Sales Hustle is now Sales Transformation
Dec. 4, 2020

Episode #28 S1 - EP28 Coldest Caller In The Game with Geno Oliva

Collin Mitchell welcomes Geno Oliva as he joins this episode of the Sales Hustle podcast. Geno shares a little background about himself and how he got into the world of sales. He also shares some of his daily sales practice and tactical SDR & ADR skills to help sales folks bring in some sales fire.

Geno Oliva is an Account Development Representative at Udemy. Udemy is the leading global marketplace for teaching and learning, connecting millions of students to the skills they need to succeed.

With over 4,000 updated and engaging courses ranging from technical skills to professional development, Udemy is the best way to develop your employees continuously. Whether you are looking to stay on the cutting edge of technological innovation or have a comprehensive e-learning platform for your company, Udemy is the platform for you.

You can find out more and connect with Geno Oliva on his LinkedIn at

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.

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Episode 28

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

[00:00:30] I'm your host, Colin Mitchell. What is happening in sales hustlers. Welcome to another episode of sales hustle. I have got a fantastic guest for you today. I've got Gino. He is the coldest color in the game, and he's going to bring nothing but sales fire. Uh, I found Gino on LinkedIn came across a post. I was super impressed with some of the things that he's putting into practice on a daily basis.

[00:00:57] Um, and we're going to talk a little bit about that. Gino. Welcome to the show. How are you doing? What's going on guys. It's um, it's awesome to be here, man. It's uh, I'm really stoked to talk about this dude. I honestly love sales development and my different tactics to try to get meetings and things like that.

[00:01:12] So, um, it's really honored for me to be here. I love talking to people who are passionate about this as well. I'm really want to grind and get those meetings. So, um, listen to a few of your episodes. Absolutely love it. And just, you know, can't be more excited to be here right now. Awesome. Well, we're glad to have you Gino, just tell folks a little bit about yourself, how you got into sales and what you do.

[00:01:31] Keep it short and brief so we can save as much time for the tactical stuff as possible. 100%. I, uh, I got into sales development about a year and a half ago. Graduated in college at a couple of buddies. Um, who were older than me, got into sales and were like, dude, you gotta check this thing out. It's a, it's a really great way to hustle.

[00:01:51] Make them make a good amount of money. Um, learn new things, try new things out. I was like, why not? Um, started at the super small company called T-Mobile 20 people calling a hundred plus people per day doing this crazy stuff. Um, now I'm at a more established company for about a year now called you to me.

[00:02:07] Um, and just, you know, keeping the grind that I got from that super small startup and, uh, you know, applying here. Awesome. What are some of the early things that you learned in your sales career that have kind of stuck with you? Um, so far? Yeah, I mean, there's such a difference between working as SDR, BDR at like a small startup, like 50, 150 plus people, um, at a more established company like you, to me, it was like 200 plus people.

[00:02:34] Um, even that's not that big, but I think the biggest thing I learned was just like, um, you have to get after it, like it's second day, second day I started, I was on the phones. Um, you know, my, my friends buddies like really encouraged me. Um, and I think you've just got to like try new things. Get after it as much as you can, don't get it like hard on yourself.

[00:02:53] We all fail in this like sales development role. Um, I feel like pretty established now, but like today, like it's hard. Um, so I think just like getting after it every day and just like trusting that it'll be okay and not beating yourself up too much at all. That's pretty much it. And then from there you can get into more like tactical stuff and like get like a little bit more established.

[00:03:12] Um, but especially just starting out, just like do everything and anything you can, I'm going to see what works for you. Yeah. Give me some examples of some of the things that you're doing that are, you know, you are finding successful with what you do. So one big thing I wanted to talk to you about. And everyone listening that I think is like pretty slept on in the sales development community.

[00:03:33] Um, it's blind calendar invites. Um, I think emailing is just kind of dying. It's kind of going by the wayside a little bit. Um, it's like, I mean like a good open rate is 30%. I was just kinda like what's going on here. So what I've been doing most like three or four months, I'm going to make a post on LinkedIn in a little bit, but is sending calendar invites.

