Cold Email Tips from a #1 Tech Sales Account Executive

Kyle Asay breaks down why cold emails fail: generic messaging, feature-first pitches, fake ROI claims, and boring tone. Instead, lead with a specific pain point, name one outcome, add proof, sound human, and follow up across channels. Video works only after you've already got their attention.
I know what you're thinking. Great. Another video about best practice for cold outreach. But here's the thing. Despite these kinds of tips being all over your feed, I still get hundreds of sales emails a month and most of them are absolutely terrible. I don't even read most of them. So I want to walk through from my point of view, what makes really bad outreach not stand out and how you can actually get somebody's attention that might end up being a champion for your solution. The first and biggest mistake is, is everybody sounds like everybody else. Every cold email, regardless of the solution, regardless of the value prop, sounds like all the other emails that I get. A really good gut check for this is can you find what you put in your email almost word for word on your website, or even worse, your competitor's website, if you can. That means you're being too high level, you're being too generic and you're not going to stand out. Another big mistake is people explaining what they do do compared to what you help people accomplish. It goes back to the tip of, look, if somebody says, hey, what does your product do? They're never asking that question. They're actually saying, hey, how can your product help me? Specifically, if you find yourself writing out in your email, we are a seamless, best in class platform that does da da da da da, stop. We tune out, we archive it, we eat, we delete it, we don't care. Another massive mistake people make is they make these incredible claims. Like I got one once, it said, hey, we can help triple your revenue in the next six months. And this was when I was at MongoDB and I'm like, okay, our revenue right now is like 1.4 billion. So you're saying that you could triple our revenue from 1.4 to 5 whatever billion dollars in six months. That's absolutely unbelievable. I know that's impossible. If they thought about it, they'd know it's impossible. Now I'm not saying that everybody is making ridiculous claims like, we're going to triple your revenue in six months. However, any claim that you're making, you need to back it up with evidence. If you're making the claim of ROI of value, I need to see a proof point relevant to me that I care about to give me confidence that you're actually worth talking to another one. That's a huge pet peeve of mine is the hey, I'm not trying to sell anything, or this is a complimentary diagnostic of your current practice. Right? Like first off, everyone is trying to sell something. You're either selling yourself, you're selling your brand, you're selling your company. To some extent, we are trying to get people to make decisions favorable for how we engage with them. So the second you say, I'm not trying to sell anything, even if you wrote the best cold email or cold email after that, I'm tuned out because you just lost all credibility. So never ever say, hey, a free diagnosis or a free demo or a free discovery or I'm not trying to sell you anything. I know that you're trying to build trust. You're trying to add validity to the outreach. Like, well, I really think there's something so strong here. I'm not even gonna try to sell you anything at first, but really, you just come across as a little bit untrustworthy and maybe a little bit cliche. Another one is being too logical. Like, when I'm skimming emails, I'm not looking for logic. I'm not looking for proven roi, boring figures that lack context. I'm wanting something emotional. I'm wanting something that will catch my attention and either make me really scared that I'm missing out on something or really excited about something that I could be adding to my toolkit to make me much more effective as a sales leader. So as you're looking at your outreach, if you're trying to get logic to help somebody make the decision, make sure you're failing. Because people don't make decisions based on logic. They make decisions emotionally and then validate with logic. So the earlier you are in the sales cycle, especially with cold outreach, emotion first supported with logic. If there's no emotion in your cold outreach, your response rates are going to plummet. Also, when I'm opening the email, don't give me a list, don't give me bullet points. That just screams marketing. It's also a little bit overwhelming and a little bit unbelievable if you listing like seven different positive business outcomes, even if they're all relevant, chances are if you have that many, they're generic. Going back to one of my first tips here, if I can find exactly what you put in your email on your website or your competitor's website, it's not going to stand out. But it just screams that it's not unique. It screams that it's not well thought out. It screams like you're just trying to throw mud at the wall to see what sticks. Hey, here are all the things we might be able to help you with. Let's see if any of them are worth it to you. And then let's Take your time to prove if we actually can do any of those things. Don't try to find one, maybe at most two positive outcomes to put in your cold outreach. Never use a bulleted list. Another pet peeve I have is a video first outreach. Now, this is not me bashing video. I like video. It's a great way to