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Caleb Sinn is Cold
Episode 19912th September 2022 • INSIDE Inside Sales • Darryl Praill
00:00:00 00:37:41

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Ready to learn how to give your cold outreach a health check in 5 steps?

Join Darryl and Caleb Sinn, Founder @ SocialBloom as they look at how to check your emails aren't landing in spam (and what to do if they are), the two checks your data needs to pass, the messaging technique to make your buyers feel seen, the secret ingredient for standing out, and why there's still a place for the phone.


Find Caleb on LinkedIn, or at

Connect with Darryl on LinkedIn.


Are you in sales, but you're not using a sales engagement tool? Then you're probably losing out on revenue because you are not engaging with prospects at the right time, with the right cadence, and with enough persistency. You need VanillaSoft.

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What is the most disputed, discussed, argued, emotionally passionate topic that you constantly encounter in the sales cycle, in your sales team in the pit, whether that be live in person, cuz maybe you've gone back to the office or virtual because you're still working from home and you talk to your colleagues on teams or slack or whatever it might be as, as you talk. And this will come up often.

I'm gonna, I'm give you the answer for the way in a minute folks, but this can come up often talking to sales, leadership, talking to the marketing folks, talking to the, to the rev op folks. What is the most emotionally charged topic? Beyond is the phone dead or not, cuz Hey, that's always emotionally charged.

So we're gonna go what's the think about that one. So you ponder that and then I'm gonna turn around and to give you some time, I'm gonna say welcome to another episode of the inside inside sales show. I am so glad you're here. I've missed you. It's I've had a good week. I've had a busy week. I've been so busy. Making content and getting the word out there. I hope you're enjoying some of it on LinkedIn, et cetera. I have some great productions or I'm talking to some amazing people. It's a lot of fun.

One of the things that came up over and over and over again, when I was head sales or I was the chief revenue officer from a sales point of view was messaging. It was always messaging over and over again, it was messaging. I thought I just did a LinkedIn post about this. The post I did on a related front was talking about sequencing and it was saying you have to continually optimize your sequencing. You know, you can sit back and get the sequencing that's given to you the messaging, for example, on your phone and your social and your email.

And you're gonna bitch and moan and say it doesn't work. And my bad results or my weak pipeline is because the sequence sucks. And to which I said to that in the post, I said, that's bullshit. Because you have control on that. You can iterate on that, but instead of iterating on that and trying to understand and get behind the numbers and do an AV test and, you know, within a matter of weeks or a month or two, and say within a quarter, let's be really crazy.

You have it all figured out. No, no, we don't do that. We wanna bitch and moan and then we wanna do one of these shortcuts. We wanna go steal what other people have done because they're smart and damn it. If it worked for them and it worked for us and I'm gonna defend that shortcut till I'm blue in the face.

Yes, I've implemented the shortcuts and the sequences still suck. The messaging still sucks that my results still suck. It all sucks. But that's not my fault. I took it from the expert and what that is, my friends is that's not iterating and that's not optimizing. That's not improving. That's not a best practice.

What that is is just, that's just taking a shortcut. That's just stealing somebody else's work. And here's what you need to understand is when you steal somebody else's work, that means that work has had to bubble up and come to your awareness. And someone's trying to say, socialize this technique, this message, this approach, and you finally see it.

And then you, and it takes a little bit longer to implement it at the same time that timeline is progressing. It's also already in the inbox, in the, whether it's email inbox, social inbox of all your perspective prospects, and they know the formula. And that's why it doesn't work when you steal it because the same time.

Realized it, the buyers realized it. Now they're filtering out that one. I, I had this conversation with my team here at AgoraPulse where I'm like, Hey, when you say ABC Inc, less than greater than a AgoraPulse in your subject line. Cuz you've heard somewhere that really opens, well, I already know the formula and I've got 42 emails alone today from all different vendors using the exact same subject line.

And therefore I just. So don't steal you iterate. But what I'm getting at here in a nutshell is the most passionate thing is messaging. And what are the best practices too many of you are heavily invested in your own point of view. You would rather be right than be rich. You would rather prioritize your ego and your vanity over your results and your take home. And I get it. I get it. I was young once too, but then you get a mortgage sheet of kids and all of a sudden take home, pay matters. It's funny how that works.

So where am I going with this? I'm going with the following. We can debate is phone or dead or not. I'm not gonna debate that today. We can debate a social selling. Functional it doesn't work or not. In fact, I would tell you as a marketer, it's not social selling it's social marketing because I've never bought a damn thing on LinkedIn. I have bought something over email and I have bought something over a phone, but I've never bought anything over LinkedIn. I have accepted a meeting over LinkedIn, but I didn't buy it over LinkedIn. I bought it on the phone. So the social selling and social marketing, I don't know.

