Cold Email: Lessons from Real Outbound Campaigns in 2025

This episode is brought to you by Zttle. We're halfway through 2025 and one thing's clear. We've been feeling this firsthand for sure. Events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking, breakfasts, everyone's all in. Everyone's leaning into in person. Events have become a core part of our playbook here at Exit 5. So far we've hosted two virtual sessions. We do them twice a month. We do one large virtual event, sometimes two a year. One in person meetup. And we're deep in the trenches right now planning drive our annual conference coming back to Vermont in September. We use Zuttle to help us run a smarter event strategy. They help us with driving, registrations, managing invites, automating, communications, reminders, analytics, tracking. They do it all. They have a salesforce integration that also makes it easy and simple to report on pipeline and revenue from events without having to pull an op. So you'd know exactly how your events performed. On top of that, the differentiator with ZTTL is how their team is insanely good at supporting us. They always go above and beyond for us and that's how we've been able to keep the momentum going with 12 events this year already and just a small little team here at exit 5. So if events are a part of your marketing strategy like they are ours, you should check out Zuttle to see how Companies like Zillow, CrowdStrike and Iterable are using the top event platform for business events in 2025. Head over to zuttle.com exit5. That's z-u- dash dash l.com exit5 to learn more. You're listening to B2B Marketing with me, Dave Gerhardt.

It is our last session of the day, the ultimate roast of told emails. This is the one we got by far the most submissions for. So I am very excited. And we have again another stacked lineup to close out the day of roasters for us. I'm really excited about who we've got here. Tell me in the emails, have you liked today? Are you excited today, Carrie? It is a Lego typewriter in the background. I'm a big Lego nerd, so thank you for noticing that. Amazing. So today, cold emails we got Zoe Hartsfield. She is at Apollo. You probably follow her on LinkedIn. She's got a great following. She shares great tips for cold emails. So very excited about that. We then have Will Allred. Am I saying your name right? You can tell me when you get on in a second. He is the co founder, CEO of Lavender, which they do some of the best content in the game. If you need content inspo like, please go look at Lavender. They're doing amazing things. And then we have Max Greenwald. He's a CEO at Warmly AI. He's fantastic as well. And I told him that he had to wear that hat as part of attending. And then we have Alex Fine, who's the co founder of Understory, which is an agency I've actually used in the past. So I reached out to him and had him get on here. So I am very excited. All right, I got Will and I got Max. You guys are coming on.

Hey, hey, hey.

Oh, my God, the hat.

It's here.

I love it.

What's up, everybody?

Kind of joking, but he's actually wearing the hat. This is amazing.

Oh, why would I not wear the hat? I mean, this. First off, this thing is glued to my head. I can't take it off.

It's amazing. Where is it from?

Got it in Scottsdale, Arizona.

Beautiful. I love it. As you can tell, I love a good hat. I have them all over my background.

Yeah, Danielle, it's not too late for you to wear a hat, but I guess it might be hard with the headphones.

It's hard with the headphones. I. You know, I could maybe grab one. Oh, we got Alex, and we got Zoe, so I'm gonna kick you guys both on. There we go.

Better late than never.

Perfect. Sorry about the links, guys. That's on me. Event organizer. Are you guys excited to roast some cold emails?

Let's do it.

Love it.

Why do cold emails suck? Like, why do. Most of them absolutely suck, and we hate them in our inboxes. Looking for real answers, guys?

I'll give my short answer. Unless, Alex, you want to go first?

Oh, go ahead.

So, hey, y'.

All.

I'm Will. Danielle. You did get my last name right. A rare moment. The amount of people who say Alfred, like, blows my mind.

There's no way.

I get Daniel all the time, so don't worry about it.

There you go. Well, that's just a sign that people don't read. Just like, they don't actually read any emails that you put in their inbox. The big thing that I think of when I think of, like, why do most emails suck? I think one people don't know how to write a good email. I think that's, like, a simple truth. They don't necessarily think about it from the perspective of, I get these emails, I would not like to receive These emails, How can I write emails that don't do this? But the other piece is like who you're contacting and like if what you're actually saying is relevant to them in this moment. I think most of the time that's actually very wrong.

Agree with that. Zoe, what do you think?

I think like, to Will's point, targeting is like a big issue. But I don't know. I think back to the fact that I was in college five years ago and everything I was taught about writing a professional email does not translate to sales or marketing copy. Maybe an internal email to your boss or maybe like a different type of communication. It made sense to be that overly professional, that long winded, that detailed, but that's not the way that Cold Outbound works in any way. So I think people like come out of school either with incorrect information or they never learned how to do it at all. And yeah, so I think it's just like, it's a lack of education around like what Good look.

Yeah. In my mind most people just talk about themselves and that's a big problem. It's like you're solving for someone else's problem, not telling them who you are. This isn't it. You're not dating somebody. You're not saying, hey, here I am. Get to know me a little bit. You want to solve for their pain. And I think most people just completely miss the mark on that. And then if you screw that up in the very first line, your toes from there. No one's reading the rest of the.