[00:03:53] Like the first time I'm reaching out to someone I'm sending the email directly to my calendar invite saying, Hey, can we talk right now? It bypasses the whole email thing. It stands up to people's inboxes and it's been working really well. I'm seeing about like 10 to 15% accept rate for these blind calendar invites that I'm sending.

[00:04:09] Um, and it's just really more effective. I'm trying to get away from. Email, even personalized emails as much as I can, because I just don't think it's working now. And I don't think it's going to be working in the future. Wow. That's really pushing the limits. So tell me a little bit about this. So you're just blindly sending an invite for a time and basically seeing if they'll accept or not.

[00:04:31] Yeah. So I'm, I'm mostly doing it for people warmer ish. You know what I mean? Um, so ideally it's someone who had talked to brush me off on the phone, like in the first 30 seconds, someone who, you know, we had a close loss, close loss off with like two years ago or something like that, or some like vague connection to my company at all.

[00:04:51] Um, those people are connected with on LinkedIn. Those people I'm always sending calendar no matter what. Um, and also people like, yeah, like my tier one accounts where I really want to get into the, these accounts, I'm just sending invites to anyone and everyone it's like a part of my cadence. Now it's a part of my steps.

[00:05:06] Um, and it's been really effective and I can't promote it enough. Is that something that you just came up with on your own or somebody was. Doing it and saying, Hey, this, this is working and you just said, Hey, you'd give it a shot. Or how did you come about starting to implement this sort of strategy? Yeah.

[00:05:23] So me and my buddies from my first company, um, we have like a, like a group chat. Yeah. We all moved out to different places, but we talk like all the time, just about different sales, development, tactics and things like that. And what's working and it's something I kind of preliminarily tried when I was first getting into sales, you know, it's like kind of like, Oh, wow.

[00:05:41] Count me in my Bubba. Wasn't getting much success with it. So recently establish a framework around it, you know, um, like. Leaving the voicemail, sending an email, directing them to the calendar and by kind of getting my wording and phrases exactly how I want to do it. I'm kind of made it more of a science out of it, sort of testing it.

[00:05:58] Um, so. I kind of did it a little bit when I started, but now it's like a full fledged process and, uh, you know, uh, part of my, my daily steps pretty much. All right. So listen up sales hustlers for those out there that are, you know, open-minded like myself and willing to try new things. This is something that Gina has been trying and getting pretty good success with.

[00:06:19] Now, I'd imagine that there's. There's some, um, you know, you mentioned that you have a bit of a process around it now and a bit of a framework, you know, I'd imagine that there's some best practices or things that you've tested as far as like how far out to send it. Right? Like typically people's calendars.

[00:06:37] Are kind of booked up usually the week of, are you typically sending those out like a week out in advance? Um, or what sort of window where it's not too far out, but not too soon where, you know, it's going to get rejected to have to break that down a little bit for me. Yeah. That's a great question. Um, so I usually try to send it out, um, like four or five days in advance.

[00:06:57] Um, Friday afternoons have been killing it for me. I'm not too sure why. Um, I usually say, okay, on Friday afternoon, I'm going to send you a calendar invite. Um, let me know if this time works for you, but anytime after like three or four days, cause I'm reaching out to like VPs and director levels and stuff like that, their calendars are usually pretty full.

[00:07:15] Um, but an important note is like, usually what happens is like people just don't accept the invite. Then you have a meeting like that. Usually they suggest a new time and you're like, okay, great, thanks for suggesting this new time. And it's a calendar invite that works for them except the schedule and the AER things like that.

[00:07:31] So. I would say the specific time for the calendar invite isn't as important as just sending it out, but you definitely want to be respectful of people's times and putting it out three to four days in advance. Okay. So three, four days is kind of the key window. Um, and then, so a lot of these people are basically seeing this and then she's suggesting another time, I'm curious to find out what the show rate is on these meetings.

[00:07:57] Yeah. So the show rate, it hasn't been too drastic to like my regular cold call or like email meetings. I'm hovering about like a 70 to 75% show rate, which I know is kind of on the lower end of like the sales development kind of like world. Um, and that's just because, um, I'm like booking anything. I can, you know, I get any interest that there's there.

