Episode #7. How to Write Cold Emails for the C-Level Executive with Todd Caponi

Episode #7. How to Write Cold Emails for the C-Level Executive with Todd Caponi


The guest of the day is Todd Caponi.

Managing Director of Chicago’s VentureSCALE.

Todd is the author of the award-winning & international best-seller, The Transparency Sale. He's also a speaker & workshop leader as Principal of Sales Melon LLC.



VentureSCALE, the Midwest's first & only Growth Accelerator

What will you learn?

  • How C-level executives prioritize their work with inbox;

  • What is the most important part of a cold email;

  • How content helps in nurturing sales.

Todd’s book: 

The Transparency Sale




Michael: Sales calls, especially the first demo introductory calls that 99.9% of all the salespeople do. I would argue, but these are probably 95% of all the calls or all the new sales that are happening right now. They go through this first introductory stage where you first meet the customer. We talk, and this is very important because as far as I did my homework, your transparency book, as well as your whole approach, is built on creating this first storytelling and then giving this impression of the openness, friendliness, and kind of building this relationship from start. And I think there's nothing more important than having this first demo call where you build the rapport, and the relationships and then continue progressing that relationship over the call.

Todd: So obviously you know about the book, I brought it just in case. There's a step before it that might be interesting for us to talk about too, which is email prospecting. And so like what I see reps do wrong with email prospecting and how they seem to have a lack of empathy for the C-level buyer that they're selling to. That might be an interesting topic too because when I talk about that people are like, Oh, I have to hear that because I wrote a book but my last 15 years before writing the book were in C-Level roles.

Michael: So, you wanted to chat about emails. Why cold emailing doesn't work or argue that why email marketing still works?

Todd: Yes. It's that but the stuff that your audience is probably going to love is the concepts around embracing transparency when it comes to email marketing. So here's the thing, as you know, Chief Revenue Officer, but the thing that everybody in your audience needs to understand is that like as you grow in your career, so you're a sales rep or an entrepreneur or whatever, and then you get promoted to a manager and then a director and then a VP and then a C-level at each rise in your career, your volume of email goes up. So maybe you're getting 10 to 15 emails today, but as a C-level person, I was getting 150 emails a day, so 150 emails a day. And then I had 30 to 35 meetings per week. So I'm in and out of meetings. I always viewed email as playing the instant lottery.

And so it'd be an instant lottery as you'd go to Walgreens, you buy an instant lottery ticket, you scratch it off and maybe there's a winner in there, but odds are it's a loser. And that's how I feel about email is I had to check it because odds are there's a winner once in a while there's a winner. But odds are it's going to be a loser. So with that in mind, I'm checking my email all day long. I'm checking it on the way in, check out on the way out. Now I understand how a C-Level executive prioritizes what emails they'll open and which ones they won't. The ones they'll open are, first of all, but one big thing that everybody needs to realize is that subject lines don't matter like they used to.

So I know growing up in sales for myself, we used to optimize the subject line, but if you pop open your Gmail or your outlook or even look at your email on your phone, you'll see a preview of 10 words of the email. That's what we need to be optimizing. So what I did as a C-Level exec and all my buddies, everybody I know does this. They look through their email inbox. They look at those first 10 words and go, alright, my top three priorities are my team, my prospects and my customers. Those three. If the email has to do with my team, my customers, or my prospects, those are the ones that get opened first.

The next category of priority is my investors, my board, my peers, other employees, partners, all those people. And then there's another tier that is current vendors and known potential vendors all the way at number 14 on my priority list is unknown potential vendors. When you're emailing me, you're coming in at number 14 I'm only opening the ones that have to do at the top three. My team, my prospects, and my customers. So if you start your emails with, I wanted to, or I just was checking in or I sent you five emails before and you didn't open them. I wanted to make sure you got, I wanted to bubble to the top. All those emails that start with 'I' or 'we' and I don't know who you are, those are getting deleted instantly. Those get torpedoed instantly.