stand out. But selfishly, here is why I don't like it. When I get some, When I. When somebody reaches out for the first time and it's a video, I can't skim it. I don't know what the video is about, I don't know who the person is. I know nothing about them. And if I'm in a meeting, if I'm on the go, I can't just glance at it to see if it's relevant. I have to stop, I have to watch it, I have to listen to it. Now you're probably thinking, well, Kyle, that's great, the video is forcing you to pay attention. But here's the problem. I'm annoyed when I start to watch the video. So yes, you have my attention, but I'm going in giving you my attention with a little bit of negative sentiment towards you. So instead, make sure that you're using a video, not to somebody that has no idea who you are. Engage with their content, call them before, send them emails or notes before, get on their radar so you build some level of familiarity, maybe even a little bit of credibility and then use the video so when they go see that video, they're not like, oh, who is this? Or oh, I know that face. I'll watch this and see what they're all about. Something else that's shocking to me is how sellers will just use one channel. They'll use just email or just LinkedIn or just Cold calls. Again, I get hundreds of cold emails a month. I get maybe two or three cold calls. And then I very rarely get thoughtful outreach through LinkedIn and then through video. Although again, video not, not the first touch point. What I can say though is any rep that has hit me with a voicemail, has thoughtfully engaged with me on LinkedIn and has sent me an email, has gotten a response from me, okay, a 100%, 100% response rate for any seller that hit me through the three channels. Voicemail, LinkedIn, thoughtful LinkedIn engagement, and a good email, they hear back from me. It's not always a yes, but it always is. Hey, thank you for your outreach. I love the multi channel work here. Here's why we're not interested here's some recommendations for moving forward. Another one that I think plagues Sellers is you're too formal and you're boring. Right? I think for whatever reason, sellers think they can have personality on cold calls. They can start off with different opening lines that can be funny, get attention, but then the second they write an email, it's just like hyper professional, hyper formal and extremely boring. So whenever I'm talking to a rep and they're like, yeah, I don't really set a lot of meetings through email. I set most through phone call. I'll have them pull up their recent emails and I'll have them read it out loud to me and I'll just say, look, like, would you ever in your life say those words to a real person? Would you ever make a call and give a pitch like that? And the answer is always no. They just for some reason think that the second you write it down, it has to be formal and boring. That's a huge mistake. Don't think that written needs to be super structured, super formal, and definitely don't be boring. So let me give you just a few quick tips of how you can level up your outreach today and get a whole lot better at getting engagement from your prospects. The first one, master emotional relevance. When you're thinking about your prospect, think, what is the number one email they don't want to get from their boss? What is the email that they would get? And go, crap, this is terrible. Now figure out how your solution can somehow help them avoid that problem. And that's you should start your email with. You should make them think about the. Oh, crap, that would suck. Oh, here's a new way to possibly solve that. Now you have them emotionally engaged and it's relevant to their role. They're going to read that email. Then as you go in, you get one pain, one outcome, one proof point. Don't do the laundry list. Don't list out all the possible pains. Pick the one that is most likely most emotionally relevant. Don't give a laundry list of outcomes you might be able to provide. Pick the one that is most likely to be exciting to me. And then one proof point, don't attach seven case studies. Don't give me a bunch of links to case studies. One pain, emotionally relevant, one outcome you provide that solves that pain. And then one very quick story written in the email to give me confidence that you can actually solve that pain and then finally be human. Right? Like, think about the person on the other side of your outreach. They are likely stressed, they're likely busy. They are juggling a whole bunch of things that are not related to your solution, and now you're coming across their inbox adding to a pretty long to do list. If you're not human in that outreach, if you're not thoughtful of who they are as a person, you're not going to do well because people don't want to take on work from somebody else that doesn't reach out to them in a human way. So again, I know there's plenty of advice out there on good outreach. I'm just so tired of getting bad outreach. I wanted to put this video together and I hope that it helps helps a few of you out there. If you found this video helpful, let me know. I'm going the right direction by leaving a like on this video. Then, if there are any questions or topics you want to make sure I cover in a future video, leave me a comment. I read all comments and I love recommendations that will help me help you sell more. Finally, don't forget to subscribe. That way you won't miss any of my upcoming content that I'm creating to help you improve the way that you sell.