My mom's a professional matchmaker and dating coach and I think she'd say even in dating you don't want to talk about yourself so much as you want to listen and learn from somebody else. And I guess I'll just sort of end by saying that I run a company called Warmly and so I think, I think it's hopefully self explanatory why we don't like cold emails.

I love it. Someone asked, what's their success rate? Dating advice. Is this about to turn into a dating advice? Ruth?

You all can look up Rachel Greenwald online and fill out the form if you'd like to.

This is so great. All right, cool. So I want to know a little bit more about like, let's talk a little bit more about like automation versus human touch. Especially now we've got AI everywhere, everyone needs to play. Maybe not great way to make it like personal. What do you guys think about that? How do you use automation and human touch in the right way with Cold emails.

I think again, this comes down to who you're emailing and why you're emailing them. Right. Like somebody fills out a form on your website or you know they're on your website, there's automated steps to accomplish, the speed to lead, assuming your copy doesn't suck. And then there's like the flip side where this is someone you really want to talk to. Are we really going to automate that message to your tier one most important prospect?

I think that's perfect, to be honest. I think you should be tiering your account list. And I think if you have a hundred accounts that you know are the absolute perfect fit, they're your dream customers, you don't need to automate that. It's 100 companies now. You can manually do that. That's why you're getting paid. So you should be doing your job manually. But I think automation plays a massive role if you have this tier 2, tier 3 accounts that you want to get into and you are sophisticated in using a tool like clay or one of these guys tools to make that happen. But as long as you're doing the personalization, automation is still a very viable way to do things. But I would leave you to your one account side of automation completely.

I'm also currently dying at the chat with Moist Regards.

No, that would be automatic spam.

I hate the word.

I'm open to changing our company name to Moist Regards.

Moistly.

All right, I'm leaving. I'm done. Done for the day. The rest of this is canceled. We actually have a pretty good like basic question in the Q and A, like when is it okay to even send cold email? When is it okay? When is it not okay?

Are you doing marketing for your company? If so, you should be using email as a channel.

In my mind, yeah. Cold, cold email.

Yeah.

I think it's when you have a valid reason for reaching out, which really ties back to who they are, the situation in which they are in. And do you have a reasonable reason to show up and say hey today compared to or howdy if you're Maximus. And the reality is, back to Alex's point, like we show up, we talk about ourselves, we create this translation problem which back to Zoe's point, we write like we're still in college and we hope that they can translate this hyper complicated message back to their problems and their current status quo.

I think it's about like right person, right message, right time. And you won't always know 100% what that is. But I think if people thought about sending to the wrong person the wrong message at the wrong time as like a bigger risk to their company. We'd actually send fewer spammy emails because, like, you have to think about your deliverability. You have to think about your reputation with that potential buyer. And nobody's going to have perfect data 100% of the time. Somebody could have just left their job last week and you don't know, things will happen. But I think if you are trying to scale too fast, if you're trying to send out that spray and pray, catch whatever you can in like one bulk message, you actually risk a lot more than if you do take the time and try. And like, Will mentioned, like, when you have something relevant to say to that person. So I believe in sending cold email. Like, I don't think you're a bother. I don't think you're an inconvenience as an SDR for 18 months. But I do think that thinking about it in terms of when should you not send it is probably like the reframe of, like, when should I actually be saying, no, I'm not going to send these emails yet. It's not the right time or they're not the right person. And getting more specific and getting more time.

I also think the goalpost of what cold and warm means have kind of moved in the last couple years. And so, like, you could argue there's no such thing as a cold email as long as you filter for people who work in B2B. If you sell the B2B now, that's a massive target that, like, is way too broad. But in some sense you have a reason, which is, oh, you're a business person, let me reach out. And so it's like, now that we live in a world where using AI and automation, you should be able to pull some relevant data points to a person. Your email isn't cold. There's like a reason. But then it's about timing. And that's what we think a lot about here at Warmly is like using intent to figure out the right time to reach out. Because it could be a warm email that is just the worst timing. And then it's the equivalent of a cold email because you're not gonna get a reply.

Well, should we get into roasting some of these cold email submissions? Our last roast of the day. I am excited. All right, so little reminder, if you haven't been here all day, like I have, we get a little bit more information about who we're roasting. We then give our just kind of gut reactions. And then we'll give one key thing we can improve and we rate it on a scale of 1 to 10. Okay. Moist in the chat. I'm going to ban that word. I think I can do that. That's the only word I'm banning. All right, first up we got rigorous technology. They're looking to reach decision makers and or highly influential stakeholders to find good fit businesses for their robotic automation solutions. These kinds of purchases generally fall under capital equipment. They haven't identified a consistent role that routinely owns manufacturing efficiency initiatives. Can you tell? At the end of the day I'm stumbling over all my words. And this was their worst performing sequence. But even their good ones are far below average. They try to keep list small and most of them are built through dnb which is what has it done in Bradstreet. Is that the company? Yeah, they sent 58% open 0% click 0 replies. Subject line Robots for small manufacturers. Let's talk. This is the email.