[00:08:18] Any, any, any sort of inkling I'm booking the meeting, I'm trying to get there. I know my show. Rate's going to be a little bit lower than that. The quote, unquote average, but it's somewhere around 70, 75%, kind of my natural, my natural zone. Hmm. Okay. Okay. Interesting. All right. So tell me a little bit about what you do when you have a warm hot prospect.

[00:08:41] Um, because I know this is how we connected as I came across a post that you put out there and you do things a little bit differently than, than, than I'd say most people where you hit them on all channels in. Break that down for me. Yeah. I want to pull up my actual cadence so I can actually get in the weeds here.

[00:08:59] But really my approach is if it's a hot lead, if it's someone I talked to, I'm going to ask her to maybe dig a few times on the phone and they just said, email, email, blah, blah, blah. It's an old inbound. If it's like anything or a person that I think is going to respond that I really want, I'm going to do everything I can.

[00:09:15] Um, so, you know, I started off with a classic, you know, call voicemail. Like LinkedIn connect and buy targeted email, fully personalized. Try to get that. Do a bump, a classic mom, like, Hey, any feedback on my, my, uh, my email two days later than that two days later than that, I'm sending them a video. Um, either through a feed yard saying it a video through email, or it's a connected with me on LinkedIn.

[00:09:39] Hopefully they are, I'll send that video through, uh, LinkedIn. Um, after that I'm sending them another, um, email that it made for them, the company, um, Of just like, kind of like the process and breakdown of you. Me, I'm sending him another voicemail. I'm sending him blind calendar, invite another email and then a text at the end of it.

[00:10:01] I'm saying like, Hey, blah, blah, blah. I haven't been again, been able to get in touch with you the last couple of weeks, um, wanting to see if this works. Um, so I'm pretty much hitting them up on every channel. And I know it's kind of a controversial topics that people don't. Like being as a aggressive, I'm all about it, everywhere that you can.

[00:10:19] Um, so you know, it's talking about phone voicemail, LinkedIn, DM, video, text messaging. I love it. I mean, there's just so many places that you can connect with people. You don't know what's channels going to work best for any video people. So why not just use them all? Yeah, they're there and you're missing opportunities if you're not using them to your benefit.

[00:10:44] Um, Now tell me a little bit, um, when did you start implementing that and what side of sort of success are you seeing with this cadence? Yeah, so I'm saying, I really like to like my first email, it's about a 50% open rate, which is like super high for like 55% right now. Um, the reply rates, like on all of these, there's like a 30% chance that like once 35% chance at once someone comes into this cadence, um, they're gonna reply to me.

[00:11:11] Which for me is huge. You know what I mean? Like that's, that's really good for me. All my other cadences or anything that I've tried in the past. I've been like around like five to 10%. I'm like, like a good, good day. So this has taken away challenge for some people with this one is you can't fully automate this.

[00:11:27] There's some manual steps in there. And so you've got to have that mapped out and be diligent about, okay. You know, part of it, you can maybe sequence or automated. But, you know, like doing the video and things like that is something that takes, you know, a manual step. At least if you want to personalize it because sending some generic video in a sequence is, is not going to be nearly as effective as something personalized.

[00:11:50] I mean, when you're addressing their name, maybe what you talked about, something that you, you know, research on them a little bit, you know, that's going to have a much higher hit rate than, than anything else. 100%. And I don't, I don't knock like automated cadences or anything like that. I do that. Like, I still have that going on the background.

[00:12:05] I have people continuously coming in and out of that, um, I just know that's going to be a way less reply rate for, for everything that I'm doing. And these are from like top people that I want to get in touch and like in touch with, are these people that you've been engaged with previously or are these like your dream list?

[00:12:21] People. Both. Um, so I just, I just got, I just got an op with, uh, this VP software development at Hulu. So I was first and I was like, Oh dude, who was sick? I would love to get this up person went into here. Um, that's kind of like a rare occasion. It's mostly people that I've talked to in the past closed loss opportunities.