If you can make your emails personalized and valuable and valuable to my team, my prospects, my customers, you're much more likely to get open because you're number 14 and when you started with 'I' or 'we', you stay at 14 and you get deleted. But if you start with something personalized and valuable, to my top three priorities, you're moving up and your odds of getting an open go up greatly and it has to be about me and it has to be about value.

Make me smarter, give me something I can use that's going to help me with those individuals or those teams or those people that I'm trying to help. And so the advice for everybody is to get rid of the I's and we're from the beginning of your emails. Those have to go away. I don't even send out an email to my wife with 'I' or 'we' at the beginning of it. Because it's about me and who cares and then make it personalized and valuable. And we can talk about some examples of what I've seen and at Belkins you guys probably are the experts at this too that stand out as personalized and valuable.

Michael: Do you remember a cold email back then when you work as a CRO that you opened, you had a call and then you signed them up as a new vendor?

Todd: There was one company that was amazing. So we were hiring Sales Development Reps, SDRs. And so we decided we're going to open up some roles. I put them on our website, so on our careers page, sales development reps. The next day a company sends me an email that simply says, here is an SDR salary study of how much SDRs are making in the Chicago market, which is where I was hiring them. And that was the first sentence. And then I opened it. The email was still short and it had a link. They followed up by saying, hey, we noticed that you posted some roles. I thought this would be helpful. I clicked on the link and I was like, yes, this is helpful. It's salary. I'm going to hire her, I'm going to make sure that I'm paying market rate. Two weeks later, our quarter ends, I get an email from them that says, here's a board deck template that you can use to speed your time to get prepared for your next board meeting.

I opened it up. It says, Hey, I am guessing you just finished the quarter and we've had other CROs and VPs of Sales that have used this board template to help them prepare and save some time. I opened it and I was like, wow, this is helpful, and so I then, they didn't even pitch me and as it turns out, the template had nothing to do with what the company does, but I went into the signature block and I was like, who are these guys? I clicked on it. They obviously had the tracking mechanisms to know that I was clicking. They called, I engaged and we ended up, I don't remember if we actually hired them, but man, they cut through the noise. My inbox looked like white noise with the, I wanted too's, but then you get, Hey, SDR salary study. Hey board deck template and I don't make, might've done a couple of other ones that are every single time. It was like they knew me, they had the timing right and they just put in a little extra effort and that little extra effort that just jumped out at me. And that's one example of a company that really did it right.

Michael: Interesting. You raised an interesting point here. So many companies, focus on the first intro email as the main kind of email that you put your name in front of the customer. And then the follow-ups are like just popping up to put your email on top of the mailbox. The strategies are like that. You change the strategy to more educational. So the second, third, fourth follow up, you send some names, some case studies. But what you're saying right now is that why don't you start with some materials, some value that I can get from those emails. And then you transition into promotional products or services only with the third, fourth touch. So the first touch would be more educational. Show me the value.

Todd: So I'm a nerd for the neuroscience, the brain science around how we engage, how we make decisions, what motivates us. And the first thing that everybody needs to realize is that with every interaction, we're either building trust or eroding trust. And if your first email, your first note is, I wanted to, I don't know who you are, but give me 15 minutes you're starting below the line. If you start to earn that trust by saying, Hey Michael, here's something that maybe you can use with your team, here's something that is going to make you smarter in the next meeting you go into. I noticed on your website you do this.

Here's something that might help you with that, you've built it up, you built it up, you built it up, and then you ask. So instead of going right into and ask, it's given to get. Earn the right to ask for something and everybody's using email tracking mechanisms. You can see when your potential prospect is engaging and use that as an opportunity to capitalize on that. Once you've earned the right, it's just like going down the street and asking somebody to do something for you. And if you haven't earned that right, your odds of getting somebody to engage with you are much lower than if you did them a favor. You help them out first and I'm just an advocate for give to get, help them out, earn the trust, and then make the ask.