But what every single person always falls back on over and over and over again is email. It's email. So what do we know? We know email is part of that same sequence that you are so in love with. We know your sequences aren't necessarily doing well.

We know that the most passionate thing going is what's the message. And we know that email is still the top performing channel and we need to invest heavily into it yet. We don't. So why is that? I don't know, know we should do. We should get an expert. We should get an. Who can talk to us about cold email, best practices, but who could that be? Who do we know? Who could tell us what that is?



Caleb. Welcome to the show my friend.



He was selling money more and more as I was giving my intro either he was feeling loved and his, his ego was increasing in the size. As I, as I, you know, was alluding to him or he was smiling because he might have heard a truth or two in what I was saying. So I gotta ask ya, why were you smiling my friend.



The sequence had three touches. Mm-hmm , that was the sequence. It was three touches. And the sequence was doing what I just said, where he had stolen the technique from other major, you know, messaging experts out there that are prolific online. And I'm like, none of this is original. It's only three touches.

This is gonna convert like shit. And they're like, no, it works. So then I went to his boss, the head of sales and I'm like, you. I'm telling you it's gonna commit like shit. And they looked into it and guess what? It was converting like shit. And they're like, how do you know this? And I'm like, this is not rocket science.

I mean, there's a thousand sales, engaging vendors out there. A thousand email companies out there who all have the stats and what works and what doesn't just based on how things perform on their platform. And they're not following any of it. And instead of him being receptive to it, cuz it's gonna help him make more money.

He was locked and loaded that he was the best sequence writer going now. Humility is a wonderful thing. He became an amazing, amazing sales leader. But that comes with growth. So today I, I need you, my friend to walk us through how we can take our cold email cold email, because it's easy guys. It's easy gals.

It's easy people to take, you know, a warm email. And move it on, but it's a son of a bitch to do it with a cold email. So Caleb, I need you to walk us through what we need to do. And as Caleb starts to talk about this and we'll talk back and forth, you, you know the rhythm here, folks we're gonna go off in tangents.

We're gonna tell stories. We're probably gonna make fun of me at one point. You wanna look at things that Caleb's telling you, that you can introduce into your own outbound techniques. And again, you wanna AB test. I remember we opened up by saying don't steal other people's, you know, templates or techniques instead iterate.

That's where we're focusing on today. I don't think Caleb's gonna give us templates to just go use this as your subject line. He's not gonna do. Rather, he's gonna tell us what we need to do from a peer technique point of view. So where do you wanna start? What's your opening cell here, sir?





And then upon digging, where were we? We were in their spam folder. Yeah. Right. So that's a classic case of deliverability. And by the way, we ended up selling that account. You know, is there ever really dead boys and girls? All right. It's not, you just gotta be able to make sure you, you, you block, you set time.

'em off on your calendar to go pursue those dead ones to rework them. But deliver is huge. Now, if I'm a sales rep, I may not have control of my domain. So what do you mean? Like, what do I need to do to my domain? Who do I need to talk to? What do I need to tell them to make sure my stuff's getting delivered?



But the reason I was getting on fired up is because there are a lot of people. Who are freelancers who are, you know free agents who are, you know sales reps for hire I, the list goes on and, and you have to set up your own infrastructure. And these are things you don't think about, or they're small teams.

And even for example, if you are a sales leader, listening to this conversation, and you're looking at. Outsourcing some of your sales or your SDR function to an agency, a sales development agency, checking with them as part of your due diligence on their deliverability to make sure that they're okay.

Their spam scores, everything else are good, cuz they can get they can get the black, bold. I can't remember the exact term to come to me. If. An agency, an agency represents multiple clients. And if one of their clients, if they're doing a boatload of email, basically spam, that's gonna affect their overall deliverability score.

So all their other clients are hammered by poor deliverability because of that one client. So you just wanna kind of do some due diligence with your sales development agency. So, and the same thing. For your organization here, if any of you sales reps know that there's someone on your team, who's doing a shitload shitload, it's a technical sales term, a shitload of of just spamming, just like, you know, I don't care about quality.

I'm gonna, I'm gonna send out, you know, a hundred thousand emails you're gonna get reported. Your domain will get reported for spam. And then everybody in the team. It's gonna have low deliverability. So this is something that you really wanna think about hard. So, I mean, so what's the obvious signs from that, Caleb, is it just that I should be checking and if I'm appearing in my, if it over and over again, I'm getting feedback that my emails are gonna their spam folders.