[00:12:38] They they're familiar with you to me, the tickets, some courses, things like that. Um, but I also sprinkle in some like, what are you doing? What are you doing different with closed loss opportunity, cadences versus like ones that are still in the funnel. So the ones that are still in the funnel, I am so does a couple things I do.

[00:12:56] It depends on how the meeting is going. Uh, but since you, to me, we target like multiple personas at each account. Um, what I'm doing is reaching out to other people within that account, with the open up and saying, Hey, we're talking to your. VP of it. Um, I wanted to see if you, as you know, like a applications leader would be interested in our content for your team.

[00:13:15] So something a little specific to you to me because we can reach out to so many different personas. Um, so I don't know how applicable that is to, you know, the. The general, you know, sales, uh, sales, development life. Um, but usually I'm kind of holding off on those actual people into my take takeover. Um, if it's a closed law, any like close off or like they wore a hot lead in my database or anything like that is going into this, you know, high value cadence.

[00:13:42] All right. What do you tell anybody? Who's just getting into sales, SDR, BDR type of role. Um, you know, that you wish you knew when you were just getting started? Um, email is dying. Uh, I think it's still, I think it's still a little bit alive today. I think you can get away with getting some meetings over the email.

[00:14:03] I think, you know, for looking macro long-term at sales development, I don't think it's going to be nearly as effective in my five to 10 years. I think it's slowly dying. It's just my opinion. Wouldn't rely on that at all. It works well when used with other channels, you know, integrated together, right? When you're using the phone, dropping a voicemail, sending an email, sending a LinkedIn DM.

[00:14:26] So integrating with it, but not just, you know, hitting, you're hitting, play on your cadence and thinking that you're going to sit back and get a bunch of meetings like that doesn't work anymore a hundred percent. And I think a lot of reps kind of fall into the. You know, prioritizing that lane. Um, probably a lot of your listeners, if people are really into it, like aren't doing that, but I know it's kind of easy to fall behind that trap and that cadence trap and the automated trap.

[00:14:53] Um, cause you know, other channels, it's, it's more scary sending a video to a prospect. You know what I mean? It's more scary telling their mobile line, um, double dialing their mobile line. It's more scary. But if, you know, you want to be in the sales game for a long time and you know, Sales development for you and you kinda like it.

[00:15:11] Like you just got to do these lists. Let's pick that apart for a second. So you said it's scary using video and double dialing on the mobile line. Why do you think that is? I think people have a negative, um, connotation with them. Interrupting people's day. You know what I mean? I don't think people either the, our BDR that's your job, your job is to interrupt people and catch their attention.

[00:15:36] And why not use every channel at your disposal to do that? I mean, If you have a mobile number, like why would you not use it? That makes no sense. I mean, you know, I I've, I mean, I've been, I've been in sales for over 10 years. Right. And like the tools that we have today are fantastic. We didn't have that.

[00:15:55] When I first started in my first sales job, I was literally handed a list of names, a phone, a script that was garbage. And told not to use the CRM because it didn't work. You know? So like the only thing that was going to get meetings was literally hammering the phone and being creative. Right. And you're interrupting people's day.

[00:16:15] Like that's what you've signed up for. That's the gig. So why not use every tool that you have at your disposal and video is huge. Like, I don't understand why more people don't just use video. If you're you're, if you're scared to use video or you're uncomfortable getting on camera. More of the reason to start doing it because the more you practice it, the more you do it, the better that you're going to get, the more comfortable you're going to become.

[00:16:41] And you'll start to learn what works, what doesn't work. Um, you know, it, any type of role that you're in sales, you gotta be open and willing to try new things all of the time, because whatever your work you're doing now, even if it's working, it might not work in two, three months. Things might change, you know, um, So you always gotta be willing to like push the limits.

[00:17:03] In my opinion, it's a good point. And if there's like one thing that I would want anyone listening to this it'd be takeaway from is if you're not sending videos, you gotta be sending videos like you, can't not be sending videos to your prospects, getting ready to close, like at all points of the sale, you can use video.