You're going to read it for the glass or.

No, no.

I can already tell from like the open rate data. There's an obvious problem in the subject line which is it's really long. It screams marketing when I think about cold email in this format. Right. We are writing a one to one sales message and so like totally get why people think to write subject lines this way. Why to approach it this way. Because most material online, particularly material that marketers are reading, are from marketers talking about how to write a marketing email. But in reality like a sales email should reflect much more. Again, to like what you're doing internally should be like one day words in order to not raise the mental spam filter that everybody can sort of immediately flag when they see robots for small manufacturers. Okay, I know it's a sales pitch.

I mean they, they only had four people read it or open it at all out of that 50. So it's like kind of a small sample size. But just reading this first two paragraphs, I didn't even get to the end of it. Like the I to you ratio is like very, very high. I we our company. I've been speaking with other people. It's like if you don't start talking about me as like the recipient of an email I've probably already checked out because it's just like I don't know who you are. Why would I care what you think? Why would I care what your opinion is on something you've done nothing to like establish your authority as an expert in my space versus if you started talking about me and talking about what you know about my business or what you know about my pain points. Then when you make a suggestion, I'm going to be much more willing to be like, okay, maybe this person has something of value to say. But like, if I were the recipient of this email, I probably wouldn't have made it even to the second paragraph because I didn't get that vibe from those first couple of.

Yeah, you saw the subject line in like four words of the preview text and you're like, this is an at scale campaign.

Yeah. And also like they don't. Like I'm going out on a limb and guessing that I don't have a robotics team. Like, I feel you should know that.

There'S no harm in just declaring it as a statement because if you're wrong, they're not going to reply. So yeah, to confuse someone.

I mean, to me this is the most, the most common thing I ever see when we audit accounts or email campaigns that are people running internally for their company. There's two variables in here. There's contact name and there's company names. No offense to Apollo, any of those tools, but it's like if you're using the pre canned variables, you're not creating your own. And this is coming from someone who runs a clagency. Right. So we're using really crazy variables all the time. We're building really segmented lists. It's like that's going to be a problem. There's no actual personalization in there. Plus they're talking about themselves way too much. Someone said it in the chat. But that CTA is absolutely terrible. Worth exploring, is not usable. So I find it harsh.

But I've always been of the mindset, especially if someone's busy, which we're all busy, that like, if you're not asking a question by like sentence three or two, then you're losing the person because like I'm not going to make it to the email before even understanding what you want. So I always try to stick a question mark by sentence three.

Yeah. If I think about like how I'd want to reorient this in like a perfect world, right. I'm looking at open job roles. I'm looking at are they bringing people on to their manufacturing organization like you know, frontline people in the org and saying like, hey, on indeed. Looks like you're doing the following thing that typically presents an opportunity to automate with robotics. Didn't see anything online about your team having a robotics team? You know, curious is this something you've.

Explored before in this case too. You could also see if the company's stagnating. You can do a search of figuring out how many employees they had last year versus this year. Run a calculation. Are they growing? Are they not? They're not growing. It's probably a good indicator if they're a manufacturing company that they're struggling with something in terms of efficiency. So this would be a perfect message to send to somebody if you know that they're struggling with efficiency. They could use the support of robotics, but you have to build some personalization. And really in this case, the list is the message.

I also think this is probably a technical recipient. I mean, they're talking about robotics. Like, I don't know anything about robotics, but like the language. This is just like at like a reading level that I don't know. I think you could use like more plain English. You could use simpler words like it doesn't have to be and fewer, like, I don't know what you call them, but like low hanging fruit. Too many hats out on a limb like those, like funny little. You don't need three of those in the email. Like you could just say what you're trying.

Yeah, I don't know if it like stood out from how I was rewriting it in my head, but the length of this is obviously problematic. The length of sentences are problematic. We've got the data that shows shorter emails are better. Each long sentence is going to reduce your chance of response by about like 17%. So it's these comma. You're just really running on with your sentences. But the big thing is that monster paragraph in like that first one. They are going to. My phone's right here, right? This is where they're going to read it for the first time. They're eight times more likely to have their first impression on the phone. And so that message is going to look like the monstrous long text from an ex girlfriend when they open it up on their phone. And that's just something that they're going to opt out of before they even start to go to read it.

Now I'm guessing that's a bad advice for matchmakers.

Well, I'd be happy to give your ex girlfriend some advice on not stalking her ex. But assuming this person doesn't have a lot of intense signals or like, you know, specifics to reach out to this prospect on, I would almost argue that a CTA about talking is a little too soon. And one sort of hot take here would be maybe the Goal is to like get them to just understand the problem exists, to give them a resource to learn more. Send them to your website. If you're open to including a link, we can talk about sort of the, you know, reply rates around like including links or not. But I would want to learn more. If I was a quote, small to medium sized manufacturer though I don't wake up in the morning thinking I'm a small to medium sized business. I just think I'm a business. But yeah, I'd probably try to send them to your website. Would probably be my goal here. Assuming they don't have much more personalization to go off of now. If they've opened up three ads, if they've visited their website five times, if they talked a year ago, then you could sort of try to get them right away to a call. But this, this feels too early for that.

