#249: Cold Email: Lessons from Real Outbound Campaigns in 2025

#249 Cold Email | In this episode, Danielle is joined by four experts in B2B outbound: Zoe Hartsfield (Apollo), Will Allred, (Lavender), Maximus Greenwald (Warmly), and Alex Fine (Understory). Together, they dive into the good, bad, and “please don’t ever send this” of cold email strategy. Each guest brings firsthand insight from scaling outbound at fast-growing B2B companies and helping clients do the same.

Danielle and the crew cover:

• The biggest reasons cold emails flop and what great ones do differently
• How to use personalization, targeting, and timing to get replies (not unsubscribes)
• The right way to blend automation and human touch in your outbound strategy

It’s an inside look at how marketers and founders approach outbound messaging, across strategy, execution, and scale.

Timestamps

• (00:00) - — Intro and guest lineup
  
• (03:41) - — Why most cold emails fall flat
  
• (05:41) - — Common copy mistakes: too much “I,” not enough “you”
  
• (07:11) - — The automation vs. personalization debate
  
• (09:26) - — When *not* to send a cold email
  
• (11:41) - — What targeting gets wrong (and how to fix it)
  
• (13:41) - — Teardown #1: Robotics email with 0% replies
  
• (15:56) - — Subject line issues, tone, and CTA feedback
  
• (18:11) - — Teardown #2: CRM campaign with profanity
  
• (19:56) - — Why this email screams “marketing,” not “outbound”
  
• (23:19) - — Teardown #3: Direct debit email repurposed from a nurture
  
• (25:49) - — Why HTML-heavy emails kill deliverability
  
• (27:34) - — Teardown #4: Founder-led cold email from Breakout
  
• (29:49) - — What worked: relevance, format, and intent
  
• (32:19) - — Teardown #5: Cybersecurity email to bank execs
  
• (34:19) - — Final takeaways on relevance, timing, and strategy

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Dave Gerhardt [00:00:00]:
You're listening to B2B marketing with me, Dave Gerhardt.

Danielle Messler [00:00:17]:
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, are, 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.

Danielle Messler [00:00:48]:
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.

Danielle Messler [00:01:04]:
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.

Danielle Messler [00:01:29]:
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.

Will Allred [00:01:38]:
Hey, hey, hey.

Danielle Messler [00:01:40]:
Oh, my God, the hat.

Will Allred [00:01:41]:
It's here.

Maximus Greenwald [00:01:42]:
I love it. What's up, everybody?

Danielle Messler [00:01:44]:
Kind of joking, but he's actually wearing the hat. This is amazing.

Maximus Greenwald [00:01:48]:
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.

Danielle Messler [00:01:52]:
It's amazing. Where is it from?

Maximus Greenwald [00:01:54]:
Got it in Scottsdale, Arizona.

Danielle Messler [00:01:57]:
Beautiful. I love it. As you can tell, I love a good hat. I have them all over my background.

Maximus Greenwald [00:02:03]:
Yeah, Danielle, it's not too late for you to wear a hat, but I guess it might be hard with the headphones.

Danielle Messler [00:02:06]:
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. There we go.

Alex Fine [00:02:18]:
Better late than never.

Danielle Messler [00:02:20]:
Perfect. Sorry about the links, guys. That's on me. Event organizer. Are you guys excited to roast some cold emails?

Alex Fine [00:02:26]:
Let's do it.

Will Allred [00:02:27]:
Love it.

Danielle Messler [00:02:28]:
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?

Will Allred [00:02:39]:
I'll give my short answer unless, Alex, you want to go first?

Alex Fine [00:02:42]:
Oh, go ahead.

Will Allred [00:02:43]:
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 ad.

Danielle Messler [00:02:50]:
I get Daniel all the time, so don't worry about it.

Will Allred [00:02:53]:
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 guess like a simple trick 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.

Danielle Messler [00:03:27]:
Agree with that. Zoe, what do you think?

Zoe Hartsfield [00:03:29]:
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.

Alex Fine [00:04:08]:
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.

Alex Fine [00:04:20]:
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.

Maximus Greenwald [00:04:27]:
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.

Danielle Messler [00:04:46]:
I love it. Someone asked what's their success rate? Dating advice. Is this about to turn into a dating advice? Ruth?

Maximus Greenwald [00:04:51]:
You all can look up Rachel Greenwald online and fill out the form if you'd like to.

Danielle Messler [00:04:57]:
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's play. Maybe not a 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?

Will Allred [00:05:18]:
I think again this comes down to who you're emailing and why you're emailing them.

Maximus Greenwald [00:05:22]:
Right.

Will Allred [00:05:22]:
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?

Alex Fine [00:05:41]:
I think that's perfect, to be honest. I think you should be tiering your account lists 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 those 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.

Alex Fine [00:06:06]:
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.