[00:17:21] Yeah, like so much easier than to type an email, to just flip on a camera and talk at them. It's more enjoyable for me too. It's like, dude, I don't want to spend five minutes typing up the email going over, like the grammar, things like that. I'd way rather pop a video on 30 seconds later, send it out. It's literally that easy and so much can get.

[00:17:41] Lost an email, like people don't te people's attention spans are so short, like send them a big, long email, regardless of what phase of the sale that they're in, whether it's cold and you're just outreaching to them for the first time, or there's somebody that you've already gotten through discovery and maybe through demo or through trial or whatever the case is, you know, and you're trying to hit them bunch of points.

[00:18:06] They're going to read, not most people aren't going to read all of it. But why not make it easier for them extra that they get everything, you know, that you're trying to help them understand to get to them in the next phase. Put it on a video type, a short email and link a video in there. And you will be quite surprised how much more successful that actually is.

[00:18:31] Yeah. The, the difference is dramatic. Um, so like if reps aren't doing that, they have to be doing that. Another thing that I think has slept on it is w we talked about at the beginning, the calendar invites, you know, said put some time down four or five days away, um, from, from your prospect saying, Hey, I sent you a couple of emails I've called you.

[00:18:50] Haven't been able to get in touch, hoping putting down some time on your calendar is a better way for us to connect. Um, I I've sent over 200 of these, these out, um, and it's around a 15%, et cetera. Um, when I'm leaving a voicemail, I sent them an email. Um, you gotta be doing that, um, because just so much more effective than any email you could send.

[00:19:12] Um, so Johnson, the videos you gotta be sending videos to. Aren't trying to just book some time in your prospect's calendar. Just put some time down. Um, I mean, what are they going to do? Decline it. And it happens. It's not a big deal at all. Like different I'll tell you that, you know, the only things that are working are things that are different that are standing out.

[00:19:31] So, um, you know, I'm, I'm somebody who like is always open to try new things and pushing the limits. The blind calendar invite is something I personally have never done. Um, I'm going to give it a, try myself and have our reps, give it a shot and see what happens. You know, this is with a qualified prospect though, not, you know, some top of funnel person that you've never spoken to before, you know, just lining up, you know, time on calendars.

[00:19:58] That's going to be wasted, right? This is qualified opportunity. This is somebody you've spoken to before. Maybe they're ghosting you. And you're like, Hey, get it. Understand. Maybe you're busy. I went ahead and just made it simple and sent you an invite if the time works great, but it doesn't feel free to propose a different time.

[00:20:15] Right. So is there any specific copy that you've tested that works better than others when sending these out? Yeah, I have actually, um, let me pull it up cause I want to get that exact verbiage. Right. Um, because I've tested a lot of different things. Um, and the ending here, um, is pretty critical and I've seen like a pretty big increase and it's like, Hey, whatever.

[00:20:36] I've been trying to reach you out via email and your phone in the last few weeks, hoping funding down some time on the calendar to talk to you is a better way to connect one sentence of like a personal thing to that prospect. Whenever I'm reaching out to him specifically, if he's done anything with my company or anything like that.

[00:20:50] And then the last sentence is always feel free to say no. Comma, but if you're open to connecting, please, just to the invitation or suggest a new time that works better for your schedule. Um, if this works, I'll add the meeting, like a details, hoping to talk to you soon, Gino that's like the best messaging found around this kind of blind calendar.

[00:21:07] And I think pretty people feel free to say no. Um, but if this works for you accept or suggest a new time, um, I've never had someone get angry over it or anything like that. The worst thing that's happened is people say no. Um, but. Yeah, like I said, I can't cam promoted enough. I literally can't. I liked, I liked the copy.

[00:21:26] So let's break down the copy again. Uh, just for a second for the sales hustlers listening. All right. So listen up sales, hustlers. It's it's very short and sweet copy, which I love that about it. Um, it's, it's personalized. Um, and it's low pressure, right? So it's basically, you know, you got your intro, you're being very clear about what your intention is.