Agreed.

Yeah. All right. Scale of 1 to 10, 1 is like stop sending emails. 10 is amazing. No notes. What do we guys think in the chat? And then also when you rate it like the one key thing you would improve. I know we've talked about a lot, but what do you think would really move the needle here? Zoe, you go first.

I'd probably give it like a, like a two. I think before you write any more emails, you have to get your targeting straight. They said it in the disclaimer like they don't really know who their Personas are. They aren't 100% sure. Get super clear on your ICP and who your best customers are because targeting happens before messaging and I think like that's just going to continue to be a problem they run into until they dial that.

I'd give it a three. I think there's simple things you can do to change the message is important, but also who you're targeting. In this case, I like Will said you could do something by going on indeed figuring out who's hiring for what, if they're hiring for this type of role, that this solves for it's probably the right person. Like I said, do some sort of enrichment to determine whether or not they're growing year on year. If they're not growing year on year, plus they're hiring for that role. Say something along the lines of, hey, notice you're hiring for this role and looks like you guys have been a little bit stagnant last year. So wondering if automation could have a place in your operations moving forward. If so, happy to send over a video about how rigorous robotics helps something like that. Low friction. You're not asking them from a call, you're just sending them something to tell them more information without them having to do anything.

Awesome. Max, what do you think?

I'll give it two. And my joke answer of what they could do better is the sign off should be Warmly Chelsea instead of Best Chelsea. Sorry, Moistly Chelsea. Say that three times fast. Honestly, that that might get a reply. Think about that for a second. I'd reply for sure but I'll go with the point that Zoe made earlier which is too much. I I think biggest win here is to switch to tell me about me.

I think it would be nice. I'm going to give it a 02, which is about the reply rate that I expect this to have. When you try to scale it so it's too long, it's too complicated. I love Joey's point on like you gotta know your targeting. I think there's some things you can do around messaging that can soften the fact that you're a little bit lost. The fact that you don't know if they have an inbox in house. Robotics team I think like using CTA language where you're like have you looked into robotics? Can be an easy way to open up conversation.

Love it.

The point to that response? See robots for manufacturing and they're already in market. They're probably already in conversation with competitors.

Yeah. To the next one Workbooks CRM trying to get the attention of senior sales and marketing leaders to have them consider switching their CRM generally from HubSpot or Salesforce. They won an award with this campaign. I think we chatted this one in our prep call, but it was good. So I wanted to put it in here again and it was part of a full activation. Key thing we had here was that a lot of the replies they got were profane and telling that they'd never consider them and others said got your attention. Subject line was stuck with a bullshit CRM. And then here's the email. There we go. Got literal. A man being covered in shit after video. Lots of bullet points.

I hope it wasn't actually, you know.

Yeah, right.

I know they won an award for this but like it's just kind of. I guess it's technically a marketing campaign. But this email screams marketing. Like, screams marketing. And so like if it were me, I would close it out before I read anything. Like the photo at the top, the multiple links in the email. Like I just wouldn't even read this to be totally honest, because it just looks like a marketing email off the rip and I'm a fan of cold emails. Feeling a little bit more, I don't know, not so marketing. But that's just like my first impression.

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I would assume someone bought my email address if this was in my inbox.

I totally agree. This is not a cold email.

Yeah, I think there's a couple things that folks in marketing should probably know about an email like this. And that is the image, the hyperlinks, you know, those show up from a technical perspective as HTML. And so the likelihood that this gets filtered to someone's promotions, if not their spam filter, is pretty high. So, like, it's not going to land in their primary. And so the likelihood of get seen is a little bit lower.

A lot lower. Yeah, a lot lower.

I also just think it doesn't talk to any pain points. For me. Like, as a marketer who works in CRMs, one of the ones they said was bullshit. I don't know if like the top one, like an overly complex implementation, like, okay, I'm already implemented, so that's not going to be a pain point. That's going to make me move. And then it's like, what is a bullshit CRM? There's just a lot of CTAs. I don't know. This one wouldn't get me. It would be spam marker.

To be honest, I could see this crushing on ads, but this isn't the roast of ads.

Yeah, ads as a full campaign and marketing, I think it's good.

We see this a lot from our customer base where folks will come up with, let's pretend for a second that you love the whole, like, profanity play to get someone to reply. So it's like, hey, we have a good idea. We're going to go with this bullshit idea. And great. And then I think what Alex is saying is then you have to flavor that per channel. And then you also have to like, dig a little deeper if your channel is one where you're expecting someone to read. And it feels like. I think it's like four times they use the word. They were just so excited to stick that, you know, little asterisk in there. And so it's like, cool. Like, we get it. Like, the general campaign idea is great, but I don't think this was tailored for email too much other than like, you know, shortish. Email got some good bullet points, but I would sort of go deeper to like you said, Danielle, kind of flavor it to pain points. And yeah, use the word bullshit once. But then like, tell me Something that I care.