Will Allred [00:06:15]:
I'm also currently dying at the chat with Moist regards.

Danielle Messler [00:06:18]:
Well, no, no, that would be automatic spam. I hate the word.

Maximus Greenwald [00:06:23]:
I'm open to changing our company name to moist regards.

Danielle Messler [00:06:31]:
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 a cold Email. When is it okay? When is it not okay?

Alex Fine [00:06:44]:
Are you doing marketing for your company? If so, you should be using email as a channel.

Danielle Messler [00:06:47]:
In my mind, yeah. Old email.

Alex Fine [00:06:50]:
Yeah.

Will Allred [00:06:51]:
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, 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.

Zoe Hartsfield [00:07:23]:
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.

Zoe Hartsfield [00:08:30]:
And getting more specific and getting more time.

Maximus Greenwald [00:08:32]:
I also think the goalpost of what cold and warm means have kind of moved in the last couple of 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.

Maximus Greenwald [00:09:02]:
There's like a reason, but then it's about timing. And that's what 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 going to get a reply.

Danielle Messler [00:09:18]:
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.

Danielle Messler [00:09:49]:
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. Hey, Shell, 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 lists small and most of them are built through D and B, which is what has it done in Bradstreet.

Danielle Messler [00:10:23]:
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.

Will Allred [00:10:34]:
You going to read it for the glass or no?

Danielle Messler [00:10:36]:
No.

Will Allred [00:10:38]:
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 like 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. It's 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 over Words in order to not raise the mental spam filter that everybody can sort of immediately flag when they see robots for small manufacturers.

Will Allred [00:11:28]:
Okay, I know it's a sales pitch.

Zoe Hartsfield [00:11:29]:
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 eye 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.

Zoe Hartsfield [00:12:14]:
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.

Will Allred [00:12:22]:
Yeah, you saw the subject line in like four words of the preview text and you're like, this is an at scale campaign.

Danielle Messler [00:12:27]:
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.

Maximus Greenwald [00:12:35]:
There'S no harm in just declaring it as a statement because if you're wrong, they're not going to reply. So yeah, confuse someone.

Alex Fine [00:12:45]:
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.

Alex Fine [00:13:05]:
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.

Maximus Greenwald [00:13:19]:
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.

Will Allred [00:13:36]:
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.

Alex Fine [00:14:08]:
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.

Zoe Hartsfield [00:14:34]:
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.

Zoe Hartsfield [00:14:55]:
You don't need three of those in the email. Like you could just say what you're trying.

Will Allred [00:14:59]:
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 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.

Will Allred [00:15:29]:
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 it's just something that they're going to opt out of before they even start to go to read it.

Danielle Messler [00:15:45]:
And I'm guessing that's a bad advice for matchmakers.

Maximus Greenwald [00:15:48]:
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.

Maximus Greenwald [00:16:30]:
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.

Alex Fine [00:16:44]:
Agreed.

Danielle Messler [00:16:44]:
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.

Zoe Hartsfield [00:17:00]:
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 a hundred percent 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.

Alex Fine [00:17:22]:
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.

Alex Fine [00:17:58]:
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.

Danielle Messler [00:18:03]:
Awesome. Max, what do you think?

Maximus Greenwald [00:18:06]:
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. Chelsea. Sorry. Moistly Chelsea. Say that three times fast. Honestly that that might get a reply. Think about that for a second.

Maximus Greenwald [00:18:23]:
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.

Will Allred [00:18:32]:
I think it would be a nice. I'm gonna 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.

Danielle Messler [00:19:01]:
Love it.

Will Allred [00:19:02]:
The point to that response see robots for manufacturing and they're already in market. They're probably already in conversation with competitors.

Danielle Messler [00:19:09]:
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.

Danielle Messler [00:19:35]:
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.

Will Allred [00:19:48]:
I hope it wasn't actually, you know.

Danielle Messler [00:19:51]:
Yeah, right.

Zoe Hartsfield [00:19:52]:
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 markety.

Zoe Hartsfield [00:20:21]:
But that's just like my first impression.

Danielle Messler [00:20:23]:
I would assume someone bought my email address if this was in my inbox.

Alex Fine [00:20:27]:
I totally agree. This is not a cold email.

Will Allred [00:20:29]:
Yeah, I think there's a couple of 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.

Alex Fine [00:20:53]:
A lot lower. Yeah, a lot lower.

Danielle Messler [00:20:55]:
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. 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.

Danielle Messler [00:21:19]:
It would be spam marker.

Alex Fine [00:21:21]:
To be honest, I could see this crushing on ads, but this isn't the roast of ads.

Danielle Messler [00:21:25]:
Yeah, ads as a full campaign and marketing, I think it's good.

Maximus Greenwald [00:21:28]:
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 bullshit. They were just so excited to stick that, you know, asterisk in there.

