Totally. Um, because you're also gonna earn a lot more respect from your team as well. If they see you not just being, you know, a sales leader, but a sales Dewar as well.

[00:28:41] Yeah, definitely. All right. Awesome. Ryan, thanks so much for coming on today. Tons of great nuggets in there for you sales, hustlers that are listening. Um, before I let Ryan go, I'm going to let him tell you where you can connect with him, learn more and what he has for you guys. So listen, I really appreciate it.

[00:28:58] It was a great conversation. Um, you can definitely connect with me on LinkedIn. I'm going to be putting more content on other platforms, but I put out very goofy and sometimes educational content about sales, sales, development, sales, leadership, coaching, and training. Um, and I love to communicate with people on the LinkedIn platform.

[00:29:21] So you can always count on me to respond to messages, content, and that's really where I love to connect. Awesome. Thanks again for coming on. If you're listening to the podcast, please subscribe, share with your friends, write us a review, and we're listening for your feedback. Thank you for tuning in into this episode of sales hustle.

[00:29:41] Are you a sales professional looking to take your sales career to the next level? If the answer is yes, then I want you to go over to sales, check us out. And if you feel that you are ready, set up a time to talk with me. And my co-founder Chris, I'm your host, Colin Mitchell. And if you enjoyed this episode, feel free to leave us a review and share the podcast with your friends.