I also think it's kind of interesting. Like, all of the pain points they're like, trying to target have nothing to do with the product or the experience with the product. They're going directly after, like, the team. They're like, their implementation sucks. Like, it's really, like targeted against, you know, and they're. They're going up against Salesforce HubSpot. Like, these are big freaking companies who have objectively been successful in some manner. I think those are real pain points. But, like, if you're going to call out the CRM for being bullshit, you should probably address how the product, like, the problems the product solves, not just like, immediately go after, like, their onboarding team sucks. Your customer service team's terrible. The prices go up. Like, it tells me nothing about how many use the product. And then the one that I remember when we did the preview call, the syntax of like, what could be their strongest sentence is just bananas. Like, too many sales and marketing leaders, 64%, according to our latest global survey, feel trapped. Like, who writes like that? Who reads like that? It's a probably a decent point of social proof, but I would work it up maybe higher in the email. I would reword it entirely because it's too long and it's very weird to read.

Also, if, if you do feel trapped by your CRM provider, you're trapped. Like, you're not gonna switch.

Yeah, I was gonna point out the 64% thing too. Zoe. We've got the data on our side. Like, as much as I love reading stats out against other stats, but, like, this shows up as an informative tone. Right? I'm just talking at you. And so for every informative tone, we see response rates go down about 26%. And so it's just like you lost one out of four just because of that one sentence. Not saying that one out of four responses on this type of email, but it just immediately starts chipping away at your chance of getting response. This could much easier or much more easily be. Hi, Dax, not sure if your salesforce renewal is coming up. Find most of our folks feel trapped. Built a solution that helps with X, Y and Z. We want to see how very similar company is made the switch.

Yeah, I'm a. I'm like a one. Just a marketing email. Yeah, I would just completely rewrite this. That's on me. What are you guys at?

I think if you go one, you can't go any lower.

Really?

Because I think zero is not, you know, can't multiply zero by anything still zero. So I'm gonna give it a two but mainly because I agree that it's a marketing email. Zoe, I'm challenge you a little bit. I think poor customer service and significant price hike that causes me to leave different software products. CRM is obviously trickier because it's super sticky. It's a nightmare to swap around your CRM so you do need to know which kind of software you're playing with here. But yeah, I mean if it was a cold email I'd rewrite it by doing a technographic search to figure out what companies are using HubSpot, Salesforce et cetera and then talk to the pains of each of those products individually and say this is how Workbooks is different. Something like that. But that's not this this is a marketing email.

So two to back some of the folks in the chat I see Natalie Horner and Greg Whitaker. I think both are accurate here of like the I think the campaign idea is cool. Like I think bullshit CRM. Like some people are going to find that profanity annoying but your goal is not to get everyone, it's just to get a good number of leads and so I think campaign idea is solid. It'll probably get a lot of clicks and opens but yeah, as soon as you see the banner image I think that's really cool.

Yeah I'm just not going to rate this one because it's not a cold email.

It's a marketing marketing email. Who won?

All right, this one is from Zento. It is a CRM implementation company help people upgrade their system to new software and use their technology better. They are launching the marketing and this is the first email about the direct debit guide. The aim is to get people to download the guide and fill in their own details. The email will be to current clients and prospects so I guess prospects too Target associations, membership organizations, unions, job titles, roles, blah blah blah. This hasn't been sent yet so we don't have any staff here and subject line or direct debits causing you stress. We got some emojis in there choosing a direct debit provider and here it is also super small but again this is a marketing email looks like to me.

So this is an opt in list based on what you just showed they.

Said I think client current clients and prospects so I think that they're also sending this cold to people in their list.

Yikes.

It's not a cold email but this seems to me like an opt in email is there I I see slide 6. It's blocking this out for me. I can't tell. Is there like an unsubscribe button down there?

Yeah, I think so.

I need the Zoe Yikes button for future reviews.

Well, I felt yikes when I saw the subject line had two emojis and a question mark in it and was like seven words long. But even when opening it, like, I'm thinking about will your comment earlier. People are looking at this on their phone. Like how much of this is actually even. Are you even seeing on that first swipe of your phone?

I'm not sure. Especially if they use Outlook. Like none of those images are going to load, so it's going to be a nightmare.

Yeah. So I think that they're just kind of sending this also cold it is a marketing email, but they're repurposing it as a cold email. I was just rechecking the things. But yeah, separate email. Not just use the same one.

The fact that I have to lean in, I'm like, oh, this is that song formatting. That's the email.

I know we moved on, but I think even like when I was looking at the subject line in the preview text, the odds of me even opening this email. Yeah, subject line and preview text. Like I would never even open this email. If it even made it to my primary inbox. It's like step big.

If I think this is like what Will said, this is going straight to the promotions folder. How do you go straight to spam, spam or promotions? I could see it going to promotions too, to be honest.