Maximus Greenwald [00:21:56]:
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 get.

Zoe Hartsfield [00:22:13]:
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.

Zoe Hartsfield [00:22:35]:
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.

Maximus Greenwald [00:23:14]:
Also, if, if you do feel trapped by your CRM provider, you're trapped. Like, you're not gonna switch.

Will Allred [00:23:21]:
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 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.

Will Allred [00:23:57]:
Find most of our folks feel trapped. Built a solution that helps with X, Y and Z. Want to see how they very similar company is made the switch.

Danielle Messler [00:24:08]:
Yeah, I'm a, I'm like a one. Just a marketing email. Yeah I would just completely rewrite this the company. What are you guys at?

Alex Fine [00:24:17]:
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 going to give it a two mainly because I, I agree that it's a marketing email. Zoe, I'm going to 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.

Alex Fine [00:24:41]:
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.

Maximus Greenwald [00:24:58]:
So too to back some of the folks in the chat I see Natalie Horner and Greg Whitaker, I think both are accurate here of like 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 what you lose people.

Will Allred [00:25:19]:
Yeah, I'm just not going to rate this one because it's not a cold email, it's a marketing.

Zoe Hartsfield [00:25:24]:
Yeah, marketing email. Who won?

Danielle Messler [00:25:26]:
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.

Danielle Messler [00:25:52]:
This hasn't been sent yet so we don't have any staff here. And subject line or direct debit's 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.

Alex Fine [00:26:09]:
So this is an opt in list based on what you just showed.

Danielle Messler [00:26:12]:
They said I think client current clients and prospects. So I think that they're also sending this cold to people in their list.

Zoe Hartsfield [00:26:21]:
Yikes.

Alex Fine [00:26:21]:
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?

Danielle Messler [00:26:31]:
Uh, yeah, I think so.

Will Allred [00:26:32]:
I need the Zoe yikes button for future.

Zoe Hartsfield [00:26:35]:
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 wipe of your phone? I'm not sure.

Will Allred [00:26:52]:
Especially if they use Outlook. Like none of those images are going to load so it's going to be a nightmare.

Danielle Messler [00:26:57]:
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, for a separate email. Not just use the same one.

Alex Fine [00:27:10]:
I can't.

Will Allred [00:27:11]:
The fact that I have to lean in.

Danielle Messler [00:27:12]:
I'm like oh, this is that song formatting.

Will Allred [00:27:17]:
That's the email.

Zoe Hartsfield [00:27:18]:
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 is like steps big if.

Alex Fine [00:27:35]:
I think this is like what Will said. This is going straight to the promotions folder. How do you straight to spam, spam or promotions? I could see it going to promotions too to be honest.

Maximus Greenwald [00:27:43]:
All right, let's say we strip out the emojis and the subject line and all the images and stuff, all. 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?

Will Allred [00:27:55]:
So like inside the email?

Maximus Greenwald [00:27:56]:
Yeah, inside the email.

Will Allred [00:27:58]:
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.

Zoe Hartsfield [00:28:18]:
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 mark.

Alex Fine [00:28:26]:
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.

Danielle Messler [00:28:40]:
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.

Alex Fine [00:28:47]:
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.

Will Allred [00:28:59]:
So I call that like the Triumph emoji.

Danielle Messler [00:29:02]:
Yeah, the little smush at the nose makes sense.

Alex Fine [00:29:06]:
Yeah.

Danielle Messler [00:29:08]:
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.

Zoe Hartsfield [00:29:17]:
Yeah, 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.

Will Allred [00:29:26]:
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'd approach it.

Danielle Messler [00:29:52]:
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.

Zoe Hartsfield [00:30:01]:
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.

Danielle Messler [00:30:29]:
All right, let's move on to the next one, which actually is a cold email, I promise.

Maximus Greenwald [00:30:32]:
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.

Danielle Messler [00:30:48]:
The subject line. Session 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?

Will Allred [00:31:07]:
So I actually appreciate the like, hey, I'm building this to solve this problem. Type messaging. 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.

Will Allred [00:31:27]:
Right. I've seen this. I do think the subject line and the first line are redundant, but let's.

Maximus Greenwald [00:31:33]:
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.

Maximus Greenwald [00:32:01]:
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.

Zoe Hartsfield [00:32:12]:
Yeah, I was going to say that line is the most compelling part of the email for me. Like that. 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 SE R 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.

Zoe Hartsfield [00:32:34]:
So, like, that's not going to hit the same way as the person building the product.

Will Allred [00:32:37]:
So I. Yeah, I guess you know, the founding team. But yeah, see that point.

Alex Fine [00:32:42]:
I'd move that first line that Zoe's 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.

Alex Fine [00:32:58]:
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.