What recourse do I have?


And a lot of times you can see if those warmup emails being sent are landing in spam or the inbox. So then you can take a good guess, like, Hey, if 70% of my emails on this tool are landing in spam, probably my everyday emails are as. At that point, you have a couple directions go into, if you're using like a one off domain that isn't used for anything else, you can kind of just buy a new domain and start fresh if you want with the best practices. Or there are people obviously that can help kind of take it off the black list. Right. And you're kind of starting fresh that way too, but you still have the same domain at that point.


They hit a certain score their Dean marketing qualified, and they hand it off to you, the sales team, then over to you to do your thing. And now you're gonna start your sales sequence with them. What you may wanna do is talk to your marketing team as well about making sure. As they initially get that content information, whether it's from a form or it's from a tool like a zoom info, or it's a purchase list, there's two things they should, they should do, which will help you ultimately in your deliverability.

One, what they should do is they should be enriching that data. So you can use a tool like a clear bit. There's lots of tools out there that will upend clean the data. But the process is also still checking the email address just as an.

The second thing you can do is you can use other tools. I think it's like one comes to mind is never bounce or bounce zero don't quote me in that one, be get the idea. And what they're doing is they're fundamentally, they're warming it up. They're sending an email to the server just to see if the server responds back saying yes, that account is legit or that account is not legit because. Marketing is doing too many bulk emails and there's too many hard too many softer, hard bounces. Then again, they penalize your domain and that affects you in sales.

So deliverability huge, not a simple answer, but if you're seeing your open rates are not where they should be and you think you do have a kick ass. Cold email message to be heard and it's not happening. Then start there. Brilliant advice.

So it main, this is, this is great guys. This is for the first time in my podcast history, I may be able to say, it's not you, it's your deliverability. And that's there. Therefore, nothing for you to fix here. It's somebody else's fault. All right. But you all stuck about accurate data. So I was kind of basically bridging into that. So talk to us about accurate data.


So you don't bounce, but also too, like making sure that your data is accurate to your ICP. If you target, like, I don't know gym management software companies, so that's like who you're target. but all your contacts don't fall under that ICP. I mean, that's inaccurate as well. You know, your message just isn't gonna resonate with them. So there's like two parts to it.


Across the board are like this sucks. It's the wrong phone number. It's the wrong email. It's not the individual. It's going to a switchboard or it's a gatekeeper. We need better data over and over again. Let me on the data thing. So what are my options for getting accurate data? So, like I mentioned, you mentioned, we both mentioned zoom info, but that's like a Cadillac.

Yeah. That's like a, and, and it comes with a Cadillac hell. It comes with a Lamborghini price tag. So are there other tools out there that I can use I can utilize or I can pitch to my management or I can pitch to my ops team to use to help me get the data I need to to succeed.



If you're in Europe, another one is a company called cosm they're big in Europe. So that's another one you can look at. Then there's couple other ones,, again, more so north American, but they've really done well. Now these vendors all have degrees of accuracy and they all have different features and functions.

And then of course you can there's solutions. Casper, not as good, a quality, more of a credit based system, but if you're in a budget that might be what you need. And then of course, zoom info is, is coming with the gold standard right now. But even that I wanna set expectations. Okay. Even that the expectation is, is any data from anybody, any vendor, no matter how often and frequently they claim to clean it and review.

Is typically at most like 60% ish accurate, just so you know. So when you bitch Amon, you say, my data's not accurate. Well, is it like is one in four legit? It's two and four or three and four, you know, if it's two and four. Okay. You might have an argument, but if three and four are, are, are legit. Then you don't have an argument, just so you know, you're, you that's as good as you're gonna get and you have to do your job.

All right. So we talked about accurate data. All right. This is, so that kind of sets us up. Do I have the data to send the email? And is it clean? Will the email be delivered? Boom. What's next? I, now I'm writing the email. What's my next best practice..


I know, like in the beginning you mentioned about not talking about templates and this isn't really a template, but it's more of like how you're gonna form your email. Right. So so like if we talk about personalization or like that opening line in your message a lot of people do personalization and usually what that is, is like, you know, Hey, I saw on your website.

you have a lot of great reviews. And then they all of a sudden go in like a pitch on their message, but that doesn't really have flow. And it doesn't really like, yeah, it, it has no like relevancy. Right. But when I think about relevancy, I think like, like if you host a podcast and you reach out to somebody else who was just on another podcast and you're saying, Hey, I saw you on X podcast.