All right, let's say we strip out the emojis and the subject line and all the images and stuff. All place everyone. What's everyone's take on emojis and email at all? Cold email. Are all emojis banned or you allowed to use one emoji? What do people think?

So like inside the email, inside the email. Thumbs up if used. Right. Exclamation marks increase response rates. Right. It increases like the level of friendliness, warmness of tone. And so it's one of those things that we've just seen work across the data. It just has to be applied. You can't just take that like carte blanche and run with it, but you have to apply it in a way that's creating warmth and familiarity between like a one to one relationship.

I would hard pass in the subject line though. Like in the body of the email. Absolutely. But in the subject line. I've just never seen it not look like a market.

I think it also depends if it's a one to one email or if it's automated. Because if you're doing automation. Absolutely not. I'm never including it for any of my clients. I'll never do that because their inboxes get destroyed, it becomes a nightmare for us. But for one to one emails, yeah, it's fair game. It's totally fair game.

Yeah. I think it depends on like the voice and tone, but like using them as bullet points here. Just like someone said it in the chat, just like screams chat.

GPT wrote, depends which one you use. So I have like signature emojis, like the handshake emoji that blows smoke at your nose. So it's like, I don't know, those aren't AI emojis.

So I call that like the Triumph emoji.

Yeah, the little smirk at the note makes sense.

Yeah.

All right, so again, I'm probably a one on this one. It's not really something you should send as a cold email. It's going to end in your spam folder or promotions tab.

I mean, there's like six links in there. Maybe I'm miscounting at least six links in this. Like, there's no shot it makes it to my inbox.

My gut instinct is just based on what I'm seeing if I'm reaching out to. So I'm going to try to use like a comparable business and be like, hey, Richard, I was talking with so and so over at very, very similar company. Here's exactly what they were dealing with. We helped them create a new income stream based on direct debits. Is this something you've explored? And that's based on the limited context that I have, but that might be how I approach it.

Yeah. And it does seem like they're sharing something valuable here. Right. They have this whole guide, assuming it's like useful, like, hey, we put together this guide. Maybe you want to check it out. It'll help you in your decision.

I also think, like, what Will said, adding that context before the kind of question makes the question more meaningful because they start with, are direct debits an essential stream of income for you? Like, I don't know that it provides enough because then I'm just going to be asking myself like, yes, no. Okay. And then I'm done reading versus, like the way he kind of framed it. There was like a little bit more contextual lead up to that question that made it more compelling than just being like, is this a problem? Because they might think, no.

All right, let's move on to the next one, which actually is a cold email, I promise.

All right, Danielle, while you're pulling it up, I'll read the Breakout this part. Director and VP marketing for B2B companies that have relatively high amount of website traffic. Breakout offers a website agent that engages with website visitors and helps you grow inbound pipeline through that. We're a very early stage company. Just came out of stealth.

The subject line is fashion gear. Founder, CEO at Breakout. That's the subject line. I put it in the chat and it's about 50 recipients, only one booked. Thanks, Max, for stepping in and reading it there. And here's the email. What's the size?

So I actually appreciate the like, hey, I'm building this to solve this problem. Type messaging. Like, Max, I'm sure you've sent messages like this before. I know I have. I remember, like, trying to get our first hundred people to like sign up for the prize. Like, hey, here's what we're building. Like, here's the problems that we solved. Would love your feedback. Right. I've seen this. I do think the subject line and the first line are redundant, but let's.

Start to get some of the good stuff here. So things that I like in here, you know, in the first or second sentence, there's a number that sort of stands out. 2x founder. There's a bolded piece, around 40% increase. They have social proof with a couple of. They call them design partners. And then if you look at the personalization online, like 6 or 7, I see that Gretel, the company they're reaching out to is 8,900 monthly traffic. And that could mean blah, blah, blah, ROI every month. And even cooler, I put together an agent for you and there's like a link. And so that's kind of interesting. It's like, oh, you built the product for me already. So those are some of the things that I like right off the bat.

Yeah, I was going to say that line is the most compelling part of the email for me. Like, that's your reason. I would just move it higher up in the email. And also, like, my one caveat is y' all are founders in here. I could never as like an SDR write an email like this. Like, it only works from the founder. So not to say that it doesn't work, but this would not be advice I would give to like, I'm the first sales rep that. So, like, that's not going to hit the same way as the person building the product.

So yeah, I think founding team. But yeah, to that point I'd move.

That first line that Zoe was just talking about. I see that Gretel gets 8,900 monthly traffic. Sounds weird, but you can fix that. Move that up to the very first line. Lead with that. Remove. I am founder CEO at Breakout. All the stuff about him. I'm sure Sachin's an awesome guy, but it's like just put Sachin co founder at Breakout. If they're interested, they're going to look you up on LinkedIn. So you've got that covered. Hopefully your LinkedIn page is optimized to give everyone all the information they could ever want to know about you. But I also do love the I built a custom agent for you. What I wouldn't do is hyperlink it and I would change the cta. I'd love to get some feedback for you. Let me know if it makes sense to jump on a call. Let me know if it makes sense to send you the agent I built for you. Something like that.