Michael: It's a fair point. Although the problem here is that the technical side of the work, let's say, I want to add to link to a case study or a board meeting template or let's say a link to this study that we did for the salary of SDR in your city. The problem with the technical side of the email outreach is that whenever you attach a link to your first email, it will be blocked by a firewall because you cannot send, an external party cannot send an email with the link attached to it. So your delivery rate will go down. So that's why a lot of folks right now wanted to change that and wanted to translate that with the plain text instead of any links, attachment and all of that. Because right now you can't just receive an email from someone with the link.

Maybe 10, 15 years ago maybe it was still. But right now when you see the link, you're like, why are you sending me the link does want to get access to my bank details or something. Do you want me to catch malware or something? So how would you tackle that? So if you cannot send any attachments or links, how would you explain that? Is it plaintext? Should it be like a long storytelling email or a short one with what should be an opening by the way? The very challenge of this is what should be an opening instead of I, we or….

Todd: And so there are a couple of things there. So first of all, if you keep your emails very short and your link is just hyperlinked into the words, your open rates are still alright versus having an attachment because you probably have links in your email signature anyway, there are links all over your emails. I come from an email marketing background. I was on the sales leadership team at the exact target through their IPO and then we sold it to Salesforce for a little less than 3 billion back in 2013 but you're okay there. However, if you don't believe that, there are two other ways to think about it. Number one, when you go to a website, let's say you're going to go to Amazon or Zappos. Let's say its Zappos and you're going to buy a pair of shoes. One of the things that you notice when you look at a pair of shoes is you'll see the product description.

The product description only has three bullets and then it fades and then it says read more. The reason they do that is that when you load up a page that somebody is trying to absorb information from if there's too much text, it actually hurts like the brain cries a little on the inside. The brain looks at that and goes, well, you're giving me a lot of work. So that's why these eCommerce sites keep their product description very short and then invite you to more information because it's easier on the brain and easier on the eyes. So when you take that to the email world, the same thing happens. If we load up our emails with all kinds of content, it hurts your brain. I might open your email, but I'm going to go, oh, you've given me a lot of work, delete.

So my suggestion is always keep it short, so keep it Twitter length and then include that little link. So hyperlink one of the words or if you don't want to do that, there are two other ways to do it. The second way is to include a link in your email signature so you can link right under that. The third way is that if you want to include more content, put it under your signature block so that there's a natural block for the brain and a mechanism for the brain to go. Alright. I looked at this. I'm going to scroll down. The problem with that last one is that you don't get the click-through history and know whether somebody is engaging. However, at least that's aiding in the brain's willingness to absorb your content and then self-select whether they want to go down. Now when I talk about the email signatures, there are two ways.

You could do that link in the email signature block or there are companies out there that use technology to make your email signature block account-based. There's a company called Sigstr out of Indianapolis that just got acquired by Terminus that does account-based marketing, email signature blocks. And what this means is if I'm emailing you, Michael, the email signature block might say something. You can actually have it populate based on who I'm sending it to. So it might say why Todd Caponi loves Belkins. And at email signature send time, it'll go into the CRM, go, Oh he's with Belkins. It's going to pull that information, populate the email signature block and send it. So maybe you're going to give me some helpful info and then I'm going to go, alright, who are these guys? I'm going to see a block that's customized to me and then I'm going to engage with it.

So there's a number of ways you can do it. The problem is when you get an email that's like, please open this link and then there's a link. Of course you're not going to do that. That's crazy. But if you say, Hey Todd, here's a link to a study around SDR salaries in Chicago. I noticed that you just posted on your website yesterday two open roles. Are you going to trust that? Of course, you are. Because it's personalized and it's valuable and it's speaking to me. So that's the difference. It's not go spam a bunch of people with open this link. It'll be helpful. Personalized, invaluable.

Michael: That's so true. Can you talk to me about follow-ups? You probably hate follow-ups. You received multiple of those. Whenever I sit down writing follow-ups for the sequence, always want to kill myself from the inside saying that guys, I don't have any ideas right now. It's killing me. Maybe someone from my team can do that instead of me. Do we have a best example follow up or a sequence that you would use yourself that is less harmful and still is very effective that you can share with us?