Why not? Like join mine? And we can talk about something that's very relevant, right? Like that. That flows really well. It makes sense. And it's not like this fake personalization and you can do it at scale. Now you can't really do like personalization at scale. I don't believe so at least.


Cause I actually want to use that as an example. So gimme one second in real time, Darrow's over to LinkedIn and listen to. What he just said, relevancy. So this is not an email. This is the LinkedIn message I sent to Caleb. All right. I said, Caleb, I heard you with Ollie in the auto closed gang on their revenue month series.

I'd love to connect with you and I'd love to get you on my podcast. Any interest relevancy, fair point. Yep. Right. And then he was super would've to say yes. I mean, right about now he's in the middle of this recording going, what the hell was I thinking? Yeah, but it's too late. He's here. You can't stop him.

So that's okay. So I often, I love that you're distinguishing relevancy versus personalization. So I have my opinion on that. Can you you're you're my guess. I'll let you go first. What's the difference in your point of view and your perspective? Between relevancy and personalization?



If I, if you're selling to a head of sales and you said to me, Hey, I know that as head of sales hitting the annual revenue target is, is stress. You know, can I have 10 minutes in your schedule to talk about how we can help you achieve that goal? Well, it's personalized to me a little bit, but it's not relevant.

Yeah. But it, but if you said to me, Hey as a head of sales, I know you have the number to hit, but I know what's probably bugging you even more is the fact that your reps consistently suck at following a very simple. Discovery process that you've put in place or updating their CRM or even following your messaging guidelines.

And it probably exasperates you if I could help get rid of that short term frustration. So you could hit that long term goal. Would that be worth having us every time that's relevant, cuz it's personal and it's emotion. It's it's like, it's, it's what I'm living right now. I just got off a call with a rep.

Who's got a very simple, yeah. I want you to follow the medic or the spiced framework. And you, you did even ask what the metrics were that they were using the measure, the pain they're experiencing. What the, hell's your problem? We talked about this that's relevant to me. That's pissing me off. Yeah. And that's an example.

When it talks, we talk about not a template. I use the word framework, you know, so there's lots out there. I've put up this before. I've got a few here that, you know, a. Which is awareness consideration comprehension action. There's B before or after bridge there's pass problem, a agitate solution there's ADA, which you would know from, was it Glen, Glen, Gary, Glen Ross, which is attention, interest, desire, action.

All of these first lines, you know, Josh Bron has their, his four T's TTTT first being trigger. Then third party validation, then teach me and tell me. And so that's where relevancy comes in.

So I'll give an example. I have a, I, I have a presentation I use when I'm giving sales kickoffs, talk about these frameworks and it often comes across better with an example. So TTTT the first one is trigger. So it says Darryl. Now the first line, all right, this is relevancy, but it's also trigger. It's triggering me. Notice your sales team has changed a little since you took over as chief revenue officer, that's all it. You know how relevant that is because you're not making an op I heard you on the podcast.

He's noticing that my, the dynamics of my team have physically changed since I took over. That's subtle. Yeah. That's relevant as opposed to, Hey, I noticed you I saw you, you became CRO six months ago. Congrats. Let's personalize. It's not relevant. Yeah. So those are the frameworks that make a hell of a difference in your, in, in your actual relevancy versus personalization.

Do you have, when you're, when you're trying to teach this to your own reps or with your clients is this something they pick up on right away or do they struggle with this?



All right. So that's, I'm, I'm, I'm gonna follow proven frameworks that we know work. I'm gonna monitor my open breaks. I'm gonna make sure that my opening line is not just personalized, but in fact, incredibly relevant to my ICP P persona, I cuz. And I know that the data's good. So where do I go next?



It was a much more beyond email. It was about just, you know, when, when the regular stuff isn't working. What can you do to stand up in the crowd and be. All right. And so basically what I would call gorilla marketing or gorilla techniques to, to do some crazy. But as it relates to cold email and being creative, Victor shared with me recently, something he did after my podcast went to, went to air with him.

And so what he did was he had an, he had a sequence of which was heavily email and exactly to Caleb's point. He knew what his response rate was. Not even did he know his open. But he knew his reply rate. He knew his reply rate was, was, was, was averaging at, and he shared, he goes darryl. I won't give numbers away for confidentiality.

He said, darryl, this is my open rate. Boom. He goes, I made one change. Other words, he got creative and it's open opening line and I can pull it up here if I can find it very, here we go. His opening line was. Simple you cha. So this is more about, he goes, Hey, I'd like to invite you to listen to my recent podcast episode.