Yeah. You could break this entire email out into a sequence. Right? Follow up, would love to get some feedback. Here's a link to the agent I built. Easy way to. Yeah, follow up.

What I'm saying is I wouldn't even put the link. I'd ask them if they're interested in the link they already built.

I was thinking email too.

Oh yeah, yeah, you can do that too.

The one thing I'll note is like the monthly traffic numbers, those things tend to be a little wrong. So I might soften that. Just be like, hey, I was doing some research or maybe cut some of that fluff and just be like from XYZ source, it looks like you're getting X amount of traffic. Realize that could be totally off working with some design partners like X and Y. These agents that we build based on the site traffic should be able to convert an additional squiggly mark 35 leads per month. I can build an agent for you pretty quickly. You want me to send one over?

I think I have an email on my screen right now for one of our clients that we wrote that's like almost identical to what you just said.

Will, I think to sort of speak to folks on this call that are from like very, very early stage businesses. And speaking from experience myself, I do think that leveraging yourself as a founder and like your kind of desire to learn a more consultative approach, which I saw in the chat, which I think is smart. This design partner stuff, it's kind of clear that this founder doesn't really know exactly what works or what doesn't. But they're just like a cool, earnest person who wants to like get on calls with people. And there's certainly people out there that are responsive to cool tech in the early stage and I think that's fine. Like I think you can lean into that for sure. But if you're targeting a mid market company and I see the word design partner, I'm running for the hills, I have no interest or any time to deal with like some, you know, early hokey pokey tech that may not really work. And I think that you have to kind of decide for yourself, do we want to sound a little further along than we really are in order to kind of get more serious buyers or are we really more in the consultative just, you know, conversation phase where I don't care if this deal goes close one, I just will appreciate a conversation to learn more about which features I should build next.

Yeah, I think like for me the tone is a little all over. To your point, Max, there is an angle for the like just being earnest, being humble, being like, I would love your feedback. But starting with I'm the founder, I've been a two times founder, like I've done this rodeo before, but then being kind of can I get your help? Can I get your feedback is almost like contradictory. So like just picking a lane, either like to your point, go in with more confidence and be like, we've got this on lock, you should see it or we're earlier on and like I'm just asking for a favor kind of a thing. I think either one could work, but trying to do both is actually confusing.

Yeah, simple copy would just be from my experiences. I know how critical it is to get feedback in the early stages that would like soften that transition, make it a little more appropriate. But great call out makes total sense.

People like helping people too. So if you play it like that, a lot of people are going to respond very positively.

When we were in the early phase with our product, I think I remember doing this, but basically we would ask for, you know, I'm just a founder, want some feedback, like, you know, help me out. And we got a ton of replies and a ton of meetings. Very few converted to close one deals. But that was okay because our goal was more like conversations. But for those folks that are like, I'm trying to make sales here, going for the consultative, I'm a cool founder type approach is not going to get you revenue. So just being intentional about what you're looking for out of this sequence.

Also like I'm confused about what this does because it mentions, like, so many different things. Like, it's an AI sales rep, it can sit on my website, it can outbound email sequence, it can make ad landing pages, offer personalized engagement to prospects, it can show product demos, it can answer questions, it can automatically qualify leads. Like, that is a lot. That's like a big product.

It's one thing that's like, you're talking about that stands out to me. It's clear that this person did not go to this other person's website. Because you could look on their website and see whether or not they have a chatbot, what that chatbot does. And then I've been in that founder seat, right, where like, every deal matters, right? You can't scale at this point. You have to think about how do I get this one deal over the line? Because I get two deals, all of a sudden it's a hundred percent growth. And so the beautiful part about small numbers is they. They grow quickly.

But the.

Yeah, the thing that I look at in this is, did you actually look at my website? Do you actually see how I'm thinking about converting this traffic today? Because you could get so much more specific if you just did that little bit of work.

One thing I do like about this email is, like, the formatting of it. We saw some emails earlier that were like bigger blocks of text. It's a little long, but I found this easier to read than that first email that was like several lines blocked together. Just like, call out something that I think is positive. I do think breaking things out like this probably makes it a little more skimmable for the reader, even if it is a little bit.

Yeah, I like the bolding too. 40 increase. That's where my eyes goes first. And I'm like, ooh, increase. And then I see the rest around it, and I do like that. So, yeah. All right, what are we rate in this one, guys?

Three. But I like Sasha and I think we'd be friends. He seems like a good guy. I don't know why, but I just get a good vibe from him.

Yeah, I would have said a three.

Action. If you're out there, Alex wants to hang out with you.

I'm between like a two and a four because, like, I appreciate playing the founder card and I think that will actually get a level of response rate that plays to his benefit.

Agree. Agree with Will. And every time we take on a new client, we try to send on behalf. The alias that we'll create is usually one of the Founders. It works way better.

I'll go four.

Four. Yeah. It's probably one of the better ones we've seen so far, though, so good job session. All right, next one. AvTech Solutions Inc. MSP IT company who provides different levels of cybersecurity, managed services, C suite level, executives of banks. That's gonna be tough. Audience. 12% open, 75% click through subject line. Managing IT risk. Let's make it easy.