Todd: Yes it's a great point. I mean the first thing is the guilt trip emails are the worst where it's like, Todd, I've been emailing you for two weeks. That kind of stuff. And for me, I look at that and go, thanks for the reminder as to why I didn't open the last ones. And so don't put a guilt trip on somebody you don't know because you asked them for something without building any relationship. It’s crazy. But the second thing to think about is I got yelled at once by somebody who I was having this conversation with and they were like, Todd, why don't you at least respond to these people and say you're not interested, at least do a solid and let them know, well, first of all, when I've done that, it has earned me about five more emails from those people. It's not like I say not interested and they Tommy boy response. Okie Dokie. I'll leave you alone. That never happens. It's Todd, here is why you're wrong. Here's why you should be interested. Boom, boom, boom.

Number two is if I get 150 emails a day, I'm in 30 to 35 meetings. I have to be selective in who I respond to. And so I would literally look for the I's and we're that start each email. I would just click the little box, to lead off. The guilt trip ones. Those things filled into that category as well. If I see the guilt trip ones, they're getting a delete. So what do you do instead? Well, that's a little bit more challenging, but again, when you make it about yourself, you're not going to get much engagement. When you make it personalized and valuable, you will, and it's that I practice too. I'll give you an example.

I had a potential workshop, a customer that was asking me about a workshop, and then they went quiet. They went quiet on me. I teach this stuff and they went quiet on me. So what do I do? Well, I don't go, Hey, how are things going? Remember me? Or give them some Oh, I haven't heard from you in a few weeks or whatever kind of whiny crap I could throw at them that they don't give a crap about. Instead I write blog posts, I send them a blog post. So here's an idea around your open floor plan environment or whatever it is. They open it up and then in it says, I know how you guys are set up. Here's just some interesting research that I came upon and thought it would be helpful. They immediately responded with and like I didn't even mention the fact that they hadn't got back to me, but what did they do? They were like, Oh Todd, this is great. Sorry we haven't gotten back to you. Here's what's going on. So when I think about follow-ups in existing sales or even in prospecting, I just always go back to that personalized and valuable gift. People value with no expectation of some kind of a giveback. And you'd be surprised how many customers actually do.

Michael: While you were saying this, I was just kind of calculating the cost for this. I was like, okay, so we need copywriters to create the content, we need a designer to do some images there, we need to post when it’s time. It increases the cost of sales. Would that be valuable for the business? But at the same time, I think how much money we're spending on different tools, different CRM tracking databases.

So we have surrounded ourselves with this or all the tools and then we just forgot about actually creating the value for the customer rather than just automating the process and spending. Because right now, just imagine, right now you're spending maybe like five years ago, you still can buy something, a monthly subscription, but then now you just cannot get the monthly subscription. You need to be built annually. So you need to put your cash in front of you for the whole year, which is like $20,000 here, $20,000 there. And then at the end of the day, your cost of sales is very expensive and it doesn't work. So what you do you start sending this whiney desperate emails about I want to make my money back from the tools that I spend on this. I bought this database, so can someone respond to me so I can make a sale.

Todd: I think that you guys are in a great situation with this podcast. For example, let's say I was a target customer of yours and I was running sales like I was a VP of sales for a company. One of the things that one of my clients did, because they've got a podcast and they sell into a different space, so it's not salespeople they're focused on, it's more HR and Chief People Officers. They may have got a podcast. What did they do? Well, instead of doing traditional prospecting, they would send a note to a targeted Chief People Officer at an organization they wanted to get into and said, hey, we would love to have you be a guest on our podcast. We love the things that you're doing and your organization and we'd love to share your story. Their open rate went from 5% to 68% overnight doing that and they had a whole host of these Chief People, Officers and HR executives that wanted to be on their show.

They weren't selling themselves this client of mine, but in time as they researched and did the podcast, they got to know each other. They built a relationship and then, sure enough, a good chunk of those converted into customers. I'm not suggesting that you use it as a trick to get into these people, but it goes back to you're creating value for that individual. You're sending them a personalized note, you're making them feel good about what they've accomplished. You're not selling them, you're building the trust up and then when the time is right, you can pitch. You can talk a little bit about what you do, but you'd be amazed at how you attract customers that way instead of you trying to pull them towards you.