Will Allred [00:33:21]:
Yeah. You could break this entire email out into a sequence. Right. Follow up, would love to get some feedback. Here's the link to the agent I built. Easy way to follow up.

Alex Fine [00:33:31]:
What I'm saying is I wouldn't even put the link. I'd ask them if they're interested in the link. Say, I already built it.

Will Allred [00:33:36]:
I was thinking email too.

Alex Fine [00:33:38]:
Oh, yeah, yeah, you can do that too.

Will Allred [00:33:39]:
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 you know cut some of that fluff and just be like, yeah, 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.

Will Allred [00:34:11]:
You want me to send one over.

Alex Fine [00:34:13]:
I think email on my screen right now for one of our clients that we wrote that's like almost identical to what you just said.

Maximus Greenwald [00:34:18]:
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.

Zoe Hartsfield [00:35:23]:
Yeah, I think like for me the tone is a little all over. To your point. Max, it 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.

Will Allred [00:35:55]:
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.

Alex Fine [00:36:07]:
People like helping people too. So if you play it like that, a lot of people are going to respond very positively.

Maximus Greenwald [00:36:12]:
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.

Danielle Messler [00:36:39]:
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.

Will Allred [00:37:01]:
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 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.

Zoe Hartsfield [00:37:43]:
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.

Danielle Messler [00:38:05]:
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?

Alex Fine [00:38:16]:
3. But I like Sachin. 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.

Zoe Hartsfield [00:38:23]:
Yeah, I would have said a three.

Danielle Messler [00:38:24]:
Action. If you're out there, Alex wants to hang out with you.

Will Allred [00:38:29]:
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 place does benefit.

Alex Fine [00:38:38]:
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.

Maximus Greenwald [00:38:47]:
I'll go four.

Danielle Messler [00:38:48]:
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.

Danielle Messler [00:39:06]:
That's gonna be tough. Audience. 12% open, 75% click through subject line. Managing IT risk. Let's make it easy.

Will Allred [00:39:14]:
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.

Alex Fine [00:39:26]:
Totally.

Danielle Messler [00:39:27]:
75%. It's 12% open, 75% click through. But yeah, it's definitely that. Especially if they're emailing it.

Alex Fine [00:39:33]:
Those tools do click on all the images and links.

Will Allred [00:39:35]:
Yeah. I like Taylor's comment. Every security leader knows that threats are evolving and growing more complex.

Danielle Messler [00:39:42]:
I thought they were getting easier. Speaking of formatting, this one kind of hurts my eyes.

Will Allred [00:39:49]:
I appreciate you putting it on a phone screen.

Danielle Messler [00:39:51]:
I didn't. That's how it was submitted. So I appreciate that.

Will Allred [00:39:54]:
I appreciate.

Alex Fine [00:39:55]:
Yeah, I'd scrap it entirely. I'd hit the phones. I wouldn't send emails in this market at all.

Will Allred [00:40:01]:
I've got the data. You disagree with that, but yeah, let's disagree.

Danielle Messler [00:40:05]:
Why do you disagree?

Will Allred [00:40:07]:
I mean, I was looking at someone's data within our product. Today, they're getting 4% and that's on the email basis. 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.

Zoe Hartsfield [00:40:41]:
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 what's going. 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.

Zoe Hartsfield [00:41:17]:
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.

Danielle Messler [00:41:28]:
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.

Will Allred [00:41:37]:
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 their IT and security services. It could be an easy way to spin up a project so that you don't have to go hire XYZ roles.

Maximus Greenwald [00:42:14]:
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.

Maximus Greenwald [00:42:42]:
That's my favorite line of it. And I'd maybe put that. Figure out how to put that more obvious.

Danielle Messler [00:42:47]:
Yeah. I feel like that sentence is the only point of this is what we can actually do for you in this email.

Will Allred [00:42:53]:
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.

Zoe Hartsfield [00:43:14]:
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.

Danielle Messler [00:43:32]:
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.

Will Allred [00:43:42]:
Or recognize they're in cyber security and they will never click that link no matter how many times you ask them.

Danielle Messler [00:43:48]:
No, they're never clicking that link. All right, this is our last one, so hit me with your scores.

Will Allred [00:43:55]:
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.

Danielle Messler [00:44:05]:
Thank you. Thank you. Wayne Ray wants to go first.

Will Allred [00:44:08]:
Well, now that I said all that nice stuff, I'm going to give it a one.

Alex Fine [00:44:15]:
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.

Maximus Greenwald [00:44:28]:
I'll give it a 2. I would have been open to a 3, but they got the Twitter logo from two years ago.

Alex Fine [00:44:33]:
I didn't even think about that.

Zoe Hartsfield [00:44:35]:
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.

Danielle Messler [00:44:43]:
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.

Will Allred [00:44:58]:
Thank you. Thanks for having us.

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