And then he goes on. That was the opening line. Now I'm not saying that's the best written line. I'm not saying that's hyper. But targeting he's targeting sales reps into sales podcast. And he probably mentioned my name, you know, on with darryl inside, inside sales. So maybe he was leveraging my brand and my reach.

There's lots of reasons why this might have worked, but what matters was a couple things, a he got creative and experiment. He actually changed it cuz it was timely. It was, it was recent. The, the, the show was out there when he did. His reply rate more than quadrupled, not doubled, not tripled quadrupled.

That's such a simple technique. Now it's only gonna last for so long because then the show gets stale and. And then everybody's talking about Caleb in his episode and nobody knows what the hell Victor was, but that's what happens. That's creative. I love that. So you gotta, again, iterate, iterate, iterate, iterate.

All right. Last one, you have one. You had, I open up by saying we, we can all agree on certain things. Like the phone is dead, but. Caleb says, hold my beer because you wanna, you have a point you wanna make on the phone.



You need to go multichannel, which is phone and social. And here's the one thing I will say to every single person you heard me say, I've never bought a damn thinking on LinkedIn. Cause I always buy it on a phone or maybe email, but there's a live one on one connection taking place. It's not on social media, ultimately, what do you want as a sales rep?

Why do you send the email? You send the email to get 10 minutes on their calendar so you can use the phone or a video conference and you can have a live conversation. That's why you're sending the damn email because you know that you can tell stories. You can qualify. You can do all the wonderful stuff.

So stop hiding from the phone. We just did an episode, not too long ago with Callum B. Was it the, the, the phone qualifier? Is that what he, I can't remember what he was come up. It was a great name, but I can't remember. And Callum talked about this. He talked about how to use the phone to generate more engagement.

We had a great session with Jason bay. Jason bay talked about the whole, when you get them on the phone, how to use the self-disclosure Princip. To actually basically get permission from the prospect to have the conversation. It's incredible. So there's lots of, we, we're kind of building up here folks to, to give you all the tools you need across multiple channels and techniques, but we're spot on here.

Caleb's a thousand percent right? Do the email, then do the phone. In fact, many sequences. I, I love Jeb blunt. Jeb blunt will say every single sequence should start with a phone call. Why do you start with an email? Why do you start with a social touch? Because ultimately, no matter what channel you're using, your whole goal is to get on the phone with.

So why don't you just start from ground one with a phone call, right? Yeah. So, you know, phone call voicemail, and then boom, email, your email could say, you know, I just a PS, I just left your voicemail. You know, please check it out. It doesn't have to open that way cuz you wanna trigger them, but you get the ID or your continuity.

So I like it tie you in the phone. Don't be a woos. The phone is not dead. Caleb we're outta time. My friend Caleb is with SocialBloom. Talk to me about social. Give me the low down. Why should my crew of incredible sales peeps talk to you? What is so special about SocialBloom? And I know it's special.



Hope I'm not saying anything. I shouldn't say they're Caleb, but they are thin cuz it's incredibly competitive. It's incredibly competitive. So for them, you know, whether he drives a Lamborghini or he drives, you know, a, a, a gently used 10 year old Prius is all based on how good he does his job. And what I love about working with agencies like SocialBloom is that there.

It's two ways. I use them well, three ways. One, I would use them if I want experiment. So I would say small engagement. Let's go try a new new target market, for example, or a new ICP or a new persona. So it's an experiment that I, if, if it works, then maybe I'll staff up internally, but until then I need to, you know, try it with them.

And if it doesn't work, then I didn't hire any. That's one, two is if I want to scale. So I just wanna go nuts. Oh, we found something here. I can't hire people fast it up. Let's go. So one is experiment. Two is scale three is to learn. So I, when you find an agency, this is really good. Give them the business and then watch everything they do, and then bring as much of those best practices in, in house.

Then what you will find happens is you'll never get rid. So you hire them to learn from them, but then you realize that they add so much value, that you'd be stupid to get rid of them. So different ways of using agencies versus in house. I've done a lot of shows in this before in the past. You wanna see that?

Let me know, hit me up on social, but in the meantime, we are at a time that is Caleb Sinn, founder, SocialBloom, You can find 'em on LinkedIn. Just like it sounds Caleb Sinn with two NS, not one. My name's Darryl with two RS, not one Praill with two L. Not one, Darryl Praill. You like it. I am with the Inside Inside Sales Show. I had fun this week. I hope Caleb did too. And I hope you did too. Go review your cold email outreach that join me again here next week. Talk you soon. Take care. Byebye.

This episode was digitally transcribed.