Michael: It's a very good point. Very good point. At this point we are trying to create a lot of content, but when we entered the market, and we did this 3 1/2 years ago when there was like 100,000 of different lead generation agencies before us. So it's like, guys you're screwed, don't do this. Just save your time. You're still young. Do something different. Let's be very passionate about what you're doing and what kind of value we can bring. We were analyzing the competitors and what do we notice that to give an example, every company right now have a blog. In B2B you have a blog, and when you go to every company's blog, all of them are generic. All of them are the same. All of them use the same stock photos, the same structure. It's boring. I don't want to read this. Why do you do this? Do you convert people from the blog?

So what we did was say, listen, we're going to hire a graphic designer who will create these unique images for every blog that we wanted to send out. We wanted every blog post to know that we put effort, we put money, we put our time, and we put our minds into that. So this is the value. This is entertaining because right now it's not just about educating and also about entertaining. Because I can spend time reading this or I can watch Netflix or I can go and watch YouTube. So why YouTube is so popular because it's sort of an entertainer but podcasts are popular because it's an entertaining webinar. People would not listen to webinars when driving. They wanted to hear the podcast and jokes. So what we did, we created unique images. We created unique posts. We always wanted to before posting. Everyone is reading and everyone wanted to delete something like, okay, this is not necessary. This is what people want. This is the flow. This is storytelling. Did we explain the topic? Did person want to read more?

So once we did this and then now we are scaling this. So we have this blog as that content or platform where people can nurture and educate and it's unique and it's different. Then we build the How to Library when people have time want to look through 50. 60 pages report, eventually probably going to come up with a book. But as I've heard on one of the podcasts that you did, it's like you don't want to read the book right now. You want to postpone because you need to start with the proposal to come up with everything and then you can grow to the book. So it takes years. So we started with this how-to thing, we grow this and we see that the people specific audience engaged with that. Then we say, okay, why don't we build the Help Center when people can educate themselves on a more technical side, what is spam? How would you set up a mailbox? And plus when you do this, you work and create the content for your users. But at the same time, Google and other SEO agents are putting your website. They're putting you on top in front of all other competitors just because they give you, okay, you've created the great content, and you put your mind into this, so why don't we put you in front? And that gives you the leads. This gives you organic traffic.

So right now when we do the podcast, we do that again. We wanted to make it unique, we want to make it something that we would listen to, that we cared about and probably there would be an audience that will listen to this and appreciate this. And eventually, they will engage with all the portions of our conscious strategy or our marketing. That is also something that we appreciate something that we would put our minds into and they will say, hey listen, this is a great company like we did with the case study. If you go to the case study back in the page, you'll see like templates, conversions, numbers, all of that. Probably if some of our customers were listening to us, they will say Mike, you put a lot of information there. Well nothing sensitive in a way, but a lot of competitors can go into, hey, this is how they do this. But at the end of the day, okay, someone will choose this, but a hundred of the customers that will reach this will say, listen, I learned something. It's great. The guys are doing something they are leaders of this industry so why don't I engage with them? And we've been in the market for three years. We've been growing like 50, 25% month over month, and this is the result of this kind of mindset. Since we wanted to stand out, we wanted to be creative in a very traditional industry like sales.

Todd: It's awesome. They really go to this give to get mind-set. You can't establish credibility by pounding people with emails. You establish credibility by showing the world that you know stuff and you're building trust through giving. There’s not one thing in the book that I wrote that you can't find in either my blog. I think I've done 26 podcast interviews, almost every word in this book. It's out there somewhere. You don't have to buy the book. Seriously, I don't care. I'd love for you to buy it. I think it's beautiful. But my point is, what I'm here to do is to try to help people. I might start to advocate for this profession. It drives me nuts that the Gallup Organization puts out a list of the most to least trusted professions every year, and sales continue to finish in the bottom three every single year and it's not moving up and it's driving me nuts.