So what they think is a 75% open rate is product like Proofpoint or Barracuda, opening it up on a separate server so that it doesn't, like, drop malicious software onto there. Totally.

Those are really 75%. It's 12% open, 75% click through. But yeah, it's definitely that. Especially if they're emailing it.

Those tools do click on all the images and links.

Yeah.

I like Taylor's comment. Every security leader knows that threats are evolving and growing more complex.

I thought they were getting easier. Speaking of formatting, this one kind of hurts my eyes.

I appreciate you putting it on a phone screen.

I didn't. That's how it was submitted. So I appreciate that.

I appreciate.

Yeah, I'd scrap it entirely. I'd hit the phones. I wouldn't send emails in this market at all.

I've got the data. Disagree with that.

But, yeah, let's disagree. Why do you disagree?

Yeah, I like that.

I mean, I was looking at someone's data within our product today. They're getting 4%, and that's on the email basis. So, like, 12% response rate. When you look at it from a campaign perspective, reaching out to this exact Persona. But the difference is you're reaching out with a marketing message that's me, me, me oriented versus, like, I'm doing my research. Here's the problem that I see. I'm helping people very similar to you solve that problem. Cybersecurity is a little weird in that a lot of times you don't want to actually drop the case study, but you definitely don't want to send anything that's not plain text.

There's just like, nothing that tells me anything about who they actually reached out to. There's no. No personalization or relevance beyond just like, very, very high level. Like, they listed a bunch of things like, banks, you know, today aren't slowing down. They're growing more complex. You know, like that kind of stuff, which I guess is like, again, like, to a point, like, they didn't do necessarily any research or I wouldn't know that you did any research on My business. I think this screams like mass and actually don't even feel like it really. What's the headache of risk management? You could have gotten more specific with some of those pain points and things like that. So yeah, I think for me I just like, I would be like why would I go through the effort of clicking the link in your signature to chat with you when you provided no context about my business and the problems.

That I'm specific and like the pain points they address. It sounds like like an infomercial voice to me. Like no more scrambling before audits. No more sleepless nights.

You could hinge this on like they're hiring people in it. You could hinge this on. I mean this is a big financial services organization. There's plenty of data out there. They could be opening new branches, which could mean, you know, they're adding more locations into their security instance. And like there's so much that could be happening across this org that you could be referencing that you could tie back to a specific initiative and you could say, hey, not sure if you have any project work available related to that. Help teams manage their IT and security services and could be an easy way to spin up a project so that you don't have to go hire XYZ roles.

Yeah.

Things stick out to me. Missing social proof, missing any numbers. I'm trying to think about like when's the first sentence where they've added something of value? Like the risks facing banks today aren't slowing down. If anything they're growing more complex like eh, like broad problem. But like didn't really add value to me. I'm excited about the we take the headache out of risk management and helping you navigate all these things requirements so you can focus on keeping your bank secure, running smoothly. That's my favorite line of it. And I'd maybe put that. Figure out how to put that more obvious.

Yeah. I feel like that sentence is the only point of this is what we can actually do for you in this email.

Yeah. So it's like, hey Wayne, see your banks opening 17 new branches. Yeah. As you try to navigate GLBA, FF, IEDC, all these requirements, imagine it's creating a headache for your IT team. We've helped some other banks spin this up on some quick project work to keep everybody's head focused on larger initiatives.

Yeah. It's missing that sort of like timing, observation, like why you?

Why now?

And I think that would hook somebody in. I also think you could just get rid of the no more scrambling before audits. It's just, like, redundant. You could eliminate that three sentences right there and then change the CTA to be something stronger.

Yeah, and someone said this in the chat with, like, if you're gonna go through the hoops of, like, typing, use the link in my signature to book time with me. Just do the link again.

Or recognize they're in cybersecurity and they will never click that link, no matter how many times you ask them.

No, they're never clicking that link. All right, this is our last one, so hit me with your scores.

Well, before I give a score, I just want to say I appreciate the folks that were brave enough to put their emails out here for a roast. I know it's not fun getting cooked on the Internet, so thank you. Thank you all who did.

Thank you. Thank you. Wayne Ray wants to go first.

Well, now that I said all that nice stuff, I'm going to give it a one.

I'll give it a two. I would have led with something like some sort of mandate that's come out specific to banks in the last month or coming out, something like that. I used to sell tax compliance software, so I am so used to seeing these emails, I don't see this working ever.

I'll give it a 2. I would have been open to a 3, but they got the Twitter logo from two years ago.

I didn't even think about that.

And, like, also just all of the logos and then the links and the multiple links, whatever. I'll say. I will go with will. I'll say a one.

I would say that, too. Definitely room to improve. All right. And that is our roast of cold email. Thank you guys so much for joining. That was awesome. Gave us so much tactical things to think about as marketers. And we really appreciate you guys being here.

Thanks for having us.

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