[00:21:46] You're also letting them know that, Hey, you've been, you know, trying to reach them phone and email and hasn't worked out. So you're trying something different, which people will appreciate. Um, and then you're giving them the, okay, to turn it down or propose a new time. Um, but even if they reply, it's a win, because then you got the conversation going again.

[00:22:03] So if they say yes, no, maybe. Not now, better time, whatever the case is, you know, you're going to stand out differently and whether they accept or not, doesn't matter as much, it matters more that they get you. Get the conversation going that may be died out. Yeah. And I've had conversations where I'll call this person.

[00:22:21] I sent it like a blind calendar invite the week before I was like, Hey, I put some down time on your calendar for like 2:00 PM on Thursday. I know you can meet then. Um, but I was hoping we could talk and make some time to talk this week and it's worked. Um, the thing about it is like this, your prospect will 90% of the time see your calendar invite in their inbox because they're not getting that many calendar.

[00:22:42] Especially from like random people, you know what I mean? So they will know your name. There is a very high likelihood, they will know you. Um, and you'll be able to like have a warmer conversation regardless of the, the like results of the black calendar invite. I love it. I love it. Um, so even if they don't accept, you're going to stand out and they're going to remember who you are, so that the next time you had, you can have them the next time that you do reach them, you can have a much warmer conversation.

[00:23:12] Um, and that's the key, right. Is standing out diff you know, standing out. Reaching them in a way that people aren't and having a warm conversation the next time that you do get to speak with them. Now I'm curious to know, um, on these calendar invites, if they don't accept, then what do you do? Do you have any sort of follow-up prior, leading up to the meeting of trying to remind them to get them to show up or at what point do you realize, Hey, it's a no go on this calendar invite.

[00:23:38] Yeah. So I'll send them like one, you know, like reply inside the calendar and by email that way. So I'll send them one more of that, like a couple of hours before the actual time that they have been accepted. Um, and I played around with like different texts and things like that, but, uh, the one that's worked best for me is like, Hey, um, I'm assuming this time doesn't work for you to talk.

[00:23:59] Um, cause you haven't accepted the invite. Um, one to see if there's another time either this week or next week that works for you to talk. Um, again, everything like this is low pressure for them. I want it to be as casual as possible. Um, so hit him with that transparently. If they don't expect the calendar invite right away.

[00:24:17] When you send it, the probability of you booking a meeting with them, like sure. We're sending like an email, like that is pretty low. Um, I haven't had as much success with it, but I'll still do it and I'll still call them after it to try to get them on the phone. And if I get them on the phone, I could say, Hey, I sent you a calendar invite for this time.

[00:24:33] That conversation usually goes pretty well. Got it. Got it. Awesome. This is something that I, I highly recommend all you sales hustlers out there. Give a shot and play around, make it your own and, uh, see how it goes. Uh, Gina, thanks so much for coming on today. Let folks know where they can connect with you.

[00:24:51] Learn more about some of these things and anything else you want to let them know. Yeah, I I'm big on LinkedIn. So LinkedIn is like my place. I love it. Um, connects me on LinkedIn.  coldest color in the game is my headline. I'm happy to connect with anyone at any time. Talk about this strategy in more detail, you know, I'll send you a exact copy of what I'm actually using.

[00:25:12] Um, so I'm happy to talk with anyone and anyone, anyone, and everyone who connects with me. Um, I also am in the middle of creating a unique course for like outbound sales. One-on-one one-on-one it should be. Available on you to be not come by the end of the year. I'm taking a little bit longer than I expected to.

[00:25:28] It's actually pretty hard process making a course online course and things like that. Um, but that should be, that should be live ideally by Christmas time I'll be promoting it on my LinkedIn and things like that. Um, and I think that would be a huge help for anyone, either just starting or anyone to look into like upscale their sales development game.

[00:25:45] Awesome. Again, appreciate it. If you're listening to the podcast, please subscribe. Share it with your friends, write us a review and we're listening for your feedback. Thank you for tuning in to this episode of sales hustle. Are you a sales professional looking to take your sales career to the next level?

[00:26:02] 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 Mitchell. And if you enjoyed this episode, feel free to leave us a review. And share the podcast with your friends.