So I want to make this profession more respected. I think it has to happen. It really does. When you think about the proliferation of reviews and feedback and everything we do buy and experience and that has made its way into the B2B world. We can't be hiding flaws. We can't be telling myths through to customers anymore and expect to get away with it. So that's number one. And then you look at the brain science and when we lead with transparency and embrace our flaws, buyers make faster decisions. They make better decisions. Your win rates go up, your work deals that you should win instead of the ones that you should lose fast. You make it really hard on your competitors to compete against you.

Those two things together, the brain science around transparency, selling better than perfection. And the proliferation of feedback and reviews. We have to be honest advocates for our buyers. We need to Sherpa our buyers through the buying journey and not try to sell them, not try to pound them with emails, not try to trick them, and not try to lie to them. And when you have those two things come together, this profession is going to move up and we're all going to celebrate the wins of that. So that's the point. And I love the way that you're thinking about this is given, give, give, make people better at what they do and they'll be attracted to you. And that's exactly the way that I think

Michael: When I went to your website, preparing for the session, I bumped into the tips section where you just record 2-5 minutes videos and I opened three or five of them and I've taken some notes and it was like, this guy knows what he's talking about. It was the kind of eye-opening experience for me because sometimes when someone write the book or build their campaign or plan around certain knowledge. They want it to be consistent with their book and not creating additional content, which is like right there. So you open, you say, Hey listen, this is tips about how you need to sell on the call or what the subject line should be. And you just explained some briefly and then that's it and I think that's, that's great.

This is a great selling tool for you because you gave a value, you showed that you know what you're doing and why you're talking you shared some insights where a lot of people were not thinking about, so I've been on this, I've been doing selling and outbound and prospecting for the last seven and a half years. And to be honest with you, I've never thought about starting out with educational content first and then moving into more proactive sales. And today it's one of those days when I learn a lot. I was like, wow, okay. So I didn't read the book, I didn't read this. But I learned just by Googling, looking through some of the podcasts, which you did some videos and I learned this and I bet if I go to the book and dive into and look through it and take some notes. I will learn a lot.

So basically, you took like 15 years of your experience, you put it in the book, you said, listen, guys, you want to say 15 years, just read through this. And that's amazing. I definitely need to tap on the shoulder to my Chief Marketing Officer, Dmitriy who set up the session because what he did, and this was his homework. She follows a lot of freelancers, a lot of people on LinkedIn and she read this post from one of these freelancers. When that guy was asking, who should I record the podcast with? Leave the comment, and in the comments, there were multiple people and you Todd, was one of them.

So Dmitry reached out to you. He did the research to reach out to you and we set up the session and a lot of people knew that these were bestselling authors, but because of the competition in your space. It's also very happy. It's a very competitive space. Sometimes you just miss some of the names, but I am recording this session with you. I had a great session with James Muir who wrote the book The Perfect Close. You guys rock and I definitely think that you should have the sales library when you put your books and then whenever you have someone new that you're training, or we have this kind of ladder, promotional ladder structure where you starting out with the Junior SDR and you move into the Senior SDR you need to read certain books, go through certain training and people well educated I definitely think that we need to put one of those books just there for people to educate themselves. So great job. Appreciate that. I appreciate everyone who will be reading and is a fan of The Approach.

Todd: Well, I'll tell you the book is more about... What I've noticed is that neuroscientists and brain scientists, they've pinpointed a lot of what drives decisions in human beings. And that was part of what really started this whole thing is, we had done a study in my last role that really kicked it off for me. I ended up in a library and I'm like, wait a second. If we as human beings know how humans make decisions, would that be great for the sales and marketing and client success community to know? And so a lot of the way that I think about this is it's fewer stories of me because who cares? I feel like it's more about how do we bring data and research into the sales community and just make salespeople smarter. Because I think the neuroscience community is about seven years ahead of where sales are. And my next project is around sales leadership and taking some of the neuroscience around employee engagement and creating a sales leadership framework and bringing that to the sales world. So I'm trying to speed those things up together too. So I'm a nerd for the decision science and brain science around this. And I'm trying to spread the good word of all of that to make people smarter about their professions.

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